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Emily Henderson

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by Emily Henderson
Fashion Trends 18

It’s painfully true that there will come a point in your life where you will not understand what the youth are wearing (or why). To match your lameness, you might say something trite like, “omg, I wore that in junior high!” or maybe get to the point with a “wtf are they actually wearing?” But I don’t take fashion too seriously so I thought it would be VERY fun for my youngest team members to dress me in the trends that they are seeing and loving on their Instagram feeds. Brian thought it was April Fools. I felt like I was ready for Halloween. But I had SO MUCH FUN. So here you go: three trends/outfits my team helped pick out for me and four others on my youngest team members, plus how we all felt about them.

First up, my team really insisted on seeing me in this color we apparently refer to as “millennial purple.” Here’s how the youngins are wearing it:

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I think I don’t like millennial purple, yet. Like most things that I think look bad on me, it takes me a while to go through the following internal process:

Step 1: See the trend, hate on it verbally.

Step 2: Let time go by and allow the parasitic zeitgeist trend to burrow into my brain. Out comes an “ooh, well I kinda like this shade of it.”

Step 3: Try trend; realize that it indeed looks bad with my skin tone, as it always has. But maybe that’s also because my skin tone usually is a shade of “spray tan orange” that when resting next to this color looks BRIGHT orange. But I suppose that’s my problem, not millennial purple’s.

But this chick looks good in it:

Unnamed 1
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So we tried it out. When my team first bought a version of this look for me, they bought it as a suit (a blazer and short set) and I just couldn’t. It’s likely that if I lived in New York or had a more formal job, I would wear it because I love the idea of it, but it’s just not my lifestyle. It’s neither work wear or party wear or weekend wear.

Instead, I paired it with the obvious choice of a 40-year-old woman: skin-tight, lower thigh length biking shorts. I’m still unsure if I’m supposed to call them “biking” or “biker” shorts (wait…is it just “bike”?). Please advise.

Indeed, I liked it more and sure, and couldn’t wait to take Brian out on that hot date he’s wanted since he wrote my birthday post. I wore a vintage-style rock-and-roll shirt, I’m sorry, BAND SHIRT—that’s what it’s called now, and then we did what I’ve always wanted to do (I’m actually not joking)…put on some sheer socks and white pumps.

I think I nailed it.

Em Side By Side 01

BlazerT-Shirt | Bike Shorts | Shoes | Socks | Sunglasses | Sunglass Chain | Bag

How do I feel about it? I felt ridiculous but Ryann, Mallory, Veronica and Chandler all thought I look LEGIT COOL. I thought it was the definition of “try-hard” but again, that’s because…I WAS.

Here’s how I would “tweak” it for real life: wear the bike shorts with the T-shirt for sure, but likely wear it with Vans. And I love the socks/shoes combo, but likely would feel better about them with a dress that warranted such style. I will never wear the blazer, but my team was into it.

Next, my team dressed me in a look they are calling “festival Emily” based on these very trendy ladies:

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I get it. I like ripped jeans, boots, and vintage T-shirts so this isn’t completely off base for me.

Fashion Trends 10

Shirt | Skirt | Necklace (similar) | Sunglasses | Boots | Bag

This is how I dressed in the early 2000s and I like it, but it’s not me anymore and not because I’m too old, but because it doesn’t represent my personality any longer. I don’t think it’s ridiculous, I’m just more “Uptown Prairie” than “Downtown Rock’n Roll.” But honestly now that I think about it, I don’t think that the street-style festival look is too much of a trend that we haven’t seen before…and I guess that’s the case for most of these things. The fashion world simply regurgitates styles from the past by slapping them on fresh new faces and bodies. It’s a cycle.

Now, before we leave my trends, I had to try the biker short in another light, specifically the Hailey Bieber light. If you need more proof to believe this is actually a thing, I give you exhibit A, B, C, D, E and F.

from top left to right: image source | image source | image source | image source | image source | image source

But the image that got my team’s hearts all AFLUTTER was this one (which is evidently a Princess Di throwback):

Screen Shot 2019 09 06 At 10.19.19 Am
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People are FREAKING out about this. Of course, I think that it’s the case of “model-thin-celebrity-wears-anything-ugly-and-gets-people-cast-her-as-fashion-goddess,” but they disagree and truly think it’s awesome. So to prove for (or against) my case, here I go:

Fashion Trends 07

Sweatshirt | Bike Shorts | Socks | Shoes | Sunglasses | Purse (similar)

To say I felt uncool wearing this was the understatement of the ’80s. I felt frumpy. Silly. Embarrassed at best. But then I saw the photo and I was like, wait, is she kinda cool?

Let’s side by side it again, we need more analysis:

Em Side By Side 02

I think there is a clear winner, and it is not the one who slobbered on keys to “get the shot.” But I had hope for the bike shorts in my future. To convince my team of how I could see myself actually wearing them, I brought a sweatshirt and shoes from home.

Fashion Trends 08

Sweater (similar) | Shorts | Shoes | Sunglasses

I actually liked it! When I sought approval they said, it’s a “cute drop-off-the-kid-mom” clothes, but it’s no longer the look or trend that impressed them. I get that.

But I also think that the influence of “influencers” that are just “skinny models” is a miss and not who anyone should set their sights on or admire artistically. I challenged them to find other, weirder, more creative (and NEW) actual trends and I’d be game. I mean, I had fun but it’s literally just a sweatshirt and biker shorts from the ’80s, HOW did that break the internet? I suppose it was the idea of an influencer recreating iconic Princess Diana looks, but it still felt a little stale to me.

Despite the embarrassment of this shoot, experimenting and hanging out with my girls was fun. I will say that buying this stuff vintage makes far more sense for me (and creates less waste) because most of this isn’t even being reinvented or modernized, which is actually my biggest beef with it. That champion sweatshirt has proportions that no person would look good in—why not create a better silhouette? So that’s the good news, just head to Goodwill and you can surely find yourself some 35-year-old biker shorts…(but we’ve linked up where they got all of them, too).

Now for my crew to take a pass at this because we all wanted to have some fun. Being 25 and under, they can surely convince us all that these trends (i.e. reboots from the ’80s and ’90s because that is exactly what it is) are cool, RIGHT????

Ryann’s Trend: The Bike Shorts

Ryann Side By Side

Blazer | Shirt | Bike Shorts | ShoesSunglasses | Earrings

Her take: Yes, the bike shorts trend got to me, too (see Emily’s inspo photos earlier). As I began pulling my outfit together, more trends came into play i.e. the asymmetrical neckline, and the strappy heels and I won’t lie: I felt silly wearing this walking down Hyperion Ave posing for photos FOR SURE. When I saw the pictures, I wasn’t a complete hater because this outfit IS flattering and cute, it is just not “me.” That said, I would absolutely wear every one of these pieces again but likely not altogether like this. I am really into this blazer. The way it falls, the color, the length, everything about it. It’s really special and reasonable priced. The bike shorts are actually my favorite to wear around the house with an oversized T-shirt or sweatshirt (although I am not one to wear athleisure outside the house unless I am extremely tired or hungover lol). The sandals are very fun and I love a leopard print (plus I have nothing like them atm) and I can see myself wearing them with vintage Levi’s and a white ribbed tank top for summer or with black bell-bottoms and a tube top for a “going out” look. 

Veronica’s Trend: The Utility Pant + Tie Dye

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Veronica Side By Side

Shirt | Pants | Shoes

Her take: I’m a huge advocate for the “mom jean” trend that circled back around, and I feel like this is a comfier version of that. I felt very relaxed and cool in this, ready to skate along the beach! I would wear the shirt and shoes again and the pants only for winter because they were pretty heavy and warm. It’s all so comfortable and simple, and any of the pieces could be transferable to pair with other items of clothing. You could wear the tye-dye shirt with a pair of shorts and sandals for a summery look, the pants could be paired with a cropped shirt for a more comfy, loungey look, and the shoes can be worn with literally anything. Add a beanie on top of this outfit and a black long sleeve under for colder weather, and you’re ready to go.

Chandler’s Trend: The Jogger Pant

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Chan Side By Side

ShirtPants | Shoes | Sunglasses

Her take: I wanted to try this trend because there are so many ways to dress the outfit up or down, so I wanted to see how to get a good in-between that was still fun. I am a huge advocate of buying clothes that can function as something I can wear to the office, and then alter slightly for a Friday night dinner. These pants are comfortable and functional and I would for sure wear them again and again. They work with sneakers, but are pretty heavy and would also work with boots and a cropped sweater in colder weather, which I think would be a more comfortable way to wear them. I felt like this was a great everyday outfit with some spunk and style. It was a little edgier than my normal everyday outfit choice and I was into that. I don’t think I would wear the shirt again with these pants just because the see-through trend isn’t really my thing, but I LOVED the bra/tank I wore under the shirt. Overall, this trend is a yes for me.

Mallory’s Trend: The Midi Leopard Skirt + Dad Shoes

from top left to right: image source | image source | image source | image source
Mallory Side By Side

Shirt | Skirt | Shoes | Bag | Hair Clips

Her take: I’ve been into this leopard midi skirt trend for quite some time, so when it was time to pick a trend to try out for this post, I instantly knew it would be this. The strategy for the exact outfit inspo was this: go to the Urban Outfitters Instagram and search for the perfect leopard midi. It must have been a good strategy because I found one in 3 seconds. While wearing this, I felt like an influencer, honestly. It seemed weird that I wasn’t on Melrose with a latte in hand and my Instagram boyfriend taking photos of me in front of the pink wall. The dad shoes (which made me feel like I was Godzilla stomping through LA) PLUS the midi skirt PLUS the hair clips were a little too aggressively trendy for my taste. The top and the skirt together make a great go-to look that I know I’d wear all the time. I’d pair them with a dainty Madewell sandal over the dad sneaks (since I don’t consider myself edgy or sporty enough to pull off the FILA look).

Fashion Trends 20

Look at us. So happy with ourselves and our youth (ha!).

WHEW. That was a lot of trendiness for one day. What do you all think (I know to some of you, it might all seem silly, but playing “trendy” dress-up was honestly SO MUCH FUN)? We would love to hear your thoughts. xx

***photography by Veronica Crawford (group shots by Brian Henderson)

  1. Adorable! You all look great.

  2. I think if I had been in the brainstorm meeting for the post I would have said it was too silly but I really enjoyed it! I’m in a school run mom phase of my wardrobe life but trying to think about working millennial purple into my week now 💜

    1. ha. here’s how the brainstorm went – Ryann said, “lets try trends!” and I said “like what?” and they listed them all off and I said “there is no way, EVER, that I’ll like any of these and I don’t want it to be a post where we all legit look bad’. Thus the challenge began – to dress someone who genuinely don’t like a trend is a fun idea. I think we’ll flush it out even more next time and do a more livable version for each. xx

      1. At the risk of being a nit-picky grammar enthusiast, I think you meant “flesh it out” instead of flush.


  3. This was really cute ! It’s nice to see fashion posts and read your hilarious analysis of it. The Emily timeline of outfits post was golden for me, ha!

  4. Biker shorts are a thing? I often think there are a bunch of influencers somewhere daring each other to push awful trends to Millennials to see who can make them look the most ridiculous. This is one of those trends (along with dad sneakers and big bangs in the 80s) that people will look back on in ten years and wonder wtf happened.

    1. Yes, yes, and yes!

  5. I’m loving this post! I love seeing you all try out the trend and see how it can be “you.” I’m a big fan of your fashion posts in general.

    1. I am so not for the trends but absolutely for the post! 🙂 Fun and funny! I’ll admit I totally dress like a basic mom.

  6. Must pause, in my reading…I’m only one outfit in. I LOVE THIS POST. I’m 45, have a teenager, and this post is going to change my life! Perhaps I can incorporate something in my wardrobe (like the sunglasses chain), but for sure, it’s going to up my street cred. Also, you look great!

    1. It was super enlightening to me, too. Last night we went to a local high school football game and now I look around with more “respect” isn’t the right word but intrigue. I’m trying to channel my high school fashion trend chasing, although it was not just before instagram, but literally BEFORE THE INTERNET so I think we were only influenced by what was at the mall. It’s why I bought most of my clothes from thrift stores, to do something new and different and to feel unique, and I think that is a GREAT way to look at fashion. My parents later told me they were mortified at what I wore at my brothers college graduation when I was 26 (2007). It included a DIY sewn vintage polyester fabric navy blue and white polka dot skirt, a red sequin tube top and a camo shirt over top. But man it took time to be that “creative” 🙂

      1. Influenced by the mall…AND 17 magazine’s School feature- what was it called? They’d show up at a high school and take photos of the cool kids. (What principal approved that??). I LIVED for those real life trendsetters, especially the ones shown with boyfriends.

        1. School Zone!!!

    2. Follow up questions/comments :
      -Can I buy the lululemon bike length leggings or is that not the look?
      -What kinda dress would you the white shoe/sheer sock ruth?
      -Surely I lost my street cred by using the term street cred.

      1. 1. I think they would say no to lululemon. i think they have to be long and 80’s whatever that means
        2. I would wear it with a shift dress, or a middie that can handle that jazz. but TBH I need to experiment and test it out. I really need someone to consult … but who?
        3. I lost my streed cred by saying ‘rock and roll shirt’ (instead of band Tee). OWELL

  7. Omg! I’m a 37 year old and I am not here for bike shorts, dad shoes or scrunches! I just can’t!

    What a great boss you are! And that was fun to read. 🙂

  8. Whoops, totally didn’t mean I’m not *here* for those things and that you shouldn’t be posting them. Just that I do not like them!

    1. ha. I totally read it the right way 🙂 I’m not here for the dad shoes either, but if mallory wants to put on 7 lb (each) white cross trainers I WANT TO WITNESS IT 🙂 Its all VERY fun.

      1. Lol. Love this post. It is hilarious and just *legit* fun times.

        I just bought a set of small scrunchies from Anthro a few weeks ago. I am 36. My 12-year-old daughter witnessed me putting one in my hair this week and said, “Mom!! You have SCRUNCHIES??!! That is SO cool.” To which I immediately replied, “Um…yeah. I thought they were fun, and apparently, they are a ‘thing’ again.” She quickly responded with a clear seal of approval while I continued, “I just think it’s hilarious. These were super popular…when I was your age.” Smiling on the inside (and outside) while thinking, “Jeez, I sound old!!” 🤣

      2. It wouldn’t be a 2019 trend post without the dad shoes haha – I was happy to do my part!

    2. 🤣🤣🤣 Nailed it!

  9. Omg! This is the best post ever! (I totally wore bike shorts to go running in like 2000 lol, not sure I can say my legs look as good as yours anymore!)

  10. I often love a trend when I see it on someone else. But on me, it feels like a costume. The group shots were my favorite. Well done, Brian!

  11. The only thing biker shorts should be worn for is biking. … And get off my lawn. 😉

    1. I agree! It’s like wearing Chacos or Tevas with a dress. Those shoes have a purpose: to be worn while river rafting or doing similar activities.

      But the post was very fun.

    2. I agree! It’s like wearing Chacos or Tevas with a dress. Those shoes have a purpose: to be worn while river rafting or doing similar activities.

      But the post was very fun.

  12. As a 35 year old, I do not understand these trends. Except maybe the band shirt and cutoffs. I feel really old, but perhaps it is because I wore these clothes in a past life in the 80s / 90s?

    1. Ditto!! Biker shorts and dad shoes.. no thank you!

      1. Another 35 year old going, what is this?!? Followed by, when did I get so old!?!

  13. This is hilarious, because a few years back I went shopping for workout shorts and tried on some biker length ones I found on the rack. I liked the longer length and thought they looked good, but I didn’t buy them because I didn’t see anyone else wearing them at the time. I could’ve been such a freaking trend setter! What was I thinking?!

  14. This is hilarious! We are the same age, and I know my husband would have the same reaction as Brian. We recently moved to Sweden and I’m more confused than ever about fashion. Bike shorts are everywhere. Are they for the youngens? Or trendy? Or Nordic chic? Or totally practical because everyone bikes everywhere whilst wearing skirts? (I’m hoping for the latter, because there are so many practical things here I love), but I’m feeling old and just don’t know. Also, lots and lots of black leather here for fall. I think I’ll just head to Marimekkko and call it a day. Thanks for the laugh, your staff is a hoot.

    1. I would guess it’s both practical and intentionally stylish, like when Kate Moss made Hunter boots the bomb again by wearing them with a gown at a festival. She says it was the muddy ground that inspired them… but for real, this bike short trend does seem to be rooted in scandi chic, which is hot hot hot. So you are like at the epicenter of this trend moment, lol. Enjoy!

      1. YES. @amanda what else are they wearing??? And good call with the kate moss comparison – that is exactly right (and kinda inspiring).

  15. Such a fun post! 🙂

    Um……..Is that an eternity ring on your finger emily???
    Is that what was in the attic?!

    *huge eyes…holding breath…waitjng for an answer…*

  16. I teach high school (at an art school to be exact) and my students have been all over the Dad shoes for the past two years and I CANNOT with them. No way no how. They’re also all about the most hideous Crocs they can find. I do think it’s awesome that a lot of the trends are moving away from tight/uncomfortable into more baggy/comfortable (which is honestly how I dressed in the late 90s so they’re nailing it IMO)

    1. Oh no! We forgot crocs!

  17. I can’t look away. I am now at the point of I didn’t even realize these were trends! I think this is such a fun post.

  18. I’m obviously old… because these “trends” are hideous on everyone!!! And you are all super cute! 🤣🤣🤣 thanks for the entertainment.

  19. I should mention that my husband works at a high school and he’ll often adopt new trends because he is immersed in them in a way I am not. I will look at him sideways… like what is this??? And he’ll say… “all the kids are wearing it” I think it might be only less horrible if EVERYONE is sitting around in bike shorts….But there better be bike nearby. And dad shoes are always a bad idea. I can get behind a band shirt any day of the week. I’m very unsure about all these photos. Hahaha.

  20. This was a super fun read, and I’m glad you did it. Even with the silly trends you have a great figure and can still pull off bike shorts. But sweet-little-baby-Jesus, I am SO glad to be in my 50s and not having to worry about trends anymore! I pretty much live in jeans and t-shirts, which will never go out of style! SO much money saved, and no angsty worrying about what anyone thinks. -Aaaahhhh.

  21. Haha! As a woman solidly in the “drop the kids off at school” phase, I like Emily’s take on the bike shorts the best! I immediately thought, “now THAT’S cute!”

  22. This post was so fun to read! Being a 40 something myself, I had many laugh out loud moments as I find myself saying the exact things to my teen daughter about these styles! “Is it bike shorts? Biking shorts?” So fun to reminiscent! Thanks for the giggles! You are darling as always!

  23. This is amazing.

    I work on a college campus, specifically for a fashion department, and I always tell my students that they look adorably hip. But, this 32-year-old just.can’t.with.the.new.trends. I honestly think I like them because they are such an outrageous throwback to the 90’s and are mostly going to be regrettable in 5 years. Nonetheless, the youths really rock it, and I appreciate them for that.

    My students always say, “you’re not old!” and then I open my mouth and they’re like… okay, yeah, you’re a mom. God love ’em.

  24. I can’t even handle this. I LIVED in bike shorts my senior year of high school 88-89 (and since you asked, at the time they were strictly ‘bike’ shorts, not biking and definitely not biker!!) – so I guess that makes me the lame trite mom. I do try to convince my kids that I was pretty cool in my day. I mean, I shopped at urban when it was still a combination of Anthropologie, Urban, and a couple of racks of cool consignment (that was what we old folks called vintage). Oh my god, I have to stop – I’ve become my mom whose cool factor I was always trying to up 🤦‍♀️🤣

  25. Wait! It was junior year (87-88)! Ha I don’t know if that makes it better or worse… and I completely remember those Diana pics too. Love and seriously appreciate this post!

  26. I ride road and mountain bikes, as well as a motorcycle, these are not biker shorts. In motorcycle language bikers wear leather or specialized pants with body armor, and bike shorts have synthetic chamois padding in the crotch. This feels like yoga athleisure wear, and I have been wearing this as a bottom for years…but it is how you partner it that makes all the difference and this post so on point for opening our eyes to new possibilities. Love the story about your attire for the graduation. My family can tell similar stories about me. But as you get older one needs to devote time to career, child raising, financial stuff, these boring details of life, and we forget how fashion can be fun!

  27. I love this post and Emily I have never felt more like we are friends. Although I’ve been an avid reader of fashion since I was a teenager (I’m now 48) and I am newer to applying an “eye” toward interiors, your take on the biker shorts with blazers trend was EXACTLY mine. I JUST had this same convo with my husband last week (he humors my fashion musing, I humor his sports news). I really loved the opportunity to compare you and the model and I have to say I think it is “cool”. But I also agree that the majority of the cool factor is association with Princess Di and the model glam factor, but there is just enough sporty nerd going on to transcend into legit statement. I also want to second the whole tone of skepticism plus fun in this article. Fashion is both frivolous and art, wasteful and necessary, a connector and a divider. Even non participation isn’t really since everyone’s choices of what is available to buy is driven by those who care deeply. As someone who loves how ideas are expressed and shared in fashion and interiors I think it’s helpful to point out that it is all ultimately personal. You do you. (Talking to everyone now). Including how much you want to care and which trends resonate. In the meantime, can we just admit it’s fun to express ourselves?

    1. Beautifully put, Michelle. 🙂

  28. I’ve been wearing bike shorts for sometime now and well before it was trendy. My girls came home last month and said, ”oh look at mom being so Kardashian!” I had no idea they were a thing!

    1. Reason enough not to wear bike shorts if people think you’re doing it to follow the Kartrashian family. Yuck.

  29. You all look adorable. I have mixed feelings about trends. Playful and fun on the one hand, perpetuating disposal culture on the other. I struggle with it myself. Whenever I thin out my closets and end up donating a bunch of trendy clothes, I recommit to the capsule wardrobe/uniform. It also frees up a lot of my time and money for the things that really matter to me.

  30. I feel like exactly what you said, Emily, but I’m only 23 😂😂😂 what’s wrong with me ??😆 the biker shorts and blazer reminds me of a stay at home mom on a conference call: comfy bottoms but dressy top!

    1. that’s funny!

      1. 🤣🤣🤣 Nailed it!

  31. Cuuuuuuuuuuuuuuuuuuuuuuuuuuuuute

  32. Really enjoyed this! Took me back……LOL!

  33. Looks like fun. I’m even that much older than you, Emily, so you can imagine how ridiculous I would feel and look if I was to imitate those looks. But I am very much for always changing, trying new things, and updating. If we don’t, we get old!

  34. I love you “cute mom dropping off the kids look!!!” I mean as a 37 year old mother of 3 that’s what I’m going for most of the time. I want to see influencers that make me say “ hey I can do that” & not “oh man I’m too old for this” ha!

  35. I struggle with this because I live in the Midwest and people… haven’t stopped dressing like this long enough for it to have come back around.

  36. I actually drove by as you were posing for the shot on Rowena ave in front of the colorful bungalows and I have to say you looked lovely and like everyone was having so much fun!

  37. Super fun post!! Being even a bit older than Emily, I can so relate. My 10 year old wore a NASA t shirt the other day that I completely just didn’t get but it was a big hit at school 🤪

  38. Fab post! But I beg of you, since all of your readers aren’t 20-please make the font larger! I seriously can’t read these posts I so enjoy anymore. SO tiny! Pretty please?

    1. Hold down the ctrl and + keys (at the same time) to make fonts larger on a windows machine.

  39. Somehow these looks don’t do the same thing for me now as they did in my jr. high Delia’s catalogues!!! Hilarious post, though. 💙

    1. DELIAS!! I wanted it ALL, but could only afford the lavender(!!!) baby t with the embroidered spirograph print. <3

  40. I’ve enjoyed your blog for YEARS and have never commented until today. WHAT A FUN POST!

  41. You all look like members of the Breakfast Club in that first photo! I laughed out loud at you trying to replicate Hailey Beiber — too funny! You totally rocked the purple outfit, though!

  42. I know the story is about fashion, and what I really enjoyed seeing is that you have a woman of color in your circle. I have been following you for at least 7 years or more, and know that you have spoken into words your commitment to social justice work. I still hold the powerful memory of what you shared about Dr. Martin Luther King, so long ago. So I wanted to share this memory with you, and to also let you know in your images I see the complexity and power of accepting change, along with developing our fashion/design/gratitude/inspiration. In short, we are multidimensional, and that design lives in time and space continuum.

  43. This was such a super fun post! The pictures were great fun and I really enjoyed your commentary 😀 If you decide to do something like this again – I am *so* here for it! Also I’ve been in love with millenial purple (I call it lilac in my head) since you featured it in one of your trend posts in a super great purple/yellow/orange kitchen and been searching for a jacket in that colour ever since – so in conclusion: I want that blazer <3 😀

    1. I love that color, too, and I think it looks great on Emily. It looks great on me (maybe why I like it), because my eyes are blue, but when I wear lilac it makes them look positively turquoise.

  44. Uhhhh, these all just look like things that you would wear. You could have popped these photos up without explanation, and I’d have thought it was just your average Saturday fashion post. Maybe you’re not as limited as you think. 😉

  45. OMG, do I see Tevas with…socks???

    I had a shorts “suit” in the 90s that wore to shreds. Loved it. Comfy, but still work appropriate. Of course, that was ….mumblety … pounds ago.

  46. This is so fun! As a 33 year old former collegiate volleyball player who literally LIVED in spandex shorts (but really short ones) I just can’t bring myself back to them and feel that only super thin girls look cute in them. No one needs to see my c-section scar through my clothes! … But I thought this was creative and could tell you all had a blast doing it! It was a great Saturday read. Thanks!

  47. Wow, what a fun post! First off, when did lavender become “millennial purple???” Geez, purple and lavender have been around since forever. But that purple blazer looked so good on you Emily!! You should consider keeping it in your wardrobe. I loved it with the tee shirt and bike shorts…looked so comfortable!

    Also cracked up at the “dad shoes” term for sneakers. Is that truly a thing? They looked very good with the leopard skirt and top tho. That was one of my fave looks, along with Emily’s and Chandler’s. You guys all looked great in the trend clothing!!

  48. Such a fun trip down memory lane and education on modern fashion trends. I’m so out of the loop. Thanks for sharing

  49. I legit love this, love the risk in trying shit that looks crazy to 30+ folks, and love reading Emily’s flow of consciousness feedback and commentary! My favorite kind of posts!

  50. This post was fun to read. Honestly, my favorite look was the cute kid-drop-off mom outfit. Guess that ages me, but definitely most flattering look on you. So cute!!

  51. Hmmm, I’m 62 and sometimes never get out of my bike shorts (from Athleta) after a morning at the gym. I didn’t know it was a trend 😂. I’ll have to pop a blazer on over it and be oh so trendy! Wonder if I can pull that off? 🤔😃

  52. Ughhhhhh. Not chic, sloppy shleppy, universally unflattering. Sad. Even if your 20.

  53. I think I have your next challenge! When I was looking at some of these so-called “influencer” styles, I was thinking it looked like they just took a couple items they liked and put them together whether they should belong together or not. That said…

    What if you and your team went to a thrift store (or two) and bought outfits for each other? Draw names and that is who you shop for. Put together a complete outfit down to the shoes and accessories. Set a spending limit for each person. Or to up the game a bit, Ryann buys everyone a top, Veronica buys everyone a bottom (skirt/shorts/pants), Chandler buys everyone a “cover” (vest, blazer, jacket), Mallory buys everyone a pair of shoes and Emily picks out the purses and accessories. Then you each get dressed in the items chosen for you and see what kind of “influencer” you can each be. That would certainly bring lots of laughter and smiles!

  54. So FUN! Since I am soon to be 40 next month, I needed to see just what the “trends” are in fashion right now. So neat to see you Emily be a sport & see what they look like on you! I’d be game too. I just fill my time (when I have a minute for myself) looking at Interior Danish/SKANDI design trends mostly. Fashion design and trends are fun to see but not something I keep up with anymore. I am a mom to 3 boys! I’m BUSY. But I LOVE all the topics you blog about! Been keeping track of you since DesignStar–and I’m from Eugene/Portland Oregon too:) but currently in Texas. Would LOVE to meet you one day!!

  55. Emily, this is a great counterpoint to your 40th birthday ruminations. You are a fantastic combination of life experience and youthful exuberance. And you look great as a 20-year-old, btw.

  56. I loved this post so much! Keep it coming, I would love to see this as a regular feature!

  57. I love that sneakers are in now because I can wear sneakers and not feel like a boring out of style mom.

  58. Ugg I’m 29 but I guess I’m too old or not hip enough because I can’t handle todays trends. And I love a band tee but it better be for a band you actually like and know something about, if you’re wearing a Ramones shirt but can’t name any of their songs that’s terrible. I can’t even handle ‘mom jeans’ didn’t we call them that because they aren’t flattering on anyone? I don’t want to be that person that is still wearing 80’s hair, but maybe that’s the path I’m on because I can’t get on board with this.

  59. Emily….you are a good sport and a great boss.
    I am old enough to be your mother and I loved seeing this post. I never thought as myself as one who followed trends but just this week I saw in an advertisement a jumper with a big zipper all the way down the front.
    I had one of those in high school. Class of 1970.
    Wore it with a turtleneck and go go boots😃
    Tell your staff I expect the jumpers to be popular this winter but don’t see the go go boots on the horizon.
    Some trends are best left far behind!

  60. Fun post! I’m also so old that I was completely unaware that these ideas were current trends. However, I just want to say that all of YOU look really cute and most of the models look just sad. Underfed and depressed (I realize that that is their “look,” but it’s just sad to me).

    1. Well, I have to say that you are definitely a good sport, but yeah, all the shoes and socks are unbelievably ugly, tbh. Still, I respect you for trying them…

  61. Love this post, so fun! I was especially cracking up at the bike shorts / sweatshirt with a cute purse style. That was me all through high school in the early 2000s as a volleyball player, and what I’d wear going home after practices. I didn’t know it was even a “cool” look now! But it does look cute!

  62. I highly recommend checking out Stasia Savasuk’s instagram for fun/funky style AND encouragement to find your own style that makes your heart sing <3

  63. As a former professional athlete, I lived in biker shorts both on and off the court for twenty years or more. I’m retired now and no amount of money could coax me into them, as I prefer clothes that don’t cut off my Qi. Still, I can appreciate your post and the fun you had with your team.
    Side note: when I saw the photo of you wearing biker shorts and a sweatshirt with keys in your mouth, it sparked a memory I had of Lady Di and of course I had to google it. I found it – a photo of her coming out of her gym (in the 90’s) wearing biker shorts and a sweatshirt, keys in mouth while fumbling in her purse. She was a fav of mine and it softened me immediately. So, thank you.

  64. Gawd, I am old. I recognized when I was fifteen that bike shorts were not a good look. And I recognize it now that I am 43. It reminds me of different Jessicas and Britneys in the early 2000s wearing Uggs, Juicy Couture sweats pants with sparkles on the a** , and a thong hanging out – not a good look then and never will be a good look. Emily, you pulled the look off as much as you can, so bravo.

  65. The only piece I liked from the whole post was the lavendar blazer. It makes your hair pop. Its structured and sweet. It doesnt make you look orange, just more tan. I know I wont talk you into it but….

  66. I loved this… especially the photo match to Hailey Bieber’s outfit. Really playful and fun!! Would we wear most of those outfits?… probably no, but I think readers should let this inspire them to wear a rocker shirt with a black blazer or wear an animal print midi skirt with just a black t-shirt (or even a rocker shirt). Please continue to create fashion posts with your team!

  67. total flashback to the 90’s with these fashions. immediately thought of ‘clueless’ with that first outfit.

  68. Thank you for a fun and informative post….I like seeing current fashion trends. The eighties looks are hilarious…I didn’t know the Reebok’s and court shoes morphed into Dad Shoes! With the leopard skirt it reminds me of what we’d wear to commute in our work suits and nylons when we had to hoof 12 city blocks after getting off the train from the suburbs.
    I cannot agree with bike short in any way other than to work out or bike in. And I’m sorry, Emily, but with the sheer socks and pumps & blazer, it just looks like you forgot to put pants over shape wear.
    I guess I’m officially “old” because I can’t wear scrunches a second time in my life. Some fashion trends have a age limit, and I’m ok with that.

  69. So fun! This post was one of my favorite fashion posts of all time on your blog ☺️. I actually really love
    the champion sweatshirt and bike shorts combo!

    I have fully embraced some of these trends since early Spring and am loving them but like you talk about, I’ve made them enough my own that I don’t feel silly in them. Midi skirts and crops all the way but with vans or sandals instead of dad sneakers. Wore the bike shorts plus band tee and Vans yesterday. It’s an outfit I’ve worn multiple times but my husband noticed it for the first time I think and simply said (without any apparent feeling or judgement), are those bike shorts? 🤣 To which I replied “yep!” The first time I wore a midi skirt with a tee, leather jacket, and black Vans he said, “wow, that’s such a cool look” (he never compliments for flattery so when I receive one I know it’s legit). I lol when you talked about how Brian thought it was April fools 🤣.

    I am all about not taking ourselves too seriously and having fun with clothes and love that you live by that mentality too.

  70. This post was fun, I liked it – everyone looked cute! I’d love to see the fashion trends in this post translated into an interior design post?!

  71. Ha, I’m 38 and this post cracked me up. I had no idea bike shorts were a thing other than a kind of CYA for my toddler to wear under dresses. For me, they fall under the same category as wearing leggings as pants and that is a resounding NO. I do love the leopard print skirt though – I can’t get enough leopard in my wardrobe. Thanks for this post, I needed these giggles!

  72. I agree it’s fun to play “dress up” but some things are just wrong on ALL levels, ie dad shoes and bike shorts. No not ever! And let’s throw in crew socks while we’re at it ( those only work if you have the legs of a giraffe.) I know you design folks know what’s great for editorial usually doesn’t work in real life. But still fun, thanks for sharing!

  73. What a fun post! But strongly dislike everything but maybe the skirt sans dad shoe. What’s next in the fashion world? Z cavariccis? Hypercolor t-shirts? Now I get what my mom was laughing about when I wore 70s stuff in the early 90s. Ha!!

  74. I really liked all the looks, especially the blazer one! Millennial purple forever! All the staff members looked very cute in their looks too.

    I’ve totally been flashing back to when 70s styles were back in a big way in the 90s and my mom just couldn’t see why it was cool. And I couldn’t see how she couldn’t see it haha! As these are the first trends that are coming back from when I was first aware of/cared about fashion and style, I can relate to the difficulty of reimagining these items/styles. But it’s so much fun to see how creatively the youngs are putting things together and I have to say I really like most of it! I think young people really seem to understand color and pattern and even proportion in a way my generation did not (I’m 36). Or at least they’re having more fun playing with color/pattern/proportion. Can’t wait to see what’s next!

  75. Cute post idea but bike shorts are a strong nope for me. All I can think of is Vanilla Ice and Milli Vanilli when I see them, especially when worn with blazers or sweatshirts. That blazer on Emily is great though. I love a good blazer or jacket in general. The rest of the outfit is good too.

    I think my issue with some of these trends is that I was in my 20s when they first happened and I just can’t get into them again. I do love the dad sneaker look and have seen really cute jogger and utility pants. Tie dye? Possibly. Watching the younguns enjoy the trends in these iterations is fun, though.

  76. Biker shorts as anything but workout wear (and even then) need to die. ESPECIALLY when paired with a blazer. Sorry, but that looks ridiculous on anyone.

    As do those awful socks that hailey Bieber are wearing. Even she looks awful in them (and arguably the dad sneakers, but especially the 2 worn together outside of a gym).

    Bring on Millennial purple though. Aka lavender.

  77. I like how your office plays dress up/down together.

  78. I bought a pair of biker shorts recently, because they are great for the postpartum body and I felt moderately cool in them. My 13 year old* thought they were so cool and made me go back and buy her a pair. I’m all for her thinking I’m cool, while simultaneously hiding my muffin top!

    *Yes, I’m 40 and have a 1 year old AND a 13 year old. 😉

  79. I’m 36 and cannot even handle any of these trends! No, no, no. I definitely enjoyed this post in a What a silly-fun thing to do, omg I am out of touch with fashion trends and am super thankful about it, way. Fun enough I had to comment, horrifying enough (many of these trends) that I had to comment!

  80. Here’s how trends go in both fashion and design:

    Year X: Look at this cool new trend!
    Year X + 10: OMG this is SOOOOO hideous; we need to trash/rip out everything!
    Year X + 20: Look at this cool vintage trend (from year X) that is now so much better because it’s vintage plus this cool modern twist.

  81. you are a good sport and I’m going to file this away for when my 2 girls are old enough to have more fashion opinions…

    it cracks me up – i was in high school/college when that bike short/oversized sweatshirt trend was in the last time…of all the trends I’ve lived through since then, I can definitively say that was the least flattering and most ridiculous! To this day i have a men’s xxl sweatshirt from that era (I’m usually a women’s xs) that is even gigantic on my 6’1″ husband…I keep it at our lake house…and on the rare occasions I wear it, I never fail to wonder what the h3ll i was thinking, buying clothes that big…

  82. I’m 36 and my reaction went something along the lines of- “oh! maybe I can incorporate *one* piece from each look into my wardrobe?” but then…does the restraint make me old?!

  83. Yikes. I must be officially old because my honest response to ALL of these was wtaf is she wearing? Yeah, I’m not down with any of these.

  84. You have no idea how helpful this article was to me! I had read it on Sunday and shortly after showed up at my parents for dinner only to find my 16yr old cousin dressed head to toe in all of these trends! My mom and aunt were so confused with her white sneakers, white socks (my grandmother wore that combo FOREVER). I quickly pulled out your article and now we are all well-educated on what the “young ppl” are wearing these days lol. My cousin did confirm the Lady Di throwback image is what all her friends think is cool. I’m 33, I thought I followed lots of fashion blogs . . . I still dont get the appeal of the white sneakers and socks. Maybe it’s because I remember it the first time around?? All the other stuff is really cute though! I loved the way YOU styled the bike shorts. Might try them that way 🙂

  85. I can get on board with nearly every look in this round up EXCEPT those god awful bike shorts. Why they are popular now (OR EVER) will remain one of life’s greatest mysteries.

  86. I can’t say that I think any of these outfits are that cute or flattering on anyone (I just don’t get why we are bringing back stuff from the 90s that we KNOW doesn’t flatter anyone when we have made such strides and now have high waisted jeans, ya know?!) and they definitely feel (as you said) “try-hard” but it was still one of my favorite posts because it’s pure FUN! Why NOT try trends you have been seeing people wear and see if you like it. That’s the joy of fashion!

    Would love to see y’all do more posts like this, but maybe less trying to make something work that isn’t actually anyone’s style, and more along the lines of “how each of us would dress on Friday night” along with what y’all would likely have planned that night, or “how we dress for the Summer to Fall transitional period”.

    You have the advantage of having multiple age groups in your office with likely various style, so I think there would be something everyone could relate to or gravitate towards!

  87. thumbs down to all outfits–sorry. sad.

  88. Oh my! These trends are different than my area with the exception of the utility pant (all about the Carhardts). Maybe I’ll have to ask some of the girls, but it’s seems like they are more into outdoor wear ala Salmon Sisters and printed shirts from local artists.

  89. You KILLED the lavender blazer! It looks fantastic with your hair. The shades, the tee, and the biker shorts look perfect with it (I’d switch the shorts out for a short black pencil skirt b/c I’d feel too self-conscious, but you look great)!!
    Maybe the socks and shoes are too much with the already-eclectic outfit but I am also 40 so what do I know?

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