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Emily Henderson

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by Emily Henderson
Emily Henderson Fashion Spring Casual Outfits

The first round of spring fashion is here and while I’m not ready to go all out with florals yet (but will be so soon), this feels like a good transition from winter to spring, with a few staples that I’ve never tried (MOTO JACKET! HIGH TOP CONVERSE!). I wanted this post to showcase some outfits that would be somewhat of a stretch for me, because let’s face it, chambray-all-day habits are hard to break. Luckily, my super stylish friend Suzanne Thune helped pull together some looks that I felt good in and could actually see myself wearing in real life.

Let’s start with my first moto jacket (above) which is a big hit with the French bulldog contingent. I’ve never been that into moto jackets mainly because they never fit me well. I have secret boobs and they always felt so constricting, but this one has more room (but is still tailored) and I have worn it three times since. It edges up any outfit especially a more casual one like this (but I am sure can be easily paired with a dress for a really cool date night look).

Those shoes are my new go-to sneakers and they really up the coolness factor with the platform and I also love how long and narrow they look. Dr. Scholls also has a great pair that is much more affordable (and very comfortable, I own those, too).

Emily Henderson Fashion Spring Casual Outfits

These shorts are THE NEW SHORT for me. I love them so much I need to buy a backup pair just in case I lose them (or they fall apart…although I still have two pairs from last year that I will wear all the time, too). The top is my new favorite one from Ulla Johnson and while it is a splurge I have a strong feeling it will be like my red one from two years ago that I ended up wearing 100 times and STILL wear. It’s the right amount of boho for me and has that boxy blousy cut that I love. It’s also easy to care for because it never looks wrinkly so all I have to do is throw it on, no ironing necessary, AND works as a casual look with shorts, or a nighttime look with skinny jeans and heels.

Emily Henderson Fashion Spring Casual Outfits

These overalls are very easy to wear, they don’t hug tightly in the belly (in fact, they fall in a really flattering way) and with the boxy blouse it feels so effortless, comfortable, but definitely looks put together. Plus, it’s not denim colored which is a change for me.

The shoes are new, from Frye, and I LOVE THEM. They are headed into the western trend but not too far (no studs or decorative doodads) and have the perfect amount of heel. Hot tip: pointy toes = longer leg, if you are into that (I am).

Emily Henderson Fashion Spring Casual Outfits

This blouse is special. It’s from The Great where everything can seem a little basic and the prices are high and you think why would this be this much? but then you put it on and you are like oh, I see. These are actually the best sweats in the world. The shape and fit of everything they make is just so good. So this shirt may not look like much, but it IS. It is triangle shaped (so it’s even wider than the boxy cut—yay for me!) and the detail around the neck is lovely. Suzanne works at The Great so that’s why you’ll see a few of their pieces here (and yes I get a press discount but I do GENUINELY love the clothes and the women behind them). The brand is full of the casual, comfortable, flattering yet modern pieces that I am addicted to. So, if you like a drop crotch as much as I do, then head over to their beautiful store in WEHO and try everything on and tell me what you think. Oh, and ask for Suzanne. 🙂

Okay, up next is an outfit that Suzanne was wearing to drop off her kid at school and I ran into her at Starbucks right after and said to her “HOW DO YOU LOOK SO COOL AND WHY CAN’T I PULL THIS OFF??”

Emily Henderson Fashion Spring Casual Outfits

She did NOT agree, and shouted that of course I could wear this and insisted on getting naked and dressing me in her clothes to prove that even I could pull off wearing a gray sweatsuit out of the house. I, however, thought that I should at least swap the sweats for a ripped jean and since it was 80 degrees in LA last week, we switched the beanie to a linen baseball cap.

Emily Henderson Fashion Spring Casual Outfits

So now you need to tell me which is “cooler.” Suzanne sticks with her outfit and while I do think it looks cool, I can’t really wear that to work, so it’s more of a Saturday-morning-grocery-store-run outfit, which doesn’t seem like a very important outfit that is in need of thought. But if I wear jeans instead then I can totally wear this on a Friday or on a day when I’m styling on set.

Emily Henderson Fashion Spring Casual Outfits

PLEASE WEIGH IN BUT REMEMBER WHO YOUR REAL FRIEND IS HERE…Me. (JK I’m sincerely curious if I’m just not cool enough to wear a monotone gray sweatsuit).

Up next is a look that I hope you love as much as I do. Listen, I will admit that this boiler suit is hard to shoot so it may not come across super flattering in photos but I’m telling you right now it’s incredible.

Emily Henderson Fashion Spring Casual Outfits

The cut. The front pockets. The tailoring. The wide-legged pant. The roomy waist. The ruching in the back…it’s just so good.

I am wearing a size 1, but took it back for a 0 and Suzanne is wearing a 0. But, if I wanted a roomier, more oversized look, that size would’ve been perfect.

Emily Henderson Fashion Spring Casual Outfits

Again, you have to try it on to be convinced of how good it is. It is a splurge so if it’s not a hell yes, it’s a no, but think about it this way: it’s both a shirt and pants, and you don’t need any accessories. Let me know if you need any other purchase rationalizing in life, I’m INCREDIBLE at it and have considered having a booth at the mall for all those who need someone to help them rationalize a splurgy purchase.

Oh, and those are my new clogs that I wear every. day. Clogs are the new mules I’ve just decided. These are from Madewell and they aren’t a fortune and are so comfy. WIN WIN.

Onto my most favorite (and affordable) top:

Emily Henderson Fashion Spring Casual Outfits

It’s kinda a throwback Emily Henderson top but it feels more modern and fresh. The Victorian puff sleeves are flattering (I think) because it plays with proportions in a good way.

Those shoes are my new summer sandal. Who doesn’t love a little nurse chic, right?? What with the platform, the white sole, the blush leather AND the insane comfortability, I am sold. I’ve worn them four times since this shoot.

Emily Henderson Fashion Spring Casual Outfits

Also, the skirt is super comfy but I suggest you size down because the fabric is very stretchy.

Alright, in another not so shocking combo, we have a white blouse with, drumroll please, DENIM SHORTS.

Emily Henderson Fashion Spring Casual Outfits

Yes, I also bought those clogs in pink. They’re that good. Originally, I was unsure if the top was interesting enough but once it was on my body I really liked it. It falls well, has cute little ruffles, a pretty V-neck and cooperates with my half tuck needs.

Emily Henderson Fashion Spring Casual Outfits

I know what you are thinking and yes, my face is much lighter than my legs. I forgot to get a spray tan so I basically rubbed this brown lotion all over my legs and then they were WAY too dark a compared to other parts of my body. It was both disgusting and hilarious.

Lastly, a dress that I’m on the fence about keeping because, well, I have nine of these, but it is super flattering as the shape of it gives you nice curves even if your body falls more straight (if that’s what you’re going for).

Emily Henderson Fashion Spring Casual Outfits

To be honest, I should have worn other shoes to style that outfit better, but I had these Nisolo oxfords and I really wanted to wear them. WHOOPS. Oh well, you get the idea.

Emily Henderson Fashion Spring Casual Outfits

1. Ruffle Sleeve Blouse | 2. 501 Long Shorts | 3. Pink Clogs | 4. Floral Blouse | 5. Leather Jacket | 6. Black Leather Sneakers | 7. 501 High Rise Shorts | 8. Gray Long Jacket | 9. Beanie | 10. Pullover Sweatshirt | 11. Sweatpants | 12. Converse Sneakers | 13. Jeans | 14. Linen Baseball Hat | 15. Jumpsuit | 16. Tan Clogs | 17. Ruched Sleeve Top | 18. White Demin Skirt | 19. Platform Sandals | 20. Denim Dress | 21. Black Oxfords | 22. Black Short Overalls | 23. Moto Booties | 24. White Bottom Up

What do you guys think? Are you on board with the new “cool” Emily? (JK). Do you wanna see the outtakes? HA.

***photography by Veronica Crawford for EHD

  1. The blouse #4 is cute, also the skinny jeans and I like that Converse are back 🙂 I really want to like the jumpsuit #15 but I can’t.

  2. I think Team Beanie is cooler than Team Baseball cap but, really, you pull off both looks very well. I have had several pairs of Converse for years but I’m about to turn 57 and I just get this weird feeling that I am suddenly … too old for Converse. Like I don’t want to be one of those older women who look like they’re trying to relive their youth. But the white Converse look so cute on you. … (Of course you’re younger than me.)

    P.S. Too many great shoes here. It’s always dangerous for me to read your clothing posts. 😉
    P.S.S. I like the unripped shorts better.
    P.S.S.S. My daughter bought a great fake-leather Moto jacket from H&M and is wearing it constantly. A leather or leather-looking Moto jacket really is one of the most versatile jackets.

    1. I am team baseball cap! But with the sweatpants 🙂

    2. You’re never too old for Converse. I have a great pic of my 90+ grandmother wearing black high top Converse with a prairie skirt to thanksgiving a few years back. She’s an artist and cool and reminds me that style is ageless unless the lewk is all about boobs and bum, then it can be age driven because you can really you outgrow that overt sexuality… but Fashion leaves room for the personal exception. If you don’t like converse because it doesn’t reflect the polished you, drop them! But if you love them don’t let some idea like “age” ever stop you from doing you.

      1. I just have to shower some love on Michelle’s comment above. Yeah! I am over 40 and happily wearing my Converse low-tops (I keep finding new ways to style them.). I don’t find the high-tops comfortable on my ankles but they are very cute on Emily.

        I like the white blouse with the overalls more than I expected to and the v-neck blouse and less ripped jeans are good too. I think the boiler suit in the smaller size is very cool but it needs some subtle accessories. I too am totally surprised, to prefer the grey sweats outfit. But I agree about the overly stylized beanie look in LA, hmmm. The two “Emily” blouses are sweet but personally I would like to see some colors other than blue. The white denim skirt is a great pairing and something I would wear, rather than all the short ripped denim shorts. Lastly, welcome to team clogs!!

        Did I miss something or why has no one identified the adorable dog in the first photo???

  3. I am honestly shocked to say I like the gray sweatpants better. I am in love with a sweatsuit outfit.!? Wow..it’s really good.
    You look great in it but now wondering if I could pull it off..;)

    1. Ikr?? It’s FANTASTIC. The perfectly put-together casual outfit for chilly shopping/dog walking/etc. I want. Sweats are already sold out and coat is only available in tiny sizes. 🙁

      Warmer weather version is very cool too. I’m getting that hat.

      1. So much is sold out. Very bummed.

    2. Anyone know of any other options for those sold out sweat pants? Preferably affordable options?

      1. Uniqlo has similar options for way less. They’re my go-to for inexpensive, quality, cute clothes. Their sweatpants aren’t distressed, but they’re still cut and super comfortable.

    3. I wasn’t expecting such enthusiasm for the sweatsuit but I AM HERE FOR IT 🙂

      1. Who makes the grey sweatpants in the actual post? Looks like they’re sold out but I’d still like to keep my eyes open for when they restock. Thanks!

      2. Can you ask Suzanne for the source for the sweats?!

    4. I actually luvv the monochromatic gray outfit – for work – including sweat pants! The fact that they’re cropped and have the uneven hem, I think, makes them elevated and intentional, even though they’re made out of sweat pant material.

      Then again, I work in IT at a very relaxed dress-code place… But still, it looks very put together (and beautiful) to me.

  4. The sweatsuit and denim dress!!!!

  5. Love these posts! My body type is totally different, so I can rarely get away with the things that look terrific on you, but I so enjoy the spirit you bring to these – all about how real women think about real clothes and how they fit with bodies and also LIFE. So much better than 97% of other fashion posts out there.

    Thanks for being you, and happy Friday!

    1. Ahh such a sweet comment 🙂 Thank you Erin xx

  6. Sorry, comenting twice to weigh in on your debate. From a fashion look perspective I like the grey sweatpants with beanie. It’s a cohesive color palette and although a beanie feels ridiculous in 80 degree weather (we Minnesotans drop our hats at 30 degrees) it looks cool. That said, I too wouldn’t wear sweats to work, unless I dressed them up with heels and blazer or something that clearly showed I KNEW I was working today. So I like your updates for you and your job. I also think choosing the best fashion look isn’t the same as dressing for real life and I love that you approach this so solidly from the latter perspective. If I wanted fashion above all, I would read a fashion blog. But I like YOU so am always interested in the whole you and not just your house stuff, so keep sharing!

    1. I like the sweatpants and coat, but, I must say, as a fellow Angeleno it kills me to see people walking around in beanies when it’s not that cold out….especially when it’s clear their hair is styled underneath said beanie, that they have make-up on, etc–it’s supposed to look just thrown together, but totally isn’t, it’s a look. The “fashionable” beanie always comes off as douchie to me. Sorry! xoxo

  7. all super cute except for the boiler suit. Looks too much like a garage mechanic.

  8. LOVE the overalls outfit! So stylish!! You always give me such great style inspiration💕

    1. THANK YOU xx

  9. I just can’t with jumpsuits! It’s WAY too much effort to go to the bathroom.

  10. Ha! “Secret boobs.” Yep, I’ve got those too – small frame, long legs & short waisted. In clothes they don’t …assert their presence. Put on a bathing suit and “well hello there!”

    All these outfits suit you. I especially love the blouse from the Great, and the jumpsuit. The sweat outfit is more note worthy because it is tonal/ monochromatic and you looked fab in both versions.
    : )

    1. Ha! Yes exactly. Thank you xx I am glad someone likes the jumpsuit because I still love it 🙂

  11. Gorgeous! I love most of it (not the jumpsuit, sorry!) * especially * the sweatpants – alas they’re sold out! Also definitely beanie and norm cap with that outfit. I also wanted to say that you mentioned them being too casual for work, in which case I assume you don’t wear your ripped denim shorts, caus they’re v casual in comparison. I’m also still in love with your red shirt from 2 years ago!

  12. Team sweatpants over jeans! I have to say, I’m enjoying the fashion content. It’s basically all out of my budget (maybe some outfits from your employees, which I can *maybe* afford would be cool in some content) but I think the Saturday posts (which I love) have brought me around. Thanks for sharing!

  13. I thought for sure if you were wearing a leather logo jacket it would be nude! Or navy. But it’s nice to mix it up sometimes. You’re really selling those black overalls and it’s making me want to give them a shot, although I’m afraid they will make me feel like I’m in middle school all over again.

    1. Sorry that should be “moto” not logo.

  14. Love everything except that denim dress. Maybe it doesn’t photograph well, but it just looks so dated, heavy and uncomfortable. On a computer screen it is not at all flattering on your frame. I bought a Halogen moto jacket last summer during the Nordstrom Anniversary sale and it has been a gold mine in amping up my weekend style!!

  15. This post is so much more satisfying than the “things I’m probably returning” list! My weight is still in postpartum flux, so I know better than to splurge right now, but I still like getting ideas for shapes and looks that are functional, but not boring. Plus I have to feed my Poshmark search habit somehow!

  16. I love this post. Thank you! I am on the prowl for a black leather moto jacket, so this is helpful. I just hope I don’t feel like a poser in one. I think you get that though, and you don’t look like a poser, so I have hope!
    Also: I ordered some Nisolo oxfords and am breaking them in. So far so good. Thanks for the rec.
    And, if you’re venturing into clogs, I recommend the Sandgrens Brett clogs. You tend to go for mules, so I’m not sure you’ll be into the closed back (plus LA = warmer weather then Maryland), but they are pretty dreamy and quickly becoming my most comfortable shoe. Amazon sells them, too.

    1. Ooh thanks for the recommendation xx

  17. I normally scroll right past the fashion posts but for some reason was into this one. Love all the shirts! The moto, the blue Victorian, the print navy, the two white button downs, really look good on you. I don’t get the jumpsuit/overalls/boiler suit thing at all… and I think you rocked both the gray coat looks! I actually thought the sweats and cap version was cooler, something about the hat with everything. The jeans version is more classic and an excellent more versatile option. Me, I buy about 80% of my clothes from the thrift store and spend my little bit of spare income on home improvement and decorating 🙂

  18. I bought the pink clogs last summer, and absolutely love them. Wasn’t so sure I would wear them, but turns out the pink is much more versatile than I thought. Good to know I won’t look SOOO last year, wearing them this year. Not that I really care.

    I’m team beanie and sweats! But understand the sweats aren’t suitable for work, so jeans are the smarted investment. That grey jacket is lovely.

    1. Yes I love the pink clogs!! They surprisingly go with almost everything 🙂

  19. Hi Em

    Love the spring looks!

    When you describe the moto jacket you mention “secret boobs” what are they? Honestly feel kinda like a creeper scrutinizing all your photos looking for larger boobs on you, but you look really normal 🙂

  20. “Secret boobs” Ha!!!

    1. I have secret boobs too! That’s the best description ever! Stealing immediately.

  21. The all grey with sweatpants is way cooler. The other is a little more pedestrian. You can definitely pull off the all grey!

  22. I love your clothing posts – but that boiler room thing? It only belongs worn under a car doing an oil change. Explain what is flattering, please. in detail.

  23. I like the jeans best with the outfit! Jeans are better depending on what you plan to do that day. I would just stick my hair up in a bun rather than wear a hat, and wear some black slip on shoes. Can we get some high-low options on these outfits? I doubt a lot of people would spend $300 on a shirt… the Madewell prices are high for me, but doable.

  24. So I love all these haha I have bought too many things from your recommendations Emily!! LOL

    Sidenote, those platform blush sandals are adorable but I found a much cheaper option on Dr.Scholl’s for $70! https://fave.co/2unX5Xu

  25. Adorbs. And the sweatpants are cooler. Something about the monotone. So try gray jeans?

  26. Always dangerous to open the fashion posts!
    I love BOTH the full on sweats / beanie outfit and the one with the jeans / cap. But, if you’re looking for a vote on a favorite, I have to give the sweats / beanie one the upper hand. It’s sooo “how dare you look that cool in sweatpants?” in a way that I never would have tried but totally want to now.

  27. HERE for the sweatsuit with beanie. Dying inside that the sweater coat is sold out.

  28. Team jumpsuit forever! I love how effortless and cool the jumpsuit looks. Need it!

  29. Emily Henderson, who are you? Colored shoes, not nude? The converse are adorable on you! I like everything.

  30. Love the grey on grey on grey sweat suit. I think the reason you think it looks better on Suzanne is because of her dark hair. The grey blends with blonde. You could go with a more grey marle. Or a navy blue.
    The thing I don’t get is how everyone assumes that sweats are inappropriate for ‘casual’ office wear and the like. If you are neat, with clean clothes and bathed, I don’t get the aversion some have for certain clothes.

    1. I feel the same. How are sweat pants less appropriate than trashed shorts?

      1. Where did your friend get her jumpsuit? I love the look!

  31. I want so many of these outfits!!!

  32. The way you post just brings a smile to my face…you are so hilarious. Think the sweater looks to heavy for spring in LA, although I’ve never been there. The boiler suits, I just can’t love them. They look really comfy for painting the house, but I can’t imagine wearing one anywhere. Everything else looks great on you. You have great legs so you can carry all of those outfits off! I have taken to dressing monochromatically (not a word, evidently) at my age of 58. Something about it works well for me.

  33. OMG I want every single thing you tried on!!!

  34. You look so hot in the beanie and sweats look, honestly, Emily. You’ve never looked cooler. I agree with Suzanne.

  35. I know you like the jeans looks better with the grey jacket, but that monochromatic look seems so much more sophisticated. In the photo, the pants don’t really read like sweatpants, but does it really matter if they’re sweatpants? What if you called them cotton pants? Then they’d be ok, right? I think you look really put together in that version….more than the jeans version. And I’m not a baseball cap fan–it always reminds me of a bad hair day coverup. So maybe nothing. But that style jacket is great for you….like that coat you had for fall/winter. makes you look taller. Not a fan of the coveralls. They look too much like a sophisticated garage mechanic outfit. Or something a puppeteer would wear. Cute, but not great. I don’t think the denim dress is you at your best. Doesn’t highlight your best features or make you look particularly happy. The other outfits are cute, though. Too much commentary???

  36. WHat size in the Levi shorts are you wearing?

  37. These outfits are all adorable but your legs are the big winner! They look amazing! What are you doing?

  38. Whg about the black joggers at the very end of the video? Any chance you could tell me where they are from?

  39. The sweats and beanie are 100% cooler and you are rocking them! So much more chilled and just natural casual style. Do it! And that boiler suit on you is amazing.

  40. I was looking for the black joggers you had on. You were wearing them with a denim jacket. Can you tell me where you purchased them?
    Thanks, Wendy

  41. This articule help me 100% https://goo.gl/m1vAk8

  42. I love every outfit and every item!!! You look fabulous!

  43. Both looks are wonderful. But that jumpsuit, I’m just glad it’s comfortable! That is its major charm, in my book! I love that long gray coat.

  44. Double thumbs up on the moto, sneakers and all the blouses. I like both sweater looks; monotone Emily and styling day Emily. Can NOT get behind shredded jean shorts (it’s me, not you). Not wild about the jumpsuit but I’d go with it if I had to change the oil in my car (okay, that’s a little TOO snarky).

    Mostly it all looks good on you …. hello, blonde, slim and beautiful? No surprise there. But those blouses … might even make me look cool (er).

  45. My god, you look cute in EVERYTHING (so not fair!!). I bet you could totally rock a diaper and get away with it …

  46. I love your style posts! Always inspiring, but for some reason this one really got me. I am going to actually buy some of these things! Or similar since others have said the items linked to are sold out

    Finding new style ideas and clothing brands (also new music – is this just me?) in my 30s is so hard for some reason. So anyway, THANK YOU

  47. I am 1000 percent obsessed with the gray on gray look and need to know the link for both the sweats and the jacket. I went to The Great but can’t pinpoint which sweats you have on. I love this look so much, but also love your version. I agree that the gray on gray isn’t something you can wear past 10am. However, I am a mom of two boys here in Los Angeles and needs this in my arsenal when I’m dashing out in the morning to tackle errands before the kids get cranky. Thank you so much for sharing your Spring wardrobe!

  48. Love these posts!
    Some thoughts:
    1. Clogs are the new mules, yes. And the new sandals, and the new sneakers. Yes to #cloglife .
    2. I really like the “you” version of the gray sweats outfit. It’s tomboyish and cute and comfortable and you look like yourself, not someone else, but you’re both cool!
    3. I love summer and can’t wait to wear all my pretty, float, summer blouses. These sensible wool sweaters have been killing me.
    You look great, as always!

  49. Em… The MOTO jacket is YOU more than any other piece you have shown us in this post. YOUR styling of Suzanne’s long gray jacket with jeans and a ball cap is definitely a much “cooler” look! Okay, you might have nine denim dresses, KEEP this one, anyway. It looks fabulous on you, truly fabulous! It’s timeless and as far as I’m concerned, one can never have too many denim dresses, especially one that fits as well as this one fits you!

  50. I think Emily could pull of the sweatsuit option with a statement necklace or earrings or different shoes and then it could be work friendly.

    After a childhood spent having to wear tights or nylons to church every Sunday, I can never think of jeans as appropriate for a business casual environment–especially ripped jeans. If jeans are appropriate for the EHD office, then she could totally rock the grey sweat pants if she dressed it up with jewelry and/or shoes.

    On another note, did Emily do NOOM? I was wondering about all the soup. Emily, you look great. Whatever you are doing, keep at it. It’s inspiring because I’m about the same age and have kids the same age as you and also work for myself in California.

  51. But what were the black joggers you were wearing at the end of the video?

  52. Loved this shop session SO much!! I bought quite a few things from this list because of you. Thanks and keep up the great posts. I really love how you mixed Madewell and The Great pieces the most.

    One more thing, can you have The Great restock the striped jumpsuit because it’s sold out in almost all the sizes now. I think your post made it sell out 😉 I need a 0 as well 🙏

  53. Wow. I knew we lived in different universes, but this post really hammers it home. I just bought some things yesterday–consignment. $5 for flats; $8 for a top. 🙂

  54. The UIlla blouse you are wearing the the one you linked are a bit different. I think this is the one you are wearing. https://ullajohnson.com/kati-blouse-midnight#.

    Important because the Kati blouse is 100% cotton while the one you linked is silk. While I love Ulla’s silk tops, I find myself reaching for the cotton ones more because..well, kids!

  55. I LOVE the sweats outfit! I schlep kids around all day so it is my goal to look cool while still wearing my sweats :). Any chance you remember what size that grey coat is? I’d like to order it but haven’t ever ordered from Aritzia before. I also love the Ulla top so very much.

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