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Emily Henderson

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by Emily Henderson
Emily Henderson Fashion Evolution Header

My genius team did it. Last night, they unintentionally did a “style diagnostic” on ME. In an attempt to understand my fashion style better, I pitched the idea of doing a “fashion evolution” post of the last 10 years of me wearing clothes on the internet—without a clear thesis. Once the post was prepped with all the photos, I had no real clarity. I went to bed last night (Friday) without writing the post which is a bummer to everyone. (Listen, I had a big week with a lot of shoots, so after we wrapped yesterday we had friends come up to the mountain house and well, I got distracted by 4 kids and a tequila-grapefruit in my hand/throat). So when I opened up my laptop at 6 am and saw the “opener image” (above) with “UPTOWN PRAIRIE”  on it, I was like—WAIT, wtf …that’s it!!! That is my style and frankly maybe it always has been. I always knew I had some Footloose in me, being raised in rural Oregon in the ’80s, but it’s less “country” than it is, yes, prairie—which has more of Victorian, 18th-19th century bent, keep reading and you’ll see. But first, since we did all the work to find all these pics of me wearing clothes the last 10 years—let’s watch the “progression” and see how I got here, or more importantly, analyze if maybe “Uptown Prairie Emily” has been here the entire time.

2010

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Exhibit A. This is one of the first photos of me ever, on the internet (hence the spectacular quality) wearing a vintage ’80s dress that I still have and love and a Ban.do flower from their first collection. It’s very “me” but certainly a younger version of me—brighter blue, pink, gold and camel leather, with princess sleeves and menswear-inspired shoes. CHECK. Check check. None of this has changed. YOU GUYS. I THINK THIS IS STILL MY STYLE AND PROVES THE “UPTOWN PRAIRIE” STYLE POINT! But let’s keep going.

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image via HGTV

Same. Blue/gold/brown leather. There is always something feminine and delicate about it, ruffles, mostly, and I like having sleeves, and a neckline that dips with a hemline that rises. I still have that dress and honestly would STILL wear it, sans belt. OOH maybe I should do a post about that.

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I love this look, while knowing it’s full “clown flight attendant.” My colors don’t really change (blue, gold, pink), something feminine—bow—and still menswear-inspired shoes. Sure, I added some pattern and a HEAVY dose of whimsy around my neck (it’s literally just ribbon for wrapping presents) and yes, that vest is actually a reversible vintage ’60s flight attendant vest. It’s so thick and polyester that it’s really, really slimming. I JUST realized that I actually have the vest and skirt still, too!

2011

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image via Check Out My New Fashion Digs

This is what I like to call my ’70s wide-leg/wooden heel phase. I’m still in it but it’s a big one for me.

2012

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image via A Lovely House Makeover in Studio City

More of the vest. And why not with green wide legs?

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image via Cover Girl, HGTV Magazine

Not sure what this says about my fashion but if you ever wondered if I intentionally try to match a set, the answer is YES. ALWAYS. Sometimes, it’s subconscious but I always dress in the style and color palette of the project that we are photographing.

Emily Henderson Fashion
image via Six Month Pregnancy Update

I used to joke that I either dressed like a flight attendant or an equestrian, with a blazer and boots (still “Uptown Prairie,” for sure).

2013

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image via New Product Lines From My Talented Friends

Here, I tried to match Bri’s house that I had designed with lots of bright colors. This actually wasn’t “me” and I didn’t feel like it either. Those big pink beads made me uncomfortable even then.

2014

Emilyfashion Evolution 2014
image via A Guide To A Well Hung Gallery Wall | image via Oh Joy’s Nursery/Office Reveal

Here, above, was a bit of a “basic” phase. I think I had just had Charlie and discovered the “mom blouse.” This wasn’t or isn’t me at all. I think I was literally just trying to put clothes on my body so I didn’t leave the house naked.

But I kept on with the vest, which you can see below…

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image via Lisa’s House: The Office Reveal | image via The 17 Most Noteworthy Things That Happened this Year

The photo on the write is continuing the elements that I love—a form of blue/pink, conservative shoes and a pattern. But no ruffle or princess sleeve.

2015

Maternity Fashion
image via The ‘Work’ Outfit

2015 is when I started doing more fashion posts with actual photography and yes, I tried harder to have more of a curated look.  I also discovered that you can put a hat on your head and distract from what might have been a more mediocre outfit. I still have that red crop top by the way and love it.

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image via Six Weeks ‘Til Baby | image via Modeling Maternity
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image via How To Find Your Style | image via Saying Yes To A ‘No Retouching’ Policy

The above photos are from Darling magazine where a fashion stylist put me in all these neutrals, which I loved, but no, they did not feel like “me.”

2016

Emily Henderson Fashion Trench Celine Bag
image via It’s In The Bag
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image via It’s In The Bag | image via My New Life (And Closet) Changing Secret
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images via Styling Luxury Handbags with Trendee
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images via Styling Luxury Handbags with Trendee
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images via What I’m Wearing.. My Favorite Fall Pieces

2017

2017 is where I A. discovered Ulla Johnson and B. realized that I’m most comfortable in a boxy top and slim pant/short.

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images via What I’m Wearing (kinda)

Remember that crazy top? It’s DEFINITELY Uptown Prairie. Also, this might have been “the year of the mule” and maybe where my love for chambray really came to a head.

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images from left to right via Playing Dress Up With Urban Outfitters | My Summer WardrobeMy Fall Fashion Wardrobe

If a chambray culotte jumpsuit (or denim modernized overalls) isn’t Uptown Prairie, I’m sorry but I can’t help you. HOW DID I NOT KNOW THIS WAS MY STYLE UNTIL NOW? (Also, remember platinum blonde Emily? I’m still recovering.)

2018

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image via A Romantic Glam Makeover with Opalhouse | image via A Boho 70’s Inspired Bedroom

The above two shots were from our Target Opalhouse shoot, and I’m fully in “matching set” action. My wide-leg pant obsession was back, except with a higher waist (which I kept buying and then never wanting to wear because they are suffocating).

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image via My Summer Basics | image via Summer Soiree On The Patio

This year, I did A LOT of fashion. You guys were really engaging with the stories on both social and the blog, so we did more professionally photographed posts where it was less “this is what I’m wearing” and more “here are some outfit ideas that have been fully thought out.” That Ulla Johnson dress above is something I pull out of my closet over and over again. Flutter sleeve, high-neck…it’s like…prairie goes to prom.

Emily Henderson Nordstroms Anniversary Sale Fall Essentials 2018 Modern Victorian Blouse Red Levis Wedgie Fit
images via Fall Fashion On My Body
Emily Henderson Summer Fashion Basics Yellow Mule Slides White Button Down
image via My Summer Basics
Emily Henderson Nordstroms Anniversary Sale Fall Essentials 2018 Blue And Tan Striped Sweater
images via Fall Fashion On My Body

I’m not sure if the dropcrotch pant is “prairie” but I mean, it’s KIND OF cowgirl?

2019

Here we are. 2019. I’m still mostly wearing ruffly tops and ripped jeans and now I know why: UPTOWN PRAIRIE.

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images via Why I Am Suddenly Dressing Like A Toddler
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image via How We Staged A House (To Sell) With Some Soul
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images via Ripped & Distressed Jeans Roundup
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image via My “Casual Comfortable Cool” Spring Weekend Wardrobe
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image via My “Casual Comfortable Cool” Spring Weekend Wardrobe
images via My “Casual, Comfortable, Cool” Summer Wardrobe
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image via 5 Fun & Unexpected Summer Work Outfits
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images via 5 Fun & Unexpected Summer Work Outfits
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image via A Fashion Review: New Clothing On My Body

Okay. That was a lot.

But I truly think I do have some clarity. Maybe it’s being up in the mountains (and Mountain Emily is certainly a thing, and a thing that we love). When looking back, I realize that where I still look like “me” is with less whimsy (but with some pattern), less “glam” (but still ruffly) but mostly it’s laid back, casual country, vintage-inspired, Victorian vibe, wearing blues/pink/black/white/plaids and leather in some form. It’s super fun to change up the look and I’m certainly not one to stick to anything, but I actually think that I’ve always been “Uptown Prairie” in some form, I just didn’t know it…

What this means is that I can purchase with a little more confidence if it falls in this vibe. I can know that I will wear the pieces and can mix and match them together. I suppose it’s the same rules as a home: find your style/styles, create a color palette and then you can shop with confidence.

So what brands do I look to for inspiration (or to purchase) in this style? Well, I have a few. Some of these I follow for inspiration and some yes, get my repeat business. Most of them are yes, high end but these designers are, in my opinion, setting the trends, designing the clothes that every other brand is knocking off. They are artists and creating special pieces (hopefully sustainably) should be expensive. While I love Madewell, I know that they are literally just copying every season of The Great, and while I buy from Free People all the time, I know that they are heavily “inspired” by Ulla Johnson. I think it’s important to buy within our means, but it’s important to appreciate the designers creating the beautiful, forward pieces. I feel like I just gave a “Devil Wears Prada” cerulean blue lecture. I also know that this conversation is a lose/lose as I’m criticized when I buy boutique clothing and also when I buy mass market. My general thesis is always this: buy smaller, local, American-made brands that will last and you’ll wear over and over if it’s in your budget. I’ve drastically reduced my fashion consumption this year and only buy/keep anything that is a “hell yes.”

Alright, lecture/apology over.

Here are the brands I’m currently LOVING and watching for inspiration.

Ulla Johnson

Ulla Johnson 1

Gemma Blouse | Alessandra Dress

Ulla Johnson 2

Liv Dress | Romilly Dress

I just realized that Ulla Johnsons is my brand. I think I discovered her in 2017 and every single piece that I’ve bought from her, I still have and wear consistently, 2-3 years later. Why? Because it’s beautifully made, with incredible patterns and colors, and I feel like a million bucks while being super comfortable. She plays a lot with volume and proportions, which can be really slimming on certain body types by enhancing areas that I personally like showing off. I also really look to her for inspiration with pattern, color and style in general—for instance I bought that red dress (and have been wearing it non-stop) but would have NEVER put it with snakeskin boots, but I love it. So if it’s in your budget or not, check her out for inspiration (and yes, Free People has more affordable versions of her vibe).

Zimmerman

Zimmerman

1. Espionage Silk Utililty Shirt | 2. Sabotage Bell Sleeve Top | 3. Espionage Lantern Sweater in Lilac

Zimmerman is a brand that I’ve never bought but I always admire and follow on social media. It’s total fantasy, and over the top in a really fun way. Sure, it’s a bit more “pirate” than “prairie” but still from the same era and the same Victorian vibe. If I had a really special occasion, I would consider shopping here. It’s impeccably designed and in person, I was so impressed with the details.

The rest of these brands are still in the vibe, but more everyday, wearable than Zimmerman.

Doen

I love everything they design, and boy does it sell out fast. I have to try things on because not everything fits or flatters me (and size down, for sure). I’m very excited that they are opening a store so that I can actually try things on before ordering. But the vibe is a HUGE thumbs up and every piece that I have, I wear consistently and even the pieces I bought three years ago I wear all the time.

Christy Dawn

Cristy Dawn

The Theo Dress | The Lottie Dress

Christy Dawn is in the same vein and I’ve never actually ordered her clothes because I don’t know what size I am here (they have a store in Venice, but that’s over an hour away). I’ve promoted this brand a few times because they use deadstock fabric so it’s much more sustainable. Plus, their pieces come in the most beautiful packaging. I just love their ethos, and vintage vibe, so I follow, but now I’m going to start trying some on.

Nili Lotan

Nili Lotan

Shon Pant | Shon Jean

I discovered Nili Lotan when I bought my first dropcrotch pant 2 years ago (which I wear 2-3 times a week), and while I don’t actually love a lot of the other pieces, I’m a HUGE fan of those pants above. Yes, they make you look bow-legged, but UPTOWN PRAIRIE EMILY actually rides bulls so it’s very appropriate. Brian hates them, I love them. Kristen Bell DM’d me that she loves them, so there’s that.

The Great

The Great 1

The Western Smock | The Cowboy Boot

The Great 2

The Eyelet Apron Dress | The Ranch Dress | The Song Top

The Great is a brand I discovered 3 years ago and love very, very much. Again, everything I’ve bought from them I still have and wear consistently so I can trust that it’s timeless. If $180 sweatpants aren’t in your budget (!!) skip those and go for what I love, like the pieces above that feel more special (but yes, the casual basics are strangely good). They are made in America and designed by Emily and Merritt who are two women/best friends whose ethos I love and appreciate. They are also a brand that I look to for trends and inspiration, even if I’m not purchasing.

Trovata – Birds of Paradis

Trovata

Brett S/S Bohemian Blouse Multi Stripe | Colette L/S Bohemian Blouse Antique White |

I just discovered Trovata’s newer brand “Birds of Paradis” and I have loved a few of the pieces (they are oversized, so go smaller). I have been wearing both of those shirts, above, over and over and over.

Rachel Palley

Rachel Pally

Willa Top | Chiffon Eros Top

I haven’t purchased anything from Rachel Paley yet, but it’s certainly fitting my vibe, so I’m going to start checking it out and seeing if anything is an actual fit.

So there we are.

I’m very excited now to embrace this Uptown Prairie, Modern Mountain Emily and I feel more confident shopping knowing that I know my style. I’m going to start combing the flea market for vintage ’70s dresses and ripped Levi’s asap and I think some modern cowboy boots are in my future.

A huge thanks to my team for helping me come to this conclusion. It will likely shift and change as styles do, but I feel a strange sense of relief and pride seeing that I’m not THAT different than I was 10 years ago.

Would love any other brand recommendations that fall in this vibe, or if any of you have a style that you’ve always been (just different/updated versions) I’d love to hear it.

Happy Saturday….:)

  1. I like Uptown Prairie better than what I was calling your style – Boho Baby Doll!

  2. Your clothes are beautiful, but I could never justify spending over $100 on any one item of clothes when I can’t afford daycare for my son. It would be cool if you did a post where you talked about budget options that are similar in style. Or if you did a post about online used clothes options that you like the best. Just a thought. Love your blog though.

  3. Not that you asked for opinions, but my favorite phase for you, hairstyle, hair color, make up, et al, 2011/2012
    You looked natural and uncostumed and uncontrived.

    1. In the same category of unasked for opinions, I love her maternity looks. I think Emily should consider a maternity line!

  4. Whatever you’ve worn, you’ve never been boring! I love how your clothes are an extension of your designs. Architectural, interesting, and sometimes weird! 🙂 Keep embracing your individuality!

  5. I always enjoy your fashion posts! In fact, you have become my fashion icon. A few months ago, I purchased a blue printed babydoll dress from H&M. When I saw it, I thought, “this looks like something Emily Henderson would wear.” A few days later, you were wearing it in your summer dress roundup! It made my day. I love “Uptown Prairie!”

  6. That was a really fun post! Enjoyed every photo and the commentary. I think creative people often struggle or come late to finding their specific look when it comes to clothes. It’s easier to be super specific with what you like in a room, for instance, and why you like it, than pinpointing one’s specific sartorial style. You’ve inspired me to hone in on what I actually like to wear/feel good in/actually look good in. Thanks!

  7. You say “wide leg”, I say “bell bottom” and I like it. I like your current style and all the straight-leg and skinny leg pants, too!.

  8. I love this post! Makes me want to figure out my style. I kind of thought I would see Reformation on your list. Super excited to dig into a couple of these brands.

  9. Fun post, interesting to see your style develop! I would caution away from cowboy boots, however. Wearing a more modern shoe is what makes your look seem contemporary and “uptown.” Wearing a cowboy boot might push the whole prairie thing into costume. Just my two cents. 🙂

  10. Remember when you almost went home at the beginning of Design Star and Genevieve Gorder was like, “I know you have talent – look at how you’re dressed!” (I’m paraphrasing.) Uptown Prairie to the rescue!

  11. Your fashion posts are my very favorite and I love the curated looks you do with your friend. I have copied them and feel so confident in the loom when i do.
    Thank you.

  12. Sorry but I loved you in the neutral Darling pics. And your hair in that deep side part!

    1. Agree 100%

      1. me too! I love that last look in the black – so chic!

  13. Rachel PALLY. “Write” and “right” are two different words. A good eye isn’t just for dressing and styling—it helps communicate your message, too.

    1. True, but she may well have been tired when writing this post. It doesn’t hurt to give the benefit of the doubt when reading.

  14. Rachel PALLY. “Write” and “right” are two different words. A good eye isn’t just for dressing and styling—it helps communicate your message, too.

    1. Ouch! Why be so snarky?

  15. I love your style (except for those drop-crotch pants). It’s not my style. I’d feel uncomfortable in prairie anything, but it works for you. And thanks to this blog I’ve been introduced to great ethical brands like Nisolo that ARE my style.

  16. The “write” side?

  17. Wow. I just realised I have been following you for a loooooooong time! Thought it was a good opportunity to say thank you. My 9 years reading has certainly taught me so much. And when I think about how much my home (and even my fashion) has changed as a result, I have a lot to thank you for! Your site is always the first thing I read every day. Thanks Emily!

    1. 100% ditto to this. Thank you.

  18. This was interesting. I would love to have someone analyze my tastes in fashion! have a very different body type from you (I tend to highlight my upper body and cover my lower) but we share similar tastes in button downs and shoes. One brand I thought of while scrolling through your photos was Sezane. It’s like “uptown prairie French girl” and so lovely.

  19. I enjoyed your commentary on high end vs mass market. Thanks for bringing it to my attention.

  20. “rides a bull”
    HAHAHA!!
    love it.

  21. WOW! What a fun post! I love your hair in the “full clown flight attendant” photo!!

  22. Thanks for this fun post and all your posts! I enjoyed that you found that your style hasn’t changed through having this unintentional ‘style diagnostic’. I’m encouraged to keep figuring out what my style is. Both in fashion and in my home.

  23. Well, I think you look cute in everything

  24. I love how your style is so uniquely and unapologetically YOU! It’s refreshing to follow someone who is pretty mainstream but not a slave to fashion trends. However, as a woman who grew up in a ranching and rodeo family in Eastern Montana, I can assure you that there is nothing cowgirl about a drop crotch. I giggled when I read that. I don’t know where drop crotch fits other than some kind of urban aesthetic because there really doesn’t seem to be anything practical about it.

  25. I didn’t expect to love this post so much, what a fun idea!

  26. Emily. Your hair! This post reminded me of how luscious your hair was and I know how hard it’s hit you.
    I thought of you while chatting with friends about hair issues about four monyhs ago, namely thinning and breakage.

    The outcome of this chat was/is this:
    Estrogen and Progesterone massively affect women’s hair. Progestrton increase when you’re pregnant, makes hair gloriously thick and shiny. Too much Estrogen can cause hair thinning and breakage. Balance is the key.

    Emily, have you had your hormones tested to see whether your levels are in balance? A friend recommended Swisse Hair, Skin and Nails and several of us now take it….with results! Actual. Results in a few months!
    But, still, hormone levels are the foundations of our hair.
    Hope this is helpful for the EHD Sisterhood. 🙂

    1. What a passive-aggressive and mean spirited comment. There is nothing wrong with her hair. “Helpful for the EHD Sisterhood” my foot.

    2. Thanks, Rusty! I know numerous women who’ve been struggling with thinning hair and lots of breakage. Will definitely look into the product you mentioned. This “sister” found your comment helpful, and I’d venture to guess that Emily might, too. Given that she’s secure enough to have shared her concerns regarding changes in her hair, I assume she’s okay with readers offering respectful advice. Thanks again.

  27. I’d love to see posts about the different decor styles and inspiration photos AND different fashion styles and inspiration photos. Maybe more in depth- breakdowns in style, sort of like the modern Victorian posts from last year. I love that stuff and honestly have no clue what my fashion style is or how to figure it out.

  28. I love your style posts and your design posts–thank you for all that you do! I appreciated your commentary about buying more expensive clothing that you love and that is a work of art. I try to abide by this as well, but it is a real struggle as a woman on the cusp of plus size (generally a 14, an XL in tops). For example, I’d love to buy from The Great, but their clothes mostly only go to a size 10, while Madewell has a MUCH larger range of sizes. Just wanted to give you a quick head’s up that most of the designers you highlighted do not sell clothing above a size 12 (shout out to Rachel Pally though, whose clothes are GORG and feature a whole plus size selection!)–there is unfortunately still a gap between what’s available to ‘standard size’ vs plus size and many of the higher end designers exclude anyone above a 12! Just wanted to give you a head’s up if you didn’t already realize this! Thanks for continuing to post great things, and I loved watching your style evolution!

  29. “Uptown Prairie” — yes! That’s my style, too! Perhaps its because I hail from Nebraska, but that’s me, too. Really enjoy your humor in these posts, too. I think you look lovely!

  30. i loved this post so much! it was so much fun to see what evolved and what stayed the same over the years. i’ve been thinking a lot about my personal fashion lately and this post was super inspirational to me. i’ve had my style pegged for a little while – a little classic, a little androgynous, mostly solids, statement jewelry – but have mixed it up lately and am trying to peg down a new balance. i recently started a new job that is business casual again (last job was manufacturing and completely casual) and i will be getting tattoos that need to be covered in the work place sometimes, so how do i want to adjust to this? i’m loving all the fitted pants and flouncy shirts!

  31. Can we get a hat post? Your hat game is on fire 🙂

  32. It cracks me up that you bought something in 2017 and are “still wearing it,” as if this is something unusual. I thought everybody kept clothes for more than a season or year. I feel like I’ve just landed on earth in a space ship when I read your fashion columns, as the vast majority of what is shown is simply not for me. Fortunately, you are cute enough to wear anything in any combination and pull it off.

  33. Emily, I sincerely LOVE your style so much and everything you wear is awesome. I’m a relatively new reader/fan (only a couple-ish years), but looking back at all this, I wish I had found out about you earlier because it looks like the evolution of your design and fashion would have been so fascinating to watch at the time. This was a fun read and it has inspired me to get back to dressing like “me” again! I’ve always loved fun and interesting looks/clothes with lots of bright colors, but i think that the last several years of motherhood and work and adult stuff has just sucked that out and my brain has not had time to even entertain it (and my mom bod has definitely changed what I wear as well). Since I’m turning 40 this year, I’m doing a lot of contemplating about “me” before kids and finding that again. And that includes my style. Thanks for the inspo.
    Also (sorry for the long comment), boutique/designer prices are not my budget, but I totally agree with your stance about paying the actual designers and buying sustainable and American-made instead of mass-market crap quality (if it’s in one’s budget). Even if your budget is not my budget, it’s fun to see what you’re wearing and just using that as inspo when shopping. So, keep up the message of sustainability/quality/fair prices (which does not mean cheap to the consumer).

  34. Style is a way to express yourself, show your tastes and demonstrate a magnificent vision of the world! But what if the end of inspiration for new ideas? I also asked this question until I found a wonderful site Texelprintstore. I ordered a multi panel wall art and it brought me back to life! Now every day a bright head and pure thoughts. This is a special place, a storehouse for new ideas. Everyone needs something special)

  35. Hi Emily!
    I love these posts. I love that your style is chic but accessible, and I love the mix of high (Ulla)- lowish (Madewell). I also wanted to say thanks for inspiring me to step outside my style “box” a little bit – these posts are a great reminder that style and fashion are fun, and it’s ok to take some time to just enjoy it. Oh, and I have tried on Zimmermann – love it, but seems like it’s made for the super tall and thin. Ulla for the people!

    The bull comment made me laugh too!

  36. Somehow, I am having a struggle imagining riding a horse in a pair of drop crotch trousers. 🙂

  37. So fun to see the common thread woven into your evolving style! And amen to the mom blouse- when I was a first time mom, I couldn’t figure out how to drape clothing over my “bloomed” body 😆 pics from that era are a bit…hmmmm… thanks for sharing your journey and inspire!

  38. I love this – Thank you for sharing your evolution. I have always described my style as Uptown Stables. 🙂

  39. OK. You have not changed at all in 10 years, in a good way. Like anyone else would show a picture from 10 years ago and cringe.
    This style obviously works for you so well, and love how you can go back at any of these looks and wear them and look good today.

  40. Love this post. I see a lot of my style and what I’ve always loved in there too so it actually even helps me feel more confident about what I’ve always loved. I’m less prairie, maybe more pirate. 😉

  41. Loved this post. Definitely check out Rebecca Taylor’s clothes if you’re a Ulla Johnson fan. Thanks for sharing !

  42. I’ve always loved your fashion sense, so it was super interesting to look at the pictures and read your commentary! I think your shoes are the winning factor in almost every ensemble—they perfectly tie together your outfits. Lots to be inspired by in these photos.

  43. Have you ever considered seeing a stylist. I had my personal color palette and corresponding style recs done by David Zyla and he is an artist, with such great vision. I would love a post about you, an interior stylist, seeing a fashion stylist.

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