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Turns Out My “Uptown Prairie” Style Is All Over The Internet (And Affordable, Too)

The “Uptown Prairie” look, my officially diagnosed 2019 style and possible “forever style” does not exist just in my closet; nay, it’s all over the internet (oh zeitgeist I’m your victim AGAIN). I’ve historically said that I’m a mix of Footloose-meets-Mad-Men-meets-Wes-Anderson-meets-Marie-Antoinette (in both home and fashion) and I think that the only thing I would take out now is Wes Anderson. I wish I had elements of that amazing weirdness, but not sure I do in my fashion anymore. ANYWAY, in case you are wondering what “Uptown Prairie” is, it’s a mix of country (ripped Levi’s, boots, plaids with ruffles, anything that feels you could ride a horse/bull in), Victorian (puffed sleeves, bohemian patterns, billowy silhouettes) with a slight hit of rogue Ren-Faire/Pirate/Outlander. The trick is to make sure that it’s not a costume, so I mix it with vans, sneakers, modern jackets and, of course, some basic T-shirts. It’s typically casual, but when needed can be elevated. Most of my uniform involves some sort of ripped pants/shorts, and a top from Ulla Johnson, The Great, or Doen which are three American-made brands that make high quality, long-lasting clothes that I wear for years and years. They are expensive, yes, so we wanted to do a roundup of a more affordable Uptown Prairie for all those who are interested in dabbling into the trend without making such an investment. (Of course, I understand “affordable” is relative, and some of below pieces are still not exactly “budget” but certainly not $300 for a top.)

So my team ordered me a few pieces, some of which I think worked; others were more Uptown Pirate than Uptown Prairie but I know someone who would love that—one Charlie Henderson. I have such a Nurse Betty brain though, guys, and as I am marathoning Outlander and legitimately obsessed with this 18th-century style, it has wormed its way into my wardrobe (and language and LITERALLY EVERYTHING I DO). So, now I’m like “Do I like this shirt or do I just want to be an extra on the boat as we sail to Jamaica to find Young Ian?” Aye. It can be confusing to me, too. But as for the three looks we did, I really liked a lot of the pieces and can vouch for their “Uptown Prairie” vibe.

Emily Henderson Affordable Prairie Fashion Trend 2

Shop the Look: Shirt | Shorts | Hat | Shoes

First up, I like this shirt, I do, but it is oversized so just size WAY down. I’m wearing an XS if that helps you at all. I was coveting a few other shirts from Free People (here and here), but we couldn’t get them in time. (I’ll keep you updated if they are a “hell yes” when they come.) THAT HAT THOUGH. We all agreed that the hat is GREAT. It’s extremely lightweight and almost made out of that same material as Chilewich placemats (in a good way). It’s really breathable and I would even say really packable so you don’t have to be like me and wear 2-3 hats in the airport and on the plane because you don’t want to ruin them in your suitcase nor do you want to succumb to hat boxes.

Next is more of my “Uptown Chambermaid” look, hmm…or maybe just “Chambermaid.”

Emily Henderson Affordable Prairie Fashion Trend 6

Shop the Look: DressScarf (similar) | Shoes (similar here)

Wait. This is more appropriate:

Emily Henderson Affordable Prairie Fashion Trend 8

I just need a wee bairn on me chebs! (Translation: a little baby on my breasts.)

I have to say I felt kinda sexy in this, but it could be because I’m channeling my inner Claire and awaiting Jamie to get back from the stables, while I tend to me garden. The dress falls really nicely but I fear that my bosoms might be too large for me to be comfortable wearing in public… in this century anyway.

For the last look, we ventured back to the year 2019 and went with a more basic and simple slightly on-look chambray dress, with cute little princess sleeves and a really flattering silhouette (am I not allowed to use the word “flattering”? I forget the rules to modern feminist PC at times…we didn’t have such restraints in 1754 Scotland—nye).

Prairie Lores 14

Shop the Look: Dress | Shoes | Scarf

I kept saying that it’s so good for church—so comfortable, easy to wear and wrangle kids in, but modest. And yes, I’m back to going to a church. Excited to hear the “journey” and see what denomination if any I’m currently liking?? Stay tuned… But yes, it’s a perfect “farmers market to church to Sunday supper” kind of dress and I know I have a lot of my LDS ladies reading so that one is for you. 🙂 I like pairing it with sneakers instead of sandals to dial down the sweetness a bit (but I like these clogs, too).

None of these are really IT, but they are all cute and great and definitely hit the mark. I may order some more pieces to really dial in the look for you and replicate that higher-end look. It just may take some digging and a few more trips to Free People.

But here are a bunch of pieces that I like, some of which I already ordered (and I’ll let you know how they turn out).

Emily Henderson Affordable Prairie Fashion Trend Tops

1. Flannel Leysfield Popover Shirt | 2. Printed Evening Button-down | 3. Indigo Ruffle Hem Top | 4. Perrine Waisted Blouse | 5. Ruffled Cotton Blouse | 6. Ditsy Smocked Blouse | 7. Apiece Apart™ Vera Pleat-Sleeve Pullover Sweatshirt | 8. Courtyard Ruffle-Hem Top in Metallic Plaid | 9. Balloon-Sleeve Peasant Top in Clipdot | 10. Abercrombie & Fitch Cropped Prairie Blouse | 11. Build Me Up Buttercup Top | 12. Fine Knit Sweater | 13. Central Drapey Shirt | 14. Ruffle-Yoke Top in Metallic Plaid | 15. Meadow Shirt

Emily Henderson Affordable Prairie Fashion Trend Bottoms

1. High-Rise Belted Corduroy Paperbag Pants | 2. One Way Pants | 3. Plaid High-Rise Straight Trousers | 4. Wide-Leg Cord Shorts | 5. Printed Pleated Skirt | 6. Julie Cropped Pant | 7. Drapey Pleated Wide Leg Pants |  8. Mid-Rise Straight Leg Paperbag Pants | 9. High Waist Straight Pants | 10. Petite Prairie Button Front Midi Skirt | 11. Twill Pants | 12. Stretch Denim | 13. Sailor Jean | 14. Brecan Pant | 15. Skinny Overalls

Emily Henderson Affordable Prairie Fashion Trend Dresses

1. Floral Print V-Neck Tie Front Midi Dress | 2. Floral Print Sleeveless High Crewneck Midi Dress | 3. Denim Slim Coverall | 4. Long Sleeve Lace Trim Midi Dress | 5. Denim Pleat-Waist Midi Dress | 6. Ruffle Tier Midi Dress | 7. Short Sleeve Scoop Neck Midi A Line Dress | 8. Ruffled Printed Dress | 9. Corduroy Pinafore Dress | 10. Long Sleeve Boiler Suit | 11. Velour Stud Button Mini Dress | 12. Long Sleeve Ruffle Tier Midi Dress | 13. Short Ruffled Dress | 14. French Connection Prairie Midi Dress | 15. Luciana Floral Tiered Maxi Dress

Emily Henderson Affordable Prairie Fashion Trend Jackets

1. Belted Workwear Denim Jacket | 2. Fringed Wool Blazer | 3. Slouch Coat | 4. Double Faced Jacket | 5. Faux Shearling Long Coat | 6. Women’s Sherpa Moto Jacket | 7. Corduroy Swing Chore Coat | 8. Sherpa-Lined Corduroy Swing Chore Coat | 9. Faux Shearling Collar Plaid Jacket | 10. Record Breaker Collarless Faux Leather Moto Jacket | 11. Coat with Tie Belt | 12. Faux Shearling Appliqué Jacket | 13. Pile Jacket with High Collar | 14. Checkered Sherpa Lined Harrington Jacket | 15. Rust Corduroy Shacket

Emily Henderson Affordable Prairie Fashion Trend Shoes

1. Rylie Faux-Leather Heeled Open Bootie | 2. Heel Leather Mules | 3. Wenda Cut Out Bootie | 4. Lace-Up Leather Boots | 5. The Ayanna Clog | 6. The Jess Slingback Mule | 7. The Marlo Slingback Clog in Leather | 8. Heel Leather Ankle Boot | 9. The Brady Lowcut Bootie | 10. Kensley Microsuede Platform Slip On Sneakers | 11. Makana Faux Leather Heeled Mule | 12. Indie Faux Leather Heeled Bootie | 13. Warm-Lined Boots | 14. Cassandra Combat Boots | 15. Slip On Shoes

I’m still working it out but frankly having so much fun working with my team on fashion posts. They have given me a few trend challenges that I’m trying to execute, namely the bucket hat, the crop top (I know it’s been around for a while but I haven’t dabbled yet in its horror), and I want to explore more “socks with shoes” looks because I LOVE A SOCK WITH A SHOE…I mean open-toed or low socks with heels. I just realized most people, including my children, typically wear socks with shoes.

SO, do you have any weird/tricky trends that you guys want to see played out here? We are down and the weirder the better.

***photography by Veronica Crawford

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3 years ago

I have read all the Outlander books and seen every episode. Your references were cracking me up!

3 years ago

Young ian lol. I binged in an effort to catch up before the last season, and like you, it affected everything. I called my cat a “wee bonny lass,” complete with accent. Do na fesh, it seems to be par for the course. 😉

Ellen Switzer
3 years ago

I think it’s funny/odd that you never link up or try anything at J Crew. There is SO MUCH “uptown priarie” stuff there right now. Great ruffled, button up, floral tops, good dresses. Branch out to J Crew!

3 years ago
Reply to  Ellen Switzer

Emily has mentioned her “secret boobs” in the past, and JCrew doesn’t seem to work for anyone over a B cup. That’d be my guess, anyway! It certainly doesn’t work for my not-so-secret boobs!

Ellen Switzer
3 years ago
Reply to  Deborah

I am a double D and i am able to wear everything there! how odd! bodies be crazy!

Sherrie S
3 years ago
Reply to  Deborah

I agree. I can’t fit my secret boobs into J. Crew – I wish, but the cut all their tops too straight and narrow through the top to accommodate anything over a B cup – well stated.

3 years ago
Reply to  Ellen Switzer

So what you are really saying here is that we should all watch Outlander, correct?

3 years ago

Och. Dinna fash about yer boobies in that dress. They look great. ? I may or may not have ordered some nightgowns like Claire’s to wear to bed and I feel very outlander in them. Ya ken? Love all this. Hahahaha

3 years ago
Reply to  Simone

Oooooo Mmmmmm Gggggggg!!!!

3 years ago

I just recently came across the company ROOLEE that has affordable clothes that have some uptown prarie pieces. I bought two midi skirts for $100. And, they are a small, Utah based company.

3 years ago

I look forward to your Saturday posts all week…. thank you for including our bodies in your styling!
Just bought 3 things. Without fail, the things I buy from your cadjin posts I LOVE. Sometimes they don’t suit my body, but I that’s me. What I keep, becomes a fast favorite in my wardrobe.

Emily and team, what happened TJ the collaborations with the other woman (she has a dog and kids at your school)? Those lewks were NEXT LEVEL and included combos I hadn’t yet thought of, but instantly LOVED.

Would be thrilled for MORE PF THAT!!!
Or does she have a blog? Or are there fashion sources/blogs on the internet you recommend?

Love all you do!

3 years ago

Ooh, I love top number 4 in the round up. Too bad it’s polyester. As I get older my body will only tolerate more natural fibers, fabrics that breathe. I don’t mind since it turns out micro plastics wash out of polyester clothes, but it does make clothes shopping harder. Anyone have any brands to recommend for natural fiber clothes made sustainably?

3 years ago
Reply to  DM

Pyne and Smith, Elizabeth Suzann, Jamie and The Jones, amongst many other slow fashion brands that make ethical clothing that are in natural fibers.

3 years ago

These comments are great. I kinda don’t want to hear about your church journey at all but am so curious I guess it would be worth a read. Most who leave Mormonism end up atheist because we feel so betrayed. Maybe because you left peacefully, and young because it didn’t fit, rather than dedicate your life to it and find out it isnt true via the CES letter that you’re able to not throw the baby Jesus with the bathwater? I dinna ken.

3 years ago

Aye…Oi too, foind meself glued to ye box, watchin’ those thar stories from yonder past!!!
You cracked me up! I remembered each bit you mentioned. Such a grand program with a tantalizing goid plot!
Love this style so, so much that I’m game for trying my ladies in a prairie top (thanx to you!). My partner doesn’t really go for the look, but me thinks…I care not….for ’tis not twee….it’s for me (damn it!), ha! 🙂
Fun post, thanks!

3 years ago

I’m not a hat person (they’re usually too small for my giant head) but that hat you’re wearing in the first pic is awesome.

patricia blaettler
3 years ago

In regard to thinking in another accent because of TV: I just finished Derry Girls and it was adorable.
Anyone who attended a Catholic girls school will definitely get a kick out of it.
You can thank me later!

3 years ago

Derry Girls – not catholic, but enjoyed it sooo much, very funny!

3 years ago

Oh and thank you for linking to those black platform sneakers at Target. I’ve been drooling over the Vince platform sneakers for months but I just can’t afford the $225 price tag … so $30 is amazing. Ordered. Now I hope they fit. They’re faux leather which is great and the kind of thing you can wear in the rain without worrying that the shoes will be ruined.

So thanks once again to your team for doing my shopping for me!

Mariya Zafirova
3 years ago

You look amazing in all outfits!

Mariya |

3 years ago

#13 top link works, but it is Madewell rather than West elm….l o l…I clicked that so fast.

3 years ago
Reply to  Anon

I LOLed at that too! I was like, wait, West Elm makes clothes now?!?

Roberta Davis
3 years ago

There’s a shirt labeled West Elm and I thought, so West Elm is selling clothing? Nope- it is from Madewell. I could never wear this style but you carry it off so naturally! Thanks for putting in more reasonably-priced items. I was looking for Nisolo shoes here and realized- too pricey. Some nice, similar, alternatives.

3 years ago

Socks with heels? Hmmmm, not my jam at all, but it will be interesting to see how you play it. I love the looks here!! And you looked adorable in everything. My favorite was the blue dress at the end.

3 years ago

On a completely unrelated note, can we have a backyard update?

3 years ago
Reply to  Dez

Agreed! Looks like there is shade, so those demolished trees must’ve come back!

3 years ago

Being Outlander obsessed for years, I’m with you on the outfit homage. All I can say is if you like the TV series you LOVE the books. Diana Gabaldon is an amazing writer.

3 years ago

I’m loving this fash moment too, and yes, there’s a fine line between Uptown Prairie and Uptown Pirate, ditto Uptown Prairie and Uptown Pajama top (hence, I’m avoiding ditsy florals). Also, mmmm Jamie

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