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.

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.”

Shop the Look: Dress | Scarf (similar) | Shoes (similar here)

Wait. This is more appropriate:

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).

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).

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

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

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

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

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