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Styling Cowboy Boots with Dresses

Girl in babydoll dress with cowboy boots looking stylish
Babydoll Dress by Sonia Rykiel, boots thrifted

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Cowboy boots are timeless footwear that can be worn with almost anything. They keep making a major comeback every decade and I'm here for it, especially considering I'm pretty much always in sneakers or flats all year. It's nice to fall back in love with cowboy boots for the mere sake of variety especially when styling dresses. They can be worn in every season and I believe their versatility is why they're so resilient in the coming years of fashion.

Plus, not everyone is a high heel wearin' lassie

Girl looking stylish in sunglasses and jean dress.
Michael Kors Sunglasses & Vintage Blouse

Here are a few examples of how to style cowboy boots with dresses:

  • A denim mini dress with a pair of brown suede cowboy boots is a great way to dress up a casual outfit. I loved pairing this vintage scalloped collar blouse under this Sonia Rykiel ruffled jean dress. You can even add a casual blazer jacket if it's still cooler out in the evenings which looks mega cute with the shorter babydoll dress shape. I tossed on a blue crossbody wallet bag by Kate Spade and loved the monochromatic look of it. The sunglasses are Michael Kors.

  • A flowy maxi dress can also be paired with cowboy boots and is perfect for a summer day out thrifting or strolling the local shops. Add a straw hat and some sunglasses to style it up a bit. There's something so dreamy about the boots with a ruffled flowy white maxi, it's just embodying that farm girl woodland witch fantasy.

  • A leather mini skirt with a pair of black cowboy boots is a great way to dress up for an evening out or show. I love this look with a worn T-shirt or a boho blouse. Just think contrast of textures. Imagine the smooth leather with a relaxed top and the boots- it's giving "effortless cool chick, you want to be friends with". I wore a similar outfit in this lookbook post.

Girl in denim dress and sunglasses by a brick wall for a fashion blog.
Denim Dress with Kate Spade Crossbody

Where to find cowboy boots:

  • I've lucked out and found a pair at Goodwill and Value Village for under $40. WHAT ARE THE ODDS? They were both brand spankin' new, one pair light suede, the other black leather snakeskin. When I searched the original retail cost of the boots they ranged from $100-$150 so I got a really good deal. Now that I have the basic colors in my wardrobe I can start looking for cool colors too, which I'm definitely on the hunt for red. Cowboy boots tend to be pricey brand new off the shelves in typical retail stores so looking in Goodwill or Value Village first is worth a shot.

  • Local boutique thrift, vintage, and antique shops. Although they tend to cost quite a bit for vintage, if you really want some unique badass boots, drop some cash on some real leather old-school boots.

Vintage store with tons of cowboy boots.
Grand Leader Mercantile, Everett WA

Vintage shops are always crawling with them and you can often negotiate a price. They will never go out of style, they will always be a collector's piece, and you will likely get complimented on them every time you wear them. They will retain their resell value too.

  • Then there are apps like Thred Up and Poshmark where you can search for some thrifty options. Sometimes you can score a deal on items marked down that the seller is trying to move out to make room for more inventory.

  • Online shops like Nordstrom, H&M, or DSW. I noticed right now some over-the-knee cowboy boots are having a moment and am considering which pair I might snag to try out. I think these would look killer in Autumn with yoga pants, kind of like a spin on the typical stretch pants and knee-high boots that we see every season.

Welp, that's it paht-nas!

Those are just a few tips on how to style cowboy boots with dresses and where to find them. With a little creativity, you can create a stylish and unique look that is custom to your particular taste and expression. They aren't meant to be rules (because I firmly believe fashion should have none) however, you can still have a sort-of guide to what might be cute right now with the beloved Western footwear we've embraced for so long.

Fashionable woman leaning on brick wall in denim dress and cowboy boots.
Old Movie Theater, Proctor District Tacoma WA

Ya'll come back now ya hear? Oh my god I'm such a dweeb.

xoxo Seanna

I did my best to find links to items similar to what I have on. Because 99% of this outfit is thrifted, I had to find pieces I thought would be cute recommendations instead. Hope that helps!

*some links are affiliated and fuel this blog, thanks for your support!

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