Cowboy boots with jeans and feathers
Emily’s outfit

So, what DO you wear with cowboy boots? That was the question we posed in our Style Challenge last week, and here are your answers. The outfits submitted feature everything from pretty dresses to casual jeans, and from glamorous evening gowns to classic cowgirl style. We think the answer to the “what to wear with cowboy boots” question, then, is “whatever you want!” If you treat them just like any other pair of boots (which is, after all, what they are), you’re limited only by your imagination. We’ve put all of your sets into one post, which means we couldn’t add a poll, so please feel free to nominate your favourite outfit in the comments section, and let its creator know you appreciated their work! Thanks to everyone who took part!

Cowboy boots with white dress and bangles
Kathry’s outfit

Suede & Leather dress with cowboy boots
Ellie’s Outfit

cowboy Boots with skinny jeans
Teodora’s outfit

Cowboy boots with black dress
Tara’s outfit

cowboy boots with butterfly print dress
Nicole’s outfit

Cowboy boots with leggings
Tanya’s outfit

Coral strapped dress with cowboy boots
Hannah’s outfit

Cowboy Boots with grey skinny jeans
Ghostie’s outfit

Stampede Parade cowboy boots with levis
Riali’s outfit


Rachel X’s outfit

Cowboy boots with pink dress and straw hat
Rock Hyrax’s “outft” :p

Blue skinny jeans with swede top and cowboy boots
Soe_the_arts’ outfit

Cowboy Boots
Chris’s outfit

boho outfit with cowboy boots with floor length dress
Georgie’s outfit

Cowboy boots with mini patterned dress
Trix’s outfit

Blue Butterfly Day
Beth’s outfit

Challenge: What to Wear With Cowboy Boots how pants
Katie’s outfit

What to wear with cow boy boots white dress
Kookakicha’s outfit

cowboy boots!
Elsa’s outfit


Moni’s outfit

19 COMMENTS

  1. I like Hannah’s, Tara’s and Kathryn’s outfits best.
    It’s amazing how many totally different styles you can create around one single pair of boots…

  2. The ones I would most like to wear myself are the outfits of Kathryn and Hannah. I kind of feel like getting me some cowboy boots now. :-)

  3. I love so many of these outfits, especially Emily’s, Teodora’s and Chris’, but I think they would all look much better with different shoes. I despise cowboy boots so much, I couldn’t even try to tackle this challenge. Rock Hyrax’s set is exactly how I feel about them.

  4. Naturally, I like my own, and thanks, Natasha, for the compliment! I, too, hate cowboy boots, as you may be able to tell from the name of my outfit. I have to vote for “Stampede Parade” because it’s so hysterical! I love the name.

  5. Elsa, Kathryn, Cloots and Ghostie… So many to choose from! I don’t like cowboy boots either, but some of these outfits could persuade me to wear them. If I had to pick one, I think Elsa.

  6. Actually, if I was given the choice of cowboy boots or barefoot, I’d feel quite happy in Gwendolyn’s outfit.

  7. I love the boots with dresses look. I am 60 and still a fashionista. Any suggestions on dresses that would go with the boots?

  8. Moni’s outfit is great only I’d like a skirt a few inches longer with less flare. Katie’s is my favorite. For those of you who “dislike” cowboys boots, you should try a good quality pair ($200+) and get a higher heel. They form to the shape of your foot bc a good pair has ridiculously high quality leather. Get them in black and BAM…you have a sexy winter boot that will last you for the rest of your life. Forget the sexy black boots in the department stores…all have a short expiration date. Get a pair of Dan Post boots or Ariat boots and your feet will love you for it :)

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