What to Wear With Cowboy Boots: the result!

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


  • July 13, 2010


    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…

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    • July 13, 2010

      The Fashion Police

      I know! I always love looking at the results of these challenges, because you get so many different styles of outfit – people are so creative 🙂

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  • July 13, 2010


    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. 🙂

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  • July 13, 2010


    Kathryn’s the best! By a milestone.

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  • July 13, 2010


    I like Beth’s the best.

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  • July 13, 2010


    I love Theodora and Taras outfits!

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  • July 13, 2010


    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.

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  • July 13, 2010


    I like the variety! (I still like my own best.)

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  • July 14, 2010


    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.

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  • July 15, 2010


    Kathryn entry gets my vote. Still wouldn’t wear cowboy boots in a million years however.

    To each her own.

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  • July 15, 2010


    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.

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  • July 15, 2010


    Chris and mine of course hehehe 😛

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  • July 15, 2010

    Rock Hyrax

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

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  • July 15, 2010


    Ellie and Nicole – i can’t make up my mind between the two.

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  • July 16, 2010


    i love Beth’s. it’s the closest to my style 🙂

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  • July 18, 2010


    I like Tara and Cloot’s the best.

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  • August 9, 2010


    I loved almost all of these. Well done, people!

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  • September 19, 2011


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

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  • July 20, 2013

    Dyman Shepherd

    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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