9 Surprisingly Cool Outfits That Make Cowboy Boots Feel So Tasteful

Cowboy boots can be tricky to style, so if you're interested in dipping your toe into the trend, we have eight inspirational outfits for you right here.

Maxine Eggenberger's avatar
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Last updated In Features
A collage of cowboy boot outfits.
(Image credit: Who What Wear UK)
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Some shoe trends are harder than others to fully embrace without feeling like you've completely overhauled your personal style. Exhibit A: cowboy boots. If you're not a desert dweller (or one at heart), trying to work these very specific Western-inspired shoes into your wardrobe isn't a walk in the park.

That said, cowboy boots have lasting power and have been a trending boot style for a couple of years now. They're also a fantastic transitional piece, as we shake off the last temperamental days of spring and work our way towards summer. Whether paired with midi or mini-length jean skirts, double denim looks or dresses, it's much simpler to introduce cowboy boots into your daily rotation, even if your usual style is the polar opposite of ranch attire.

An image of cowboy boots.

(Image credit: @emmaleger)

I understand if you find cowboy boots a little too costume-like for your taste, but there are plenty of styles from the best boot brands that offer a subtler nod to Western-inspired styling via a buckled belt, Cuban heel or swapping the traditional stitching for a fun cow print. Personally, I don't think you can go wrong with a classic black leather pair, which is sure to go with everything you own.

Whether you're planning your next music festival outfit or are looking to embrace your inner Dallas Cowboy Cheerleader, pulling inspiration from these nine cowboy-boot outfits below will ensure no one will assume this is your first rodeo. (And earn you several "yeehaws" at your next outing.)

What to Wear with Cowboy Boots, According to a Fashion Editor:

1. White Mini Dress + Cowboy Boots + Suede Bag

An image of @emmaleger wearing suede cowboy boots with a white dress whilst in New York.

(Image credit: @emmaleger )

Style Notes: When you don't know what to wear, you can't go wrong with something textured. Start with a pair of suede cowboy boots before adding visual intrigue with a knitted or crochet white mini dress before tying it all together with a matching suede bag. Plus, rich browns are an ideal colour palette for a Western-infused ensemble.

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2. White T-Shirt + Black Mini Dress + Cowboy Boots

An image of @francescasaffari showcasing what to wear with cowboy boots.

(Image credit: @francescasaffari)

Style Notes: Personally, I think cowboy boots were made to be worn with thigh-grazing hemlines. (I'm sorry to all the Levi's 501s I've offended in the process.) But there's something so darling about pairing a more practical shoe with a flirty dress length. I'm taking cues from this look through summer by experimenting with layering and pairing my cowboy boots with my favourite designer bag.

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3. Cropped Trench Coat + Wool Trousers + Cowboy Boots

An image of @lefevrediary wearing a cropped trench coat with trousers and cowboy boots.

(Image credit: @lefevrediary )

Style Notes: Cowboy boots are a staple come summer, but given the unpredictability of London weather, it always pays to have several looks up your sleeve that can fit any forecast. This ensemble strikes that transeasonal note, whilst still keeping the cowboy boots a central part of your look.

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4. Cape Blouse + White Skirt + Cowboy Boots

An image of @chiarasatelier wearing cowboy boots with a white skirt and black cape top.

(Image credit: @chiarasatelier)

Style Notes: If you don't want to wear your cowboy boots in a way that looks like you've just come from a Kasey Musgrave concert, though you've obsessively been playing her latest record "Middle of Nowhere" on repeat, take notes from this sleek look. Opt for a pair with a razor-sharp heel and point to lean into the sophistication inherent to elevated wardrobe essentials like white pencil skirts and a cape blouse.

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5. Leather Jacket + Floral Dress + Cowboy Boots

An image of @emmaleger wearing a floral dress from Khaite with a leather jacket and boots.

(Image credit: @emmaleger )

Style Notes: Wearing cowboy boots is sometimes a lesson in contrasts. Wearing them with jeans and a tank top feels like the obvious choice, so the most tasteful dressers are always finding innovative ways to style them to ensure their looks feel fresh. This is exactly why pairing cowboy boots with an ethereal, floral dress and a leather bomber jacket feels surprisingly perfect; it's all about taking cues from unexpected places and piecing them together to create a totally new silhouette you can rely upon.

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6. Black Vest + White Skirt + Tan Boots

Influencer wears white skirt with tan boots and black vest

(Image credit: @meganadelaide)

Style Notes: For warmer spring days, call on a laid-back vest and miniskirt combo and add a pair of cowboy boots. This pair is reminiscent of Frye boots and other brands that were at the cutting edge of developing the style. It's another type of cowboy boot with a square toe and top edge shape, which makes it a little more classic.

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7. Bomber Jacket + Handkerchief Skirt + Cowboy Boots

An image of @gracealexandriaa wearing cowboy boots with a bomber jacket and handkerchief skirt.

(Image credit: @gracealexandriaa)

Style Notes: This is one of the easiest and coolest transitional-weather looks I've seen. Suitable for both Nashville and Dalston, pair a handkerchief skirt (a favourite of certified cowgirl Bella Hadid's) with a bomber jacket and consider your work done. This ain't Texas, but it might as well be the closest thing to it.

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8. White Dress + Oversized Sunglasses + Cowboy Boots

Influencer wears a white dress with cream coloured cowboy boots

(Image credit: @ali_tate_cutler)

Style Notes: A pair of cream-coloured, croc-print cowboy boots is an easy way to lighten up your wardrobe for spring and create a blend of muted shades that work beautifully together. Of course, you could always wear an all-white outfit, which is always a reliable and chic summer look.

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9. Leather Jacket + Midi Skirt + Black Boots

Influencer in a white midi skirt with black cowboy boots and brown leather jacket.

(Image credit: @frannfyne)

Style Notes: Softer neutral colours like cream and chocolate brown make a pair of black boots feel more fitting for spring. This outfit is a perfect example of how to incorporate cowboy boots when your style doesn't typically lean Western; slouchy boots with a midi skirt and relaxed jacket make for a more contemporary silhouette.

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Maxine Eggenberger
Maxine Eggenberger
Deputy Editor

Maxine Eggenberger is Who What Wear UK’s Deputy Editor and has over fourteen years of experience in fashion journalism. She been creating engaging and authoritative content for Who What Wear UK since 2018, covering runway reports, emerging trends, long-form features, talent interviews self-styled shopping stories and columns, including her edit of the best new-in buys. She ensures the highest editorial standards are met across the site, leads the editorial team in their search and keyword planning, works closely with the fashion and beauty team on strategy and continues to pen many of her own articles. Prior to Who What Wear UK, Maxine's contributed to publications including Grazia, InStyle Marie Claire, Elle and Look, amongst others.