Cowboy Boots Can Be Tricky to Style—7 Cool Outfits That Make It So Easy

Some 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 for spring as we shake off the last chilly days of winter and work our way towards summer. Whether paired with midi or miniskirts, denim-on-denim looks or dresses, it's much simpler to introduce cowboy (or cowgirl) boots into your daily rotation, even if your usual style is the polar opposite of ranch attire.

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 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.

Pulling inspiration from these cowboy-boot spring outfits will ensure no one will assume this is your first rodeo.

1. Leather Jacket + Midi Skirt + Black Boots

White midi skirt with black cowboy boots

(Image credit: @frannfyne)

Style Notes: Softer 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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2. Black Vest + White Skirt + Tan Boots

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 differing toe and top edge shape, which makes it a little more classic.

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3. Denim Jacket + Jeans + Cow-Print Boots

Denim on denim outfit with cowboy boots

(Image credit: @aimeesong)

Style Notes: Cow print is in the same realm as cowboy—both are equally as emblematic of ranch style. To bring fun cow-print boots into a modern-day wardrobe, copy Aimee Song's outfit (above) and choose a knee-high pair to wear over the top of a denim-on-denim look.

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4. Long-Sleeved Top + Patterned Skirt + White Boots

White cowboy boots with long-sleeve top

(Image credit: @ada_oguntodu)

Style Notes: In the UK, spring sunshine isn't guaranteed. For the days too cold to wear T-shirts, a long-sleeved top with a flowy skirt will offer a little more coverage without feeling stuffy. A plaid or patterned skirt brings out the prairie aesthetic, and white cowboy boots are the perfect pick to brighten and modernise it all, as Ada Oguntodo proves above.

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5. Dungarees + Quilted Jacket + Ankle Boots


(Image credit: @gracealexandriaa)

Style Notes: This is one of the easiest and coolest spring looks I've seen. Grace Halksworth pairs her dungarees with a floral quilted jacket and black ankle cowboy boots. No doubt I'll be wearing this exact look this weekend…

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6. White Dress + Croc-Print Cowboy Boots

White dress with 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, just as Ali Tate Cutler has done here.

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7. Brown Dress + Brown Handbag + Brown Cowboy Boots

Brown monochrome cowboy boot look

(Image credit: @frannfyne)

Style Notes: When you don't know what to wear, you can't go wrong with a monochrome outfit. Franny Monzemba's dress and boot combo (above) is the perfect 'fit for transitioning from winter to spring. Earthy brown is an ideal colour palette for a Western-infused look.

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This story was originally published at an earlier date and has since been updated.

Maxine Eggenberger
Deputy Editor

Maxine Eggenberger is Who What Wear UK’s deputy editor and has over thirteen years of experience in fashion journalism. She been creating engaging and elevated style content specifically for Who What Wear UK since 2018, covering runway reports, emerging trends, long-form features, 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 SEO strategy and keyword planning, works closely with the beauty team on content initiatives, represents the brand at industry events, and regularly contributes to social media, including her own Who What Wear UK TikTok franchise, French Style Fridays. Previously, Maxine appeared on ITV's This Morning in her own fashion segment and has interviewed countless celebrities—everyone from Victoria Beckham to Oscar winner Lupita Nyong’o.

Prior to Who What Wear UK, Maxine’s career began when, after completing her first-ever internship at Look magazine, she was offered a position on the brand's fashion desk. She accepted, leaving university a year early in the process. Her passion and natural talent for writing and styling meant she swiftly rose through the ranks to become the title's fashion news and commercial content editor, with a stint as’s fashion and beauty writer along the way. She later served as Look’s acting Editor in Chief, overseeing both print and digital, before embarking on a successful freelance career, working with Grazia, The Pool, and Marie Claire amongst others.

Maxine is based remotely from her countryside home near Edinburgh where she spends her downtime renovating her house, walking her dogs, hosting friends and trying to master the art of making Old Fashioned cocktails.

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