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 shoe 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 toward summer. Whether they're paired with midi or mini skirts, denim-on-denim looks, or minidresses, 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 life attire.
I understand if you find cowboy boots a little too costume-like for your taste. But there are also plenty of styles from the best boot brands that offer a subtler nod to Western-inspired styling via a Cuban heel or swapping in the traditional stitching for a fun cow print. I personally think you can't 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 with this footwear.
1. Leather Jacket + Midi Skirt + Black Boots
Style Notes: Choosing softer colours like cream and chocolate brown make a pair of black boots feeling 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 all make for a more contemporary silhouette.
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Swap your dark denim skirts for cream-coloured versions to match the season.
2. Black Vest + White Skirt + Tan Boots
Style Notes: For warmer spring days, call on a laidback vest and miniskirt combo. To infuse a little Western flair, just add cowboy boots. This style of is reminiscent of Frye boots and other brands that were at the cutting edge of developing this shoe. It's another type of cowboy boot but with a differing toe and top edge shape, which makes them a little more classic.
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No spring or summer wardrobe is complete without a white skirt — and it goes perfectly with cowboy boots.
A square top edge is less costume-y than the scalloped edges of traditional cowboy boots.
3. Denim Jacket + Jeans + Cow Print Boots
Style Notes: Also in the realm of cowboy boots are those in a cow print, which are equally as emblematic of ranch style. To bring them into a modern-day closet, copy Aimee's outfit and choose a knee-high pair to wear over top of a denim-on-denim look.
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A relaxed denim jacket is a match made in heaven when paired with cowboy boots.
These jeans work with shorter cowboy boots but the slim fit can slide into taller pairs too.
A high heel and knee-high height give cowboy boots more glamour.
4. Long-Sleeve Top + Patterned Skirt + White Boots
Style Notes: In the UK, spring sunshine isn't guaranteed. For the days too cold to wear T-shirts, a long-sleeve top with a flowy skirt will offer a little more coverage without feeling stuffy. A plaid or patterned skirt brings out the prairie aesthetic, but white cowboy boots serve as the perfect pick off your shoe rack to brighten and modernise it all, as Ada proves.
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5. Dungarees + Quilted Jacket + Ankle Boots
Style Notes: This is one of the easiest, and yet coolest, spring looks we've seen. Grace 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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One-piece outfits like dungarees make spring dressing so easy.
6. White Dress + Croc Print Cowboy Boots
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 ensembles that work beautifully together, just as Ali has done here.
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White cowboy boots get an upgrade with the crocodile texture.
7. Brown Dress + Brown Handbag + Brown Cowboy Boots
Style Notes: When you don't know what to wear, you can't go wrong with a monochrome outfit. Franny's dress and boot combo is the perfect fit for transitioning from winter to spring. Earthy brown is an ideal colour palette for a Western-tinged look.
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This dress works in a Western context but slots into any other style you're opting for.
Although this bag isn't inherently Western, the hardware reminds me of a horse-bit.
A muted suede material never goes out of style. The star debossing is darling too.
This story was originally published at an earlier date and has since been updated.
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 InStyle.co.uk’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.
- Melissa EpifanoContributor
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