Imani-Nia Francis-Tsolaki
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.
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 relive your Eras or Cowboy Carter tour fantasy all year round, pulling inspiration from these eight 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. Leather Jacket + Midi Skirt + Black Boots
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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Embrace the funnel neck jacket trend with this style. The relaxed fit is comfortable and ideal for layering.
Come summer, throw off the jacket and style as COS has here with a double-stacked tank top. Or, if you're looking for a change, swap your woolen midi skirt for a cream satin version this season.
As Nancy Sinatra sang, these boots are made for walking...
2. Black Vest + White Skirt + Tan Boots
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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A black vest is the perfect contrast against a white skirt, and I love how this one brings in a barnyard flair through the addition of suspenders.
No summer wardrobe is complete without a white skirt, and Free People's Lowen skirt is our top pick for 2025.
The rounded square toe paired with a wooden block heel feels fun and fresh.
3. Denim Jacket + Jeans + Suede Boots
Style Notes: Cow print is in the same realm as cowboy—both are equally as emblematic of frontier style. To bring fun cow print boots into a modern-day wardrobe, copy Aimee Song's outfit (as seen above) and choose a knee-high pair to wear over the top of a denim-on-denim look.
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A relaxed denim jacket and cowboy boots are a match made in heaven.
These jeans work well with shorter cowboy boots, but the slim fit can slide into taller pairs too.
If cow print is a touch too maximalist, try another animal-print pattern like these Khaite snake-effect ankle boots. (Dua Lipa and Kendall Jenner both own a pair, too)
4. Black Sheer Dress + Black Hat + Brown Boots
Style Notes: If sunshine is guaranteed, this sheer dress offers a little less coverage without leaving you feeling over-exposed. Layer a bralette and slip skirt underneath to create a warm-weather-appropriate outfit that still feels polished and sophisticated. Add a pop of colour with a hat to complete an otherwise monochromatic look, just as Lou Northcote perfectly demonstrates above.
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On warmer days, this sheer dress can be layered over shorts and a black bikini; on cooler days, wear it over a t-shirt and jeans before topping it all off with your favourite woven leather bag.
If the blue feels too adventurous, make it more 2025 appropriate with this on-trend straw style.
The intricate design and turned-up toe give this French-designed a desert-ready feel.
5. Dungarees + Quilted Jacket + Ankle Boots
Style Notes: This is one of the easiest and coolest transitional-weather 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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One-piece outfits like dungarees make summer dressing so easy.
Perfect for peeking out from under dungarees.
A floral quilted jacket softens the look of Western boots. But if you're not into the botanical print, try one of the other 11 prints, including red tartan and black and white gingham.
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 shades that work beautifully together, just as Ali Tate Cutler has done here. Of course, you could always wear an all-white outfit, which is always a reliable chic summer look.
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The puff sleeves, functional buttons and lace detailing are a nice touch.
Oversized sunglasses—one of the biggest sunglasses trends of 2025— will never be considered outdated. And if you're looking for an investment, this designer style from Celine is a gorgeous option.
Cream cowboy boots get an upgrade with suede 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 Monzemba's brown summer dress and boot combo (above) is the perfect look for moving through the season. Plus, earthy and chocolate browns are an ideal colour palette for a Western-infused ensemble.
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This dress will prove to be so versatile.
A saddle bag is fitting and the hardware reminds me of a horse bit.
I adore how these are more English countryside than American south, making them perfect for Glastonbury and winter dressing in the Cotswolds.
8. White T-Shirt + Black Mini Dress + Knee-High Cowboy Boots
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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This exact COS t-shirt comes highly recommended by Who What Wear editors.
The perfect LBD doesn't exist—
How could we exclude Ganni's viral cowboy boots from this list?
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