How to Wear Cowboy Boots in 2022 Like a Style Pro

20 Best Cowboy Boot Brands of 2022

If you’ve lately found yourself wondering how to wear cowboy boots so you like more like a street style star and less like Daisy Duke, you’re not the only one. Searches for the western footwear have been steadily on the rise this winter, according to the global shopping platform Lyst. But outside of simply pulling them over a pair of blue-wash skinny jeans and knotting a flannel shirt at our waist, we’re still figuring out exactly how to make the trend work. Luckily, we found 20 stylish women who appear to have cracked the code so we can bookmark and Pin their outfits to copy ASAP.

ARE COWBOY BOOTS IN STYLE FOR 2022?

You betcha! Cowboy boots have been wavering onto and off of our shopping list for the past few years, but they’re definitely back for another spin in the spotlight in 2022. Best of all, there isn’t just one style that is reigning supreme. So whether you prefer the look of classic brown soft leather or metallic silver or even red with embroidered flowers, all fit right in with the trend.

DO COWBOY BOOTS GO OVER OR UNDER PANTS?

Realistically you can do either, but either option requires a different leg silhouette. If you want to tuck, stick with skinny jeans, leggings and other slim fits. They won’t look bulky or bunch above the top of your boot and will help your legs look long and lean. On the flip side, wide-leg styles and, obviously, boot cuts will easily flow over the top of your boot. Save those middle-of-the-road styles, like straight legs, for another day and a different type of trendy footwear (like chunky loafers or retro ‘70s sneakers).

HOW TO WEAR COWBOY BOOTS IN 2022

 

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1. RANCHER HAT + SHIRTDRESS + CLASSIC BOOTS

Let’s start with the basics—rather than go all out western, mix your brown or black boots with a shirtdress in a heavier fabric (like denim or flannel) and top it off with a felt rancher or similar wide-brim hat. The result is a fabulous blending of true cowboy style and city chic.

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2. BLACK DENIM JACKET + BLACK SKINNY JEANS + CONTRASTING BOOTS

If you’re more of a pants gal, try a fresher, reworked version of the Canadian tuxedo (aka, denim on denim) by way of clean black washes with no distressing. Keep your accessories on the modern side (yes to a structured lady bag, no to a fringe-trimmed tote) to really amp up the style factor.

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3. WHITE BUTTON UP + PATTERNED SKIRT + BLACK BOOTS

Cowboy boots tend to feel like a standout piece (at least in the city and suburbs), but they don’t have to be the focal point of your outfit. Pair them with a boldly patterned mini or midi skirt and a classic white blouse and suddenly they’re as easy to wear as any other black knee-high styles in your arsenal.

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4. BLAZER + MIDI DRESS + COWBOY BOOTS

This date-night look is so much more walkable than strappy stilettos but just as cute for making a good first impression.

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5. PATTERNED COAT + PATTERNED BAG + PATTERNED BOOTS + SOLID-HUED DRESS

A handy tip for figuring out how to mix and match prints like a pro is to start with a solid, neutral-hued base, like a black dress or white jeans and a white T-shirt. Then you can work outwards, piling on all the fun plaids, zebra stripes or colorblocking you want without looking too over the top. (Another pro tip is to make sure all your printed pieces have a least one color in common.)

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6. BLACK DRESS + INTRICATE, COLORFUL BOOTS

If you want to make sure your red embroidered boots are getting all the attention they deserve, pair them with a simple little black dress and minimal accessories to really give them the spotlight.

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7. SWEATER DRESS + KNEE-HIGH BOOTS

Winterize your western boots by pairing them with a cozy knit dress. Chunky, looser sweater dresses are trending in 2022, but thinner knits will also look cute, provided they hit below the knee.

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8. SILK SCARF + LEATHER GLOVES + BOOT-LEG PANTS + ANKLE BOOTS

Add a touch of old-Hollywood glamor to your look by knotting a pretty silk scarf under your chin and slipping on a pair of luxe leather or suede gloves. And while you could tuck skinny jeans into your booties, we think this look works best with wide-leg pants that can glide over the top of your boot for just a touch of western.

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9. PRINTED MINIDRESS + STARK WHITE BOOTS

Give the cowboy trend a ‘60s spin by picking up a pair of simple, stark white boots and pairing them with a flirty mini that would make Twiggy proud.

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10. STRUCTURED JACKET + T-SHIRT + SHORTS + COWBOY BOOTS

Yes, you can wear shorts with cowboy boots and not wind up looking like Daisy Duke. The key is to choose both shorts and boots with a more polished vibe. Think longer hem lengths, clean washes or non-denim options paired with black leather or suede that doesn’t slouch. Top it off with a structured jacket—like a blazer—that hits within two inches of your hips and voilà!

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11. WHITE TOP + WHITE SKIRT + WHITE BOOTS

When in doubt, try a monochromatic look. Head-to-toe brown or beige can often fall flat, and brighter shades might be a bit overwhelming, but white clothes paired with white boots makes for a chic ensemble that even the most minimalist fashionista will feel comfortable in. Play around with different textures or subtle patterns, like denim with white-and-silver snakeskin, to add some depth to the look.

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12. BLACK TOP + BLACK SKIRT + BLACK BOOTS + GOLD HARDWARE

Of course, if you’re going to go the monochrome route you can’t discount the power (and ease) of wearing all black. That said, so much darkness can sometimes obscure your shape and leave you looking a little like a blob. Add in a few hints of gold, either by way of a gold belt buckle, a chain necklace or even as a decorative cap on the toe of your boots, to shake things up a bit and add interest.

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13. SILKY MIDI DRESS + LEATHER BELT + TALL BOOTS

Sleek workwear and rugged boots may not feel like an obvious match, but adding in a dressy-casual piece, like a leather belt, can help bridge the gap between the two. Also, be sure to choose a dress with a hem that hits one or two inches below the top of your boots for maximum style points.

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14. DENIM SHIRT + KNIT MIDI SKIRT + HEELED ANKLE BOOTS

We adore this cozy fall combo for chilly autumn afternoons. Hot tip: Sporting white boots or another light color rather than dark hues can help lighten the vibe, so you don’t look quite so weighted down by all that fabric.

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15. HEADBAND + PREPPY MINI + COWBOY BOOTS

Embrace your preppy and ranch-loving sides by choosing pieces that all fall within the same color family. A black headband, black boots and green-and-black plaid dress work beautifully together, but so would a brown-and-yellow floral headband, brown boots and a pale yellow mini skirt.

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16. WHITE DRESS + BLACK BELT + BLACK-AND-WHITE BOOTS

Or you could wear a black dress with a white belt. The point here is to embrace your inner Cruella De Vil (her fashion sense only) and sport only black and white for an elevated finish.

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17. PATTERNED TOP + CONTRASTING PATTERNED BOTTOM + BLACK-AND-WHITE BOOTS

For those who love a good maximalist moment, try pairing your bold cowboy boots with two equally show-stopping prints. If you’re not aiming to have a through-color included in each piece, opt for patterns with similar sizes or styles, like two large contrasting plaids, rather than going too out there with your selections.

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18. SWEATER VEST + MINI DRESS + CLASSIC BOOTS

Combine two hot 2022 trends—sweater vests and cowboy boots—for one uber trendy ensemble. We suggest layering a solid-hued knit over a dress in the same color to keep things simple but chic.

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19. TURTLENECK TEE + MIDI SHIRTDRESS + MID-CALF BOOTS

We love a good layered look, and this combo is one of the best. Slip a thin turtleneck on underneath a button-front midi for added warmth without added bulk. Then opt for boots that show just a few inches of skin under the hem of your dress to balance out your top layers.

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20. ANYTHING GOES

The point of bold fashion pieces like cowboy boots is to have a little fun with your clothing. So really, at the end of the day, wear what makes you feel good. If that means tucking corduroy skinnies into burgundy boots and topping it all with a floral-embroidered denim vest, then so be it.

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Krista Jones
Former Harper's Bazaar editor, Krista Jones is always sporting some of the coolest brands, and is a constant source of inspiration for her unique New York style.