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Don’t underestimate ankle boots with jeans. Here are 8 outfit ideas that prove they’re a match

Getty Images / InStyle
It’s almost time to break out your ankle boots for fall. Credit: Getty Images / InStyle

The duo doesn’t have to look dated.

The duo doesn’t have to look dated.

The Gist

  • The right styling gives ankle boots and jeans a modern refresh.
  • Ahead, two stylists share how to reimagine the duo with Western-inspired fringe touches, pops of juicy color, and fall-ready layers.

Alt hed: Ankle Boots and Jeans Are the Ultimate Summer-to-Fall Transitional Pairing

Fall still feels far away for now, but before you know it, you’ll be crunching across leaves on your evening walks and saving pumpkin loaf recipes to bake on chilly weekends. While you don’t have to shelve your sandals and sundresses just yet, it can be helpful to start taking out pieces that can ease your wardrobe in the direction of cooler days—i.e., ankle boots and jeans.

The pairing was popular throughout the ‘90s and early 2000s, then again in the 2010s with the rise of Chelsea boots and skinny jeans. Now, the duo is getting the modern twist it deserves with Western-inspired silhouettes, wider-leg denim, and unexpected pops of color. Consider playing with texture and finish by pairing light-wash blue jeans with a dark snakeskin pair, or contrast distressed denim with slick patent leather booties.

Ahead, find eight ways to wear ankle boots with jeans, with stylist insight that will keep the combination from looking dated.

Meet the Expert

  • Christina Stein is a personal stylist and image coach.
  • Naina Singla is a Washington D.C.-based stylist and fashion expert who has spent over a decade styling women.

01 of 08

Breezy Boho

guest wears a black camisole, blue straight-leg jeans, a black and pink patterned long cardigan, oversized aviator sunglasses, carries a red Balenciaga City bag, holds a smartphone, and black pointed-toe ankle boots outside Elie Saab show
Credit: Raimonda Kulikauskiene/Getty Images

Lean into Americana charm with a pair of classic blue jeans and cowboy ankle boots. This guest pairs hers with bohemian touches, including a sweeping embroidered duster and rust-colored purse with fringe details. Aviators further cement the outfit’s Western-inspired roots.

02 of 08

Opt for Oversized

Boots With Jeans Oversized
Credit: Jeremy Moeller/Getty Images

Personal stylist Christina Stein loves an oversized denim moment, but especially if your favorite pair is then paired with heeled boots, a bodysuit, and a cozy, longline knit cardigan. “The wide-leg cropped denim hitting at the top of the bootie with a blouse and blazer is also super chic and easy,” she says of the combination. “If you’re just trying out the angle boot trend you’re bound to have either of those styles in your closet to try!” 

03 of 08

Pop of Color

Aleali May wears long wavy black hair, pink aviator sunglasses, a white tank top with a neon red graphic print, orange leather flared pants, a gold squared handbag, white snake leather ankle heels boots shoes, outside Amiri
Credit: Edward Berthelot/Getty Images

Another 2010s-coded trend having a resurgence? Colorful denim. This guest pairs white ankle boots and an airbrushed tank top with coated jeans in a freshly-squeezed shade of orange.

04 of 08

Lug Sole Boots

Boots With Jeans Lug Sole Boots
Credit: Christian Vierig/Getty Images

Lug boots are a classic Chelsea style that’s been reimagined with a treaded sole platform and block heel. “You can easily style this for a casual look with cropped denim and a knit top,” says stylist Naina Singla.

05 of 08

Make it Minimal

Boots With Jeans Make it Minimal
Credit: Christian Vierig/Getty Images

For a minimal and neutral approach, Singla recommends throwing on a pair of slim straight-leg black denim with pointy-toe heeled black ankle boots. “You can layer this with an oversized off-white turtleneck sweater and a cute ivory clutch.”

06 of 08

Denim on Denim

A passerby wears an oversized light blue denim shirt open at the chest, a tan leather belt, light wash straight-leg ripped jeans, a black quilted chain-strap shoulder bag, dark brown suede ankle boots, small rectangular dark sunglasses, and wavy light brown hair worn loose during the Milan Design Week 2026
Credit: Valentina Frugiuele/Getty Images

It’s hard to go wrong with denim on denim. The pairing transcends all decades, and is easy to replicate with pieces you already own. You can wear contrasting washes, as this guest does, or opt for matching denim for a monochromatic moment. Ground the look with neutral booties.

07 of 08

Prioritize Polish

Boots With Jeans Polished
Credit: Edward Berthelot/Getty Images

For a refined aesthetic, Singla envisions a classic straight-leg high-waisted 90’s style mid-wash denim with a black almond-toe ankle boot and thin grey knit tucked in. “To elevate the look,” she says, “add an olive-colored relaxed-style blazer and a black top-handle bag.”

08 of 08

Cuff It

A guest wears medium-length wavy dark brown hair, olive khaki button-down shirt, dark chocolate brown blazer, structured shoulders, notched lapels, light wash blue straight-leg jeans, cuffed hem, leopard print pointed-toe high heels, gold hoop earrings, black smartphone in hand, bracelet on wrist before Mondepars fashion show
Credit: Mauricio Santana/Getty Images

The quickest way to draw attention to a statement shoe choice is with a hefty pant cuff. This guest team understated neutrals with loose, wide-leg denim for a relaxed edge, then completes the outfit with fiercely chic leopard print boots.

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