How to Wear Ankle Boots With Jeans

Trending Videos

A woman wearing ankle boots and jeans — Photo:
CHRISTIAN VIERIG/GETTY IMAGES

Though ankle boots with jeans might be a look associated with the '90s and early 2000s, this era can’t take full credit for this classic pairing. Rather, the duo was a recycled trend, stemming from the late '60s and early '70s—and it’s come back around heading into winter. Expert Christina Stein tells InStyle that the resurgence is expected to combine influences from throwback periods, Western aesthetics, and modern trends like metallics.

According to fashion stylist and expert Naina Singla, this resurgence also comes at the perfect time: winter. “This popular style shoe has become an easy go-to into the colder months,” she says. “If there's ice or wintry weather, you want to consider shoes that are water resistant, offer traction, and have a stable base, so I always recommend my clients wear ankle boots this time of year.”

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.

The upside to incorporating boots into your jeans outfits is that there are many styles, colors, and prints to choose from. Ultimately, the best pair to wear with your favorite denim bottoms is the pair you feel your best in. That said, we asked Singla and Stein to break down which styles are expected to be everywhere in the upcoming season.

01 of 08

Square Ankle Boots

Singla expects the square ankle boots from the 90s era to influence our wardrobes heading into the New Year, but notes they’ll be an especially popular pair to wear with jeans. “It’s both a comfortable and wearable style,” she tells InStyle.

02 of 08

Western-Style Ankle Boots

The Western-style inspired boot has been trendy for a little while, but Singla has a hunch the style has largely stuck around as long as it has due to Taylor Swift strutting in these types of boots throughout her Era's tour. Still, the modern interpretation of a cowboy boot “has less details and a more streamlined look,” Singla says. “It’s also being worn in varying shades of metallics such as silver.”

03 of 08

Metallic Ankle Boots

While we’re on the subject of metallics, Stein is especially enthusiastic about the illuminated look. “Metallics still cannot be beat,” she confidently states, adding, “They’re not going anywhere anytime soon!"

04 of 08

Brown Ankle Boots

Red might hold the top spot for the “it” color of the season, but brown isn’t too far behind on that list, especially, Singla says, regarding footwear: “This is a top color trend as seen on the runway for Fall/Winter 2023 and this has translated to footwear as well. It's a great neutral option that offers an unexpected alternative to the classic black ankle boot.”

05 of 08

Lug Sole Boots

Singla defines lug boots as a classic Chelsea style that’s been reimagined with a lug platform and block heel. “You can easily style this for a casual look with cropped denim and a knit top,” she says.

06 of 08

Opt for Oversized

Boots With Jeans Oversized — Jeremy Moeller/Getty Images

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!”

07 of 08

Make it Minimal

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.”

08 of 08

Prioritize Polish

Boots With Jeans Polished — Edward Berthelot/Getty Images

For a more 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."

We Care About Your Privacy

We and our partners process data to provide:

8 Ways to Wear Ankle Boots With Jeans