Now that fall is fully in swing, there's never been a more perfect time to look for new ways to style your jeans. One of the first things to consider? The right shoes. While there are so many options that it's almost overwhelming, a timeless favorite stylists always turn to is the classic ankle boot. When thinking about how to wear ankle boots with jeans, we turned to celebrity stylist Adeel Khan. He considers this pairing a seasonal must that provides endless ways to create interesting outfits. "Contrary to fashion icon Morgan Stewart's known dismay for the ankle boot, I think ankle boots and jeans are not just the perfect fall combo but truly can work year-round," he says. "They're a great way to look polished with the potential to be cozy if you wear a thicker chunky sock inside, and can be worn with a myriad of looks for different occasions."For starters, Khan says a flat ankle boot or one with a shorter heel is great for the office, school pick-ups or errands, while a higher-heeled ankle boot can transition from daytime lunch with friends to a dinner date or even a cocktail event if accessorized accordingly. Basically, the options are endless—there's an ankle boots and jeans combo with your name on it below. While difficult, Khan managed to narrow down his list of favorite looks for this to his top seven best ways to wear ankle boots with jeans.Related: 8 Best Ways To Style Ankle Boots Over 40, According to a Celebrity Stylist
This is what Khan considers "the great debate." Generally speaking, ankle boots can be worn either over or under jeans, but it also depends on the styling of the outfit. Overall, though, Khan tends to prefer a "boots over jeans" aesthetic. He also says to consider the proportions and what the goal of your outfit ultimately is to decide for yourself. "The most flattering silhouette is jeans over an ankle boot so the boot doesn't cut off your 'leg line,'" he explains. "[You want it to] flow with the pant leg to create the illusion of an elongated leg."He also says that if you have more of a standout boot (à la Carrie Bradshaw) rather than a neutral, you'd want the boot to stand out by wearing it over jeans. "[You want to] give it the spotlight it deserves," he shares. "And if the ankle boot has a wider, dramatic shaft, it can actually give the illusion of a slimmer leg when worn over jeans."Related: 8 Best Ways To Style Cow-Print, According to Celebrity Stylists
How To Wear Ankle Boots With Jeans in 2025
The world is really your oyster when it comes to styling ankle boots and jeans in 2025. You never really run out of new ways to dress them up or down. Khan says there's a look and style of ankle boots to suit everyone."The fun thing about [pairing] jeans and ankle boots together is you can constantly reinvent and create new outfits by playing with different jean silhouettes," he shares. "If it's a straight-legged jean, try rolling up the cuff to hit right at the top of the ankle boot for a vintage look."Khan adds that wide-leg jeans can be a great choice as well, adding drama to an outfit. Long-length jeans in a legging fit can be extra chic when scrunched up under an ankle boot to create a stylized ruched look."Ankle boots have been around since the eighteenth century and jeans have been around since the nineteenth century," he continues. "So each era since has worn both in such inspiring ways—it's fun to go through each decade to gather ideas and mix and match what works for you!"Related: A Celebrity Stylist Is Begging Women To Follow the ‘3-Color Rule’
7 Best Ways To Wear Ankle Boots With Jeans, According to a Celebrity Stylist
1. A monochrome boots and jeans look
According to Khan, wearing a monochromatic boots and jeans look is a great way to spice up your fashion approach. He looks to designers and fashion houses like Anthony Vaccarello, Yves Saint Laurent and Valentino for inspiration here. "[You can pair] an ankle boot that is the same color as your outfit, whether it be black, navy, burgundy, grey, brown or more daring colors and tones like reds, greens, pinks and purples with matching jeans [and] a top," he says. To top the look off, you can add statement earrings and rings to add boldness to your look.Related: 7 Best Jeans Styles for Women Over 50, According to Celebrity Stylists
2. A boho chic look with ankle boots
Khan says that pairing flowy and modern silhouettes with a pair of ankle boots is the perfect way to channel designer-chic looks from Chloe, Stella McCartney and Phoebe Philo. You can opt for a breezier top with statement sleeves or a loose-fitting trench and layered jewelry. "[You can even] try a jean short or miniskirt paired with a flowy top—channel your inner 2010 Sienna Miller!" he says.Related: These Are the Best Shoes To Wear With Wide Leg Pants, According to a Celebrity Stylist
3. Printed jeans with metallic or crystal-studded boots
For when you're in a flashier mood, Khan recommends trying a printed jean with statement boots. "[Channeling] a '90s Cindy Crawford, Naomi Campbell or Donatella for Versace vibe is always fun," he says. "Go for a printed jean with metal or crystal-studded ankle boots, a chunky belt and a simpler button-up or tank to let the other parts of your outfit shine."Related: 9 Best Ways To Style Loafers, According to a Celebrity Stylist
4. An oversized blazer, jeans and ankle boots
If you need a quick, low-maintenance outfit, Khan is a huge fan of the "model off-duty look." This involved pairing simple yet chic staples that make you look put together without a ton of effort. "[It's] easy to attain," he adds. "[You] just need a great fitting t-shirt with an oversized blazer, blue jeans that work for your body type and any ankle boot will do." If you like to add a dash of mystery, Khan also says you can do a lace bootie with dark wash denim jeans, a lace or ruffle neck top and a structured blazer with crystal accessories.Related: 7 Best Jeans for Women Over 60, According to a Celebrity Stylist
5. Pastel-colored jeans and ankle boots
A softer jeans and ankle boots look would include a bit of color—pastels, to be specific. Khan says to try pastels like lavender, seafoam green, light blue and light pink jeans with your look to add femininity. You can opt for a statement jacket or choose to go with something simpler, like a cardigan. To add to the look, he recommends ivory or cream ankle boots and modern pearl jewelry.Related: 5 Essential Tips for Date-Night Style if You’re Over 50, According to Model & Beauty Mogul Molly Sims
6. A denim-on-denim look with ankle boots
Khan calls this look "urban cowgirl." Wearing denim-on-denim with an ankle boot is a great way to keep things simple yet interesting. "Try an ankle boot with leather-etched detailing and a Canadian tuxedo—AKA your favorite blue jeans paired with a coordinating blue jean button up, accented by leather, silver and turquoise accessories," he adds.Related: 5 Essential Tips for Wearing Jeans if You’re Over 50, According to Model and Style Mogul Molly Sims
7. Floral-printed jeans and ankle boots
There are so many ways you can wear floral jeans with ankle boots. Khan says that you can go for a more retro-style look, a crisp outfit with a collared shirt or a more urban-style look. Floral denim looks great with a bomber jacket and sweater for the fall season, but Khan also loves to brighten things up and try a preppier style."Try going preppy with floral printed jeans, a polo shirt with sleeves rolled up and a cable knit sweater wrapped around your shoulders, completed by an ankle boot in a color that coordinates with one of the shades in your floral jeans," he shares.Up Next:
Related: 5 Essential Tips for Wearing Boots if You’re Over 50, According to a Celebrity Stylist
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Adeel Khan is a celebrity and editorial fashion stylist who has worked with celebrities such as Tori Spelling, Mischa Barton and Jennie Garth.Hence then, the article about 7 best ways to wear ankle boots with jeans according to a celebrity stylist was published today ( ) and is available on Parade ( Saudi Arabia ) The editorial team at PressBee has edited and verified it, and it may have been modified, fully republished, or quoted. You can read and follow the updates of this news or article from its original source.
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