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Boot season comes and goes, and with it comes the yearly debate about which boots look best—and, just as importantly, what to wear with each one. Because of that, it can be a little tricky knowing what you should and shouldn’t pair with them. One of the most confusing footwear trends is how to wear ankle boots. There’s just something about their height that can make or break an outfit, especially as you get older. To make things easier, we’ve rounded up not one, but eight of the best ways to style ankle boots over 40, according to a celebrity stylist. With decades of fashion experience dressing Hollywood icons like Fran Drescher, Jamie Lee Curtis and Molly Shannon, stylist and author Brenda Cooper has mastered the art of dressing women. That’s why she’s the perfect person to dish out fashion advice. She not only offers tips on what looks best with ankle boots, but she also shares where some of the outfits can be worn to as well as some fashion no-nos. That way, you won’t find yourself wearing a combination that isn’t flattering. So, if you’re a fan of ankle boots, get ready to get a quick fashion lesson from one of the biggest pros in the industry. Thanks to her expert advice, you’ll know how to wear ankle boots if you’re over 40. Plus, you’ll feel more confident than ever picking out your fall looks this season. Related: 7 Best Ways To Style a Vest in 2025, According to a Celebrity Stylist How To Wear Flat Ankle Boots Over 40 Wearing flat ankle boots can enhance your outfit at any age, and Cooper says they look great with a lot of different pieces you probably have in your closet. “Flat ankle boots are a perfect choice for when you are over 40, as they will take you through the fall and winter seasons with comfort, style and versatility,” she explains. So, how should you wear flat ankle boots when you’re 40 and over? “Some of the best ways to wear flat ankle boots are with jeans or slacks, and when styled correctly, they can look great with a maxi skirt too if you want to dress them up,” she shares. However, she warns they don’t look good with just any style of maxi skirt. “When styled intentionally—say, with a maxi skirt that has a bit of movement in the fabric so it gives a glimpse of the boots—the look can become an effortlessly boho outfit and beautifully balanced,” she notes. Related: These Are the Best Shoes To Wear With Baggy Jeans, a Celebrity Stylist Reveals What Not To Wear With Ankle Boots Cropped pants Because ankle boots have a very specific height (your ankles), it’s not a great idea to wear something that also has a very specific length. “Flat ankle boots create a visual break at the ankle that shortens the leg line, especially when paired with cropped pants,” Cooper stresses. “Because of this, you shouldn’t wear cropped pants with ankle boots as they disrupt the vertical flow and balance of the silhouette.” Super long flared pants On the same note, you don’t want to wear anything that’s going to completely cover the star of the show (your shoes!). “Flared pants and ankle boots can feel like mixing oil and water—one’s retro and fluid, the other structured and modern,” Cooper explains. “When the flare hides the boot completely, the proportions and style story clash.” Pants that gather at the bottom If you can see a pattern here, it’s that you don’t want to have too much going on at your ankles when wearing ankle boots. And while pants or jeans that scrunch up at your ankles will show off your boots, it doesn’t look great. “When pants bunch or gather at the top of an ankle boot, they disrupt the clean line of the leg and add unnecessary bulk,” Cooper states. “The result can look untidy and shorten the silhouette, rather than elongating it.” So, what’s the fine middle ground for pants and ankle boots? We’ll get more into perfect ways to style ankle boots later. But for now, Cooper shares that it’s really all about not interrupting your leg line. “A smooth, uninterrupted line, where the pant either skims over or tucks neatly into the boot, is best as it creates a more refined, intentional and flattering appearance,” she explains. Floor-length dresses Similar to why flares don’t work well with ankle boots, floor-length dresses aren’t a great fit. “Straight, floor-length dresses can sometimes hide ankle boots and make a person’s outfit feel bottom-heavy,” Cooper says. Are Ankle Boots Still in Style? If you’re a fan of flat ankle boots, Cooper tells us you can keep wearing them (if you care about what’s in style, at least). “Flat ankle boots never go out of style, and each season brings fresh new interpretations of them,” Cooper tells Parade. “For women over 40, choosing between flat or heeled is purely personal; it depends on your style, comfort and the statement you want to make. Flats lend a relaxed, casual feel, while heels instantly elevate and refine the look.” Do Ankle Boots Go Over or Under Jeans When You’re Over 40? Whether you should wear your ankle boots under or over your jeans is a never-ending debate that people have. However, Cooper is here to set the record straight. “It’s not about a person’s age, it’s about the proportion of a person’s outfit when they are wearing flat ankle boots,” she points out. “So the answer is both. You should let your jeans meet your ankle boots or tuck them in smoothly into the boot, not bunch or bulge them over it. Clean lines always look modern, flattering and confident.” Related: These Are the Best Shoes To Wear With Leggings, According to a Celebrity Stylist 8 Best Ways To Style Ankle Boots Over 40, According to a Celebrity Stylist 1. Flat ankle boots with black leggings “Flat ankle boots work well with this black legging look because their chunky, modern style adds edge and weight to the casual leggings and layered top, balancing the outfit’s proportions,” Cooper reveals. “I like the relaxed, confident vibe—it’s easy, unfussy and has a subtle rocker-chic feel.” She tells Parade that this look can be worn to tons of places. “This look is great for casual weekends, coffee dates or running errands in style,” she shares. “To elevate it, I’d add a statement accessory like a scarf or bold earrings to bring some polish and personality.” 2. Flat ankle boots with leather leggings While ankle boots look good with leggings, they look even cooler with leather leggings. “When it comes to this outfit, ankle boots pair perfectly with it because their fitted shape continues the clean, elongated line of the leather pants, adding polish and edge without breaking the silhouette,” Cooper expresses. “The overall look works so well because it blends urban sophistication with effortless confidence.” She also notes that the fabric mixing—with the wool, leather and knitted items—also helps the outfit feel “modern and refined.” “To elevate it further, I’d add a statement watch or structured crossbody bag in a deep oxblood or metallic tone to tie in with the jacket sleeves and give it a subtle, luxurious finish,” she shares. 3. Flat ankle boots with tights “For the fall, this is a great look,” Cooper states. “It shows one way ankle boots can be worn when it gets cooler because they echo the dark tights, creating a long, continuous line that elongates the legs and balances the structure of the rich cognac leather coat. I really love this look for its effortless blend of modern polish and retro cool—it’s confident, chic and timeless.” She adds that while it’s great to wear while out and about in the city, at an art opening or to a lunch meeting, the only thing she’d incorporate would be something bold like a statement accessory, to add a touch more personality. 4. Flat ankle boots with bootcut jeans “The black ankle boots ground this look perfectly thanks to their sharp silhouette and sleek finish, which balances the casual, vintage vibe of the bootcut jeans while adding polish and structure to the outfit,” Cooper notes. “I love this ensemble because it takes classic elements—a crisp blue shirt and denim—and gives them personality with the bold, playful floral tie. It’s unexpected, creative and effortlessly cool. “ As for style changes, Cooper would just change up one thing. “To enhance the overall look of the ankle boots with this outfit, I’d just tuck the shirt a bit neater and add a tailored blazer or cropped leather jacket for a touch of refinement and balance to the playful tie,” she shares. Related: These Are the Best Shoes To Wear With Bootcut Jeans, According to a Celebrity Stylist 5. Colorful flat ankle boots “Instead of dark-colored ankle boots, you can always go with a brighter pair,” Cooper states. “The mustard ankle boots in this outfit add a vibrant pop of color that instantly lifts the neutral camel coat, creating a sophisticated yet playful contrast.” She shares that she likes the timelessness of this outfit and how polished it is. But at the same time, it “still feels modern and full of personality.” “The mix of classic tailoring with a bold accessory also shows confidence,” she says. There’s just one item that Cooper says would make this outfit even better. “To make it even sharper, I’d add a structured hat to echo the color of the ankle boots and pull the whole look together with a touch of Parisian flair,” she explains. 6. Flat ankle boots and high-rise jeans “I’m a fan of the ankle boots with this look because it’s classic, comfortable and effortlessly chic as the tucked-in checkered shirt, high-rise jeans and crossbody bag paired with the black ankle boots create that perfect off-duty balance of style and practicality,” Cooper states. While there’s not much she says she’d change, she tells Parade, “adding a bright red lip or statement sunglasses would give it a little extra pop!” 7. Flat ankle boots with skinny jeans “Brown ankle boots work beautifully with skinny jeans, like in this look, especially when paired with a leather jacket, as their earthy tones will tie seamlessly together and create a warmth,” reveals Cooper. Where does she suggest wearing this look to? So many places. “It’s the perfect look for casual Fridays, travel days or weekend lunches,” she says. “To make it even better, I’d add a bold scarf in a rich jewel tone or pattern to elevate the overall polish of it.” 8. Flat ankle boots and a skirt “If you want to dress up ankle boots, this is a good example as the ankle boots’ dark tone elongates the legs when paired with opaque tights under the teal skirt, creating a polished, uninterrupted line,” Cooper shares. “The draped, asymmetrical coat also softens the structured silhouette.” How would she enhance the overall look? “I’d just add a statement brooch or a patterned silk scarf at the neckline to draw attention to the face,” she tells Parade. Up Next: Source:
