Fashion | 08.31.2022

40+ Style: How To Wear Ankle Boots Over 40

Woman wearing stylish heeled ankle boots over 40.

By Christina Lyon

Style doesn’t dry up and die as we get older. It only gets smarter with age.

Just ask any woman over 40. We know how to work our wardrobe, and we’ve got the confidence to boot (pun very much intended). So when it comes to one of the most versatile footwear options out there—ankle boots—we rock ’em like no one else can.

If you’re ready to make the most of this style staple, keep reading. We’ll show you how to wear fashion-forward booties like a boss.

Do’s And Don’ts Of Styling Ankle Boots For 40+ Women

There’s no denying that booties are a wardrobe staple for women of all ages. They’re comfortable, stylish, and can pair seamlessly with just about anything. But when you’re over 40, the last thing you want is to look frumpy or dated. Fashion trends are current and ever-changing, but that doesn’t mean you can’t keep up. It just takes a little bit of know-how.

A woman wearing black boots with a feminine skirt.

Whether you’re teaming your lace-up booties with skinny jeans or a flowy dress, we’re here to help you master the art of styling this footwear option. Here are a few do’s and don’ts to get you started on learning how to wear ankle boots over 40.


  • Pair opposing styles. A chunky, masculine boot with a silky, feminine dress? Yes, please!
  • Keep your hemline high. Flowy dresses, cropped jeans, and midi-skirts are all great lengths to show off your booties.
  • Experiment with interesting details. Think cut-outs, embellishments, studs, or unexpected materials.
  • Show off some ankle cleavage. A little lower leg peekaboo can make you look instantly taller.


  • Wear anything floor-length. We’re not saying you can never pair a bootie with a long dress or skirt. Just be mindful of the proportions to best show off those gorgeous booties.
  • Be afraid of color. A pop of color can add some fun and personality to your look.
  • Match your booties to your outfit. Unless you’re going for a monochromatic moment, there’s no need to perfectly match your booties to the rest of your ensemble.
  • Tuck your wide-length pants in. Trust me, it’s not a good look.

Now that you know what works (and what doesn’t), it’s time to get shopping.

Woman pairs black skinny jeans with ankle boots.

How To Wear Ankle Boots With Jeans

You can never go wrong with pairing one classic with another—and a jeans and booties combo is no exception. No matter what bootie style you choose, this outfit formula is always a winner. If you’re nervous about wearing ankle boots over 40, start with these classic outfits!

The key to nailing this look is choosing the right bootie for the right pair of jeans. So let’s dive into these wardrobe essentials, shall we?

Rock A Skinny Jean

Skinny jeans may get a bad rap, but nothing says fashionista like a killer pointed toe. Pair classic black ankle boots (like these from Marc Fisher) with your favorite skinny jeans for a look that’s equal parts stylish and comfortable.

Just be sure to tuck your jeans into your booties to avoid any awkward bunching, and opt for a flowy blazer or oversized top to balance out the fitted bottom.

Slide Into Some Bootcuts

Booties with bootcut jean is always a good idea. The flared silhouette will balance out the proportion of your booties, and the extra fabric at the bottom will help to create a longer and leaner look.

For a modern take on this outfit combination, try a pair of Chelsea boots. The sleek lines will add a touch of sophistication to your look. Bonus points if you grab a suede pair like these from La Canadienne.

Stylish woman wearing straight leg jeans and ankle boots crossing the street.

Channel The Off-Duty Model With A Straight Leg

Think of straight-leg jeans as the chameleon of the denim world. It’s the perfect canvas for booties of all shapes and sizes—so now is the time to play with your most daring ankle booties! We’re talking cheetah print, metallic details, and all the color.

Pairing booties with a straight leg is all about having fun with your look. So don’t be afraid to experiment with different colors, materials, and textures. Start with something a little edgy, like these green suede booties from Rag+Bone, which would pair perfectly with some black jeans.

Show Some Calf With A Crop

It may feel like you’re wearing some high-waters, but cropped jeans with booties can look quite chic. You want the denim to fall just above your booties. Too much skin, and your outfit will look more sloppy than stylish.

This slightly taller pair from Franco Sarto hits the perfect spot. Throw on a leather jacket, and you’ll be the talk of town.

Pair It With A Classic Mom Jean

The ’80s are back in a big way—and so is the mom jean. This vintage-inspired denim style is surprisingly flattering, thanks to the high waist and relaxed silhouette.

To make this throwback look feel fresh, pair your mom jeans with booties that have some modern details. We love the idea of pairing heel booties with an unexpected print, like this taupe snakeskin pair from Frye. Just look for a pair with a straight leg or slightly flared silhouette (no saggy bottoms, please).

Keep It Cozy In Boyfriend Jeans

Oversized, relaxed, and comfortable—what’s not to love about boyfriend jeans? This slouchy style looks great with chunky combat boots, and there is no better brand than a pair of Stuart Weitzman. But I get that they’re not for everyone.

For an elevated take on this outfit combination, try a pair of ankle boots with some unique details and a block heel. These cream-colored fabric booties also from Stuart Weitzman have just the right amount of personality.

Outfits To Wear With Ankle Boots Over 40

While I love a good denim moment, there are more options for styling booties than just jeans. If you want to shake things up, try one of these other unexpected bootie pairing and outfit ideas.

For Running Errands: Leggings

Leggings are the gold standard of comfort—and they can look chic when styled correctly. To make this outfit work for running errands or casual Fridays at the office, just pair your favorite booties with an oversized sweatshirt or duster coat. Make sure your leggings are long enough to tuck into your booties, and you’re good to go!

For Networking Events: Dresses

I know it feels totally weird to wear ankle boots with something short, but trust me on this one. Booties with dresses can actually look quite stylish—especially if you play with proportion a bit.

Try pairing a pointy bootie with an above-the-knee dress or skirt. The extra leg coverage will help balance the shorter hemline, and you can always add tights if you’re feeling a little exposed. Your dress is the true star of the show here, so a classic pair of black booties like these from Phillip Lim will do the trick.

For Hitting The Town: Jumpsuits

Whether you’re going out for drinks with friends or heading to a fancy dinner party, a jumpsuit is comfortable, flattering, and easy to wear—plus, it looks like you put in way more effort than you actually did. Just make sure the silhouette of your jumpsuit is slim and tailored. You don’t want anything too baggy or boxy.

A pair of stylish booties only elevates the look. These leather-heeled booties from Cole Haan are the perfect finishing touch.

A flowy skirt is paired with heeled, black ankle boots for a date night outfit.

For Date Night: Skirts

Is there anything more fun and unexpected than booties with a mini skirt? This styling trick is an easy way to add a touch of edge to any outfit. Just make sure your skirt is on the shorter side, like a mini to a midi length. Maxi skirts will make your booties look a little out of place.

And if you’re looking for a bootie with some personality, check out these sleek leather booties from FARYL. They’ll add just the right amount of flirtatious attitude to your outfit.

For A Board Meeting: Trousers

Keep it polished and professional while you’re running that board meeting or nailing that client presentation with sleek and simple black leather booties. A low, chunky heel will keep the blisters and achy feet at bay while you’re hustling around town.

These leather ankle boots with a rounded toe from Phillip Lim will look great with a pair of tailored trousers or trendy wide-leg pants and a turtleneck. And the camel color will match just about everything in your closet.

For Your Day Off: Shorts

Yes, booties with shorts can work! Just make sure you keep them loose. Both your shorts and your boots. Go for a slouchy pair, or a pair with cutouts like these from Sorel to balance out the denim perfectly.

Not feeling the denim shorts? No problem! Khaki, black, or even a fun patterned pair will work just as well. Just try to keep the heel of your boots smaller if you’re trying to achieve a casual look. High heels will dress up your look, even if you’re wearing a t-shirt.

These Boots Were Made For… Everything!

Now that you have some styling tips for wearing ankle boots over 40, it’s time to get out there and put your new skills to the test. Just remember to have fun with it and experiment with different styles until you find what works best for you.

So go ahead and give them a try! You might be surprised at how much you love the way they look.

Need more fashion over 40 tips? We’ve got you covered! Browse the latest in fashion from Finer Things.

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