Step Into Style with These 16 Outfits: How to Wear Ankle Boots Over 40

Ankle boots are a wardrobe basic that every woman should have in her closet no matter what her age. A good pair of ankle boots can be incredibly versatile, they add an extra boost of height without compromising comfort or style, and you can wear them for most occasions and across seasons. We’re sharing a roundup of 15 ways to style ankle boots for women over 40 (or any age!) below. Most of these looks are older, but you can take these outfit ideas and make them your own with pieces you already have in your closet!

How to Wear Ankle Boots Over 40

There are SO many different types of ankle boots out there…pointed-toe ankle boots, square-toe ankle boots, rounded-toe ankle boots, flat ankle boots, heeled ankle boots, Chelsea boots, stiletto boots, lug-sole boots, black ankle boots, brown ankle boots, white ankle boots…you get the point! The key is finding a pair of ankle boots you absolutely love that work seamlessly with the rest of the pieces in your closet. Bonus points if you can wear the same pair of ankle boots for every season!

For example, Erin’s ankle boots above are a gorgeous brown suede with a stiletto heel. Erin wears lots of neutrals so brown is ideal for her wardrobe, and she’s 5’4” so she prefers to wear heeled booties to add height. But if you’re a woman who mostly wears black, has young kids you’re chasing after, or can’t wear heels, a pair of black, flat ankle booties would be ideal for you. Let’s dive into some of the outfits you can create with your ankle booties…

#1) Ankle Boots with Baggy Jeans & Button-Down

In this first look, Erin’s wearing the brown suede ankle boots with a pair of baggy, super wide-leg jeans by Mother. You’ll see ankle boots styled with pretty much every jean style out there in the following outfits but wearing a pair of wide-leg jeans is a fail-safe way to style ankle boots. She completed the look with a classic white blouse by Frank & Eileen, and a brown waist belt to add some definition. You could wear this look on casual Friday at the office or to dinner or lunch.

#2) Ankle Boots with Cuffed Jeans & Printed Blouse

This is another fun ankle boot outfit that would be perfect for dinner, lunch, or brunch. Erin is wearing a pair of baggy cuffed jeans that shows off a pair of white ankle boots by Schutz. Erin loves these boots so much, she also bought them in black! On her top half, she’s wearing a beautiful printed blouse by Ulla Johnson and the same brown belt from the previous look. You could recreate this look with any booties, cuffed jeans, and printed blouse.

If you’re looking for more tips on wearing jeans and boots, make sure you check out this post next.

#3) Ankle Boots with All-White

Erin took the same white Schutz boots and created a gorgeous all-white look with a pair of cropped jeans by Mother and a white cable-knit sweater. If you don’t have white ankle boots, that’s okay! You can recreate the look with tan, black, beige, brown, or whatever color ankle boots you have in your closet. All you need is a pair of jeans or pants and a top in a similar color family to your boots.

#4) Ankle Boots with Flare Jeans & Sweater

In this look, Erin’s wearing the black version of the Schutz ankle booties she loves so much. But this time she styled them with a pair of flared jeans and an asymmetrical sweater. As you can see, wearing ankle booties is really SO easy when you’re wearing them with any pair of jeans! Complete your ankle boots and flared jeans outfit with your favorite sweater and you’re ready to go!

#5) Ankle Boots with Ripped Jeans & Sweater

This is another super easy look to throw together and a great example of how to wear your more tapered and slimmer-fit jeans with ankle boots. The easy answer? Don’t do any tucking or cuffing…just leave them alone! In this look, Erin’s wearing a pair of super ripped tapered jeans with a pair of brown suede western-inspired boots. To complete the look, she threw on an oversized sweater and voila… an easy ankle boots outfit!

#6) Ankle Boots with Straight-Leg Jeans & Blazer

This is one of our favorite outfits of Erin’s…EVER! She’s wearing a pair of classic straight-leg jeans with black stiletto ankle boots, a silky blouse, and a double-breasted blazer. This is something you could wear for casual Friday at the office or to dinner. It’s SO chic and sophisticated and an easy way to style your ankle boots.

#7) Ankle Boots with Tapered Jeans & Blouse

In this look, Erin’s wearing a pair of tapered jeans by Moussy Vintage with a pair of lug-sole ankle booties by Steve Madden. Erin bought these boots back in 2021 and purchases the new version that the brand puts out every year because they’re just that good! They’re versatile, comfortable, stylish, and aren’t too heavy. She’s worn these with everything from skirts and dresses to jeans and pants. Throw on your favorite blouse and you’re ready to go with a chic, edgy look.

#8) Ankle Boots with Skinny Jeans & Trench Coat

Don’t worry…this is the last jeans and ankle boots outfit on the list and then we’ll dive into some other more unique options. We wanted to show you what your ankle boots can look like styled with skinny jeans even though we’re seeing a movement away from skinny jeans. You can see that the length of the skinny jeans just perfectly hits where the ankle boot begins. But that’s not usually the case, and that’s where the issue of tucking, rolling, or cuffing your jeans can come into play. This post has a really helpful graphic to make it easier!

#9) Ankle Boots with Sweater Dress

If you’re looking for a way to wear your ankle boots NOT with jeans…consider sweater dresses! In this look, Erin’s wearing an Isabel Marant sweatshirt dress in a cool charcoal color. We love a mini dress with ankle boots and Erin played up the on-trend western vibe with a pair of Isabel Marant boots with a cool silver-toe detail. They have a low cone heel and a cool western look. You could wear any western-inspired ankle boots you already have or try edgy combat boots or lug-sole ankle boots too.

For more tips on how to wear a sweater dress with boots, check out this post next!

#10) Ankle Boots with Tights & Mini Dress

If you’re worried about being cold or showing too much skin, wear your mini-dress with a pair of tights. In this outfit, Erin’s wearing a pretty polka dot mini dress with patterned tights and a pair of pointed-toe ankle boots. She’s wearing a belt to add waist definition and a cool handbag to make the black and white pop. This look is really dressy, sexy, and a wonderful way to really dress up your ankle boots.

Find more ways to wear dresses with boots in this post.

#11) Ankle Boots with Leggings & Sweater

Another way to style your ankle boots is with a pair of leggings. Erin’s wearing a pair of faux leather leggings by Spanx, but you could wear any leggings you have in your closet. Throw on a sweater long enough to cover your bum, and you’re ready for a day of running errands or a quick coffee run. Erin’s wearing the same pair of Steve Madden lug-sole booties featured in a previous look.

#12) Ankle Boots with Leather Pants

This look is a great example of not compromising fashion and function. Erin’s wearing a pair of patent leather ankle boots by Aquatalia that have a low heel so they’re easy to walk in. Plus, they’re waterproof…making them seriously functional! She styled them with a pair of sexy black leather pants, a classic black top, and a tweed bomber jacket. You could make this look your own by wearing black jeans, a black top, and whatever your favorite piece of outerwear is at the moment.

#13) Ankle Boots with Jumpsuit

Does anyone remember this fun Paris Fashion Week look Erin put together? She’s wearing a pair of fun black and white ankle boots by Balmain that look so cool paired with anything. But Erin styled them with a silky black jumpsuit. The jumpsuit has a straight-leg silhouette so Erin tucked it into the boots to make a jogger-leg effect. She belted the waist for some definition and grabbed a go-to handbag. This look is so simple, but Erin’s few styling tweaks make a big difference. Wear this to an event, to dinner, or out with the girls.

#14) Ankle Boots with Midi Dress

In this look, Erin’s wearing a gorgeous blue and white midi dress styled with a pair of ivory, pointed-toe, wedge ankle boots by Paris Texas. If you’re headed to a wedding or event and want to wear something a little unexpected (or just don’t love traditional heels), this is a wonderful alternative!

#15) Ankle Boots with Midi Skirt & Blouse

Remember the Isabel Marant western-inspired boots from Look #9? Here they are styled with a cool ruched leather midi skirt and shimmery blouse. This is a dressier way to wear your ankle boots on a night out or to dinner. We love that you can really see the boots and that they have a moment to shine in this look.

#16) Ankle Boots with Printed Midi Skirt & Leather Jacket

If you liked the last look but want a skirt and ankle boots outfit that’s a little more casual, this is a great example. Style your ankle boots with your favorite midi skirt, a classic tee, and your favorite leather jacket. Erin’s wearing a pair of stiletto ankle boots but she could have easily swapped them for a pair of flat booties to make the look more casual.

Which of these ankle boot outfits are you going to try to recreate? Let us know in the comments below!

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