Expert Advice on Wearing Ankle Boots When You're Over 40

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Styling tips for ankle boots, plus cute outfit ideas

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IN THIS ARTICLE

1 Cuff your jeans to show off your boots.

2 Try some cropped pants with a nice blouse.

3 Spice up a sweater dress with combat boots.

4 Pair a patterned t-shirt dress with solid ankle boots.

5 Stay warm in a trench coat and chunky boots.

6 Wear wide-legged trousers and heeled boots to the office.

7 Pair pointed-toe ankle boots with wide-legged jeans.

8 Wear ankle boots with a blazer and mini skirt.

9 Try skinny jeans with fun, patterned ankle boots.

10 Rock jeans and a T-shirt for a timeless, casual look.

11 Wear ankle boots with tailored trousers and a cable-knit sweater.

12 Pair faux leather with ankle boots for an edgy look.

13 Show off your confidence with a body-con dress.

14 Wear ankle boots with a wrap dress in warm weather.

15 Rock a bomber jacket and graphic tee for a youthful look.

16 Keep it simple with a fashionable jumpsuit.

17 Go for a boho look with bell bottoms.

18 Pair your boots with a floral dress and denim jacket.

19 Look classy with a slitted maxi skirt and a turtle neck.

20 Turn heads with bright boots and a monochrome outfit.

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Co-authored by Candace Hanna and Raven Minyard, BA

Last Updated: April 18, 2025 Fact Checked

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Who said you can’t rock ankle boots after you turn 40? You don’t have to sacrifice your style because of your age—if anything, you’ve just had more years to perfect your look! If you want to know how to wear ankle boots over 40, look no further. We’ve gathered the best outfits to wear with ankle boots so you feel comfortable, confident, and stylish. Plus, we talked to fashion experts Candace Hanna and Joanne Gruber for all the best styling tips.

Styling Tips for Ankle Boots

• Pair ankle boots with tailored trousers and a nice blazer or sweater for a professional look.
• For a casual look, rock ankle boots with a tee and your favorite jeans.
• Or, dress up your ankle boots with a nice wrap dress or a slitted maxi skirt.

Steps

1

Cuff your jeans to show off your boots.

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1. 
   This classic look highlights your ankle boots. Unless your jeans are super skinny, the fabric can bunch up and look bulky. So, cuff your jeans just above your boots to show them off. This look pairs nicely with a light sweater or a soft T-shirt. Throw on a scarf or a wide-brimmed hat to accessorize.

   • If you do wear skinny jeans with your ankle boots, tucking them into your boots can actually make you appear taller.
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2

Try some cropped pants with a nice blouse.

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1. 
   Cropped pants show off your favorite booties. You’re sure to get compliments on your boots when everyone can see them! This look is versatile and can be dressed up to look more professional or dressed down for a day of running errands. Try a silk blouse with some dark, cropped dress pants, or go for a casual button-up with some cropped jeans.

3

Spice up a sweater dress with combat boots.

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1. 
   Use opposite aesthetics to create a dynamic outfit. Sweater dresses are soft and feminine while combat boots are edgy and more androgynous. Wearing combat boots automatically accessorizes your outfit and creates a unique, edgy ensemble.

   • Play up the shape of your sweater dress by adding a stylish belt.
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4

Pair a patterned t-shirt dress with solid ankle boots.

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1. 
   Use ankle boots to add flair to a casual outfit. A T-shirt dress is a comfortable, cute wardrobe staple and the key to styling a T-shirt dress is adding accessories. Try some heeled ankle boots for a feminine touch or opt for flat ankle boots (like Doc Martens) to add a bit of attitude. Finish off your look with a few cute pieces of jewelry, like a necklace and bracelet. Add a fashionable belt to show off your shape and personal style.

   • When wearing ankle boots with a dress, choosing a boot with a heel can make your legs appear longer!

5

Stay warm in a trench coat and chunky boots.

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1. 
   Beat the cold-weather blues with a jacket and boots. Choose a bright-colored trench to add pizzazz to your look and stand out in a crowd. Pair it with your favorite jeans and chunky ankle boots for a cozy, stylish outfit.
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6

Wear wide-legged trousers and heeled boots to the office.

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1. 
   Ankle boots are a great option for work. Opt for heeled ankle boots to elongate your figure and add shape to your outfits. Pair them with some wide-legged trousers and a tailored blazer or a nice sweater, and you’ll be the office fashionista!

7

Pair pointed-toe ankle boots with wide-legged jeans.

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1. 
   Show off the toe of your boot when the rest is hidden. When you can’t see the whole boot, it’s important to create shape with the toe. A square toe might get overshadowed by the wide leg of your jeans, but a pointed toe lengthens the leg line and adds some extra style to your look.

   • Rock a graphic tee for casual outings or go with a button-up blouse for a more professional look.
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8

Wear ankle boots with a blazer and mini skirt.

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1. 
   Show off your legs while keeping it classy with this 'fit. Blazers have made a comeback in both professional and streetwear. If you want to stay on top of the trends, pair one with a tailored mini skirt and rock some black ankle boots. Be sure to leave the blazer open to show off the rest of your outfit and create movement.

   • Add some tights or leggings if you’d prefer to have a bit more coverage for your legs.
   • If you don’t care about trends, that’s okay, too! Fashion expert Candace Hanna says, “Your style is about you, and fashion is about the world. Focus on style, your preferences, what you love, and what you hate. Even if fashion tells you ‘This is what is in right now,’ you can bypass it.”

9

Try skinny jeans with fun, patterned ankle boots.

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1. 
   Let your boots be the star of the show with this look. Ankle boots come in all sorts of fun patterns, including animal print, snake skin, and floral. Having a good statement piece is essential, so why can’t it be your shoes? Pair some fun ankle boots with a pair of plain denim skinny jeans and a solid-colored shirt or blouse.

   • Fashion expert Joanne Gruber says a classic skinny jean with a full, standard-size inseam is best to pair with ankle boots. “You typically want it to be tucked in,” she says, “so you see the silhouette of the shoe.”
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10

Rock jeans and a T-shirt for a timeless, casual look.

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1. 
   Pair your favorite style of ankle boot with this outfit. There’s no wrong way to style it. Try combat boots, westerns, Chelseas, heels, or any other style you have in your closet. Play around with the jeans, too, and see if you prefer skinny, bootcut, or wide-legged. Rock a graphic tee or keep it simple with a solid color.

   • Because this outfit is basic, play up the accessories. Add a funky jacket or a nice cardigan, and layer on some necklaces or bracelets. Add statement earrings or a cute bag to finish off your look.

11

Wear ankle boots with tailored trousers and a cable-knit sweater.

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1. 
   Choose this look for a perfect fall weekend. You can be casual and still look tailored and classy. Dress down some fitted trousers by pairing them with a soft sweater and your favorite booties. For an autumnal look, opt for some plaid trousers, a cream sweater, and brown or tan ankle boots.
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12

Pair faux leather with ankle boots for an edgy look.

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1. 
   Wear faux leather to add texture to your outfit. While you can opt for faux leather ankle boots, you can also pair some black booties with a faux leather skirt, jacket, or even pants. Dress the look down with a T-shirt, or dress it up with a patterned blouse.

13

Show off your confidence with a body-con dress.

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1. 
   Ankle boots are the perfect shoe for this form-fitted option. If you’ve got it, flaunt it! Pair a mid-length black body-con dress with a leather jacket and some heeled ankle boots, and you’re sure to turn heads. Add a sleek pair of sunglasses to really feel like a fashionista.

   • Fashion expert Joanne Gruber stresses how important it is to feel confident in what you’re wearing. “Your look comes from the inside out,” she says. You’ll look your best when “you’re wearing it confidently and you feel great in it.”
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14

Wear ankle boots with a wrap dress in warm weather.

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1. 
   Ankle boots are a staple you can rock all year long. There are plenty of fashionable ways to rock ankle boots in the heat. Not only are wrap dresses cute, but their breezy fabric helps you stay cool. Opt for a patterned or light-colored dress and pair it with a pair of brown or tan booties for a perfect summer look.

15

Rock a bomber jacket and graphic tee for a youthful look.

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1. 
   Let your spunky personality shine through. Graphic tees are a cute and comfy way to show off your interests, like your favorite band, and a bomber jacket can give your outfit a little edge. Play up the rocker look with some ankle-length combat boots or choose an ankle boot with a bit of a heel to add a feminine touch.
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16

Keep it simple with a fashionable jumpsuit.

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1. 
   Adding ankle boots can make any outfit look trendy. Jumpsuits are a great option for when you don’t feel like trying to match a top and a bottom; throw one on and you automatically look put together. Ankle boots work well for any jumpsuit silhouette, but if you’re hoping to show off your boots, opt for a cropped jumpsuit.

   • If your jumpsuit has a bold pattern, choose a simple black or brown boot to avoid clashing.

17

Go for a boho look with bell bottoms.

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1. 
   If you’re a free spirit, rock some ankle-length western boots. Pair them with denim bell bottoms and a fringe vest to fully embrace your style. Earthy tones generally look best with outfits like this, so opt for tans and browns, and throw on a turquoise necklace for a pop of color.
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18

Pair your boots with a floral dress and denim jacket.

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1. 
   Choose this outfit for a casual, feminine look. If you’re looking for a way to wear ankle boots in the spring, this look is perfect for you. Don a mini or midi floral dress, especially with pastel colors like pink and purple. Add a light denim jacket or some tights or leggings for those chilly evenings, and you’re good to go. Any style of ankle boots works well for this look, from flats to heels.

19

Look classy with a slitted maxi skirt and a turtle neck.

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1. 
   Make the look more dynamic with stiletto ankle boots. The slit in the skirt (especially if it’s a slip skirt) paired with the heel of the boots creates a sexy, elegant ensemble perfect for a night out on the town. If heels aren’t your thing, dress the look down with some faux leather or suede flat ankle boots for a more cozy daytime look.

   • If you’re tall, you can still rock heels. Fashion expert Candace Hanna says heels help create a more feminine silhouette regardless of height. “I think for taller women, maybe go for a lower heel,” she says. “It’s not about height; it’s about that silhouette. It doesn’t have to be a huge 4-inch stiletto. It can just be a small heel to create that angle.”
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20

Turn heads with bright boots and a monochrome outfit.

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1. 
   Don’t be afraid to add a splash of color to your look. Monochrome outfits can give you a sleek, stylish vibe, but sometimes they make you blend in when you want to stand out. If you’re wearing all black, try mixing it up with a pair of bright red booties. This is also a great way to add some color to your world when it’s gray and dreary outside, like in winter.

   • If you’re looking for other ways to style your favorite ankle boots in the winter, try adding a trench coat, some gloves, and even a beret.
   • Fashion expert Candace Hanna stresses the importance of accessorizing during winter: “Accessories are a really easy way to have fun in the winter especially because, if you're in a full-length coat—which a lot of people are—you’re going to need accessories.” She recommends wearing a scarf for some extra color and a stylish hat.

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• Don’t let anyone tell you that you can’t wear something just because you’re a certain age. Wear whatever makes you feel confident and comfortable.
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