This article was co-authored by Candace Hanna
and by wikiHow staff writer, Raven Minyard, BA
. Candace Hanna is a stylist and style expert based in Southern California. With 16 years of experience in the corporate fashion and personal styling realms, she runs Style by Candace, a personal styling agency that focuses on helping individuals find their personal expression through clothing. Her work has been featured in magazines such as Shoutout LA and VoyageLA.
There are 15 references
cited in this article, which can be found at the bottom of the page.
This article has been fact-checked, ensuring the accuracy of any cited facts and confirming the authority of its sources.
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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
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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. [1] X Research source
- 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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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. [2] X Research source
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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. [3] X Research source
- Play up the shape of your sweater dress by adding a stylish belt.
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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. [4] X Research source
- When wearing ankle boots with a dress , choosing a boot with a heel can make your legs appear longer!
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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. [5] X Research source
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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! [6] X Research source
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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. [7] X Research source
- Rock a graphic tee for casual outings or go with a button-up blouse for a more professional look.
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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. [8] X Research source
- 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.”
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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. [9] X Research source
- 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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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. [10] X Research source
- 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.
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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. [11] X Research source
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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. [12] X Research source
- 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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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. [13] X Research source
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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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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. [14] X Research source
- If your jumpsuit has a bold pattern, choose a simple black or brown boot to avoid clashing.
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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. [15] X Research source
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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. [16] X Research source
- 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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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.
Expert Q&A
Video
Tips
- 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.Thanks
Other wikiHows
Expert Interview
Thanks for reading our article! If you’d like to learn more about fashion and personal style, check out our in-depth interview with Candace Hanna .
References
- ↑ https://www.nikiwhittle.com/2016/10/12-ways-to-wear-ankle-boots.html
- ↑ https://www.jessannkirby.com/how-to-style-cropped-pants-in-winter/
- ↑ https://www.froplusfashion.com/sweater-dress-combat-boots-winter-outfit-idea/
- ↑ https://hellogiggles.com/how-to-wear-ankle-boots/
- ↑ https://youtu.be/1xUrepJNaSM?t=89
- ↑ https://www.marieclaire.com/fashion/how-to-wear-ankle-boots/
- ↑ https://youlookfab.com/2018/08/08/the-pros-and-cons-of-pointy-toe-footwear/
- ↑ https://brunettefromwallstreet.com/blazer-mini-skirt-booties/
- ↑ https://hellogiggles.com/how-to-wear-ankle-boots/
- ↑ https://youtu.be/1xUrepJNaSM?t=53
- ↑ https://thefoxandshe.com/how-to-style-ankle-boots/
- ↑ https://www.sistersletter.com/style/got-curves-how-to-wear-bodycon-after-40
- ↑ https://www.silkfred.com/blog/how-to-style/3-dresses-made-ankle-boots/
- ↑ https://www.stitchfix.com/women/blog/fashion-tips/what-shoes-to-wear-with-jumpsuits/
- ↑ https://youtu.be/7Oh6LItgg_k?t=326
- ↑ https://www.harpersbazaar.com/fashion/trends/g7958/how-to-wear-ankle-boots/?slide=11
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Anonymous
May 8
"As a soon-to-be 42 yrs and busy Mom of one, I am trying to work in two pairs of ankle boots into my wardrobe. This article helped me see how to style them in many different ways. Now I am looking forward to buying more ankle boots!" ..." more
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