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7 Tips for Wearing Boots Over 60, According to Style Experts

You can style them for everything from the office to date night.

In the summer, getting dressed is easy. You throw on shorts and sneakers or a dress and sandals, and you're ready to leave the house. But in fall and winter, things get challenging. Layering comes into the mix, leaving us to wonder what pairs best with what and how to accessorize our outfits in the most stylish way possible. Our biggest dilemma? Boots. But fear not. Here, we spoke to personal stylists to learn all the tips for wearing boots after the age of 60. Read on to start your most stylish decade yet.

RELATED: 9 Coat Styling Tips If You're Over 60.

Try a trusty ankle boot.

Close up of a woman's legs walking along the street in black python ankle boots.
fortton / iStock

It wouldn't surprise us if an ankle boot was the most-worn shoe in your closet right now.

"Known for versatility, ankle boots are a wardrobe workhorse for most women from fall to spring, especially women of 60," says Elizabeth Kosich, personal stylist at Elizabeth Kosich Styling.

"Pair with a bootleg cut pant and cropped jacket for a classic look, or with leggings and a long blazer or sweater coat for a more casual, layered effect," she suggests. You could also pair the style with a long skirt or dress.

RELATED: 6 Tips for Wearing Boot-Cut Jeans Over 60, Stylists Say.

Or a knee-high boot.

Close up of a woman's legs wearing jeans and black knee-high boots with orange leaves on the ground.
Voyagerix / Shutterstock

Knee-high boots are having a moment in the trend cycle, but they're also totally classic.

"My favorite way to style knee-high boots for any age, but particularly for women over 60, is with an above-the-knee pencil skirt," says Holly Chayes, a personal style coach and consultant. "A couple of inches above the knee is enough, but it really depends on the person's comfort level."

With a pair of tights underneath, this look could take you anywhere from the office to the apple orchard.

RELATED: 6 Ways to Style a Belt If You're Over 60.

Consider a heel for date night.

Close up of a woman bending over to try on boots in a shoe store
miljko / iStock

Date night is your time to push boundaries and feel your best. So, opt for a heeled boot if you'd like.

"Anything goes for boot style—bootie, three-quarter height, or knee-high—as long as it's sky high," says Kosich. "Go for fun colors, metallics, embellishments, patent, or python since it's date night, and follow the lines of your body to pick your best style—pointy-toed if you're angular, round-toe if you're not; stiletto heel if you're slender, tall block heel if you're not."

Pair with flirty dresses and skirts to complete your look.

RELATED: 10 Tips for Getting Out of a Clothing Rut After 60, Stylists Say.

Give riding boots a try.

Woman Zipping up Riding Boots

"Classic riding boots are elegant, timeless, and stylish, proving they're worth the investment," says Kosich.

To really make them last, though, Kosich says to shop premium brands for matte-finished, high-quality leather that hides scuffs. Sensible and stylish boots like these are essential when it comes to winter wardrobes.

RELATED: 6 Jean Jacket Styling Tips If You're Over 60, According to Stylists.

Go conservative for the office.

older woman at the office reviewing document

For days at the office, you'll want to keep it conservative.

"Office-appropriate boots will depend a lot on your office environment, but a good rule of thumb is to stick with an understated ankle boot in a traditionally office-appropriate color," says Chayes. Black, tan, and charcoal always fit the bill.

"Start by pairing this with a work outfit you'd usually wear with a closed-toed shoe and adjust from there," she adds. Most boots can be teamed with everything from trousers and denim to skirts and dresses.

RELATED: The 6 Best Clothing Brands If You're Over 60, Stylists Say.

Try something trendy on your day off.

Female legs in black tights and black combat boots on a grey street background.
galyakiss / Shutterstock

Just because you're getting older doesn't mean you can't experiment with trends. For women over 60, Kosich suggests western and combat boots.

If you decide to give the Wild West a go, she recommends a cowboy boot with a knee-high shaft. If you'd prefer to style combat boots, pair them with dresses to make the outfit more casual and modern, Kosich says.

RELATED: 6 Winter Wardrobe Essentials You Need at Every Age.

Find styles that are lined.

An older woman standing in a shoe store and choosing new boots.
BearFotos / Shutterstock

Keeping your feet warm during the winter is incredibly important, which is why Kosich recommends looking for classic Chelsea or engineer-style boots with shearling, sherpa, or faux fur linings for a rugged-meets-luxury mashup.

Not only will your toes be toasty, but you'll also have a versatile pair of shoes that can be worn with just about any outfit.

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Courtney Shapiro
Courtney Shapiro is an Associate Editor at Best Life. Before joining the Best Life team, she had editorial internships with BizBash and Anton Media Group. Read more
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