5 Tips for Wearing Boots Over 65, According to Style Experts


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 65. Read on to start your most stylish decade yet.

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Try a trusty ankle boot.
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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 65," 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." You could also pair the style with a long skirt or dress.

Or a knee-high boot.
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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 65, 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.

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Consider a heel for date night.

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.

Go conservative for the office.

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." Most boots can be teamed with everything from trousers and denim to skirts and dresses.

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Try something trendy on your day off.
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Just because you're getting older doesn't mean you can't experiment with trends. For women over 65, 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. Each style is playful, interesting, and unexpected in the best way.