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My Favorite Fall 2024 Footwear Styles for Women Over 50

Get a seasonal upgrade with boots, booties, kitten heels and loafers that are comfy and fashionable


spinner image Various shoes, heels and loafers for women
Photo Collage: AARP; (Source: Saks Fifth Avenue; The Gap; J.Crew (2); Target; Bloomingdale's)

After wearing flip-flops, sandals, espadrilles and slides all summer long, it’s kind of a relief to put on a structured shoe or boot. Arch support, ankle support, a solid or low heel go a long way when it comes to comfort ... and confidence.

My footwear choices have evolved since I retired. After teetering around on high heels for decades (when I worked as a fashion editor in NYC), I am firmly grounded. I still embrace a graceful, leg-elongating pointy-toe pump, but it will probably have a kitten heel instead of a stiletto. I love a little bit of added height — again, to lengthen my silhouette — but my boot will likely have a sturdy block heel. A badass ankle bootie speaks of my self-assurance at this stage of my life. Comfy loafers nod to my newfound freedom to spend my days as I wish — sometimes loafing but often still running around. I have a lot on my schedule even if I no longer get a regular paycheck, and I need to be quick on my feet.

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Kitten heels

spinner image Jeffrey Campbell Women’s Persona Calf Hair Slingback Pumps in Cheetah
Jeffrey Campbell Women’s Persona Calf Hair Slingback Pumps in Cheetah
Photo Collage: AARP; (Source: Bloomingdale's)

Thank goodness, this ladylike style is popular again. When I have an occasion to get dressed up, my go-to heel height is 1 to 2 inches. Look for pumps with a pointy toe and deeply cut vamp (the top part of a shoe) for maximum leg lengthening, such as this one: Talbots Erica Kitten Heel Pumps — Suede in Black ($149, talbots.com). Sam Edelman Women’s Blanka Slingback Kitten-Heel Pumps in Black Suede ($140, macys.com) are a must.

Perhaps consider a pair close in color to your skin tone as an alternative, such as the Nine West Arlene Pointy Toe Pumps in Blush Leather ($71, ninewest.com). Choose a “nude” shade (close in color to your legs). They will make your legs look longer, and flesh tones go with almost anything. An animal pattern, such as Jeffrey Campbell Women’s Persona Calf Hair Slingback Pumps in Cheetah ($116, bloomingdales.com) is surprisingly versatile too.

Block-heel tall boots

spinner image Blondo Tessa Waterproof Knee High Boot in Black Cow Leather; DV Dolce Vita Women’s Finnegan Over-the-Knee Block Heel Boots
Blondo Tessa Waterproof Knee High Boot in Black Cow Leather (left); DV Dolce Vita Women’s Finnegan Over-the-Knee Block Heel Boots (right)
Photo Collage: AARP; (Source: Nordstrom; Macy's)

The best thing about tall boots? You don’t have to wear tights to stay warm especially if you choose a style such as DV Dolce Vita Women’s Finnegan Over-the-Knee Block Heel Boots in Mushroom ($99, macys.com). In leather or suede, a tall boot with a solid stacked heel such as the Vince Camuto Sangeti Boot in Black ($229, vincecamuto.com), the Nine West Barile Boots in Dark Brown ($142, ninewest.com) or the Blondo Tessa Waterproof Knee High Boot in Black Cow Leather ($220, nordstrom.com) will give you a nice long line as well as comfort and support. Wear them with knee-length or midi dresses and skirts or wide-leg trousers.

Chunky ankle boots

spinner image Women’s Kyrie Chunky Heel Ankle Sock Boot in Tan; Gap Vegan Leather Moto Boots in True Black
Women’s Kyrie Chunky Heel Ankle Sock Boot in Tan (left); Gap Vegan Leather Moto Boots in True Black (right)
Photo Collage: AARP; (Source: Target; The Gap)

Booties with lug soles, such as Women’s Kyrie Chunky Heel Ankle Sock Boot in Tan ($40, target.com) and the MIA Jonna Lug Sole Chelsea Boot in Black ($80, nordstrom.com), pack some serious punch. Bonus: Lug soles provide traction on slippery surfaces. A buckled motorcycle boot such as Gap Vegan Leather Moto Boots in True Black ($78, gap.com) or the Born Midway in Dark Castagno Distressed ($160, bornshoes.com) show that you’re still a rocker at heart. Both styles demand to be worn with jeans, cords or cargo pants and attitude.

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Penny loafers

spinner image Bernardo Tabitha Penny Loafers in Safari; J.Crew Winona Penny Loafer in Spazzolato Leather in Black; Eastland Patricia Women’s Penny Loafers in Camel
(Clockwise from top left) Bernardo Tabitha Penny Loafers in Safari; J.Crew Winona Penny Loafer in Spazzolato Leather in Black; Eastland Patricia Women’s Penny Loafers in Camel
Photo Collage: AARP; (Source: Saks Fifth Avenue; Kohl's; J.Crew)

What’s not to love about a loafer? Easy-on, easy-off, these menswear-inspired classics are having a moment. G.H. Bass introduced them to America in 1936, calling them “Weejuns” (a play on the shoe’s Norwegian origins), and it is still making them today. The brand even offers an updated style with a trendy lug sole, such as the Women’s Whitney Super Lug Weejuns Loafer in Wine ($185, ghbass.com).

The J.Crew Winona Penny Loafer in Spazzolato Leather in Black ($110, jcrew.com) and the Bernardo Tabitha Penny Loafers in Safari ($268, saks.com) have a preppy vibe that makes them a great accent to a blazer and jeans — or pullover and flannel trousers.

The Eastland Patricia Women’s Penny Loafers in Camel ($90, kohls.com) resemble a driving moccasin. Again, a great companion to jeans.

The penny loafer purportedly got its name way back when college students would pop a coin in the shoe’s slot in case they had to make a phone call. Doing that these days would definitely date you!

There are no hard and fast rules about dressing your age. It’s really a question of what you do, where you live and your personality. But when it comes to footwear, comfort and support become increasingly important factors in how you dress as you get older, so be ready to embrace new options.

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