We’d be willing to bet that if there’s one style of shoe you slip on from late-August through mid-April, it’s a pair of ankle boots. This makes sense: Ankle boots are flattering on the leg, look as good with a dress as they do with jeans, and if you land on the right pair, are just about as comfortable as a pair of everyday walking shoes can get. But, like all wardrobe staples — whether it’s a white button-down or the perfectly vintage-inspired pair of blue jeans — there’s a vast sea of ankle boots to pick through before landing on the ideal pair. To get a lay of the land, we reached out to 23 cool and stylish women, from the coach of Downtown Girls Basketball League to the founder of a luxury sock company, to hear about their favorite-looking pairs that have also stood the test of, well, standing — and plenty of walking, whether through slush in the winter or on long treks in the spring.
Best under-$150 ankle boots for women
Writer and senior podcast producer at the Boston Globe Amy Pedulla told us she first bought Dolce Vita’s suede ankle boots when she was at college in upstate New York, and despite the “muddy” environment, the boots held up: “They are super durable, and I found that the heel lasted for over two years without much wear and tear,” she says. Pedulla first spotted the Dolce Vitas at Marshalls in 2010, where they caught her eye because “they looked kinda like Isabel Marant,” but at a much lower price. A decade later, Pedulla still loves Dolce Vita’s suede ankle boots, and says she recently bought a new pair in an apricot shade. And despite the reasonable price, the quality is high. “The suede doesn’t fade much, and the heel is low enough that you can get away with them for everyday wear and long walks.”
“ASOS, for whatever reason, makes the perfect ankle boots,” says Charlotte Palermino, co-founder of Nice Paper. Palermino told us she owns “just about every pair” of shoes from ASOS’s Western series, and that when she wears boots from the collection she gets “accosted every time I go out in public.” Her favorite pair is currently sold out, but this constrast-stitched, hardware-adorned pair is similar. Palermino’s boots are often mistaken for Balenciaga, she says (though if you do want to splurge for the real deal, designer Melody Ehsani named Balenciaga’s Ceinture Derby as her favorite ankle boots) and have held up well. In sum, Palermino says, “These have been hands-down my favorite shoe of the blessedly mild winter season, and will transition into spring/the grave for me.”
“I tried on a ton of ankle boots last winter, including the Rachel Comey Mars booties that I really had my heart set on, and I just didn’t love any of them,” says Strategist senior writer Karen Iorio Adelson. “Either they weren’t comfortable to walk in or they just hit my ankle at a weird spot.” But then, on a whim, Adelson ordered the Vionics — and they were the one. “They are great — they’re supercomfortable, they look sleek, and the leather is water-resistant, so you can wear them in the rain and snow,” says Adelson. “They’re affordable, too.”