The 10 Coolest Boots for Fall, According to a Stylist

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As your flip-flops, Birks, and Tevas begin to collect dust in dark corners of the closet, it’s time for your boots to step into the winter sun. And rain. And snow. But let’s not get ahead of ourselves—we’re still in that autumnal sweet spot when leaves blanket the sidewalk and the brisk air smells of spice and sap.

Before worrying about footwear that’s weatherproof and insulated against the elements, how about you take a new pair of polished Chelseas for a ride? Or keep it casual and office-ready with a suede chukka? And by the time the first flurries hit the ground, you’ll want to keep the stylish kick going with a rugged but presentable (never clunky!) snow boot.

We tapped NYC-based fashion stylist Seppe Tirabassi to curate a solid list of fall and winter boots that’ll satisfy your needs until the clock springs forward. And being a Maine native, he knows a thing or two about keeping the ankles covered most of the year. “At the end of the day, you definitely want a boot that’s going to last several years, maybe even a decade,” Tirabassi says. “But comfort and quality should always be paramount.”

Here are 10 handpicked boots across a range of styles and budgets for fall and winter.