The Best Chunky Boots to Wear All Winter Long

Is there any trend from the '90s that hasn't been revived at this point? Barely-there slip dresses, completely see-through sheer tops, and the oh so controversial low-rise pants are all trending. But it's the chunky boot, the preferred shoe staple of the time, that is having a particularly major moment. It's been on every runway from Prada to Rick Owens. It's been on the feet of trend-setters like Bella Hadid. And it's, no doubt, all over your TikTok FYP and Instagram feed. But unlike other trendy pieces from the early aughts, it'll actually stand the test of time thanks to its versatility. You can wear the best chunky boots with ultra-trendy trends like the mini-est of mini skirts, and trusted wardrobe essentials like a classic pair of straight-leg jeans.

“Chunky boots are definitely a winter wardrobe essential,” says NYC-based stylist Seppe Tirabassi. “They can withstand the elements while allowing you to remain fashion forward and cool with an attitude." Tirabassi also notes that the chunky sole gives a nice boost in height that isn't as hard to balance in as a stiletto heel.

As for his go-to pairs, he calls out brands like Ganni, Loeffler Randall, and 3.1 Phillip Lim, all of which have modern takes on the tall combat boot. “We’re also seeing minimal styles with a top zipper from brands like The Row and Proenza Schouler. Isabel Marant gives us a great classic combat with its own spin on the ankle strap. Brunello Cucinelli's embellished boots make for a fun addition [to any wardrobe]. Other brands are playing with proportion and using materials other than classic leather like nylon and rubber,” he says.

At a loss on how to style them? Don't fret! NYC-based stylist Calvy Click suggests working with your existing winter wardrobe: “A quilted style that has more refined hardware can dress up a more casual wardrobe, while a broken-in Dr. Martens [boot] can add a cool factor to buttoned-up coats, floral prints, or floaty layers.”

Clearly, there's endless possibilities for dressing a chunky boot up or down, although one thing is certain: most pairs almost never come with an invitation to hike. With sky-high platforms, delicate lace-up shafts, and funky wedges, chunky boots are truly made for being seen in—especially our 26 favorite below.