The 5 Winter Boots We Swear by

I’m not gonna lie: maybe it’s because 2021 hasn’t exactly been the drama-free year that I had hoped (yet!), but I have been majorly binging on Friends lately, simply to retain my sanity. And that first season, when Rachel says: "'I don't need a job, I don't need my parents, I've got great boots' boots”??? Even though I’ve got a job and haven’t relied financially on my parents in over a decade, I felt that


There IS something about great boots that can turn your frown upside down. So, in honor of winter (and Ms. Rachel Green), we’ve rounded up the best winter boots out there—all beloved by SwearBy’s decidedly well-heeled curators. 

Hunter Original Refined Waterproof Rain Boot

If Rachel ever swapped her heels for wellies, she’d *definitely* go for Hunters—the brand much of the British royal family Swears by. These are literally fit for a queen: Queen Elizabeth II, to be exact. “I’m from New England where the weather is highly unpredictable and there’s a good chance it could rain at any moment,” says Stephanie Perry. “I love these Hunter boots (which I’ve owned for over ten years) because they’re lightweight enough for a warm spring shower, but they’re also durable enough for a winter blizzard. Plus, they look cute with jeans, leggings, or even dresses.” She recommends adding the perfectly-fitting Hunter Boot Socks for added warmth on life’s inevitable frigid days. 

Everlane The Boss Boot

You’ve heard of a LBD, but these are my LBB (little black boots),” says Stephanie Perry. “They’re my go-to throughout the fall and winter months and look great paired with jeans, leather leggings, dresses, skirts, and more. Plus, the heel height is manageable enough for walking around the city all day.” We love that they’re made of super-supple, 100% Italian leather. Did we mention that, as of press time, they were on major sale? Run, don’t walk, to Everlane dot com for your pair.

Summit Herringbone

Claudia Tang gets major points for inventively testing her winter boots: “I compared these to lots of other boot brands by filling a bucket in my bathtub with water and stepping in,” she says. “This was the brand that didn’t leak.” Bogs Summit, which she purchased while living in snowy Montana, won by a landslide. “I have a different color of these Summit boots and I really do ‘swear by’ them…They are soft and lightweight and have held up great for four years so far. The bottoms are flexible instead of with heavy lugs for traction.” Plus, they’re rated to 14 degrees—and machine washable. 

Women's L.L.Bean Boots, 8" Thinsulate

There’s a reason these are classics: they WORK. L.L. Bean’s boots have been handmade in Maine (and keeping generations of people warm and dry in inclimate weather) since 1912. “These are my winter boots that I live in,” says Boston-based Chelsea Bates. “They are comfortable, cozy, waterproof, and they may not look like much in the picture but pair these with cute leggings and it’s actually a super cute outfit.” Kylie DeLaO loves them, too. “My feet stay warm and dry in them. I think these are a must, especially if you live in a colder climate.” Bonus: they’re made of premium full-grain leather and lined with super-cozy Thinsulate. 

Red Wing Shoes Harriet Boot

My husband and I once rolled past Red Wing, Minnesota on Amtrak, and let me tell ya, “idyllic” doesn’t begin to describe this town (population: 16,338) where Red Wing boots have been made since 1926. “These were a little bit of a splurge, but totally worth it,” says Caitlin Kimmet. “I was looking for a nice pair of leather boots that would be lifetime-boots. I’ve been steering away from fast fashion and really angling for more sustainable, long-term purchases. These were not cheap, but they are the highest of quality. They’re still handmade in the US, and both look beautiful and feel beautiful. They took a little breaking in, but are now my ideal shoes.” Plus, the Vibram outsole means they’ll work wonderfully in all seasons. Bring on that Minnesota snow!

Hi! [Insert waving blonde emoji here] I'm a Colorado-based freelance writer, and I'm Niles Crane-level picky about everyyyyything.