by all it fall, call it winter, true fashion lovers know there’s one true name for the chilly months of the year: boot season. And while we could wax poetic about the many styles of boot that we’re stocking our closets with this season, there’s no denying that one particular silhouette that stands out about the rest year after year-the knee high boot.
From traditional riding boots to sleek heeled versions to pair with your sweater dresses, the knee high boot is a must for stylish cold weather wear. Here, we’ve rounded up some of the irresistible versions of the look we’ve got our eye on this year. Add them to your cart ASAP to make the most of the most wonderful time of the year AKA boot season.
Loeffler Randall Indy Tall Boot
“If there’s only one pair of boots to expand the possibilities in your wardrobe, it’s the Indy,” says T&C Deputy Digital Lifestyle Director Roxanne Adamiyatt. She favors this easy, pull-on style for its versatility, explaining, “Worn with a day dress these pull a look into an elevated space, but worn with something a bit more frilly, they keep the look grounded and polished, without feeling like they can’t transition from day to night even though the heel is modest.”
Gucci Boot with Slim Horsebit
Everybody loves a classic neutral boot, but sometimes you just want something a little extra. Enter: These cherry red, block-heeled, knee high boots featuring Gucci’s signature horsebit detailing—the perfect statement boot for winter.
Stuart Weitzman 5050 Gisele Knee High Boot
A slightly shorter version of Stuart Weitzman’s iconic 5050 boots, these knee high options bring both comfort and style with a subtle 1 inch heel that gives just a hint of lift for all-day walking, as well as a leather front and elasticized back panel to offer a custom fit.
Penelope Chilvers Tassel Knee High Boot
Need some royal style? This pair, with its tasseled zipper and scalloped detail, is a favorite for Kate Middleton; so much so that she’s been sporting them for over two decades.
STAUD Wally Boots
These bestsellers by Staud are destined to be a regular part of your boot rotation. With a wide, slim kitten heel and pull-on styling that’s neither kitten nor slouchy, they are a trend-defying silhouette you’ll return to not only day after day but season after season.
Aquatalia Ricarda Weatherproof Knee High Boot
Of course you want your feet to stay dry in even the wettest weather, but you also don’t want to tromp around the office in rain boots all day. Luckily, Aquatalia has made a name for themselves with weatherproof leather boots that look as good on sunny days as they do when the storms roll in.
Sarah Flint Perfect Riding Boot 30
These boots have achieved “most worn pair of shoes” for Adamiyatt, who adds, “They just look good with everything.” Given that they come from Sarah Flint, who also makes one of Meghan Markle’s favorite pairs of heels, that style star status isn’t entirely shocking.
Sam Edelman Wyatt Knee Boot
For a subtler take on the Western trend, these soft, vegan suede boots bring some classic cowboy boot details while still maintaining enough minimalism to be wearable with any style profile.
La Canadienne Boden City Dry Knee High Boot
Cold weather can be unpredictable—and, more often than not, wet. Hedge your bets with these waterproof boots, which feature a sturdy lug sole and 2 inch heel; ideal for battling snow and slush while staying stylish.
Schutz Maryana Up Slouch Boots
Slouchy boots are making a comeback and these supple versions by Schutz are a perfect way to dip your toe into the look. With a suede upper and 3.25 inch stiletto heel, they add rich texture that instantly upgrades your basic outfits.
Frye Campus 14L Boot
Seeking something a little more rugged? Balance out femme dresses or lean into the rustic aesthetic with Frye’s classic pull-on style. As an added bonus, the brand has updated the sizing with new wide calf options so those with athletic gams can get in on the game too.
