These Classic Knee-High Boots Will Elevate Your Winter Wardrobe
Whether anchored in stilettos or grounded with lug soles, there's a style for everyone.
I have, let's say, an extensive lineup of boots—so vast that both of my parents told me off for bringing home more boots when I was in college. But now that I'm an adult, I need to take stock of everything I own and assess any gaps in my assortment. And if there's one boot trend that I must pick up this season, it's a pair of classic knee-high boots.
Luckily for me (and unfortunately for my bank account), this lengthy style appeared everywhere across recent runway collections. Designers like Isabel Marant and Christian Dior sent playful slouchy versions down their catwalks. Meanwhile, other labels such as Hermès and Gabriela Hearst showcased utilitarian stompers, like English country style riding boots and Western-inspired cowboy boots.
During the Fall 2024 fashion week circuit Isabel Marant championed slouchy knee-high styles. Months later, across the Spring 2025 runways, Hermès and Gabriela Hearst revealed knee-skimming silhouettes in the form of riding boots and cowboy boots.
With an abundance of footwear inspiration, I decided to craft a list of all the knee-high boots that are going straight on my shopping list. Given that this cold-weather shoe style is one of the building blocks of my winter capsule wardrobe, the list ahead is quite extensive.
Shop the Best Knee-High Boots
If you dress in all neutrals and are looking for accessories to boost the color of your wardrobe, Staud's Wally boots are for you. This cult-favorite pair of boots is the ideal wear-everywhere option. The heel clocks in at just over two inches, and it comes in several colors, including this burgundy suede and an olive green, plus a classic black option.
If you're reading this between August and April, there's a 95 percent chance I'm wearing a pair of boots from La Canadienne. I have a version of this lug-soled pair that doesn't come with shearling on the inside, and they are, hands down, the most comfortable pair of boots I own. These have lasted me through 18-hour days of running around during New York Fashion Week and show virtually zero signs of wear. The leather has never left a blister in the year I've had them. This shearling pair comes in two colors (brown and black) and I think I may need to splurge on them for even more comfort.
Taylor Swift recently wore this pair of knee-high boots from Larroude to a football game, but she's hardly the first A-lister to showcase them. Vanessa Hudgens, Alicia Keys, Olivia Munn, Selena Gomez, and more have all been spotted in these shoes over the years. Swift recently wore the black leather iteration—which is somehow still in stock on the brand's website.
Another Swift favorite is this pair of Loeffler Randall knee-high boots, which come in three neutral colors. Swift is partial to the dark brown shade (she's worn them a few times now while out and about), but they also come in black and a light tan colorway. The stacked heel measures 85mm high (three-and-a-half inches) and the shaft measures 16 and-and-a-half inches around with a pull-on style. The leather and rubberized footbed offers maximum comfort, too.
Meet the ideal riding boot from Reformation. Available in three colors and retailing for shy of $450, these are the timeless staple your wardrobe is missing—and you can shop them in sizes 5 through 11 now. I would go full boho and style these with knee-high socks peeking out from underneath.
These suede boots from Paris Texas are, in my opinion, the adult-ified way to master the Western boot trend. Plus, the small heel is ideal for all-day wear. I would personally tuck a pair of skinny or straight-leg jeans into these boots for a cool-girl look that doesn't appear too styled. Or, lean into the horse girl aesthetic and wear them with a prairie-inspired white skirt or a flouncy dress.
These boots from Jeffrey Campbell scream '70s fashion. The enlarged buckle detail and thick, sturdy heels are begging to be paired with a supremely cozy knit dress and tights. While I am partial to the red pair, they also come in a timeless black colorway. The soft leather looks like it will show signs of wear with time, which is truly one of my favorite things about it.
Follow Acne Studios' footsteps and pick up a pair of snake-print boots from brands like Schutz. This exact style has been an influencer favorite and comes in tons of colors and prints, some of which are currently on sale. The heel measures 3.5 inches, so it's a good option for those of us who are not constantly heel-wearers.
Not many things can be dubbed timeless, but I've wanted these boots for nearly a decade and a half. And, after all these years of pining and saving all my pennies, I might actually make the splurge this winter. They're made from buttery-soft leather panels for added comfort and have a low enough heel for long-haul wear. They fit close to the leg, making them perfect for wearing under almost anything. The silhouette is the epitome of trendless shopping, so it's no wonder they’ve been on my to-buy list for so long.
If you're over wearing the same black and brown boots, consider this olive green pair from Madewell. These shoes prioritize comfort with a tiny kitten heel and a cushioned padding around the sole. And because the shaft is crafted from sturdy materials, these boots will maintain their shape.
These under-$200 boots from J.Crew are the perfect medium between cowboy boots and regular riding boots. They have the pointed toe and stacked heel of a Western boot without the bells and whistles that they normally come adorned with. The only hint of drama comes from the topstitching at the sides, which is beyond charming.
I love French brand Sezane for their knitwear selection, but I've learned not to overlook their range of boots. The label's Theodora Boots are designed with soft cowhide leather that's extra sumptuous. Plus, they boast an inside zip fastening which makes slipping on these shoes extremely easy.
These boots are low-profile enough to wear daily thanks to the 30mm heel. Not to mention, they mold to the foot and leg and are made from a buttery soft leather material.
Ask any fashion girl, and you'll know that this pair of Ganni boots has been *the* knee-high boot of the last few seasons. Easy to style and comfortable to wear all day thanks to the rubberized lugged sole, this pair is the end-all-be-all if you want to incorporate rugged pieces into your wardrobe this winter. Plus, they work just as well when worn with white summer dresses.
Rain boots can be trendy! Hunter is known for their famous rubber knee-high boots, but this glossy take is a welcomed high-fashion twist on the style. They're lightweight and sturdy, just like the classic matte pair (I've had mine for nearly a decade without fail), but the updated finish on this pair also adds an easy-to-clean layer.
