11 Winter 2023 Boot Trends That Walk the Walk

The most covetable item of the season is a pair of sophisticated, versatile, and functional boots. Boots speak to the power of versatility: These styles work beautifully with—and elevate—tailored trousers, midi skirts, and sweater dresses, and, of course, a great pair of well-worn jeans. They work for every occasion, from early morning coffee meetings to attending holiday parties, with elegance and ease.

We’ve done deep dive investigations of the fall/winter runways and of notable street style trends that are soon to be everywhere to highlight the dominant looks of the season. Each of these styles is having a moment in the limelight—some are even subversive, but also classic enough to serve as a worthy investment and a go-to footwear option for years to come.

For extra warmth and a luxurious, discreet touch, wear your boots with a pair of classic cashmere socks or tights.

Ready to step brazenly into the hottest trends of the season? Here, eleven hyper-chic boot styles, with our product picks at every price point.

Sky High

Reach for the stars in a pair of attention-demanding, disco era-esque platform boots. Wear these with a skirt, tights, and a button-down or turtleneck and we can guarantee that all eyes will be on you. ‘Tis the season to stand a bit taller, and a pair of platform boots will inject your cold-weather outfits with a dose of fresh, punchy verve and girl power. It’s never too late to reach new heights, and we recommend doing so in one of these daring pairs.

Sock Market

Sexy, versatile, and very of the ‘90s, sock boots are tight-fitting, elongating, sleek, and sophisticated. They’re a great minimalist go-to boot for a date night, and their narrow silhouette is ideal for wearing with slim-fitting trousers or jeans. We obviously love boots, but at times, certain iterations can feel a bit bulky—especially when worn with layers upon layers of winter clothing. The sock boot is a perfect, delicate solution to this issue.

Color Me Mine

Fend off the winter woes and dreary, pale weather with bright, colorful boots. Pair with an all-black outfit for an incredible, artful ensemble, or invigorate your sweater and jeans uniform with a brush of rich pigment. Flashes of cherry red, bubblegum pink, mint green, and sky blue bring welcome gusts of warmth and brightness when sunlight and foliage are sparse. Pick your favorite flavor and run with it.

Rain or Shine

Rubber boots were born out of practicality: They deflect water, they’re easy to clean, and they’re simultaneously sturdy and flexible. The rubber boot is nothing new—the Wellington, as they’re commonly referred to, was invented in 1817 by the 1st Duke of Wellington, Arthur Wellesley, and it quickly became a staple shoe for the British aristocracy and middle class.

In more recent history, designers have elevated the rubber boot with design details, sophisticated silhouettes, and unexpected colorways. Whether you’re looking for a discreet, short boot in a neutral tone or a bright, knee-length option, the market is raining with incredible, stylish options. This season, the most on-trend iteration of the rubber boot is discreet, short in length, and neutral in tone.

These Boots Are Made For Walking

Flat boots will serve you well on the dance floor, at work, and on walks around the block. They’re balancing when worn with a more feminine silhouette, such as an A-line skirt, and they’ll make you look effortlessly put together when worn with jeans or trousers. The flat boot of the season is similar to an elf boot—in a great way, and they’re comfortable enough to let you prance around, creating magic. If you tend to live in ballet flats, this is a simple cool weather transition move. These boots may be flat in form, but they’re anything but anticlimactic.

Hello, Horses

Enter the grand stable of equestrian-inspired footwear, and you’ll find that both English riding boots and Western-inspired boots are having a moment. Both styles are timeless—riding boots are refined, preppy-in-a-good way, and can be worn with anything (they’re especially fantastic when worn with slim-fitting pants or a minimalist black or plaid mini skirt). Western boots are more playful and wild—and it’s relatively easy to find a hand-painted or custom pair.

Pointed Question

Sharpen your image with a pointed toe. Pointed-toe boots pay a nod to the beloved ‘90s minimalist style, and will make any outfit more chic and sultry—even daring. Sharp, bold pumps are a classic bombshell, powerhouse heel, and these boots evoke the same bite—but they’re designed to withstand the cool weather.

Wedged In

Take a bold stance in a sleek wedge boot. This minimalist style presents a number of contradictions: They’re dressy but not too formal; bold, but more reserved than a stiletto. They’re sophisticated, to be sure, but also subversive. They’re not obvious—and we welcome this during the winter, when our incredible outfits are often hidden beneath cocoon-like jackets. Practically speaking, they’re also an extremely comfortable alternative to a high heeled shoe or boot. They’re ideal for work and evenings out—slide them on with slacks or a sweater dress and a necklace, and you’ll look pulled together in mere minutes.

Buckled In

This season, the classic punk-inspired combat boot was upgraded, and laces became a thing of the past. The emphasis is now on their bold, shining buckles: Gleaming expressions of both form and function. Buckle boots exude a downtown toughness and confidence with elegance. These styles are elevated, thoughtful nods to their punk origins.

Wild Things

Take a walk on the wild side and play with jungle prints, space-age colors, and interesting textures. Sumptuous suede, wild animal prints, velvet, and glistening metallic boots made their way down countless runways, transforming each ensemble that they punctuated into a work of art. Each of these finishes, though unexpected, is a neutral, so you can wear them with just about anything. A statement print, shimmering metal finish, or textural boot is a super simple way to recast your go-to winter outfit as something spectacular.

Lug Around

The base of lug-sole boots features a notched, rubber sole—a structural fixture that’s ideal for trudging through rain, snow, and the dreaded “wintery mix” with poise. The good news? They can also be incredibly beautiful. Slip them over jeans or wear them with a skirt and a pair of warm black tights and, just like that, the most functional shoes in your collection are actually chic enough to wear to drinks and dinner.