As the days grow shorter and the air turns brisk, outside beckons with the promise of autumn adventures. Whether you’re wandering through a vineyard in Tuscany or navigating a crisp New York City morning, it’s the perfect time to embrace a wardrobe that’s both functional and effortlessly chic—and no piece is more essential to this transformation than a great fall boot.
From cobblestone streets to country roads, boots are your passport to style and comfort. Imagine the understated elegance of a classic riding boot paired with rich, textured layers, or the bold confidence of a sleek combat boot cutting through the urban sprawl. Ankle boots, versatile and stylish, are the workhorse of the season, transitioning seamlessly from daylight adventures to evening outings. And, of course, you’ll need a pair of rain boots, because autumn’s unpredictable weather won’t stand a chance against style this season.
Wherever your travels take you, these boots will be there ready to ground you in every sweet autumnal moment. Read on for the best fall boots that will elevate all kinds of journeys this season.
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Ankle boots
Ankle boots are some of those autumn fashion staples that never go out of style (see also: cashmere sweaters, cardigans, and cozy joggers). That said, there are oodles of amazing ankle boots for every occasion. Of course, the best ones combine comfort and style, be it in the form of a lug sole for traction, water-repellent construction for durability, or sheepskin lining for extra warmth. Below, find our favorite ankle boots to wear wherever your travels take you, whether that’s a work conference, a night out at the bar, a long-haul flight, or an afternoon trekking through a new city.
Over-the-knee boots
Slipping on a pair of over-the-knee boots is an easy way to elevate any outfit. What’s more, these statement-making shoes, which can be dressed up or down, work especially well with mini dresses or skirts (paired with tights or leggings in cooler weather) or your favorite pair of straight-leg jeans. Keep the rest of your accessories to a minimum so as not to take away attention from the shoes. Ahead, a few of our favorite picks—including wide-calf options—across an array of price points.
Most notable feature: Waterproof design
Rain boots
While rain boots are a must-have for any season, the best ones combine fashion and functionality, shielding your feet from puddles, water, rain, and slush sans any bulkiness (which is key when traveling and preserving precious suitcase space!). Classic rubber rain boots are great for casual everyday wear, while those made with waterproof leather offer a slightly elevated look and feel—stylish enough to be worn on dry days, too. Most options feature thick rubber soles for grip and traction to help prevent you from slipping in the rain. All you need is a lightweight rain jacket to complete the weatherproof look.
Under-the-knee boots
Under-the-knee boots, also known as riding boots, are the fall essentials that keep making a comeback year after year. Some western-inspired, others sleek, these styles effortlessly transition from day to night, adding a polished touch to everything from jeans and tees to flowy dresses. Classic riding boots, with their clean lines and timeless appeal, are a wardrobe staple, while calf boots, which fall around the half-calf area on the leg, offer a more playful, relaxed alternative. This season, expect a variety of styles to hit shelves, from Vince Camuto’s sophisticated leather options to Steve Madden’s subtly edgy designs featuring chain accents. If you’re looking to switch it up, Dolce Vita brings in chic vibes with rounded toes and delicate tonal stitching.
Sam Edelman
Drina knee-high boot
Most notable feature: Block heel
Combat boots
With their lace-up design, chunky soles, and leather construction, combat boots practically ooze cool—and best of all, they’re actually practical. A quality pair of combat boots can last for several seasons and provide optimal comfort and foot support for hours on end, making them ideal for travelers looking for a functional and fashion-forward footwear option. And, despite their striking silhouette, these shoes are pretty easy to style: They look great with (almost) anything, from jeans and joggers to loungewear sets and leggings, as well as dresses or skirts of varying lengths. For a fun take on the trend, consider springing for a pair with fun embellishments (like the option below from Frye).
This article has been updated with new information since its original publish date.