Chelsea Boots Are the Most Timeless Winter Shoe Style for Travel-Shop 10 Versatile Picks, From $27

Trends come and go, but it’s the lasting styles that are the ones most worth investing in if your goal is to build a timeless wardrobe. For the fall and winter, Chelsea boots are one of those classic looks that never seems to lose their wearability, so if you’re working to make your packing list resistant to passing fads, you’re in the right place.

Whether you’re seeking the perfect pair of platform boots or an upgraded rain shoe that you can wear regardless of the weather, we’ve rounded up the 10 best Chelsea boots worth adding to your seasonal wardrobe. We’ve uncovered pointed-toe, classic, and even fur-lined styles all available for under $160—with discounts reaching up to 53 percent off at Amazon, Nordstrom, and more.

Athlefit Chelsea Boots

Many Chelsea boots are easy to slip on and off, making them essential for your fall and winter travels. What makes these Athlefit Chelsea Boots  even more convenient are the thick, knit elastic bands at the entrance of each shoe that stretch to provide a comfy yet snug fit that’s almost sock-like. Chunky outsoles are made slip-resistant with lugs that’ll keep you safe on slick city streets and uneven terrain, while rounded toe boxes offer ample room for your feet to sit comfortably. Best of all? They’re on sale for under $50.

Mia Panola Chelsea Boot

For an elevated take on this timeless seasonal style, the Mia Panola Chelsea Boots are a beautiful choice thanks to their rounded toe-boxes and sturdy, rugged outsoles. The heeled, platform style looks great with jeans, trousers, and even a flowy maxi skirt, but they’re functionally made with stretchy elastic at the entrance of each shoe for maximum comfort. While stylish, they’re still easy to walk in so you don’t have to rely on sneakers for your next sightseeing day, and at $70, they’re a worthwhile investment.

Toms Bennet Chelsea Boots

With colder weather on the way, these faux fur-lined Chelsea boots are a must-have addition to any suitcase. They feature the brand’s CloudBound insoles for extra cushioning and support during your travels, and the addition of a plush lining keeps your feet well insulated against the elements. A pop of contrasting tan along the soles makes them stand out from other boots in your collection, and they even offer a slight platform that’ll give you some height while remaining easy to walk in. According to shoppers, they’re “comfortable right out of the box,” no break-in period required.

Caslon Miller Water-resistant Lug Chelsea Boots

Lugged outsoles and reliable, water-resistant uppers make these Chelsea boots an excellent alternative to traditional rain boots—and they’re so stylish you’re not going to want to take them off, even on sunny days. The moderate platform on these boots provides a slight lift in tandem with impressive traction thanks to grippy lugs, plus loops at the heels make them especially easy to take on and off. The simple, versatile style can be easily dressed up or down (really, they look exceptional with everything in your suitcase), and they’ve even earned thousands of five-star ratings at Nordstrom Rack.

Timberland Brimfield Chelsea Boots

Switch up your look with this beautiful, tan pair of Timberland Brimfield Chelsea Boots that just went on sale for a whopping 53 percent off. Most Chelsea styles come in black and deep brown shades, but this lighter color will still wear well with the majority of your travel wardrobe while remaining endlessly comfortable. The suede exteriors channel a softer, more feminine look that’s still suitable for everyday wear, while the insoles are lightweight and ultra-cushy for vital support while you’re on your feet.

Steve Madden Sawyer Chelsea Boots

A sleek men’s style, the Steve Madden Sawyer Chelsea Boots are made with rich black leather or tan suede exterior that’s understated and easy to wear in numerous ways throughout your next vacation. Now on sale for just $50, these slip-on shoes are travel essentials with their roomy toe boxes, well-cushioned insoles, and sturdy design. They effortlessly combine fashion with function, looking just as great with a nice pair of slacks as your favorite worn-in jeans, and they’re so comfortable that you won’t want to take them off. If you’re limited on packing space, these are a solid wear-with-everything option.

Chooka Waterproof Chelsea Bootie

A best-seller at Amazon, the Chooka Waterproof Chelsea Boots are a far more wearable alternative to true rain boots—and they’re now on sale for just $25. Crafted to sit right above the ankles and lined with faux fur, these cozy, utilitarian boots are a great addition to your seasonal packing list if you’re headed to a rainy destination. However, even on sunny days they’ll be easy to style thanks to the simple black exteriors. Non-slip outsoles offer the traction needed to stay safe on slippery streets, and the waterproof exteriors are exceptionally easy to clean.

Dr. Martens Rometty Fashion Boots

Dr. Martens excels at creating high-quality boots that are designed to last for years on end, so we’d be remiss not to mention the platform Rometty Boots as an edgier Chelsea boot style to score for the fall. This pair has a chunkier outsole that’s still comfortable to walk in, and, as with all other boots from the brand, they’re slip-resistant and incredibly durable. Shiny leather exteriors make the quality of these boots evident to the eye, and they’re well worth the price tag at $101.

Vepose Women’s 936 Chelsea Ankle Boot

With durable, grippy lug outsoles, the Vepose Chelsea Ankle Boots provide good traction even on slippery surfaces—all in total comfort, thanks to the memory foam insole. The moderate platform on these boots provides a slight lift, plus loops at the heels make them especially easy to take on and off. The simple, versatile style can be easily dressed up or down (really, they look exceptional with everything in your suitcase), and they’ve even earned over 500 five-star ratings at Amazon.

Goldnut Platform Chelsea Ankle Boots

Add style to your cozy winter boots with these platform Chelsea boots made with a plush faux fur interior. They slip on and hug your feet in fuzzy warmth like your favorite pair of Uggs, but they offer the same look of a classic Chelsea boot so you dress them up a little bit. The slip-on and off design makes them ideal for flying days.