10 Best Chelsea Boots I Found at Amazon to Make Fall Packing Lists So Much Easier — Starting at $29

I try my best to be a minimalist packer, but it gets tricky when deciding which shoes to bring, especially in the fall when luggage space is already limited because of warm sweaters and jeans. However, thanks to my favorite shoe style of all time, the super versatile Chelsea boot, I’m saving precious space.

When it comes to comfortable boots, I’ve always found this style gets top marks. Chelsea boots often have lug soles, so they’re grippy and easy to walk in (even if it rains), and usually hit mid-ankle, offering some support — especially on uneven cobblestone streets. But what makes Chelsea boots particularly ideal for travel is how versatile they are — I’m anticipating taking my trusty Madden Girl Karley boots (which are unfortunately no longer available) straight from vintage market shopping to a birthday dinner and a night out during my upcoming trip to London. Water slides off the faux-leather exterior, so I won’t have to worry about London’s on-and-off drizzly weather, and the only other shoe I need to pack is a comfortable sneaker for extra-long days on my feet.

Ahead, I rounded up some of the best Chelsea boots I spotted on Amazon, all for under $100. They’re perfect for your fall or winter travels and are guaranteed to elevate any outfit in your suitcase.

Cushionaire Women’s Sasha Slip-on Chelsea Boot

An all-over black boot is essential in my closet, and these Cushionaire shoes feature a memory foam insole so they’ll be just as comfortable as they are versatile. Made of faux leather, they’re water-resistant and will be durable enough to carry you through the season and beyond. The two-inch heel also adds some height, so they’re easy to dress up for a night out. One reviewer even compared the style and comfort to high-end boots like Dr. Martens and Ugg.

Athlefit Women’s Chelsea Boots

Chelsea boots often come in suede, and this light tan pair will be perfect for matching just about any outfit in your travel wardrobe. The faux suede is stylish while keeping the boots affordable, and the stretchy elastic around the ankle makes them easy to slip on and off. Many shoppers rave about the comfort of these boots, with one noting their versatility for fall and winter wear.

Asgard Women’s Ankle Rain Boots Waterproof Chelsea Boots

If you’re headed to a rainy destination, then these waterproof Chelsea rain boots are the perfect pair to pack. They’re versatile enough to wear even when it isn’t wet outside, thanks to the sleek matte finish. Shoppers agree that these boots hold up in the rain — even a “heavy downpour” — and remain comfortable all day. “The cushioned insole provides excellent support, ensuring that I can wear them for extended periods without discomfort,” one person said. “The boots are also lightweight, making them ideal for all-day wear.”

Steve Madden Women’s Howler Chelsea Boot 

A slightly pricier pick is the Steve Madden Howler Chelsea Boot, which is available in 12 stunning shades, including taupe suede, fur-lined tan, white and tan, and more. Like most of the boots on this list, it has the signature Chelsea boot lug sole and elastic around the ankle to easily slip them on and off. One reviewer who wore them to Portugal said, “[I] knew I’d be walking everywhere, but didn’t want to wear sneakers throughout my trip — these were comfortable and excellent quality for heavy walking or a cute boot for a casual fall/winter night out.”

Dream Pairs Women’s Low Heel Chelsea Ankle Boots

If you’d prefer a lower heel, then these Dream Pairs boots are perfect for you. They’re relatively flat, yet still have a lug sole to offer sturdiness and support. Several reviewers note that they wore these shoes while traveling, with one person saying they wore them for a week straight on a winter trip to Austria. “I was backpacking so I [had] very limited options to bring shoes. I bought these shoes and LOVED them!” they wrote. “I was able to bulk them up with two pairs of socks and ended up being super super warm and very comfy. They are totally worth the price and good quality!”

The Drop Women’s Campbell Sherpa Chelsea Boot

A rich cognac finish screams cozy fall, and the sherpa lining on these boots is the cherry on top (but don’t worry — everything is faux and vegan-friendly). The lug sole provides plenty of stability and support, while the interior lining will keep your feet toasty and warm, especially if you’re headed to a chilly destination. One person said they’re “comfortable and perfect for all-day wear” and that they run true to size. They’re also available in other neutrals, including taupe, black, and patent leather black.

Fitory Women’s Chelsea Boot Mid Heel Elastic Ankle

Get a little extra room in your shoes with these Chelsea boots, which offer a more elastic ankle than usual, making them a good fit for anyone with wider ankles or calves. With a majority of five-star reviews, these boots are said to be comfortable, and many people note wearing them for long periods of time without pain. In addition to faux leather, the boots are also available in several suede hues.

Mysoft Women’s Chelsea Boots

A chocolate-colored boot is a versatile pick to add to your closet if you’re looking to expand your footwear collection beyond black. This rich color is bound to get compliments, while the nonslip sole and lightly cushioned interior will keep you comfortable and confident. Shoppers mention buying these shoes for various trips, from a European vacation to a New York City winter getaway. “I wore these all over New York City. About 20,000 steps a day for a week,” one person wrote. “No blisters and kept my feet warm and dry on rainy days … Love them!”

Dream Pairs Women’s Chelsea Ankle Boots With Pointed Toe

Make a statement with these sleek pointed-toe Chelsea boots, which come in neutral shades like black, tan, and white, plus an eye-catching red suede. They’re only the second boot on this list without the signature lug sole, so they’re good for anyone who wants to dress up their look a bit more. Still, they have a sturdy block heel for navigating cobblestone streets or wet surfaces. “My toes are not smooshed up into the pointed toe area and my sock fits in comfortably,” one shopper noted, adding that they sized up a full size so they could wear socks.

Firelli Women’s Fashion Platform Chelsea Boots

To add a little drama to any travel outfit, try this platform Chelsea boot that features a cream upper and contrasting black sole. The 3.6-inch heel is roughly an inch taller than most other boots on this list, but many reviewers agree that they’re pretty comfortable to walk in. Although they might not be your go-to travel shoe, they’re a fun choice to pack for wearing on nights out at your destination. Numerous shoppers advise sizing down, so keep that in mind when buying!

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