The Best Chelsea Boots in Every Price Range

From baggy jeans and dad sneakers to the return of the velour suit, fashion is wild out there. As trend cycles churn away, this winter brings us an unexpected favorite that isn’t exactly new to the scene. Chelsea boots have entered the chat, and they are having a moment.

Chelsea boots originated in the 1800s in the United Kingdom. Queen Victoria, tired of laces getting stuck in her stirrups while she rode, was among the first to don them. They featured an elastic gusset to make it easier to slip on and off, as well as vulcanized rubber, a new innovation at the time.

With a savvy marketing campaign featuring his new royal customer, shoemaker Joseph Sparkes Hall’s “Patent Elastic Ankle Boots” soon became the high fashion of the West. Even 1800s society understood the value of a celebrity endorsement!

The trend endured through the 20th century. By the 1950s and '60s, rock stars such as The Beatles and The Rolling Stones popularized the style again, and it became associated with the Chelsea district in London, hence the name Chelsea boot.

Popular in both women's and men’s styles, the Chelsea boot is seeing a resurgence again. Or perhaps it never really went away. During the colder months, these boots are a closet staple.

Here are our picks for this season’s hottest Chelsea boots in every price range.

Madden NYC Women's Lug Sole Chelsea Boot

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Walmart

Easy to slip on, easy to wear, and easy on the wallet, the Madden NYC Lug Sole Chelsea Boots from Walmart are a bold statement that are also easy on the eyes. This bootie features classic side elastic for easy on-and-off accessibility, along with an updated and fashionable 1.25-inch block heel.

Soda Pilot Chelsea Boot

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Amazon
starting icon Starting at $28 from Amazon
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This classic style has a lug sole and 3/4-inch platform heel. The boots come in eight color combinations including the black on black seen here, as well as tan, brown, and off white. Shoppers report they run true to size.

Kamik Isabella Lo Boot

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Kamik
single icon $140 from Kamik
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The Isabella Lo women's boots go with everything, and thanks to their waterproof construction, they can handle everything you can, from rainy mornings to slushy afternoons and anything else your day might have in store. Featuring eco-friendly leather and the brand’s high-performing Grip traction and EVA comfort insoles, these boots are the closet staple you didn’t know you needed.

Wearwell Merida Boot

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Wearwell

Featuring calf-skin lining and memory foam insoles, these Nubuck leather classic boots are made to order by Guatemalan artisans. They are available in women’s sizes 5 to 12, including half sizes and width options. Although they are near the top end of the price range for this list, the Merida Boot is designed to last a lifetime because they can be fully resoled.

Jabasic Chelsea Boot

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Amazon
starting icon Starting at $50 from Amazon
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If you prefer your Chelsea boot with a heel, this is a fantastic option. The block heel is just uder 3 inches and the upper is made from a warm faux suede. It comes in four colors including a bright burnt orange. The elastic side panel makes these boots easy to put on and take off.

Alterre Black Suede Chelsea Boot

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Alterre

This Black Suede Chelsea Boot from Alterre has the right buzzwords in high-quality luxe footwear including a kid-suede upper and leather lining. The customizable boots also feature a 3/4-inch heel made of recycled plastic and a cushioned foam midsole for supreme comfort. Best of all, you can create an entirely new shoe by incorporating the equally luxe detachable straps (sold separately).

Ariat Wexford Waterproof Boot

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Ariat
single icon $175 from ariat
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Ariat was the first brand to integrate the concept of athletic footwear technology into its boot, providing a highly functional and stylish boot for equestrian athletes. The Wexford Waterproof Boot is not only the most functional boot on our list but also the most stylish. Made from 100% leather, the Wexford also features enhanced food support and nonmarking Duratread sole. It's available in women’s sizes 5.5 to 11.

Chooka Waterproof Plush Chelsea Boot

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Amazon
starting icon Starting at $34 from Amazon
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Chelsea boots are an excellent option for trekking around in the rain and snow while still looking stylish. This waterproof option is also lined with faux fur to keep you warm, and the sole has a tread to keep you from slipping on ice and sleet. It comes in five colors.

*Psst: if you choose to purchase an item from this post, CafeMom.com may receive a small cut. Each item and price is up to date at the time of publication; however, an item may be sold out or the price may be different at a later date.