2022 Winter Fashion Trend: Chelsea Boots

Of all the winter boot styles available this season, one trend outranks all others: the Chelsea boot. With their lightweight soles and stretchable sides, these ankle boots are comfortable, sturdy, and—most importantly—stylish. 

Check out our collection of Chelsea boots HERE.

It’s believed that the Chelsea boot was invented in the early 19th century by Queen Victoria’s shoemaker, Joseph Sparkes Hall. They were initially designed as horse riding boots that were easy to slip on and off. However, they quickly became a notable high fashion trend that extended far beyond equestrianism. They remained a popular style until the beginning of the 20th century. After gaining traction again in the 1950s, they were worn by stars such as The Beatles and The Rolling Stones. In the past few years, Chelsea boots have made a comeback and are a highly admired shoe trend this winter.

Chelsea boots are comfortable and functional, but the best thing about them is how versatile they are. You can style them with a wide range of outfits, whether you want to dress up or down. As Abby Hepworth says in her PureWow article, "How to Wear Chelsea Boots in 2021 Like the Stylish Fashionista You Are," "There are few fall boot styles easier to pull off than Chelsea boots. Literally—the signature stretchy gussets on either side make it a breeze to slip into and out of this classic bootie, making them an absolute must-have."

If you’re looking for ideas of how to style these beautiful boots, then you’ve come to the right place! We’ve curated some Chelsea boot outfit boards that are sure to inspire your winter outfits for the remainder of the season.
Chelsea Boots outfit 1 - neutrals mix: turtleneck, wide crops, Clarks Rock Knit Chelsea Boot, trench coat, chunky necklace

 

SHOP CLARKS ROCK KNIT BOOT - $180.00 - 2 COLOR OPTIONS

 

Chelsea boots outfit 2: long knit dress, MJUS Morgana Chelsea Boot, Pixie Mood Vegan Convertible Backpack, small hoop earrings

 
Chelsea boots outfit 3 - denim chic: polo top, cropped frayed denim, Bos & Co Lock Chelsea Boot, Pixie Mood Bubbly Clutch

 

SHOP BOS & CO LOCK CHELSEA BOOT - $244.95
SHOP PIXIE MOOD BUBBLY CLUTCH - $85.00 

 

Still looking for the perfect Chelsea boot to wear this winter? We’ve selected some of our favorite styles available at simonsshoes.com with free shipping, as always. 

Our Favorite Chelsea Boot Styles for Winter 2022

BLUNDSTONE 1316 SUPER 500 BOOT

The weatherproof outsoles, moisture-wicking comfort footbeds, and chic red accents make this Chelsea boot durable, comfortable, and stylish. 

SHOP 1316 SUPER 500 BOOT TODAY - $209.95

MJUS LEATHER ANKLE BOOT

These gorgeous Italian Chelsea boots are crafted with durable nubuck leather, and the lining is made from recycled fabric. They are the perfect complement to your outfits any time of year, and they’re eco-friendly! 

SHOP LEATHER ANKLE BOOT TODAY - $219.95

BOS & CO MASS WATERPROOF BOOT

This trendy Chelsea boot is perfect for winter. It’s waterproof, lined with soft Suapel microfiber, and comfort rated to five degrees Fahrenheit. It also contains a beautiful leather upper and chunky heel with a non-slip rubber sole. The Mass Waterproof Boot is a practical winter shoe that will keep you warm and stylish throughout the season.

SHOP MASS WATERPROOF BOOT TODAY - $199.95

LA CANADIENNE CHARLIE WATERPROOF CHELSEA BOOT

The Charlie Chelsea boot is made with a beautiful, waterproof leather upper, microfiber lining, and a memory foam footbed that will keep you cozy all winter. And, the studded detail will add an extra flair to any of your winter outfits. 

SHOP CHARLIE WATERPROOF CHELSEA BOOT TODAY - $524.95 

SHOP OUR FULL COLLECTION OF CHELSEA BOOTS HERE

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