2022/23 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

Rock Knit Boot

$98.00
$180.00

CHELSEA BOOTS OUTFIT #2: LONG KNIT DRESS

Morgana Mid Boot (M58229)

$160.00
$239.95

Leila Backpack

$104.95

CHELSEA BOOTS OUTFIT #3: DENIM CHIC

Lock Boot

$185.00
$249.95

Bubbly Shoulder Bag

$75.00
$94.95

Our Favorite Chelsea Boot Styles for Winter 2022/2023

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. 

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.

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! 

BLUNDSTONE 1316 SUPER 500 BOOT

Forever in season, the iconic Blundstone Original #510 Chelsea Boot features legendary comfort and outstanding durability; proof that sturdy and straightforward never goes out of style.