Men’s Journal aims to feature only the best products and services. We update when possible, but deals expire and prices can change. If you buy something via one of our links, we may earn a commission. Questions? Reach us at [email protected].Sponsored content
If there’s a perfect boot for fall, we’re putting our money on the Chelsea. Comfortable, casual, and darn good-looking, Chelsea boots seem to find that ideal mix of protection and style. If you’re thinking about changing up your boot game this autumn, we’ve got you covered with our Chelsea Boot Guide for Fall.
Renowned for their elasticized side panels that allow for comfortable movement and quick on and off, today’s Chelsea boots make use of modern materials, varying heel types and toe shapes, and color. And while they all may appear similar from a distance, get up close and you’ll see—the devil, as he often does, is lurking in the details.
Why “Chelsea Boots”?
The trademark footwear of the Swinging 60s and the downtown New York scene in the 70s, the history of the Chelsea boot actually dates back to the mid-19th century. As legend tells it, Queen Victoria requested a pair of riding boots without laces; hers kept getting tangled in her stirrups. The invention of vulcanized rubber allowed her shoemakers to develop a riding boot with stretch material on the sides. Now her majesty was able to slip her riding boots on and off easily, without tangles.
For decades, they were called paddock boots. In the swinging 60s, they became popular as London streetwear and were soon sported by everyone from the Rolling Stones to the Beatles. The kids called them “Chelsea boots,” mostly because of their association with trendy King’s Road. And the legend was cemented.
Modern Chelsea boots are much more varied than the one’s Mick and Keith and John and Paul wore. Thanks to contemporary design and materials, they come in all shapes and colors. Which makes them the ideal boot for autumn.
Work boots are great, but they’re sometimes too clunky for casual wear. Dress boots are gorgeous—but you don’t wanna wear those everyday. If you’re searching for the perfect shoulder-season boot, check out some of these Chelsea boots for fall. Many of them are on sale; all of them are quality-made. Some of these brands—and prices!—are amazing.
You ready? Slip on a pair of Chelsea boots and hit the streets this fall. Maybe you’ll start swinging, too.
Check out all the products and gear we recommend to Men’s Journal readers
For access to exclusive gear videos, celebrity interviews, and more, subscribe on YouTube!