The Timeless Boot That Deserves a Spot in Your Suitcase This Fall

What exactly is a Chelsea boot, you ask? Well, it’s the little ankle boot that seems to have figured out all of our travel wardrobes: sleek enough for dinner, sturdy enough for a day of wandering, and easy enough to slip on when you’re running through the airport. With its close-cut shape, elastic side panels, and pull-on design, these stylish booties look equally at home on a rainy sidewalk in London as they do hopping from art gallery to dive bar in New York City.

A brief history of the Chelsea boot

Chelsea boots are hardly a new discovery. The style has been around for more than 150 years, first developed in England by Queen Victoria’s shoemaker, Josepth Sparkles-Hall. His mission? To create an elastic-sided design that made the boots easier to pull on and off, and that he did—even the Queen herself wore them. Commonly known as the “paddock” boot, the style was soon adopted by equestrians and countryside folk worldwide.

Its name arrived later, when the boot became associated with London’s cool Chelsea neighborhood; by the 1960s, the Beatles and the Rolling Stones had transformed the practical boot into a rock-and-roll staple. While there have been many renditions of the Chelsea boot, from hot new prints to chunky platform versions, its functional features and signature silhouette has remained.

My introduction to the Chelsea boot came from my mother and her Dr. Marten’s. She has always been a sucker for ’90s NYC style, with most of her outfits consisting of the classic downtown vibe: effortlessly cool and a little bit edgy. A New York rocker at heart, she was the first person to tell me that Chelsea boots are iconic. I would borrow her pairs through my angsty teenage years, and somewhere along the way, they became a staple in my own wardrobe.

Why Chelsea boots are a travel staple

I pack a pair of these bad boys everywhere—and that’s the beauty of a Chelsea; there’s a version of them for any trip you can dream up (minus a beach vacation). Whether your next vacation involves walking, unpredictable weather, dinner somewhere fabulous, or simply wanting your jeans to look a little cooler, there’s a Chelsea boot ready to come along. The dozens of pairs I’ve had over the years have followed me around the world, from the timeless Dr. Martens 2976 Chelsea (one of my favorites) to Blundstone’s classic pull-ons that I bought in Australia, and at this point, more Sam Edelman iterations than I can count.