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 bootCommerce writer Jessica Chapel is wearing Steve Madden's Klayton boot Jessica ChapelChelsea 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 stapleI 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.Dr. Martens2976 Classic Calf leather Chelsea bootsBlundstoneClassic Chelsea bootsThe versatility of the Chelsea boot is exactly why travelers all over the world trust them. They can be the dependable pair you walk miles in, or the goes-with-anything shoe that makes a simple travel outfit feel like a look. And unlike so many shoes that promise to do both, the Chelsea boot has the history and rockstar lore to back it up.My latest Chelsea obsession is this pair of chunky heels from Steve Madden that are surprisingly comfortable for their height, which makes them a dream when a quick walk turns into a few miles around a city. But after rocking them everywhere over the last three years, I’m more than ready for a refresh.The Chelsea boots I’m eyeingThere are lots of excellent Chelsea boots out there right now. Classic leather, lug soles, chunky platforms, sleek low-profile versions, and weather-ready pairs from brands I love and trust. Below, I’ve rounded up a dozen travel-friendly Chelsea boots worth packing this season—many of which I’ve got my eye on.Dr. MartensFlora Smooth Chelsea bootsThis year-round staple can handle whatever is on the itinerary, rain or shine.VagabondBlanca bootConsider these for a more classic Chelsea silhouette.Sam EdelmanLaguna Chelsea bootThis classic Sam Edelman style offers comfortable, waterproof support.Thursday BootsLegend platformWalking all day? These actually support your foot with shock-absorbing memory-foam insoles.Dolce VitaSimaya H2O bootsCooler weather calls for this cool, structured lug boot.MaeveCap-Toe stretch ankle bootsSleek and stylish, these ankle boots are for dinner dates and holiday parties.DingoRoxy leather bootieDingo does boots right. These brown ones are comfy and go with everything.VivaiaRound-toe chunky platform bootsMade specifically for travel, consider this fashion-forward design.Steve MaddenEralyn BrownThese comfy block heels are perfect for leaf peeping this fall.CamperMilahA classic style to pull on and off easily.Steve MaddenKoah2o blackThese platform booties offer support while giving you some height.AthlefitWomen's Chelsea bootsThis beige Chelsea boot is on sale for just $40 on Amazon.