I can’t imagine a more versatile boot for traveling than the Chelsea boot. First made in the UK during the Victorian era (possibly by Queen Victoria’s very own shoemaker), Chelsea boots were then worn for both riding and walking. In the more modern context, these easy-to-slip-on boots experienced a comeback in the 1950s and ’60s when they were worn all over London’s Chelsea neighborhood by the likes of the Rolling Stones.
Given their history as both riding and city-stomping footwear, the Chelsea boots are the kind of shoes that can seamlessly take you from casual days out to more dressed-up evening plans. This versatility makes them a great all-purpose travel shoe. Throughout my own travels, I wear Chelsea boots often: I’ve hiked in them in the Azores (perhaps not the wisest decision) and comfortably rocked them on full days of sightseeing in Mexico City. In fact, they’re the boots I brought to Chile, where I’m writing this right now. And depending on their style (many come with sturdy, durable soles), you can even take some of these on more rugged excursions, too. In the last few seasons, designer labels as well as high-street brands everywhere have been making them in a variety of styles, giving Chelsea boot lovers even more options. But the shoe’s defining design elements—elastic gussets on the side and pull-on tabs at the back—are still intact, and make getting through airport security a breeze. And for travel lovers, that might be the most important feature.
Below, our edit of the best Chelsea boots for men for every type of trip.
This article has been updated with new information since its original publish date.
