I can’t imagine a more versatile boot for traveling than the Chelsea boot. First made in the UK during the Victorian era (potentially by Queen Victoria’s very own shoemaker), Chelsea boots were originally worn for both riding and walking before the more modern context of cool kids stomping around the streets of London’s Chelsea neighborhood with these on their feet came to be.
These are the kind of boots that can seamlessly take you from casual days out to more dressed-up evening plans. Because of that, throughout my own travels, I wear Chelsea boots often, from the otherworldly terrain of the Atacama Desert to the meandering, medieval old town of Edinburgh—in fact, I’m wearing a pair there as I type this. 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 picks for the best Chelsea boots for men for every type of trip.