The next time you step out, you should be wearing Chelsea boots. Yes, Chelsea boots. You’ve seen them on the likes of The Beatles, Ryan Gosling, and Ryan Reynolds (to name just a few famous examples), and if you don’t have a pair, now’s the time to get hip to your new favorite boot. They’re both on-trend and yet utterly timeless, with a history that stretches back to Great Britain in the 1800s.
Once favored by royalty and prized as a useful horse-riding boot, the Chelsea boot style—a pull-on boot with elastic sides, or gores, and typically a back heel tab—has taken on a number of variations over the years. Yes, The Beatles wore black leather Chelsea boots with slim tailored trousers, and you can wear yours in much the same way—if they happen to be made from sleek, shiny leather. Chelsea boots are the perfect balance of rugged and refined; they’re ever-so-slightly edgy and seriously cool.
Chelseas also come in materials like textured suede (useful for wearing with jeans) or more rough, tumbled leather (again, great with jeans or garment-dyed chinos). You can wear them in the summer months—they’re less stuffy than thick winter boots—yet they’re also easy to style in the fall and winter. With so many varieties available, you can pick up one pair that strikes the right balance between dressy and casual, or get multiple sets to suit different occasions. Whatever your strategy, these are our favorite Chelsea boots of 2022.