Let’s take a take a moment to appreciate a classic fall accessory: the Chelsea boot.
Effortlessly cool and adaptable, this iconic silhouette has been a stylish go-to ever since the mid-1800s when it was first introduced to the world by Queen Victoria’s personal shoemaker. Known for its elasticized ankle and lack of shoelaces, the Chelsea boot came to modern fame in the swinging ’60s of London, where they were worn by Mod fashion trendsetters along with the likes of The Beatles. Thankfully, the trend quickly hopped over the pond and is now enjoyed by gents all over the world. Today, you can see a pair on any urban fashionisto, including celebrities like Harry Styles and even Brad Pitt.
There are countless variations on the Chelsea boot available online, which means it’s both easier and harder than ever to find the one that’s perfect for you. Below, we’ve assembled some of our absolute favorites.
Thankfully you don’t have to break the bank to get your hands on a pair of high-quality Chelsea boots, as proven by these great shoes from Kenneth Cole. Composed of sleek black leather, they’re bound to take your style game to the next level.
Built entirely of brown suede, the Ellis from Jack Erwin is about classic a Chelsea boot as you’re likely to find on the market. With its padded insole and reinforced stacked heel, this accessory is as visually striking as it is functional. Just make sure you know how to clean suede shoes before making a purchase.
If you’re interested in a Chelsea with a slightly taller silhouette, look no further than the Blitz model from Wolf & Shepherd. Here, an exterior of either black or brown full-grain Italian leather is complimented by an ultra-soft sheepskin footbed and thermal rubber soles, resulting in a supremely comfortable shoe.
For something a bit more rugged, consider these waterproof beauties from Cole Haan. Available in an array of attractive finishes (including black leather, java nubuck, midnight gray, and mesquite), this boot is guaranteed to amp up any fall look and is more than prepared to pound the puddles.
The Anderson Black from To Boot is a stylish option perfect for the guy looking to invest in a pair of super luxe boots. Outfitted with premium Italian leather, these bad boys are sure to turn heads when paired with a suit or your best pair of dark denim jeans. While more expensive than the other boots on this list, these are keepers you’ll have for decades to come, making the initial investment worth the price.
Not every man is a fan of Chelsea boots, we get it. It takes a certain mod-style to pull off. If you’re more of a trails-and-tequila sort of guy, check out the best moc-toe boots instead. They offer rustic appeal with proven wearability.
Article originally published August 16, 2017. Last updated on October 24, 2018, to include the best new Chelsea boot options.