Think of the humble Chelsea boot as the ultimate wardrobe staple. This iconic shoe is as much a style superstar as a practical pick that adds class and sophistication to any look in your closet. The beauty of Chelsea is that it’s more than just an everyday boot—it’s footwear that subtly crosses the line from dressy to casual, and vice versa. That it offers the best of all worlds is a testament to its endurance.
Moreover, they look great with everything. Feel like wearing those well-worn jeans for the millionth time? Headed to the office in your finest? Going for more of a cool rocker aesthetic? Whatever your intention, this hip boot will complete the look perfectly—and, most importantly, it will never lose its place in your wardrobe. With its easy on-and-off styling and wide range of colors and materials, it’s the perfect addition. Here are the best Chelsea boots for 2020.
Ted Baker London Tradd Chelsea Boot
Contrasting goring panels set the Ted Baker London Tradd Chelsea Boots apart from anything else in your closet. Constructed with supple leather, these pull-on boots feature a cushioned interior to enhance your comfort. The panels are emblazoned with eye-catching paisley patterns that are subtly striking.
UGG Biltmore Chelsea Boot
If you’re after something that boasts a certain rugged quality, you’ll find it in the UGG Biltmore Chelsea Boot. This standout shoe is designed with all of the hallmarks of an outdoor performer: a waterproof leather upper, smooth textile lining, and a thick rubber outsole designed to promote superior ground grip while you’re adventuring and exploring.
Steve Madden Illen Chelsea Boot
Prefer a lower profile? Get acquainted with the Steve Madden Illen Chelsea Boot. Featuring a minimal look, these leather shoes have rounded toes that exude a traditional appearance. The subtle heel finishes the shoe perfectly, making it the perfect partner for anything from your off-duty denim to your corporate pants.
Vince Suede Burroughs Boot
Meet your everyday boot, designed to plant you firmly in the realm of the fashion-conscious. The Vince Suede Burroughs Boot is the shoe you wear to brunch with friends, first dates, baseball games, the bar, and everything in between. They’re made with smooth suede stacked on sleek soles for a striking, old-world look.
Lucky Brand Brentwood Chelsea Boot
Meet your everyday boot, designed to plant you firmly in the realm of the fashion-conscious. The Vince Suede Burroughs Boot is the shoe you wear to brunch with friends, first dates, baseball games, the bar, and everything in between. They’re made with smooth suede stacked on sleek soles for a striking, old-world look.
Blundstone Thermal Chelsea Boot
When you need a Chelsea boot that does a little more than simply look amazing, turn to the Blundstone Thermal. Made with waterproof leather and featuring waterproof elastic and latexed seams, along with thermal Thinsulate® insulation to keep you extra toasty, it’s an essential addition to your winter wardrobe. Bonus points for the detachable sheepskin footbed!
Church’s Worthing Chelsea Boot
If you’re shopping with longevity in mind, it pays to seek out pieces that exemplify quality craftsmanship and dedication to timeless design. That’s the case with Church’s Worthing Chelsea Boot, a smart and classic take on the look that is made with polished calf leather and accented by a sleek metal buckle for a pop of rocker-worthy intrigue.
FRYE Bowery Chelsea Boot
But of course! Who but FRYE could produce boots built to last…and last? The Bowery Chelsea is a dream for anyone who wants to buy the shoe and be done for good. They’re Goodyear-welted, and feature lug soles injected with rubber for extra durability and stability. The stonewashed leather finish is all class, through and through.
Maison Forte Falcon Chelsea Boot
There’s something to be said for the Chelsea boot that evokes the sophistication and appeal of a dress shoe. That’s precisely what you receive in the Maison Forte Falcon, a smart shoe that bears the same high-end polish as your favorite professional footwear. A delicate almond toe lends it a classic look, while the rich hue and smooth leather ensure it will remain a constant part of your rotation for years to come.
Sorel Madson Chelsea Boot
If you spend the majority of your time outside, you need something that will handle anything that the day brings, be it heavy foot traffic as you navigate a busy sidewalk or a sudden downpour. To the rescue comes the Sorel Madson Chelsea Boot, which is made with waterproof leather and features a sturdy rubber sole that keeps you on your toes.
Bed Stu Cortado Chelsea Boot
Channel your inner cowboy in a pair of Bed Stu Cortado Chelsea Boots. These effortless shoes are everything to the man who craves something just a little less posh and a little brawnier. The vegetable-tanned leather offers an enduring look, while the stacked heel and intricate stitch work on the upper channels the cowboy boot of your dreams.
Zanzara Eric Chelsea Boot
For those who’ve been seeking the perfect everyday shoe for what feels like an eternity, the Zanzara Eric Chelsea Boot ticks every single box. Few boots play so well with both rugged jeans and tailored pants with such authority, but these—with their smooth leather upper, sturdy rubber sole, and flexible goring—are the ultimate choice for anything on your agenda.