I still remember a couple of years ago around 2016-2017 when Chelsea boots were essential in every man’s closet. I personally had 3 or 4 different pairs and they were my go-to boot. I loved how they could complement any outfit and easily dress up a pair of jeans and a white tee. Often worn by celebrities and style icons like Harry Styles and Kanye West it was no question that these were THE boots to wear. Since then the Chelsea boot has evolved into something different. It is no longer just a suede leather boot in tan, brown, or black. Many brands have turned this style into an all-weather, more stylish rain boot. Sure, the classic leather Chelsea boot still has a place in every man’s wardrobe, but the new stylish waterproof Chelsea boot is making way as the new trend of footwear to wear in the rain and snow.
What Do I Look For In a Waterproof Chelsea Boot?
When creating this list I had to consider what a Chelsea boot is, to me it is an ankle-high boot, with no laces, and sewn-together leather at the upper. I also have to consider what material these boots need to be made out of since they need to be waterproof. The boots listed below will be made with materials like rubber, high-quality leather, Vibram soles, and other water-resistant materials. I made sure each and every boot can handle the wet elements with ease. Lastly, I kept in mind budgets. I know we all wish we could spend $1,000+ on a pair of designer boots (I have a couple on this list) but I also wanted to feature some budget-friendly picks for around $100 for the frugal fashion enthusiast.
Diemme Balbi Bad Weather Boot
This boot is the perfect combination of the duck boot and Chelsea boot. The strong rubber outsole makes this boot perfect for wet and rainy conditions. The suede upper adds the classic Chelsea boot look we all know and love.
Rick Owens Black Beatle Bozo Tractor Boots
This boot is Rick Owens unique take on the classic Chelsea boot. Sure, it looks quite different from the classic silhouette but it still features the attached leather on the upper and the ankle-high style all Chelsea boots have. The treaded sole and rubber outsole makes this boot waterproof.
SOREL Caribou Chelsea Waterproof Boots
These boots were made to be waterproof. These boots feature a premium full-grain leather upper, seam-sealed waterproof construction, and a rubber outsole. Look good in the rain whether it’s a workday, weekends, or anything else in between.
Clarks Morris Up Waterproof Chelsea Boot
This functional Chelsea boot was designed for year-round wear. Not only is it water-resistant but it looks great on foot. Wear this boot to the office, dinner, or the big game. It is truly a versatile boot that fits in any wardrobe.
Bottega Veneta Tire Chunky Sole Boot
A combination of high fashion and functionality. The chunky sole makes sure water stays out and the butter-soft leather upper guarantees comfort for all-day wear. Plus the pop of color not only comes in green but also purple, yellow, blue, brown, and more.
Sperry Cold Bay Chelsea Boot
This boot is not only perfect for rain but also for the cold. It has a microfleece lining on the inside of the boot to keep your feet warm on bad weather days. The lugged rubber sole creates added traction so you can avoid slips and falls while walking on slick grounds.
A.P.C. Sacha Boots
This ankle-high boot features buffed calfskin and a Vibram sole. Vibram soles are known to keep the water out. So you can walk and hike in rainy and boggy conditions without having to worry about your feet getting wet. These soles are known to be incredibly long-lasting so you can expect to get years out of these boots.
Blundstone BL510 Classic 550 Chelsea Boot
Beloved by art school students and farmers alike, these Blundstone Chelsea boots are some of the best all-weather boots on the planet. The leather is soft and sturdy, the outsoles waterproof, and the inside is as comfy as your favorite sneakers.
Camper Pix Chelsea Boot
Made with nearly indestructible leather and a rubberized sole, these boots are ready for whatever elements you throw at them. A classically styled boot that won’t break the bank.
Balenciaga Tractor Bootie L20
These chunky Chelsea boots are guaranteed to be a head-turner. Soft calfskin leather and thick rubberized outsoles make this boot comfy and durable for all conditions. The Balenciaga print on the toe box is a subtle but added flex for these Italian-made boots.
The classic Chelsea boots blew up on the fashion scene in the mid to late 2010s. Even though the hype has died down a bit, this stylish silhouette of a boot still has a place in every man’s closet and even if you already have a pair of suede Chelsea boots, why not level up your bad weather game and grab a pair of waterproof Chelsea boots as well. Now you can look good in the rain, snow, and the sun.