Men's Chelsea Boots

Chelsea Boots

Chelsea Boots

Chelsea boots are one of the original ankle boots for men, believed to have been designed by royal shoemaker Joseph Sparkes Hall and worn for walking, horse riding, and so much more. In the swinging 1960s, Chelsea boots for men skyrocketed in popularity and became an iconic fashion piece of the British mod (modernist) scene, worn by the Rolling Stones and the Beatles. Today, the timeless Chelsea boots are the chosen footwear of celebrities like Kanye West and gentlemen like yourself.


What are Chelsea Boots?

Chelsea boots for men are close-fitting, slip-on, ankle-high boots with elastic side panels. The elastic sides allow them to be easily and quickly slipped on and off instead of having to tie laces. This is one of the reasons why men’s Chelsea work boots are so popular. The most commonly used materials are leather and suede. At Upscale Menswear, we offer the finest suede and genuine leather, including python, calfskin, and vegan leather.  


What are the Key Features of Chelsea Boots?

You might find men’s Chelsea boots with a zipper, but the original and classic design only has elastic sides. Our unique selection of the best Chelsea boots for men are made of premium leather or suede. They’re manufactured with rubber, non-slip soles, durable stitching, two-layer insoles, and a breathable lining. You have plenty of arch support and room to wiggle your toes.

For example, our Emilio Franco Italian leather men’s black Chelsea boots are handmade in Italy with a buttery soft lambskin on the inside for superior comfort. The special tanning process produces the glossy aesthetic of this fine Italian leather.

Our Los Altos camel cowboy suede Chelsea boots for men have a hand-stitched sole and bring a Southern charm to the traditional men’s Chelsea boots.


What Should You Wear With Chelsea Boots?

Our Chelsea boots pair well with everything from a sharp suit to jeans, fitted pants, and an oversized sweater. You can wear them to the office, a casual day out, or a weekend dinner. 

Styles like our Los Altos cowboy suede Chelsea boots for men or our Paul Parkman handmade leather men’s black Chelsea boots complement fitted or cuffed jeans or chinos, a smart top, and a jacket or sweater. The legs of your pants should sit just over the top of your boots.

The glazed, polished look of these Paul Parkman brown calfskin leather Chelsea boots sets off this Cielo cognac slim-fit, vested suit


How Do You Care for Your Chelsea Boots?


Here are some top tips to prolong the life of your men’s leather Chelsea boots:

  • Gently remove excess dirt with a soft-bristled brush.
  • Dip a clean cloth into warm, soapy water and wring it out before wiping the surface of your boots.
  • Dip another clean cloth in clean water, wring it out, and wipe away any soapy residue.
  • Air-dry your boots away from direct heat or sunlight to avoid cracking or fading.
  • Use boot trees or shapers.

You can preserve the leather by using a special leather conditioner. Leather is durable and naturally repels water better than suede, which is why you can find more men’s Chelsea rain boots and waterproof Chelsea boots for men made of genuine leather.



Here are some top tips for taking care of your suede boots:

  • Gently brush your boots in one direction with a suede brush to remove dirt.
  • Use a water-resistant spray to protect from water stains.
  • Let them air dry if they get wet.
  • Use boot trees or shapers.
  • Keep them away from heat sources and out of direct sunlight to avoid fading the colors.


Frequently Asked Questions on Men's Chelsea Boots


Are Chelsea Boots in Style this Year for Men?

Chelsea boots are a timeless fashion that’s become even more popular recently. For example, the established Esquire magazine for men listed Chelsea boots as a top style for 2024.


Which Brand is Best for Chelsea Boots for Men?

Upscale Menswear only offers the best brands of Chelsea boots for men, including: 

- Antonio Cerrelli

- Emilio Franco

- Los Altos

- Mezlan

- Paul Parkman

If you’re looking for men’s Chelsea boots on sale and the best budget men’s Chelsea boots, we often have excellent deals on our top-tier shoes at Upscale Menswear.


Why are Chelsea Boots so Popular?

Chelsea boots have remained sought-after since the Victorian era because they’re stylish, practical, versatile, and easy to slip on and off.


Are Chelsea Boots Dressy or Casual?

You can wear your boots with jeans on a casual day out or with a nice suit for a dressier occasion. That being said, you don’t want to wear Chelsea boots in a formal setting if they don’t fit the dress code. 


Are Ankle Boots and Chelsea Boots the Same?

Chelsea boots are a specific style of ankle boots with elastic side panels that allow you to slip them on and off.

Read Less
  1. Home
  2. Shop By Tags
  3. Men
  4. Footwear
  5. Luxury Boots for Men
  6. Men's Chelsea Boots
  1. Home
  2. Shop By Tags
  3. Men
  4. Footwear
  5. Luxury Boots for Men
  6. Men's Chelsea Boots
1–20 of 162 items
1–20 of 162 items