7 Best Men’s Chelsea Boots to Wear With Everything

Daniel Bishop
Written by
Last update:

In this post, I’ll be focusing on Chelsea boots, their evolution and the main features you should look out for when choosing a pair of dress boots for men.

What is Chelsea boot?

The Chelsea boot is basically a highly fashionable and elegantly designed pair of boots that are perfect for both the working and leisure environments.

The boots were originally designed in the 1960s by iconic shoe designer Nils work. The original Chelsea boot design then went on to become the outfit of choice of a number of famous people in the 60s and 70s.

How did Chelsea boots became popular?

In the 1970s, fashion sources began to pick up on the trend of this popular boot and it eventually became a must have item for any fashionable male in the 1980s.

Chelsea boots were made very popular in the 1980s due to their appearance on several iconic 80s celebrities including Bob Dylan, David Bowie and Duran Duran (One Thing and Hungry Like The Wolf).

The boots have gone on to still remain popular and in vogue in modern times for both men and women.

Here are some more stylish men’s shoes, to check out and choose from.

Blundstone Unisex Original 500 SeriesBest OverallBlundstone Unisex Original 500 Series
PARTY Mens Ankle Casual Chelsea BootsBudget PickPARTY Mens Ankle Casual Chelsea Boots
Thursday Boot Company Duke Men's Chelsea BootUpgrade PickThursday Boot Company Duke Men's Chelsea Boot

1. Blundstone Unisex Original 500 Series

Our rating: 9 / 10

Blundstone Unisex Original 500 Series

Check Price on Amazon


  • The great leather and rubber soles provide added protection to your feet
  • The comfort and stability of these boots is amazing
  • Resistant to water, oil, and chemicals
  • The soles are made out of polyurethane and are great for excessive use
  • Very durable


  • Some people find that the boots run small
  • The boots are more expensive than similar other models

With the Blunderstone 500 you can choose from four different colors, they are the smooth chocolate, smooth cigar, rough dark bark, and rough light bark.

The boot has a rubber sole that makes standing on hard surfaces less painful than when wearing just regular shoes. The boot is also waterproof, which protect you if you are caught walking in the rain.

These boots are excellent for business use and they have a sleek design that women too can enjoy. If you have a long commute and have to take public transportation you will enjoy having these comfortable boots in your life.

2. Bruno Marc Men's Suede Leather Chukka Ankle Boots

Our rating: 8 / 10

Bruno Marc Men's Suede Leather Chukka Ankle Boots

Check Price on Amazon


  • Will last a long time
  • Nice quality
  • Priced well, especially considering the brand
  • Looks nicer than regular chukka boots


  • Looks bigger than most men’s chukka boots
  • It’s more like a women’s boot than a men’s boot

The Bruno Marc Men’s Suede Leather Chukka Ankle Boots are a nice casual boot. They have a stylish design that makes them look better than regular chukka boots. They are made with high-quality materials. The suede leather upper makes the boots look great and feel comfortable to wear. The boots are also durable, since they are made with welted construction. The inside is smooth and soft for comfort. This boot can be worn with virtually anything.

The boot runs a bit big. The color looks a bit darker in person than what is shown in the picture. If you have to wear a formal suit to work, this is not the boot for you. This works best for casual wear.

3. Thursday Boot Company Duke Men's Chelsea Boot

Our rating: 8 / 10

Thursday Boot Company Duke Men's Chelsea Boot

Check Price on Amazon


  • Constructed with high quality leather
  • Good value for the price
  • Good, comfy fit
  • Ample ankle support
  • The sole is non-slip
  • Available in various colors and sizes
  • Waterproof
  • Sits well above the ankle
  • Waterproof and breathable lining
  • You can polish and clean with ease


  • The tongue can dig in a little
  • Not for wider feet
  • The lining seems weak, could tear easily
  • The front strap is plastic and rattles

When you're looking for a quality men's Chelsea boot you want a boot that is constructed well, with high-quality materials. The Tuesday is a great boot for dress, casual or work attire. It's available in an array of colors and sizes and includes personalization options. The distressed leather on the outer of the boot gives it a nice worn look.

The fit of this boot is great for most people, but those with slightly wider feet may have issues. The laces are very long, and the top of the tongue is very high. You'll have to tie up the laces a lot to keep out water and other materials that can be harmful to your feet.

4. Skechers Mens Relaxed Fit Segment

Our rating: 8 / 10

Skechers Mens Relaxed Fit Segment

Check Price on Amazon


  • Great quality
  • Great price
  • Wide range of colors
  • Good cushioning for the bottom of the feet
  • Good arch support
  • Good traction on the soles
  • Good size widths
  • Comfy with socks


  • Won’t work for people with wide feet
  • May fit too loose for some people

The Skechers Mens Relaxed Fit Chelsea Boot is a great boot if you’re looking for a comfortable everyday shoe. They’re made in a true Chelsea boot style, which means that they’re not only easy to pull on and off, but they also have elastic panels on the sides that stretch to fit around your ankles without pinching.

These boots have very comfortable insoles, including a full length of padding for your heels that’s covered by a soft leatherette material, and a thick and soft sock liner to rest your feet on.

If comfort is your ultimate goal, then these Skechers boots are the best choice for you. They’re multisport flexible and lightweight and will provide you with the comfort you need for walking around the city, going to the mall, and running errands.

5. Dr. Martens

Our rating: 8 / 10

Dr. Martens

Check Price on Amazon


  • Superbly made with the highest quality product
  • The breathable lining is durable, soft, and comfortable
  • The rubber sole provides non-slip comfort and sturdiness to withstand everyday wear
  • Comes with an impressive 2-year warranty
  • Fashionable colors


  • The strap can be a bit stiff upon arrival
  • It sits just above the ankle
  • The heel is a bit low

The Dr. Martens Chelsea is a timeless style, something Chelsea boots were meant to be. The brilliant design boasts the trademark Dr. Martens air-cushioned sole with firm grip, but it doesn’t sacrifice style for comfort. It’s handmade by highly experienced craftsmen in the UK, and it’s handsomely crafted with the toughest and most durable material.

The design also makes it easy to clean, and it retains its shape well. Dr. Martens Chelsea boots are also good for people whose feet tend to sweat such as men who are suffering from hyperhidrosis. The lining of the boots is breathable, making them even more comfortable to wear.

6. Crevo Men's Denham Chelsea Boot

Our rating: 7 / 10

Crevo Men's Denham Chelsea Boot

Check Price on Amazon


  • Really comfortable
  • Made with high quality genuine leather
  • Found for even less than what other sellers charge
  • Extremely popular with consumers with positive reviews


  • Straight cut design
  • Could be a little more durable


What’s great about this Chelsea boot is that it’s a classic. Made with high quality genuine leather and available at a fantastic price. This boot is made with a great amount of detail, starting with the patent leather underlay right down to the lasted brass buckles.

The sole is made with rubber, so it will be durable even on wet surfaces. It also has a deep heel and a good amount of grip. What’s more is that this boot is available in a variety of sizes. So if they don’t fit you, you can easily get a different pair. The Crevo Men’s Denham Chelsea Boot is a great find if you’re looking for a stylish Chelsea boot.

7. PARTY Mens Ankle Casual Chelsea Boots

Our rating: 7 / 10

PARTY Mens Ankle Casual Chelsea Boots

Check Price on Amazon

Sizes: 6,7,8,9,10,11,12

Ultra comfortable men’s ankle boots in brown and black, made from rubber. Good support. With an ideal gripped rubber sole.

Great for everyday use, and ideal for wearing with jeans and trousers.

Frequently Asked Questions (FAQ)

What are the best Chelsea boots?

The Chelsea boot comes in many styles, but they all tend to be mid-calf or knee-high. The boots have a rounded toe and an elastic side. Traditionally, they are not meant to be worn with socks and for that reason, they were originally called ‘semi-boots’.

In recent years, they have evolved in many styles, allowing them to be worn with socks today. Since the boots are made from leather, they tend to be made more for fall and winter wear, although you may find some made with suede or other materials for summer wear. The most common of the Chelsea boots are dark brown or black, although many come in other colors as well.

What color Chelsea boot should I get?

Almost all of the Chelsea boots you come across today are black, making it the optimal color. Black Chelsea boots go with all of your casual and dress clothes, making them an easy choice if you’re on the fence about style and color. If you want something different or special, think about navy blue, brown, or occasionally tan Chelsea boots.

If you’re shopping for a Chelsea boot on a budget, look for a dark brown or black model. The next step up will usually be a lighter brown leather color, and the lightest leather on offer will be white or off-white. This will be the most expensive option, but if you select a light color you’ll be able to wear it more often.

What can I wear Chelsea boots with men?

The versatile Chelsea boot is stylish enough for formal wear and functional enough to be worn for outdoors. They pair especially well with slacks and, of course, jeans. They are not boots for heavy duty chores, but they are very comfortable to wear casually for long periods. As long as it’s a casual look, you can wear Chelsea boots with almost anything.

What color boot is most versatile?

Choose a classic color such as black, brown, or dark blue.


Chelsea boots are definitely a cool & trendy type of footwear that can be worn with both formal or casual clothing. We hope this review has been very helpful and provided you with the best tips on the best Chelsea boots for men. If you have any questions about anything that has been discussed here, do feel free to shoot us an email. We’ll be happy to answer any queries that you have, as well as hear your feedbacks.

Our Recommendation

Blundstone Unisex Original 500 SeriesBest OverallBlundstone Unisex Original 500 Series
PARTY Mens Ankle Casual Chelsea BootsBudget PickPARTY Mens Ankle Casual Chelsea Boots
Thursday Boot Company Duke Men's Chelsea BootUpgrade PickThursday Boot Company Duke Men's Chelsea Boot