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Chelsea boots first became popular when the Beatles chose them as their favourite shoes in the 1960s. Since that moment, they have never stopped growing in popularity, and nowadays they are a must for any fall wardrobe, for both men and women.

One of the best things about these boots is that they have elastic sides, which makes it easy to be worn and styled. On the other hand, you should always make sure you buy the perfect size, which is comfortable, have enough room for your toes, and can be worn with your favourite pair of socks in wintertime.

For some reasons, many believe these shoes are too formal. On the contrary, other men think these boots cannot be styled with a suit. Whether your doubts about Chelsea boots are, in this guide you will find all the answers you have been looking for.

We have investigated and found several looks you can copy or use as an inspiration to wear your Chelsea boots and make them the best piece of your fall wardrobe.


How to Fit Chelsea Boots

Finding the perfect size for your boots may be difficult. On the other hand, Chelsea boots are usually easier to fit, as they are crafted with elasticated sides. These come in handy to make the shoes fit your ankle comfortably. Besides, they are made of soft leather or suede, which makes it easier to take them on and off.

As a general rule, Chelsea boots tend to run true to your usual size. However, if you wish to wear them with cosy and warm socks, maybe you should try going for one size bigger. For this reason, you should wear the right thickness of socks the first time you try your new boots on.

On the other hand, don’t forget that shoes made of real leather tend to become looser after a while. The last thing you want is to wear a pair of oversized boots!

As usual, the best thing to do is to try different Chelsea boots until you find the best pair for your needs and your size. Don’t forget that Chelsea boots have elastic sides, which should stretch long enough to allow your feet into the shoes comfortably.

Classic Is Timeless

You don’t necessarily need to go wild to highlight your look and focus the attention on your Chelsea boots.

You can still rock your footwear by pairing your boots with some faded jeans or black cotton pants, a simple jumper, and a neutral coloured outwear.

Man wearing Chelsea boots in mink

Picture by Marks & Spencer (M&S Collection Chelsea Boots in Mink)

Chelsea Boots with Printed Socks

Socks are some of the best accessories you can play with, and Chelsea boots are really useful when it comes to trying new styles.

Pair your most colourful socks with a pair of black or brown Chelsea boots to keep your look glossy and dynamic.

Rock the Boho Style

Chelsea boots are the perfect addition to any boho-inspired look. Thanks to their vintage feel, they can be worn with either extravagant floral boho print or more subtle printed scarf.

mens going out shirt floral print

Photo by Light in the Box (Men’s Going Out Shirt Floral Print)

Bohemian revolt blair boho scraf men

Photo by Trendhim (Bohemian Revolt Blair Modal Boho Scarf)

Add an Elegant Twist to Your Style

Chelsea boots can be more versatile than you think. Try styling them with your favourite suit, or even with just a double-breasted blazer, and you will immediately have a contemporary yet elegant and stylish look.

Brown linn double breasted peak lapel slim fit jacket for men

Photo by Hockerty (Brown Linn Double-breasted Peak Lapel Slim Fit Jacket)

You will soon fall in love with these boots, which will definitely become your accessory to look fabulous in your best office attire.

Play with Different Textures

The majority of Chelsea boots are made with leather, although you can play with different fabrics and textures to enrich your style. For example, you can wear a pair of suede Chelsea boots with your favourite cotton pants, and a woolly coat or blazer.

suede pull on chelsea boots for men

Photo by Marks & Spencer (M&S Collection Suede Pull-On Chelsea Boots)

Contrast Your Clothes’ Colours

Playing with fashion trends means that you can mix and match different colours until you find your favourite combination. For example, if you are wearing a pair of black denim, you shouldn’t necessarily pair them with black shoes.

In fact, one of the best ways to rock Chelsea boots is to contrast different colours. Black boots with light-washed jeans will create one of the best outfits for your cosy days.

light wash ripped dad jeans in blue

Photo by Urban Outfitters (BGD Light Wash Ripped Dad Jeans in Blue)

Similarly, tan coloured shoes and dark pants will be a great match.

Man wearing Chelsea boots in tan

Photo by Marks & Spencer (M&S Collection Chelsea Boots in Tan)

Soften Other Leather Pieces

You can immediately make your outfit edgier and bolder with a leather jacket and even a leather pair of trousers. However, if you want to soften the look a little bit, you can try with some suede Chelsea boots and a pair of simple black or brown socks.

real suede Chelsea boots in tan for men

Photo by Boohoo MAN (Real Suede Chelsea Boots in Tan)

Go One Step Further

You may be surprised to see how many different types of Chelsea boots are available on the market. In fact, these footwears are now so popular that even high-fashion brands are promoting new styles.

From chunky boots to embellished shoes, there are plenty of looks you can try. As usual, if you go for an extravagant pair of shoes, you should keep the rest of your outfit more minimal. This will make the whole outfit more balanced, and allow your Chelsea boots to shine!

Also Read:

Sneakers From Sportswear to Fashion Legends (Men’s Edition)

How to Wear: The Leather Jacket – Men’s Edition

How to Wear: The Duffle Coat – Men’s Edition

About The Author

May is totally crazy about the 80s and everything the decade inspired! Having grown up in a household that was totally taken over by 80s music and fashion its only natural that May lives and breathes the 80s!

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