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The ultimate guide to Chelsea Boots

How to wear chelsea boots

Chelsea boots have very simple design, but at the same time they are very comfortable and elegant. One of the most versatile shoes, which every man should have in his fall and winter wardrobe. Today, I want to tell you more of my favorite boots and explain how to style and select them. 

Today, I want to tell you more about my favorite boots and explain how to style and select them. 

What are Chelsea boots?

At first, both women and men used to wear Chelsea boots for horse riding and walking. They have very simple, stylish, classic look and are very popular nowadays. A Chelsea boot is close-fitting, ankle-high shoe with elasticated sides, which can be dressed up and down easily. These boots have low heels, round toes and are constructed of two parts. Each of these parts is made from a single piece of leather: the quarters and the vamp, which are connected near the ankle. Usually Chelsea boots have a loop on the back so it can be pulled on. Chelsea boots are the right choice for the colder weather and match both official and casual looks. These sleek boots will look good on you regardless of your age and individual style. You can pair them with both jeans and a suit. Chelsea boots are timeless and you can’t go wrong if you wear them to the office, business meeting, weddings or parties.

Material and color 

As regards material, the most popular are leather and suede. If you are going to buy your first pair, I would recommend leather of a dark color, because it is more versatile. After you get your first boots, you can purchase another leather pair of a different color or try suede boots.

Simple colors are always the best. My favorite colors are black (it gives you timeless and classy look; perfect for formal outfits, but not recommended for casual style), brown (great in all shades, easy to match with many garments) and blue (perfect for casual outfits or if you want to make a statement).

Such colors work good with many different looks, gray and tan are good options as well.

How to style Chelsea boots


These boots are the best choice for everyday wear, you can easily pair it with any kind of jeans or chinos. Both leather and suede Chelsea boots work good with casual outfits, but suede boots are better for a more relaxed look.


You can’t go wrong if you wear Chelsea boots to a cocktail party, wedding or a date. This elegant footwear is just right for any look. You can pair leather boots with a nice suit or contrasting trousers and a blazer, though suede boots will match with this outfit too.


Pick a pair of elegant leather Chelsea boots and make sure the color looks good with your suit (for example, brown boots look nice with navy blue suit and black boots match with a grey suit perfectly). Your trousers should break in the right place, just above the ankle. The combination of brown suede boots and black denim will work perfectly for a more relaxed business casual look.

Best brands

My favorite shoe brands of all time are Backers and Tricker’s. They are both British companies with a very good quality/price ratio. You can find any kind of shoes in their shops and I highly recommend you to buy Chelsea boots of these two brands. All shoes are made of finest leather or suede, have simple yet sleek look. Built to stand the test of the time, these boots will be the perfect choice for you.

How to wear chelsea boots

Buying guide

Before purchasing a pair of Chelsea boots you should make sure that they are of good quality and fit you well. Below are the things you should consider before spending a decent amount of money on these boots.

  • Chelseas are close-fitting boots and it is really important to get the right size. You always should try Chelsea boots on as standard shoe size charts may not work in this case.
  • Chelsea boots always have the traditional elastic, so all the boots which have a zipper and are sold as Chelseas can’t be actually called like that.
  • Some brands offer a selection of soles, but classic Chelsea boots always have leather soles and you should stick to this option every time.
  • Chelsea boots are great in black, you should get them first and after that you can try other different variations.
  • The comfort, shape and longevity of Chelseas mostly depend on the elastic fastening. So, you should always pay attention to the quality of it before buying a pair of Chelseas.

Chelsea shoes are very versatile and easy to style. But just like all other shoes they need care. Use a hydrating cream for a leather pair few times a year and purchase a brush for a suede pair. Then, your boots will serve you much longer.

Alessandro Rocco Pietrocola is an entrepreneur, fintecher, investor, blogger and author based in London and operating mainly in Europe, Asia and Oceania with main focus on UK, Baltic Countries, Russia, China, Hong Kong, Malaysia, Singapore, UAE, Middle East and New Zealand as area of interest! At the moment is the CEO of Astorts Group. He is an UK FCA (Financial Conduct Authority) and NZ FSPR (Financial Service Provider Register) Approved Person and has great experience as director of regulated companies.
He uses to dedicate part of his life to inspire others and help them achieve the most out of their lives. Since he was 20, he had successfully founded and managed several companies operating in the field of management consulting, wealth management and fintech. He is Member of Institute of Directors in London, Member of Changer Club in Riga, Member of Fintech Association of Hong Kong, Member of Singapore Fintech Association, Member of Non Executive Director Association in London and Member of Alumni Network of Draper University in San Francisco. He loves travelling, he is a cigars lover, an amateur golfer and a dapper man.

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