How to Wear Chelsea Boots: An Outfit Guide

how to wear chelsea boots men

We are rolling out the red carpet for the one and only Chelsea boots this season. We know that the classic boots have a special corner on your shoe stand, but the Chelsea boots are an absolute must-have right now. Although they were introduced decades ago, these handsome boots are still relevant for a streamlined trendy look. 

After all, they might not be from the family of your easy slip-on; they are an individual entity as transitional footwear for morning and evening looks.

So, instead of repeating your signature boots, try the outfit ideas we have compiled below. 

Here are the outfits you need to give a shot.

Burgundy Cardigan and Beige Chinos

You might have seen many people wearing men’s suede Chelsea boots with formal suits. But that doesn’t mean it is the only outfit you are left with. Wear a maroon striped shirt with a burgundy cardigan and beige chinos for a casual look with a stylish spin. This outfit is incomplete until you wear a matching burgundy strapped watch. For this look, you can go for black Chelsea boots.

Charcoal Polo Shirt and Charcoal Jeans

Inside the wardrobe of a fashionista, you will find a bunch of polo shirts. A polo shirt is a versatile garment that lies in a category between a t-shirt and formal wear. Due to that, it is suitable for your summer hangouts and backyard parties. 

This Chelsea boots men’s outfit is a classic preppy combination with a charcoal polo neck sweater and charcoal jeans. This is a great outfit when you are on the go and can’t afford any afterthoughts. You can wear grey Chelsea boots and a black watch to match this outfit. If you are going out in the sun, wear black aviators. 

Black Pea Coat and Jeans

This is a great way of wearing jeans with Chelsea boots. You can wear a grey shirt underneath a black pea coat and top it up with a grey and black neck scarf. You must try this male black Chelsea boots outfit if you plan to travel. This look qualifies as a common British outfit

Grey Shirt and White Chinos

This is a laid-back combination that looks fabulous on most occasions. You just have to throw on a grey shirt with white chinos, and you are ready to go out. You can wear a tan brown racer jacket to look amazing in this outfit. Of course, you need to balance this outfit with black Chelsea boots, a pair of black sunglasses and a watch.

Red Shirt and Black Jeans

At times, you want a break from your favorite jeans with high tops. To that end, pick a white and red vertical striped long sleeve shirt with black jeans. The style of jeans you want to opt for is up to you. These pieces are practical and casual when you wear brown Chelsea boots. You can break up this look with a brown leather jacket too. As accessory, you can don a black beaded bracelet. 

White Shirt and Charcoal Blazer

Now, this outfit is dedicated to Chelsea boots with a suit. In this dressed up look, you can wear a charcoal suit or charcoal blazer with a white shirt. We call this an easy-to-achieve outfit because, in a men’s clothing collection, white shirts are unsung heroes. This is a refined look that you finish off with a silver watch, black tie and black Chelsea boots. 

Grey Blazer and Black Pants

If the last look was too dressy for you and you are thinking about how to wear Chelsea boots for men in a semi-formal type of attire, this outfit is ideal. You need a grey plaid blazer and black chinos, and you can elevate this look by wearing gray Chelsea boots for men.

All Black Ensemble

We know how much our men love a full black outfit, so how can we skip this outfit?

For a hip look, you can wear a black hoodie, black leather vest, and black cargo pants. This is an excellent pairing for a sharp look. There is no way that wearing all-black Chelsea boots won’t bring some extra classiness to this outfit. Besides that, wear a black beanie as well.

Black Biker Jacket with Ripped Skinny Jeans

Let’s go now with an edgy look. The most convenient rugged Chelsea boots outfit includes a black biker jacket with metal studs detailing and a few zippers with a jet black ripped skinny jeans. Underneath the jacket, you can wear a white top. To dial this rugged look up a notch, go for shiny black leather boots.

Bomber Jacket and Blue Ripped Pants

For an absolutely unforgettable off-duty look, you can don an off-white bomber jacket and any blue ripped jeans. This is a bold and carefree look overall. To stir things up a bit, add a pair of tan Chelsea boots to this outfit and add accessories like sunglasses, a watch and a silver chain.

Floral Shirt with Dress Pants 

This combination of dress pants with Chelsea boots can take on different moods based on the road you are taking for styling them. A white and black floral short sleeve shirt and black dress pants. After wearing that, you would need only a single item to get all dressed up i.e., a pair of Chelsea boots. We think that on the list of effortless styles, this outfit idea should be the second number after the men’s leather outfit.


What are Chelsea boots?

Chelsea boots are one of the most popular footwear options for guys consisting of a soft, stretchable panel on the side that makes them sophisticated and relevant for almost every occasion. 

Can you wear Chelsea boots with a suit?

If you know how to style Chelsea boots for men, your life would be very much sorted. Pick a suit of any color with the correct fit and match the boots as stated in our guide. Note that, these boots can’t be worn with tuxedos.

Can you wear Chelsea boots in the summer?

There is no doubt that Chelsea boots are fabulous for Summer. You can decide the outfits to wear with Chelsea boots and you can add some accessories like belts, chains, watches, etc. according to personal preference.

Are white boots in style 2023?

The white Chelsea boots trend is here to stay as it is suitable for many events. Any of the Men’s Chelsea boots outfit is easy to match with the outfits and look perfect at day and night parties.

Can you wear skinny jeans with Chelsea boots?

Definitely, you can wear skinny jeans with Chelsea boots whenever you feel like it. One of the cool skinny jeans outfits to wear with Chelsea boots includes a brown overcoat, white shirt, and navy skinny jeans.

The Bottom Line

Similar to the combination of burger and fries, men’s outfits and Chelsea boots are a duo that tends to make sense. Whether you want to look confident at the office or simply want to bring a new style factor to your everyday clothes, these boots need to make it to your closet. 

However, before you start doing it, you must be sure of what to wear with Chelsea boots. So, make sure you quickly memorize some of the combos from this article.

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