How to Wear Chelsea Boots

What are Chelsea Boots?

For those new to the game, Chelsea boots are a stylish and unique piece of footwear constructed with an elastic or vulcanised rubber attachment at the sides. They come constructed without laces and can easily slide on and off your foot. They typically extend to the ankle and have a small tab at the back to make pulling them on easier.

The name “Chelsea” is rumoured to come from the Chelsea region of London where the style was very popular among men and women in the 50’s and 60”s

Leather Chelsea boots

Leather Chelsea boots are the most popular type of Chelsea boots available. They are sleek and can partner nicely with a lot of clothing attire.  Wear with slim fitted jeans, trousers or well-cut chinos to narrow the silhouette. Popular colours include black, brown, beige and navy blue.

Suede Chelsea boots

Suede Chelsea boots are much the same as leather Chelsea boots regarding fit and style. Just, slightly less restrictive than leather. They are incredibly stylish but more difficult to maintain than their leather counterparts. I would suggest styling a brown pair with an untucked slim-fit shirt, and grey jeans. For a black suede Chelsea boot, partner with a black suit to help you encapsulate the monochrome combo in one look.

The versatility of the Chelsea boot makes them a favourite shoe to own. They can be paired nicely with pretty much anything you have to wear. Follow this guide for some styling examples.

Causal Vibe

Jeans and Chelsea boots are a made for each other. To slide into a casual vibe, pair with a leather or suede Chelsea boot. Although both can effectively pass for a casual look, the latter will give you a more relaxed appearance.

Think brown or black suede Chelsea boots with slim fitted blue denim jeans and a white monochrome T-shirt. In cooler months, opt for a sweatshirt layered with a lumber jacket to stay warm.

Smart-Casual

Walking to lunch, a day in the office or a casual spin in your favourite haunt? Chelsea boots and jeans can help you nail that smart-casual outfit.

Go for a smart white shirt on slim-cut jeans with a black suede Chelsea boot. If this look is too simple for you, dress the combo up with a fitted blazer to match.

With a Suit

If you just got a new suit and you don’t know to what shoes will pair in nicely, then a Chelsea boot is worth considering. You will hardly make a style mistake in one of them. Here is some style inspiration for a few of the more popular suit colours.

Black Suit

A black suit is slick, stylish and consistent.  They will never go out of style and are the favourite for most office workers and smart dressers around the world.  To add a bit of flair to the classic black suit, team it with a casual inner t-shirt as opposed to a regular dress shirt.

Leather, suede and pointed toe Chelsea boots all pair in nicely with a black suit.

Navy Suit

We often rave about the versatility of the navy suit, and herald it is an essential piece in any man’s wardrobe.

The best colour of Chelsea boots to pair with a navy suit is brown. Try to the keep the colour hues consistent, darker blue with a darker brown for example, and the two colours should blend nicely together.

Grey Suit

If you aren’t feeling the groove of a black or navy coloured suit, opt for a dark grey suit. Grey is perfect for those who regularly like to break free from the norm but still stay traditional. The colour adds a little bit of detailing with a silhouette that blends in nicely with Chelsea boots.

For a grey suit you aren’t limited to a particular colour of boot. Go for either brown or black coloured Chelsea boot as the occasion warrants.

Final Note

It doesn’t matter what type of clothes you plan to wear, as long as they are comfortable there is always a Chelsea boot to match. Chelsea boots are seasonless, timeless and will remain in trend for a long time to come. Invest in a quality pair, paying close attention to the quality and longevity of the piece. However, no matter how tempting it might seem, never tuck in your trousers into your boots.

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