How to Wear Men’s Chelsea Boots - Daniel Footwear BlogDaniel Footwear Blog How to Wear Men’s Chelsea Boots - Daniel Footwear Blog
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Style Guide

How to Wear Men’s Chelsea Boots

The jury is still out on whether Chelsea boots are better suited for smart or casual outfits. Whilst they can certainly be dressed up, they also look great when paired with jeans and a jumper. The beauty of Chelsea boots is that they can be worn in various different ways, so you can really let your imagination run wild. 

Failing that, here are a couple of fashion inspirations to ponder.

Suede Chelsea boots

Suede Chelsea boots are a great addition to any man’s wardrobe. They’re perfect for chillier weather and look great when styled with an injection of formal attire. 

Wearing Chelsea boots with a button-down shirt and jacket will achieve a sharp, professional look perfect for the office or a semi-formal event. Suede Chelsea boots evoke a less tailored, precise aesthetic without appearing too dressed down. For this reason, they’re a great piece of transitional footwear, ideal for going from office to socialising effortlessly.

Perhaps the best example of how to wear suede Chelsea boots is from the likes of Kanye West and Harry Styles. This is a casual yet stylish look that is perfect for weekend wear. 

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Pairing your suede Chelsea boots with a cosy, oversized sweater and your favourite pair of jeans will get you closer to Kanye’s look. This look is all about the relationship between streetwear and more traditional elements. Combining your suede Chelsea boots with less traditional fits is a good way to experiment without stretching the rules too much. Kanye also keeps it simple with block colours and the odd flourish of texture. If an oversized fitting is not for you, try a sleeker, more fitted bomber jacket.

Harry Styles’ approach to Chelsea boots is less streetwear and more classic rockstar. Donning a pair of black slim-fit or skinny jeans with a squarer or pointier Chelsea boot will help you achieve Styles chic. While a fedora hat isn’t for everybody, paisley print shirts and corduroy jackets should be on your list when thinking about tan or sand-coloured suede boots.

Leather Chelsea boots

When thinking about leather Chelsea boots, you can expect to appear smarter than you might with suede boots. Whilst Chelsea boots shouldn’t be a substitute for a good pair of Oxford or Derby shoes, they will make you look a little more formal.

Leather Chelsea boots are perfect for smart outfits and can be dressed up or down according to the occasion. A pair of dark Chelsea boots with a suit or tuxedo is a good idea to (within reason) break formal menswear rules. If this is the case, make sure your tux also has a little playfulness about it by, for example, opting for a coloured jacket.

If you’re going for a more casual look, pair your leather Chelsea boots with some dark jeans and a dress shirt. Alternatively, you can take inspiration from  The Beatles’ look and exchange the shirt for a roll-neck jumper in thin material.

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Tips for looking after suede and leather Chelsea boots

Leather Chelsea boots are a wonderful investment, and with the right care, they will last you for many years. In some cases, well-looked-after leather boots can look more interesting and characterful than brand-new ones. On the other hand, Suede Chelsea boots are a little more delicate. When looking after your new favourite boots, you should bear these tips in mind:

  • Avoid getting your suede Chelsea boots wet as much as possible. Avoid water and don’t wear them on rainy days. If they do get wet, stuff them with newspaper to help them retain their shape and let them dry naturally.
  • Keeping debris off your boots is key. To remove dirt, use a soft-bristled brush or a suede eraser.
  • To protect your leather Chelsea boots from the elements, use a waterproof spray before wearing them. Reapply the spray every few weeks or after you’ve worn them in rain or snow.
  • Store your Chelsea boots in a cool, dry place when you’re not wearing them. If you’re going to be storing them for a long period of time, stuff them with newspaper to help keep their shape. You may also want to invest in a shoe tree if newspaper doesn’t sound too appealing.

What kind of fitting trousers should be worn with Chelsea boots?

When wearing Chelsea boots, it’s important to ensure that your trousers are the right fit. Too tight, and you’ll be struggling to get them on and off, as well as evoking memories of indie bands. Too loose, however, and they’ll look a little bit too informal whilst also detracting from the sleekness of the Chelsea boot’s silhouette – one of its greatest characteristics.

Ideally, your trousers should fit comfortably around the waist and be slim-fitting through the leg. This will ensure that they look good with your boots whilst also guaranteeing one of the most important facets when building your wardrobe – whether your clothes feel good on you.

A few more considerations when it comes to your legwear are: to avoid tucking your jeans or trousers into the boots; rolling up the hem of your jeans for a slightly more cropped effect; making sure the jeans don’t bunch up at the bottom.

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Men’s footwear staples at Daniel Footwear

Chelsea boots are a classic example of a piece of footwear that should be part of the modern man’s wardrobe. From their ability to be dressed down or formally to their many different colours and materials, there is a pair to suit almost any man. If you’re looking to extend your shoe collection, you should look at the full range of men’s shoes, boots, and trainers at Daniel Footwear.

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