What to Wear with Chelsea Boots

by Jamie Wilson

Reviewed & updated: October 19, 2022 by Jamie Wilson BA

Chelsea boots are a staple in every man’s wardrobe. If you’re not sure what to wear with Chelsea boots, this comprehensive style guide should solve all of your worries. Read on to learn how to style them with minimal effort.

What to Wear With Chelsea Boots

Chelsea boots are a staple in the footwear game and an easy one to transition through the seasons. They’re also incredibly versatile and have been a mainstay in menswear for decades, being donned by some of the most forward-thinking and stylish men on the globe. Here we look at the history of them, the features that make them unique and the key styles out there for a range of budgets. We’ll also give you three key looks you can slot them into, offering varied styles to show their true versatility and timelessness.

The Rocker

This is for those of you looking for an alternative look but you’ll still be drawing for some classic pieces to bring it all together. Go for a leather biker jacket, jeans (with distressed effect if you want a rugged finish), a plain white tee and your Chelsea boots to finish. You could also try accessorising with some leather bracelets and try a more relaxed neckline in your T-Shirt for a really laid back approach.

The Businessman

We have The Beatles to thank for this look more than anyone else. Their custom-made Chelsea boots were always paired with grey tailoring. You can switch this look up a little with a roll neck underneath your suit jacket or just keep it simple with a plain white shirt – whatever you prefer. If you’re accessorising this look, I’d stick to a classic watch. If it’s cold outside, opt for a peacoat to keep the cold at bay but retain that classic aesthetic.

The Everyday

If you’re not after a totally distinct look like the above styles and you just want to incorporate your Chelsea boots into everyday outfits, that’s easily done as well. For this, I’d stick to other staple pieces which you should already have in your wardrobe.

It’s almost impossible not to create a classically cool look when you’re building your outfit around Chelsea boots but consider this really is a sterling example of just that. Try an overcoat or trench coat, a denim shirt, slim cut jeans or chinos and finish with some classic brown Chelsea boots. A clean outfit that will turn heads wherever you go, perfect for days or evenings out.

Key Features

The Chelsea boot has stayed relevant all these years purely because of its stripped back, no-fuss design. With no elaborate decor, a streamlined silhouette and fairly subtle heel (depending on preference) it’s a shoe that can transition into an array of looks. To make sure you’re looking at a Chelsea boot, look out for the following traits.

  • Elasticated ankle
  • Slight heel
  • Simplistic aesthetics
  • Pull tab to back
  • Leather upper

The Icons

There have been many iconic figures in both pop and sub-cultures over the decades, all of which help to solidify the boot’s popularity and relevance as time passes by. The Beatles very famously had their own style commissioned in the 60s, opting for a taller heel and a more pointed toe, catapulting the boot’s popularity for that generation. Other notable wearers include Harry Styles, David Beckham, Kanye West and David Bowie.

Your Budget

When it comes to working on a budget or splashing out, your options are honestly limitless. With such a simple design and aesthetic, it’s really easy to get yourself a pair of Chelsea boots from a discount retailer for £20 (just don’t expect them to last very long).

To make sure you’re getting a pair that will last and hold that classic aesthetic, we’d suggest spending close to £100. This will ensure the leather’s of a good quality, the stitching is as secure as it can be and the pull tab won’t rip off when you’re struggling to pull them on after a beverage or three.

Key Colours and Materials

Chelsea boots come in a wide variety of colours if you look hard enough, but we’d stick to the key colours that bring a touch more versatility. Think tan, brown, grey and black. These colours will go with all three looks we’ve put together below and offer much more versatility in terms of other colours they’ll match with.

The only other real variant you have is the slight difference in texture. For a more premium (but harder to maintain) style, head for nubuck or suede – you may just have to invest a little more. If you want an instant rugged look, there are distressed styles as well, but we always prefer to create our own wear and tear.

Further Reading: History

The Chelsea boot’s roots stretch all the way back to Victorian Britain when the Queen’s shoemaker, J. Sparkes-Hall, developed an elastic ankle boot which the Queen herself would wear. The boot was an instant success and its popularity continued to rise as the decades passed, being adopted by mods, teddy boys and rockers alike. The Chelsea boot is undoubtedly up there with the likes of brogues, derbies and loafers in terms of its timelessness and classic status.

How to Wear Chelsea Boots

  • Try out the rocker look by wearing a biker jacket with some black skinny jeans. Finish this off with a pair of Chelsea boots.
  • You can go for the business/ formal look and pair a grey suit with a set of Chelsea boots – a classic look.
  • Go for the everyday look. A denim or oxford shirt, some slim cut jeans and a pair of brown Chelsea boots are a timeless outfit.
  • Go for quality. A quality pair of Chelsea boots will cost you more, but they will last a lot longer than cheaper ones.

On That Note

The versatility of the Chelsea boot really does leave your options wide open when it comes to styling them. These aren’t the only looks you can incorporate them with but they are a good demonstration of the variety of looks they effortlessly slot into. When it comes to buying your Chelsea boots, we’d always suggest investing more than a bargain-basement amount and opt for a classic style with minimal bells and whistles to ensure they last more than a few months. If you fancy buying a pair yourself, check out our store to see what’s available.

Feature image from Pinterest

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