The Chelsea Boots’ Secret: Wearing Them With a Suit

Boots and suits—you’d expect them to be a fashion faux pas—but with the right boots, nothing could be further from the truth! Whether you’re looking for a rugged and reliable footwear option that will go more places than a dress shoe or loafer, or you simply like the aesthetic, formal men’s boots do exist. And they can look wonderful when styled correctly, even with a suit! 

The Chelsea boot, one of the most formal men’s boot styles there is, offers a versatile and daringly different menswear alternative to explore. Today, the expert tailors of the Oliver Wicks team will walk you through wearing Chelsea boots with a suit, styling it well, and caring for your footwear so you always are dressed to impress.

What are Chelsea Boots?

Let’s start with the basics. What even is a Chelsea boot? If you’re familiar with the equestrian world, the Chelsea boot is a slimline, tapered, and elegant boot, typically made from leather or suede and closely echoing the classic short-riding boot. They have the iconic elasticated side panels for comfort, flexibility, and fit, and they hug the ankle. It’s a very unisex style, dating from the Victorian era, and you’ll find men’s and women’s Chelsea boots. They were also closely associated with the mod era of men’s fashion in the 1960s.
 

They’re classed as the most formal boot style for men, which is why you can elegantly wear a suit with Chelsea boots. The only place they can’t be worn is in black tie attire with a tuxedo. Not sure what shoes to wear with a tux? We’ve answered this for you in another article! 

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What Type of Suit Goes Best With Chelsea Boots?

The Oliver Wicks slogan is, “The fit that suits you”, and the Chelsea boot is no exception! To wear Chelsea boots with a suit well, you need to pay particular attention to the fit and shape of your suit pants. You’ll need slim, tapered pants (think at least modern cut) with only a slight break, in order to showcase the styling of the boot. Your pants should hang outside the boot, not tucked into it, to maintain the correct look and elegant feel.

Chelsea boots do come in varying styles. If you want to keep a fully formal look, err towards well-finished, sleek leather with a more pointed toe and higher ankle. If you want to dress down for a casual lunch date or night on the town, you can introduce some suede for texture and visual interest, and explore a wider toe box. Steer away from thick soles, reinforced toe caps, and other features that suggest work boots, and opt for a boot where the elastic matches the shoe for the most formal feel.

If you’re looking to ace this casual look, try a lighter-colored suit, possibly in a summer fabric variation like linen, and opt for slim lapels and an unstructured form. If you can skip the tie, it’s fine for this combo. It’s the perfect smart casual!

Swapping out the traditional Oxfords for Chelsea boots is a great way to pep up a black suit and kill some of its overly formal vibes. Opt for a nice black leather to style this one. If you prefer classic gray suits, the color of the boot you choose is up to you—burgundy, brown, and black all look fantastic. As long as the boot color blends seamlessly with your suit color, you’re ready to go. A navy or blue suit with brown shoes can create an intriguing, stylish look that’s hard to beat!

How to Color Coordinate Your Chelsea Boots

As we’ve already mentioned, you can’t go wrong with this look if you stick to smart, slimline, and dressy leather Chelsa boots with your suit. If you’re still struggling to match up your look, try these classic combos

• Black suit: Stick with black leather or suede for style.
• Light gray suits: Lighter grays have a hot weather, more casual feel that you can echo in your boots, too—depending on the function, black (for formality), brown, and burgundy all work well.
• Charcoal and dark gray: With a more formal vibe, darker grays look fantastic with black or dark brown in a similar undertone to your suit—you can experiment with burgundy for less formal settings, but it would be a bit too much in the workplace.
• Navy: Almost nothing looks bad with navy—we’d lean into browns for smart-casual and blacks for a more formal look that’s work appropriate.
• Other blues: Navy isn’t the only blue man’s suit you’ll find, of course, how casual or formal this looks will depend heavily on the suit itself—you can experiment with lighter browns for more vivid blues or stick to the tried-and-true dark browns for a smart vibe.
• Forest green: A surprisingly elegant suit choice that’s often overlooked, forest green is a great go-to for functions and can even work in the boardroom—burgundy Chelsea boots add a fashionable touch, browns will always look great, and black can tone this down for a formal look.

In the end, it’s all about tonal balance. If your suit color flows well into the boot, you’re likely just fine. Do remember that bolder colors, like oxblood, pale browns, and burgundy, lend themselves more to daytime events and less formal settings. Dark brown and black are formal classics and make a great default go-to if you aren’t sure how to style yourself. Just remember to opt for a single-tone boot, rather than jazzier options with different colored elastics. 

What Type of Socks to Wear With Your Chelsea Boots

Ideally, very little of your sock choice will show itself to the world if you’re wearing Chelsea boots, especially the more formal, higher cut. It is worth remembering that nylon will be a sweaty choice in an enclosed shoe like this, and the harsher petroleum-based threads can actually damage leather over time. So, opt for a high-quality wool or cotton sock if you can. 

Another factor to remember is that a Chelsea boot looks best when it’s fitted securely to the foot like a glove. If you favor thicker socks, especially in winter, you may want to make sure you’re wearing them when you fit your boot. You may find you need to go up a half-size or size to accommodate them.

Because you won’t be flashing your socks at the world, you can choose your length to suit yourself. However, it’s usually best to opt for a dress sock that’s a little longer than the boot itself. Not only does this prevent chafing, but it also ensures that if your pants pull up when you sit, you won’t be flashing bare skin. When in doubt, opt for black, or match your socks to the boot or suit color.

How to Care for Your Chelsea Boots

When it comes to shoes, how classy your overall look is doesn’t just depend on the style you choose or the price you pay for it. If your top-end leather boots are scuffed, dull, and dirty, they’ll look cheap (and nasty) next to a less pricey pair that’s been loved and cared for. True sartorial elegance comes with knowing how to care for your clothes, as well as choose them.

When purchasing your Chelsea boots, cast an eye over the leather for marks or blemishes. This can indicate structural weaknesses in the leather, plus, who wants to pay for damaged goods? Remember that lighter leather will show wear more easily than darker hues. 

Leather and suede need a moisture-free environment to avoid mildew and mold. If you want to keep your boots in pristine condition, consider storing them with a shoe form. This prevents the toe box from crushing in storage and keeps the boots open to the air. Even if you skip the form, however, ensure that you aren’t crushing your boots under other heavy shoes, and make sure they can air out well. 

Never put your boots away damp, or with mud and grunge trapped in the sole. Make sure there’s nothing in your wardrobe area that can snag or scratch the leather, either. If you want to take your storage game to the next level, invest in a breathable show bag for your better pairs.

The elastic sides will always be a weak point on Chelsea boots, so try not to deform them by yanking your boots on roughly. Instead, place your foot firmly inside the boot and slide forward, pulling on the back of the boot if needed.

How to Clean Your Chelsea Boots

To keep your boots looking their best, get into the habit of wiping them down with a soft, scratch- and lint-free cloth before you put them away. You can use a brush with stiff bristles to clear mud and dirt from the sole. Invest in a great leather-suitable polish and shine them up after every 2–3 wears to keep them looking great. If your boots are suede, it’s a smart idea to buy yourself a special suede brush to revive and refresh them without damaging the soft leather.

If your shoes have lost their signature polish, a good clean should be enough to bring back their luster. When cared for properly, leather can last a lifetime, so it’s worth investing in the right products. Proper leather soap and a leather treatment/cream are cheap to buy and simple to use.

If you do use a leather soap on your boots (not for suede!) be sure to use a damp soft sponge, and don’t soak the leather or you’ll risk it shrinking. For this reason, if your boots get soaked with rain, wipe off what mud and dirt you can and then stuff them with newspaper or use a shoe form to prevent shrinkage. Any remaining mud can be brushed off when they are dry. 

How Long do Chelsea Boots Last?

Quality leather never goes out of style, and when properly cared for, will last decades (even a lifetime). Should you get wear-and-tear on the sole of your boot, you can look at having them resoled instead of abandoning them. The only weak point on Chelsea boots is the elastic at the sides, so take care to avoid overstretching them when you put them on and you’ll be enjoying your boots for many years to come.

As a bonus, pants from Oliver Wicks come with a built-in hem guard, to protect your pants from wearing against boots/shoes over time.

Conclusion

Hopefully, we’ve thoroughly answered a key question for you—can you wear Chelsea boots with a suit? With confidence, you can style this look beautifully with any of our custom suit options, and look great doing so! 

As always, if you have any further questions, you’re welcome to reach out to the Oliver Wicks team at custom@oliverwicks.com