Chelsea Boots – Men’s Outfit Inspirations and Buying Guide
Chelsea Boots

Chelsea Boots – Men’s Outfit Inspirations and Buying Guide

The Chelsea boot made their first debut as a legitimate style in the 1960s, when a similar boot appeared on the feet of the Beatles. Fast forward several decades, and the boot now is the perfect pairing with a Wall Street business suit.

Not only are these boots handsome — and come in a variety of leather tones from a deep burnt brown to a black coal — but they are incredibly comfortable. That’s because the Chelsea boots is known for a soft, elastic side panel that lends itself to a refined and sleek yet still versatile look. It’s perfect to add a streamlined, modern look to your dressed up look.

If you’re after a versatile shoe for every occasion, Chelsea boots are the way to go. These ankle boots are stylish, yet easy to pair up with your everyday outfits, making them the perfect transitional piece for day to night looks.

Whether you want to look dapper at the office or simply want to introduce different elements to your everyday outfits, these shoes are the way to go.

Chelsea Boots are Versatile

Chelsea boots are an absolute favorite type of boots for many guys out there. They can be worn with many different outfits and through various seasons.

These boots are also great for various occasions. You can wear them to work, weddings, casually or to business meetings. Whatever the occasion, you can wear Chelsea boots without being out of place.

These boots can be worn so many times throughout the year, making them a must-have pair of boots. Invest in a high-quality pair and it will be so worth it.

Suede or Leather Chelsea Boots?

Along the journey of your search, you will find Chelsea boots in a few different materials. Such as suede and leather.

Both are great options and you should eventually, consider having both in your footwear rotation.

If this is going to be your first pair, I recommend leather because it can be dressed up like a dress shoe and down, like an everyday boot.

Once you have the essential first pair, you can explore other options. You can get another leather pair in a different color or try a suede pair.

What Color Should I Get?

You can buy Chelsea boots in many colors. Although there is a great variety, it’s good to stick to simple and basic colors.

Simplicity is a great thing, especially when it comes to a timeless style.

For color, stick to brown, tan, grey and/or black. By having these colors, it allows you to wear it with the majority of your clothes rather than having a shoe that can only go with one single outfit.

Not only will that cause your boots to gather dust, but you’ll also feel like you wasted money on boots you don’t even wear that often.

These colors also allow for great versatility, which is important when you are building a wardrobe. You want to have flow in your wardrobe – meaning that it is easy to put together outfits, instead of having one-off pieces.

How Should Chelsea Boots Fit?

When buying these boots, I recommend actually trying them on. The reason I say that is because there are a few important things to think about when it comes to these boots. Let’s get into them.

They don’t have laces. This means you lose the luxury of tightening or loosening when a shoe doesn’t fit well. When you try these boots on, you have to make sure they fit and are comfortable.

The fit you’re looking for is a snug fit and you don’t want your toes to be squeezed together.

Instead of sizing up or down, you’ll have to change the width of the boot. This may mean going with a different brand and that is okay. Finding the perfect fit will ensure that the boots last you a long time while keeping you comfortable.

How To Style Men’s Chelsea Boots

Chelsea boots are extremely versatile and can be successfully worn with both casual and more formal styles. Their straightforward and clean design means that they can complement a range of outfits without clashing or seeming uncoordinated. So, whether you wear them with jeans or a suit, these shoes can look great.

Creating a top Chelsea boot outfit comes down to dressing for the occasion and going from there. Whether you’re aiming for a casual, smart casual, business casual or semi-formal look will affect which Chelsea boots you should wear and the items that you should wear with them.

Casual Attire

Chelsea boots can easily be dressed down for a casual look and can make a stylish alternative to sneakers. While you can wear either leather or suede Chelsea boots for a casual look, the latter will have a more relaxed appearance.

In particular, brown suede Chelsea boots project a cool casual look that pairs perfectly with other essential items from your wardrobe. Try wearing a pair with some skinny jeans, a white T-shirt, and denim overshirt for a contemporary weekend look.

Smart Casual Attire

While Chelsea boots can easily work for casual outfits, they can also suit smart casual styles well. Thanks to their sleek appearance, these boots will help elevate your classic closet pieces to appear more polished. Simple items, such as black jeans, a rollneck sweater, and a double-breasted coat, will all appear seriously suave when worn with Chelsea boots. Although both suede and leather styles can be used to create this smart casual appearance, a black leather pair will be best for achieving a sleek urban vibe.

Business Casual Attire

If you think your Chelsea boots are just for after-hours and on the weekend, you should think again. These boots are so versatile that they can also be worn with business casual outfits. The key to achieving the perfect business casual outfit with your boots is to find the right balance.

Start by choosing a leather style of boots to keep things sophisticated, but avoid patent options as they may seem overdressed. Then, keep things casual yet office-appropriate with some chinos, an Oxford shirt, and a blazer. Opting for a check or pattern on your blazer or shirt can also help give your look a smart style.

Semi-Formal Attire

Chelsea boots can make a surprisingly good footwear option for semi-formal occasions. An excellent alternative to Oxford shoes, brogues, and loafers, Chelsea boots can match well with a suit.

All you need to do is select the perfect pair. If you’re wearing a black or grey suit, stick to black boots for a formal feel and consistent colour palette. If you’re donning a navy or brown suit, you can choose between both black and brown boots to suit your style. Also, don’t forget to ensure that your trousers fall neatly just over the tops of your boots for a sleek silhouette.

Key pieces to work with

Chelsea Boots With Chinos

More dressed-up than jeans but less formal than a suit, chinos and Chelsea boots scream sophistication. The trick here, is understanding fit and layering with the right pieces. Above all else, steer clear of chinos that grip to your calves.

This has the unfortunate effect of making you look like you’ve continuously skipped leg day. Instead, opt for a pair of slim cut chinos that fit comfortably over the boot’s upper. Styles in beige, navy and khaki are great foundations for any casual wardrobe and you’ll be able to wear them all year round.

When it comes to choosing your top half, casual shirts are a good bet. To add some personal flare, look for bold colours in checks and stripes that will add a point of interest to the outfit. Pair this with a half-zip jumper or a quilted jacket in the cooler months for an effortless look.

Chelsea Boots With Jeans

Chelsea boots and jeans are a recipe for a classic, laid back look. Easy to throw on after work for drinks or dinner, a pair of these boots in a dark brown or black will instantly elevate a pair of indigo jeans and a casual shirt.

For best effect, make sure that the jeans are slim cut (not skinny) as this will allow the top section of the boot to sit comfortably under the hem without getting squashed. Pair this with a white chambray button-down shirt from the likes of Brooks Brothers or Ralph Lauren and a matching belt for an easy but elegant outfit.

If your style skews a little more to the likes of Yeezy, suede Chelsea boots can add a hint of polish to distressed denim like nothing else. Pair this with a fitted plain tee-shirt in khaki and a black bomber jacket for a more sophisticated take on street style.

Chelsea Boots With A Suit

While most would think of Oxfords, brogues or loafers when considering suiting suitable footwear, the Chelsea boot is another great option that’s often more suitable than you’d think.

Coming in a wide range of different colours, materials and finishes, there’s something that’ll work with every scenario. How about some brown leather boots with a grey suit? This will give you that effortless smart look, as London Chelsea boots with a suit is one of the most signature looks of them all.

If you prefer a classic navy or blue tailored suit, try pairing them with a dark brown leather Chelsea boot. The contrast of the brown against blue is a failsafe, complementary combo that’ll elevate any ensemble. always leave your trousers sitting over your Chelsea boots, as this makes for a cleaner, smarter look.

Nailing a brown Chelsea boot outfit can be a difficult task, but once you’ve got it right there will be no stopping you from rocking the look day in, day out. The same goes for if you’re wondering how to wear heeled Chelsea boots.

Chelsea Boots With A Winter Coat

Chelsea boots are perfect for winter, adding that extra layer of warmth and keeping the wet weather out of your socks. This being the case, you’ll likely be pairing them with a winter coat at some point. As a rule, if I’m wearing a collared shirt, I’ll opt for a more structured wool coat in either a navy or camel.

Suit Supply have a great selection as do retailers like Harrolds or Mr. Porter. Look for either mid-thigh, single breasted styles or pea coats if you’re vertically challenged.

Alternatively, if you’re going for a more casual look – with jeans and a tee for example – look at layering a light wash denim jacket or gilet over a chunky knit sweater. This has the appeal of being both rustic and supremely comfortable.

The Rules for Wearing Men’s Chelsea Boots

There are no hard and fast rules that are unique to Chelsea boots. Of course, you want to make sure that your colours don’t clash, but other than that, the main thing to remember is that generally, the leg of your trousers should sit over the top of the boot. Still, don’t forget, you’ve paid money for those boots, so don’t hide them – your trousers or jeans should sit just over the top.

What to Look for When Buying Chelsea Boots

As with any shoes, make sure they’re going to fit well. It’s not worth saving yourself a tenner just to have the shoes rub on your heels and toes, as that would be a complete waste. A decent sole is something to look for when buying your new boots – this will help to increase the life and will stop them looking worn out as soon as you start wearing them everyday.

Whether you’re going for leather, suede or a synthetic version of the boot, ensure they are made of the good stuff as you don’t want them falling apart as soon as you buy them. While we’re on the subject of good material, make sure you consider when and where you’ll be wearing them.

Suede will not be good for the wet weather but will look smarter in the evenings, whereas leather is an all rounder and will be suitable for both the autumn and winter months. If you do go for suede you can buy shoe protector and cleaner so your shoes will look newer for longer. A black version is probably the most versatile and best Chelsea boot for men.


Chelsea boots have been a firm favourite for the last 150 years, and you just cannot go wrong with them. They’re perfect for every occasion, whether you want them for a formal event, for work, or for going out in town.

Keep your colours matching and you’ll be able to do what you want with them. Mix and match different T-shirts, or shirts and pair them with jeans or trousers. Whatever your favourite outfit is, there’s a Chelsea boot to match. It just goes to show that when it comes to the Chelsea boot, the world is your oyster.

Read Also – How to Get the Skater Style

No Comments

Leave a Reply

Recent Comments
Recent Comments
Close Bitnami banner