Three Ways to effortlessly style men’s Chelsea boots

The Chelsea boot. A boot with British heritage that has stood the test of time as a seminal footwear option and essential wardrobe staple for men and women. However, if you’re having Chelsea boot fatigue or trouble styling Chelsea boots, we’re here to help! 

In this guide, we offer three ways to style men’s Chelsea boots with recommendations for formal and casual events and guidance on when to wear calf leather boots or suede and when to wear leather or rubber soles. Learn which Chelsea boot colours work best with which coloured suits to master the men’s Chelsea boot style and avoid a heinous fashion faux pas!

Table of contents

• Are Chelsea boots OK for men?
• What are the best Chelsea boots for men?
• Can you wear Chelsea boots with everything?
• How are Chelsea boots supposed to be worn?
• How to wear men’s Chelsea boots

Are Chelsea boots OK for men?

The short answer is yes, of course! Chelsea boots are a perfectly acceptable and stylish footwear option for men. From the Victorians to The Beatles, Chelsea boots have always been a classic and versatile footwear choice for men and women because you can dress them up or down. Today, Chelsea boots are a timeless boot style and an essential wardrobe staple for men for casual and formal occasions.

What are the best Chelsea boots for men?

Instead of asking, “What are the best Chelsea boots for men?”, we’re going to show you the various styles available that can be dressed up or down, depending on your occasion.

Can you wear Chelsea boots with everything?

While Chelsea boots are a highly versatile footwear option, some combinations don’t quite pair with every piece in your wardrobe. Keep these general guidelines in mind when putting together your outfits. 

• Chelsea boots are great for casual wear with jeans, chinos or casual trousers, which pair well with t-shirts, casual button-down shirts, jumpers and jackets. This may sound obvious, but avoid wearing Chelsea boots with athletic clothing. 
• You can also dress up your Chelsea boots with your formal wear. For example, wear them with trousers, blazers and suits. 
• Avoid wearing Chelsea boots for super formal occasions like black tie events. 

It’s also important to consider colour and material when incorporating Chelsea boots into your everyday wardrobe. Not all Chelsea boots are equal.

Black smooth calf leather will offer a more formal look than a brown suede pair. If you are looking for a pair of boots appropriate for multi-seasonal dressing, suede Chelsea boots in lighter colours are more appropriate for your spring and autumn wardrobe and warmer weather. In comparison, darker colours are more suitable for winter.

How are Chelsea boots supposed to be worn?

Although Chelsea boots are super versatile, there are wrong and right ways to wear them. 

Here are our top 8 mistakes men make when wearing Chelsea boots and how to rectify them. 

1. Don’t tuck! Whatever trouser type you wear with your Chelsea boots, never tuck them in like you would with your lace-up or work boots. It will look clunky and not very sophisticated.
2. Trouser style. Another mistake we see is men wearing the wrong style of trousers or jeans. Avoid wide-legged trousers or boot-cut jeans, as these will swallow the elegant silhouette of the Chelsea boots. You want to opt for straight or slim tapered trousers to create the perfect amount of stacked material over the topline of the Chelsea boots. We wouldn’t recommend skinny jeans as these don’t provide enough tapered material at the top. 
3. No cuffs! Avoid cuffing your trousers. If you feel like you need to cuff, you’re wearing the wrong trouser style or trousers that are too long for you. 
4. Get the correct size. You must have the correct shoe size and fit to achieve the ideal aesthetic. The width of your Chelsea boot should be snug but not tight, but leave enough room for your toes to wiggle to create that elegant silhouette. A top tip is to leave an inch/ inch and a half gap between the neck of the boot and your ankle. Anything wider will cause your trousers to fall inside your boot. 
5. The wrong socks. Wearing the wrong sock types or no socks is the right road to a fashion faux pas! When you sit down, people will see your socks, and there is nothing worse than showing your shin between the top of your Chelsea boots and your trouser hem. Either go for monochrome socks to match your Chelsea boots. Or, choose socks with detail to add a design flare to your outfit. Avoid ankle socks, as these will likely roll down. 
6. Variety is king. We see time and time again men wearing the wrong style of Chelsea boots for the wrong occasion. If you only have one pair, you are limited to the outfit combinations you can wear them with. Instead, opt for a smooth calf leather dress boot for suits, a suede pair for casual events and a working pair for more rugged wardrobe styles. 
7. Wrong sole for the occasion. Chelsea boots also come with various soles; some are better for formal or casual occasions. For example, leather soles are more formal, giving you the classic simplistic look of the classic Chelsea boot. However, if you wear these every day, they will wear quickly. If you wear your Chelsea boots more regularly in more casual settings, consider a rubber sole to help them last longer. 
8. Look after your investment. There is nothing worse than seeing a pair of scruffy Chelsea boots. Representing style and sophistication, scuffed leather and water-marked suede are not the look you want. Regularly brush your suede Chelsea boots with suede cleaner and a rubber suede brush, and regularly polish your leather Chelsea boots to keep them looking their best. Regular cleaning and protection will also elongate the life of your Chelsea boots.

How to wear men’s Chelsea boots

With Chelsea boots being some of the most versatile footwear in a man’s wardrobe, there are several ways to style them. Whether you opt for the sleek and sophisticated suit, effortlessly casual chino or a more out-there option, Chelsea boots are an essential boot every man of substance needs in his wardrobe. Discover what to wear with Chelsea boots below.

1. Chelsea boots and jeans

We’ve already briefly touched on styling Chelsea boots with jeans. If you want to dress down your Chelsea boots, pairing them with jeans is an excellent way to create a casual or smart-casual look.

What kind of jeans to wear with Chelsea boots?

Avoid wearing wide-legged jeans, as these will swallow the silhouette and overshadow your  Chelsea boots. Ideally, you want to choose straight or slim-tapered jeans to create the perfect casual aesthetic that shows off your stylish Chelsea boots in an understated way. Tapered jeans will also give you the best material amount to cover the topline of your Chelsea boots for effortless style. 

You should also think about the colour of your jeans when styling Chelsea boots. 

• If wearing black jeans, stick to darker leather colours like black or dark leaf. 
• Brown Chelsea boots will look better if wearing blue or light-coloured jeans. 
• Note that calf leather will look more formal than suede. 

So, whether you’re going for a casual or smart-casual look, consider the Chelsea boot material and colour.

How should jeans sit on Chelsea boots?

Your jeans should sit slightly over the top of your Chelsea boot shaft. Any lower, and they will overpower the sleek boot. Don’t tuck them in, and make sure there isn’t a gap between the boot topline and your jean hem when you stand, as this can look scruffy.

2. Chinos and Chelsea boots

Chinos are another classic men’s Chelsea boots style. Offering a more formal wardrobe option than jeans, chinos and Chelsea boots are an iconic pairing for smart casual and work occasions.

Can you wear chinos with Chelsea boots?

We would be mad if we didn’t say YES! You can pair numerous Chelsea boot styles with many chino colours. With so many colour combinations available, your outfit options are endless. For example, pair black chinos with black Chelsea boots like the Godwin Chelsea Boot in Black Calf Leather, camel-coloured chinos with plough suede Chelsea boots like the Godfrey D Chelsea Boot in Plough Suede or blue chinos with dark-leaf Chelsea boots like the Godfrey D Chelsea Boot in Dark Leaf Calf Leather.

You can also create a smart-casual look by teaming pale-coloured chinos with suede or grain leather Chelsea boots because they are more casual materials. With this combination, you can still assemble a luxurious and distinguishable look without being too formal.

3. Chelsea boots and a suit

One of the main advantages of Chelsea boots is that you can effortlessly swap them between casual and formal outfits because of their sleek and minimalist design. As a result, whether you’re heading to work or a wedding, Chelsea boots are an excellent option for pairing with suits.

What suits go best with Chelsea boots?

Chelsea boots will work well if you opt for a slim or straight-legged suit. Although you want to avoid a suit trouser that is too skinny, otherwise it won’t neatly fit over the top of your Chelsea boots. If you’re worried, opt for a straight-legged suit trouser for the optimum material amount. 

You must also consider suit colours when styling Chelsea boots. Here are our recommended pairings for different suit colours:

• Black. If you’re wearing a black suit, you’re probably attending work, a funeral or a formal wedding. We recommend choosing a black calf leather Chelsea boot like the Threadneedle Chelsea Boot in Black Calf Leather. 
• Grey. Similarly, if you’re wearing a grey suit, you mean business. Black Chelsea boots are the best option for grey suits.
• Blue. Blue is a fun-coloured suit popular for weddings, where you can experiment with different coloured Chelsea boots. Opt for a contrasting brown to make your sleek Chelsea boots stand out like the Godwin Chelsea Boot in Dark Leaf Calf Leather.
• Burgundy. If you’re wearing a burgundy suit, don’t wear burgundy Chelsea boots unless you want to look like a monochrome block. Opt for contrasting browns to break up the bold colour. 
• Brown. Similarly, if you’re wearing a brown suit, choose a shade of brown that contrasts against the brown suit shade. 
• Light sand or cream. If it’s summer and you’re wearing a light sand or cream linen suit, contrast the pale suit with dark brown or burgundy Chelsea boots to make them pop. If it’s hot, you might opt for a more breathable suede Chelsea boot for a laid-back casual look and feel like the Godwin Chelsea Boot in Rustique Janus Suede.

Men’s Chelsea boots Cheaney Shoes

Now you know what to wear with Chelsea boots for men; your outfit options are endless, with many styles and types of Chelsea boots to select. From sleek and sophisticated leather-soled Chelsea boots for the office to rugged commando-soled Chelsea boots for casual wear, these boots offer complete versatility to your wardrobe.

Remember, when styling Chelsea boots, consider style, colour and fabric to match the boot to the occasion, and you should be good to go! Discover our extensive range of classic and stylish men’s Chelsea boots at Cheaney Shoes today and complete your footwear collection. 

Related blogs:

• From Royalty to Rock’n’Roll: The History of Chelsea Boots
• Dress shoes with jeans: How to wear formal shoes with jeans
• The best shoes to wear with chinos