What Trousers to Wear with Chelsea Boots? (10 Types Of Trousers)

What Trousers To Wear With Chelsea Boots?

Footwear has always been a tricky purchase. You have to think about the occasion, the weather and of course the outfit that you are going to wear it. But there is one shoe you can’t go wrong with – the Chelsea boot.

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The Chelsea boot is one of the most versatile boots available on the market. They are smart enough to wear with a suit but also casual enough to be worn with jeans on a night out.

However, this versatility does come with a few downsides. Because they can be worn for almost any occasion, how do you know which trousers are best?

One thing that sets them apart from other boots is the fact that they can be worn with jeans and trousers alike. In this post, we will look at some of the top trousers to match your brown Chelsea boots.

So let’s get started!


10 Types Of Trousers to Wear with Chelsea Boots

Chelsea boots are the perfect combination of classic and modern. They’re a timeless addition to any man’s wardrobe, effortlessly adding a touch of style and sophistication to casual and formal outfits.

The beauty of Chelsea boots is their versatility; they can be worn with pretty much any style of trouser.

When it comes to Chelsea boots, you’re going to be wearing them often. They are your go-to boot that will feel smart with a suit and casual with jeans.

It might sound obvious, but trousers can also look great when worn with Chelsea boots and create a really smart look when paired up together. You don’t need to wear black or grey trousers either, as there are plenty of different colored options available that will work just as well and can be worn with much more casual outfits too!

Your Chelsea boots will work with a number of trousers and we have listed 10 of the best ones below:


1. Trousers with Turn-Ups

Turn-ups are an incredibly versatile addition to any trouser. They’re subtle enough to be paired with most outfits, making them the ideal way to show off your Chelsea boots!

Trousers with Turn-Ups Will Show Off Your Shoes

It’s hard to get the right balance between boot and trouser leg, but turn-ups do it perfectly. Their shape complements the sleek lines of Chelsea boots, and the double layer of fabric helps to frame them in a most pleasing way.

They Add Balance To Your Outfit

Turn-ups work well with various trouser lengths; however, if you wear short trousers on top of Chelsea boots, there can be too much skin on display. You don’t want an ankle gap as big as the Grand Canyon, so turn-ups can help you avoid this scenario. If you have long legs, then turn-ups are also great for adding some balance – a bit like a belt does for your waist.

 

Perry Ellis mens Classic Fit Elastic Waist Double Pleated Cuffed Pant, Caviar, 36W x 30L US

 

The turn-ups add a touch of individuality

Small details, like turn-ups on trousers, can make a big difference to how your outfit looks overall.

Trousers with turn-ups are a great way to add a little bit of whimsy to your look, something that’s not too fussy or over the top, but just quirky enough to be interesting. They also add some depth and character to an otherwise flat trouser leg.

The turn-ups and the Chelsea boots create a subtle shape around the ankle

The way the turn-up sits against the Chelsea boot creates some much-needed definition at the ankle. Since trousers are usually quite wide and baggy at this point, it’s important to have something that defines the ankle in a more flattering manner than just fabric falling flat.


2. Wool Trousers

Wool trousers are an incredibly smart choice of trouser that works perfectly with Chelsea boots and other smart shoes. They can be paired up with a suit jacket for a formal look, or simply styled in a more casual way for everyday wear.

How to Wear Chelsea Boots with Wool Trousers

The secret to wearing Chelsea boots with wool trousers lies in the fit. You don’t have to do much to accommodate the boot style. All you need is a pair of wool trousers that are cut slim.

Regardless of the color or pattern, as long as your wool trousers are slim-fit you’re good to go. You can pair them with any Chelsea boot style or color.

 

Woolly Clothing Men's Merino Wool Longhaul Pants 34w 34l Moss

 

Flexibility of Style

Wool trousers do not limit your style to one type of look. And neither does a pair of Chelsea boots. In fact, pairing these two together will only increase your flexibility when it comes to creating outfits this fall and winter.

A classic combination is a blue wool trouser paired with brown suede Chelsea boots, but there’s more than meets the eye. This same outfit can be worn in multiple ways, depending on what top you choose and how you accessorize it. For example, add a tan trench coat for a polished look or opt for a white hoodie for a casual getup.

It’s versatile

It doesn’t matter if you want to dress up or down – wool trousers and Chelsea boots work with everything! For a smart look, pair your trousers and boots with a blazer and shirt for work or dinner dates. For a more casual look, go for a turtleneck sweater or lightweight jacket instead of a shirt and blazer.


3. Smart Trousers

The versatility of Chelsea boots means they can be worn with a number of different trouser styles including smart trousers. Pairing black Chelsea boots and black trousers together will create an elegant style that is perfect for business meetings and other formal events.

Smart trousers are an easy way to keep your legs warm in winter, but there are plenty of other reasons why we love them too. Here are three great ones.

 

Celebrity Pink Jeans Women's Smart Trouser Uniform Pant, Black, 1

 

Dress them up or down

Smart trousers look great when worn with a suit jacket and tie, but they’re equally at home with a casual shirt and cardigan. They’re also very easy to dress down by leaving off the jacket or swapping it for a sweatshirt.

They’re versatile

Smart trousers go well with trainers and loafers, as well as Chelsea boots and brogues, so you can wear them with pretty much any outfit and still look good, regardless of whether you prefer casual or smart clothes.

They never go out of style

Smart trousers have been around for many years, which means they’re unlikely to suddenly fall out of fashion (like some bolder styles do). This makes them a smart investment that you’ll be able to enjoy wearing for years to come without worrying about whether they are still in style or not.


4. Leather Trousers

It’s not just men who have been rocking leather trousers over the past few years; women have too! We love the combination of leather trousers and Chelsea boots because they complement each other so well and create a sleek look.

Both items are versatile

Chelsea boots can be paired with many different items, whether it is trousers or jeans. And the same can be said for leather trousers. The reason I think these two items look good together is that you can create so many different looks by pairing them together.

For example, if you want to create an elegant vibe, you can pair your leather trousers with a white shirt, a black blazer, and some Chelsea boots. Or you can go for a more casual look by pairing your leather trousers with a t-shirt, a gilet, and some Chelsea boots.

 

ROLZMOR Women High Waist Faux Leather Pants Solid Color Straight Wide Leg Pu Leather Leggings Trousers (Black, X-Large)

 

They both go well with other colors

The fact that both Chelsea boots and leather trousers are neutral colors means that they work well with other colors and prints. For example, if you pair your black leather trousers with your brown suede Chelsea boots, it’s likely that your outfit will work well with most other colors and prints, as the neutral tones mean that they won’t clash with any other colors or patterns that you choose.


5. Tapered Trousers

Tapered trousers look similar to chinos in many ways, but they generally have a more formal fit. They look best when paired with leather Chelsea boots in black or brown. This type of trousers will look great on any man who wants to create a smart-casual look.

 

Dockers Men's Comfort Knit Trouser Tapered Fit Smart 360 Knit Pants, Timberwolf, 32Wx32L

 

  1. One of the benefits of wearing a pair of Chelsea boots with tapered trousers is that they are extremely comfortable. However, make sure that the trousers have enough room in the leg area so that you do not feel restricted while moving around.
  2. Another great thing about these boots is that they can dress up an outfit in a very subtle way; so if you are looking to impress someone on a date or a special occasion, try wearing these boots with your favorite pair of jeans or khakis. If you want to look even more stylish, go for a pair of black pants and dark brown Chelsea boots.
  3. The third reason why tapered trousers look good with Chelsea boots is that they give you the option to wear them with almost any kind of outfit. It is just important to choose the right one for your body type and personal style.

6. Dress Pants

Dress pants are slightly less common than chinos or jeans but still work well with Chelsea boots, especially when you want to dress them up more than usual. Keep your shoes shiny and your pants pressed, then add a shirt and jacket to complete the look.

Some guys prefer to pair black boots with black pants to help create a clean line from top to bottom, but that’s not necessary if your clothes fit well together as is.

 

Calvin Klein Men Slim Fit Dress Pant, Grey, 32W x 32L

 

Simple black dress pants and Chelsea boots

The simplest form of the modern gentleman look is with black dress pants, a plain white shirt, and black Chelsea boots. This gives you a classic look without being too loud or flashy. If you have dark brown hair and dark skin, this is an especially good option for you to create contrast in your outfit.

Black slacks and Chelsea boots

You can also wear black slacks with this style if you want something less formal than black dress pants but still want to keep things simple. A pair of black slacks will give your outfit a slightly more casual feel than black dress pants would, but they can still be worn to work and other important events.

If you are going to wear slacks instead of dress pants, then make sure they are a dark color, such as gray or brown. Also, try to avoid pleated styles because these will not look as good with Chelsea boots as flat fronts will.


7. Jeans

One of the most popular combinations is undoubtedly jeans and Chelsea boots. They’re both versatile so whatever style you decide to go for, whether it be a skinny or straight leg, they’ll still look good together. The best color in our opinion has to be black jeans and dark tan Chelsea boots – it just works!

Blue Jeans

A classic look that never goes out of style, blue jeans are an obvious choice when it comes to wearing Chelsea boots. This stylish and simple look can be worn throughout the year and works great with either brown or black colored boots depending on where you’re going!

Skinny Jeans

The classic outfit for Chelsea boots is a pair of skinny jeans. It’s the perfect combination of smart and casual and is ideal for formal events or evenings out.

Jeans and Chelsea boots go together like fish and chips; they’re the perfect match. A pair of jeans can be dressed up or down depending on which style you choose, so you can easily switch between formal and casual looks by changing your footwear.

 

Levi's® Womens 311 Shaping Skinny Maui Views 31 30

 

Trouser Jeans

Trouser jeans are similar to regular jeans but feature a more formal cut that makes them ideal for pairing up with other smart items in your wardrobe. These jeans will also look great when paired with Chelsea boots and can easily be dressed up or down depending on the occasion.

When wearing trouser jeans, opt for a darker wash and pair them with Chelsea boots and a shirt. If you really want to make an impression, throw on some braces too!

Cuffed Jeans

Cuffed jeans are another way to show off your shoes while staying stylish and cool at the same time. Pair with a plain white T-shirt and black Chelsea boots for that classic rock ‘n’ roll look!

Denim Jeans

Contrary to popular belief, denim jeans can look very smart when styled correctly. If you want to make your denim jeans look smarter and more formal, then we suggest you wear them with either black or dark brown Chelsea boots! This works well with both indigo jeans and black jeans.


8. Chinos

Chinos are one of the most versatile trouser types out there, and they look great paired with Chelsea boots. These trousers will give your overall outfit a smart-casual look that is perfect for lunch dates or socializing after work.

Chinos are also extremely comfortable, so you won’t have any problems when it comes to walking around all day. Chinos are another great fit for Chelsea boots, whether you go for black, grey, or beige. Pair with a shirt and blazer for a smart look, or add a T-shirt for a more casual appearance.

 

Amazon Essentials Men's Classic-Fit Wrinkle-Resistant Flat-Front Chino Pant, Khaki, 34W x 32L

 

Chinos are an ideal option for those who want a smart-casual look that will allow them to dress up or down depending on the occasion. Chinos are very versatile and can be worn with almost anything, so they’re perfect if you want to mix things up a bit.

They look great paired with Chelsea boots and are versatile enough for any occasion, from casual Fridays at work to a night out with friends. The one thing to be careful of is making sure the chinos aren’t too long on you so that they bunch up around the ankles.


9. Corduroy Pants

Corduroy trousers can be worn on a number of occasions, from work to nights out. In our opinion, they look best with brown Chelsea boots as it creates that vintage vibe that corduroy is so well known for.

 

Goodthreads Men's Slim-Fit 5 Pocket Corduroy Pant, Khaki, 36W x 32L

 

Smart Casual

Corduroy pants are smart enough to wear to the office (when paired with a blazer) but are just as comfortable as sweatpants. This makes them perfect for something like weekend brunch or a night out at the bar — occasions that require a step up from jeans but aren’t so formal that you need to don your suit.

To achieve this look, pair your corduroys with a white button-down shirt (or T-shirt) and a leather belt. If possible, opt for brown Chelsea boots; they’ll complement the color of your pants and add visual interest.


10. Cargo Pants

Cargo pants are growing in popularity, yet it’s still not something everyone feels comfortable wearing. If you want to try them out, pair them with Chelsea boots. They look great together and the boot helps balance out the cargo pant’s baggy shape.

 

Dickies mens Regular Straight Stretch Twill Cargo work utility pants, Black, 34W x 32L US

 

Corduroy is a classic textile that has made something of a comeback in recent years, particularly in pants form. And they look great when paired with Chelsea boots, providing you wear them in the right way.

Lighter shades work best – pastel pinks, blues, and greys – while dark corduroy trousers will look more like regular trousers than corduroy ones.


11. Khakis

Khakis are a great alternative to jeans on days when you want to dress up a little bit but don’t want to wear trousers. The two go especially well together if you’re wearing Chelsea boots in a dressier color like dark brown or black. Make sure to get the right fit so that they’re not too long or too baggy.

They Make For A Chic Look

Another reason you want to consider pairing khakis with Chelsea boots is that it makes for a chic look that is comfortable enough for nearly any occasion or use. By pairing your Chelsea boots with khakis you will really be able to get some of the best possible results from your outfit as a whole.

 

Amazon Essentials Men's Straight-Fit Casual Stretch Khaki, Dark Khaki, 38W x 32L

 

A clean, classic style

Pairing Chelsea boots with khakis are all about keeping things simple. Chelsea boots are inherently sleek, and they go great with something like khaki pants because they help create a clean, classic look. It’s the perfect way to put together a polished look that doesn’t feel over the top or overdone.

Show off your ankles

Another reason why khakis look good with Chelsea boots is that they allow you to show off your ankles. By pairing a slim, straight-legged khaki with Chelsea boots, you’ll show off your ankles and give a little more definition to your legs. It’s subtle but impactful — especially if you’re wearing skinny jeans all the time and want to switch things up a bit by wearing something like khakis for once.


In summary, Chelsea boots are an iconic men’s style. Chelsea boots are a men’s style staple that works with almost anything.

From the classic black Chelsea boot to new interpretations, such as polka dots, florals, and animal prints, this is a style that will never look out of place in your footwear arsenal.

You may also be interested in… What Shoes to Wear with Mom Jeans? and What Trousers to Wear with Doc Martens?