How To Wear Chelsea Boots And Jeans

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Under Armour - T-Shirt                             Hawksmill – Jeans                           Giorgio Brutini - Boots

Under Armour – T-Shirt                   Hawksmill – Jeans                   Giorgio Brutini – Boots


Jeans and Chelsea Boots are the two seasonless extremely important things every man should have in his clothing. Whatever your jeans of choice, they can easily be worn with a pair of Chelsea boots because they are both incredibly versatile items. Swapping out your trainers for Chelsea boots is a great way to redo your style and keep your look current.

How to Wear Men’s Chelsea Boots

The Chelsea Boot is a classic. Able to change the unpredictable weather and constantly maintaining its smooth and shiny image, it’s a shoe which can do no wrong. While it’s versatile on the feet, it’s also versatile in your clothing as well – especially when paired with a black or light wash jean. Lucky for you, we’ve narrowed down our favorite styled boots.

Leather Chelsea Boots

These pairs from Hudson have a smooth and shiny, waxy finish that makes them a touch of fancy than other styles.


Whether it’s a day in the office, a working lunch or you just want to turn up to your lectures looking smart, Chelsea boots are your number one option. In order to keep your whole outfit looking slick, you need to choose a black slim pair of pants.

Next, give your outfit the classic level of smart and choose the classic slim fit shirt. You can either go for a suit or a smart white shirt for this look. If you are wearing a suit then don’t be afraid to mix it up a little bit with color and pattern.


The beauty of black boots is that no matter where or when you wear them, they always bring a defined edge to your outfit – including your casual day-to-day looks. Wrap up for these months ahead by switching your shirt for a sweatshirt or hoodie for a downplayed and really casual look that’s great for those off days.


Steve Madden Men's Aziz            Florsheim Men's Belfast           English Laundry Men's Fort

Steve Madden Men’s Aziz                                           Florsheim Men’s Belfast                                  English Laundry Men’s Fort


Brown Leather Chelsea Boots

Another classic way to wear a pair of Chelsea boots; a brown leather pair of Chelsea boots easy to wear and go perfectly with so many outfits. Perfect for those days when you want to dress in a relaxed way and want something easy to wear, brown leather Chelsea boots work with a large number of looks and colors.

You can either go for a pair of blue jeans, navy pants or even black jeans or pants, as the Chelsea boots will work either way. Throw on a simple T-shirt or button down and you’ll be good to go.


Vogstyle Men's Trench Coat                MLG Casual Pants              Kenneth Cole REACTION

Vogstyle Men’s Trench Coat                     MLG Casual Pants                      Kenneth Cole REACTION


Pointed Chelsea Boots



DAVID ANN Classic                  Rocorose Turtleneck                    

        DAVID ANN Classic                                   Rocorose Turtleneck                         Santimon Boots


Needing a pair of Chelsea Boots for your Friday Night drink? With an undecided dress code, it can seem a bit of a headache to meet the balance of casual and smart. Like every other classic shoe, this is a middle ground.

To the Bar

Pointed Chelsea boots are the blurred lines between looking custom-designed yet extremely easy. Always providing a slick detail to any outfit, it’s the shoe that can shine your denim. Pointed toe-cap, smoothly polite design and completely wearable throughout the year.

With a slimming ankle design, it’s like these shoes are built to be worn with your favorite slim fit jeans. When traveling from work to the bar, pair your pointed Chelsea boots with skinny jeans. With the slim outline on the legs, don’t be afraid to have the hem over your boots, or tucked in – whichever is suited to you. To finish the look and to create an outfit which is seasonless with a touch of dirt

Brown Suede Chelsea Boots



APTRO Wool Coat Just No Logo Jeans   Madden Men's M-Graye

APTRO Wool Coat                             Just No Logo Jeans                 Madden M-Graye Boots


If you want to keep things casual and comfortable for a day of lectures or an afternoon pint, then jeans and a hoodie, elevated with an overcoat is about to become your new best friend.

A simple grey hoodie doesn’t have to be a boring option – it can be dressed up a little smarter. We sometimes like to opt for more earth-tones for this season, creating a neutral look which still grabs the attention to the shoes.


If the sports-expensive and fancy look isn’t for you, then don’t don’t be afraid to smarten up your whole look. You can always team black jeans with brown suede Chelsea boots. It’s a classic combination that will work for more formal occasions.

Black Suede Chelsea Boots

Black suede Chelsea boots are probably the most classic way to wear these clothing staples. The great thing about black is that it works with so many other colors and you’ll struggle not to pair them with anything. Knowing how to wear black suede Chelsea boots is easy, just like knowing what to wear with black jeans, their versatility and ease of wear speak for themselves.



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