How to wear Chelsea Boots

Written By Bakes

Avid writer on Men's Hair, Grooming, and Lifestyle!

The Classic Chelsea Boot originates from the Victorian era and were created for the Queen in response to opting for comfortable footwear for horse riding and walking. Today the boot has become a fashion item with credit to the Beatles for its revival in the 60’s. As there are now many variations of the boot we have produced a Men’s Expert Guide on How to wear Chelsea boots.

The absence of laces, ankle length, rounded toes and low heels make the boot one of the most recognizable silhouettes. Not to mention most Chelsea boots have elastic gussets making them easy to put on and slip off, a simple feature which ranks them as a favourite amongst men.

This Men’s Expert Guide will show you

  • Outfit Options suitable for each style of Chelsea Boot
  • Guideline on how to wear Chelsea Boots
  • Practices to avoid
  • Frequently Asked Questions

Our only goal is to ensure you obtain the best results which will be reflected in your outfit choices after reading our guide!

We have gone through the trouble to show & demonstrate which style of Chelsea boot is best suited for selected outfits, so you wouldn’t have too 😀 Lets get to it!


How to wear Chelsea Boots: Outfit Options

Business Attire

how to wear chelsea boots example

Chelsea boots come in many different fabrics, one of which is leather. These are typically constructed with a single piece of leather which ultimately keeps stitching to a minimum which gives the boot a clean polished look.

This look is best paired with a 2-piece suit and the leather Chelsea boot is complimentary to this outfit. For business attire your leather Chelsea boots should either be black or dark brown.


Smart Casual

how to style chelsea boots example 2

For smart casual looks the Chelsea boot provides the perfect solution as the simple silhouettes work well with other semi-formal wear. In our example we have paired dark brown Chelsea boots with slim fit jeans and an overcoat.

The difference between business attire and smart casual outfits as it pertains to the Chelsea boot is that we recommend leather Chelsea boots for business attire while smart casual options permits you the option to select leather or suede Chelsea Boots. Pair with plain t shirt or shirt.


Smart Casual 2

chelsea boots outfit mens

As I mentioned above Chelsea Boots worn for a smart casual look will allow for both suede and leather options.

The suede Chelsea boot is a great alternative to casual sneakers. Your able to pair them with a shirt or jumper (dependent on your choice) with slim fit jeans or chinos for a relaxed appearance.

This specific look works great as your also able to transition to different looks in a matter of seconds. For example, this smart casual outfit once worn with a fedora hat will become a stylish casual outfit. Great for the office and drinks after work!


Smart Casual 3

best ways how to style chelsea boots example 3

A great alternative to a 2-piece suit is a great fitting blazer & chinos.

More formal than jeans but less formal than business attire, this look embodies class and sophistication. To ensure you master this look the fit of your blazer must be in proportion to your upper body accompanied with slim fit chinos, finished off with leather or suede Chelsea boots.  

Grey, beige, navy and khaki chinos are a great start with dark brown or black chinos.


Contrast Look

contrast look

To intentionally create a contrast look will involve the combining of opposing colours on the colour wheel. In effect your going to want to select darker colour tones such as black or dark navy blue for your garments and a complete opposing colour such as light brown.

Ensure that your clothes follow the same colour theme, for our example above we have selected a dark navy jacket, chinos and t shirt all the same colour and light brown boots.

For an even more apparent look opt for beige colour Chelsea boots in suede.



casual outfits for chelsea boots

As the first half on our list has consisted of smarter looks we will now shift our focus to casual wear.  Aside from being a great quality shoe the Chelsea boot also allows for versatile outfit choices.

Most casual outfits will pair well with simple sneakers, the Chelsea boots however allows those same outfits to become dressier.

Pair your suede denim boots with a double denim outfit. The denim shirt can be fitted or baggy, with slim fit jeans. Feel free to opt for a denim jacket instead of a denim shirt.


Casual 2

casual outfit with boots

We have discovered that most people posing the question, how to wear Chelsea boots are looking for inspiration around casual styles as opposed to formal wear. This is because most people understand how to wear Chelsea boots with formal attire. Our casual outfit 2 example shows how creative your outfits can become.

Our 2nd casual outfit consists of colours that don’t necessarily match but are complimentary to each other. The focus here will be to select the same shade hat and boots with the upper and lower half different colours.


Biker Look

biker style example

I know you hate maths, WE DO TOO!

But help us work this equation out.

What do you get when you pair a biker jacket + slim fit Jeans + Chelsea Boots together?

The ultimate cool look! Correct

The combination of the biker jacket and Chelsea boots is the embodiment of sophisticated style!  Sophisticated in the sense that your Chelsea boots possess minimal style and stitching, muted tones and beautiful design while the Biker jacket is stylish & grabs attention.


We have taken it a step further and produced a Chelsea Boots Outfit photo gallery which will best serve you as a visual guide and an inspirational reference point. 


Guideline on how to wear Chelsea Boots

Now that we have covered all the different outfit options its best you keep the following styling principles in mind.

Care for your Chelsea Boots
Caring for your Chelsea boots will come in the form of investing in a simple leather hydration cream. The application of this cream will not only prevent dry cracks, scratches and stains but will increase your shoes lifetime.

– Ensure the Right Pant Length
Ensure that the end of your chinos, jeans or trousers sits just over the top of your boots.

-Choose the Right Fabric
Leather Chelsea boots for business attire & suede Chelsea boots for casual outfits.

Water Resistance for Suede
Apply water resistance sprays to your Chelsea boots to keep them looking sharp in wet weather conditions.

-Have a Rotation
Its best to have a rotation of Chelsea boots in different colours to allow you to match multiple outfits and increase the lifetime of both shoes. Start off with black and brown afterwards feel free to purchase more colours such as navy and grey.

-Invest in High Quality Boots
It should go without saying, you get what you pay for.
Poorly constructed Chelsea boots are likely to be subject to damage & wear and tear very soon. Chelsea boots in the range of $90 upwards will last longer.


Talking about investing in High Quality boots Esquire have curated a list of some of the Best Chelsea boots here – The 10 Best Men’s Chelsea Boots To Buy Now And Wear Forever

Practices to avoid

-No Shorts
Chelsea boots are to be worn with full length jeans, trousers or chinos only.

-No Baggy Pants
Baggy jeans and pants ultimately ruin the look by covering the majority of the boot. The idea is to ensure pants sit just over the top of your boots to create a fitted look. Your best options will be slim or skinny fitted pants.



-What pants do you wear with Chelsea boots?
The best pants for Chelsea boots are slim fitted chinos, trousers and jeans. Avoid baggy jeans or shorts!

-Are Chelsea boots easy to put on?
Due to the elastic gussets making them easy to put on and slip off Chelsea boots are very easy to put on. It should go without saying you will need the right size shoe for this effect, however Chelsea boots are easy to put on.

-Should you cuff jeans with Chelsea boots?
While cuffing your jeans with Chelsea boots will come down to personal preference and style it’s best you do not cuff your jeans.
As I mentioned before the pants should be placed over the boot, if you feel the need to cuff your pants they are most probably the wrong style for these boots.