What to Wear with Chelsea boots

The trusted men’s Chelsea boot is one of the most versatile footwear choices you can own as they can be paired with a variety of wardrobe favourites. Whether it’s enjoying a leisurely day in the city, or meeting up with friends for evening drinks, this classic style never lets you down. Boasting undeniable comfort and an innovative ease of wear design, here at Rieker, we’ve put together a how to wear guide so you can ensure your men’s Chelsea boot outfits make the impact they deserve. 

Mens chelsea boots

How to wear Chelsea boots

Men’s Chelsea boots are a must-have for business, casual and formal outfits. They can pair with jeans and a t-shirt effortlessly but equally be matched with a suit for chic formal attire.  Iconically styled out by the Beatles and Mick Jagger this fashion forward style allows you to be creative with your look with just one pair. When choosing your Chelsea boots you need to consider the style, material and colour to ensure they blend well with your capsule wardrobe.

Leather Chelsea boots are always a good choice as they make the transition from day to night easy as they can be tucked under your suit like dress shoes, but still be worn with a turned up jean for a more casual look. 

When considering your men’s Chelsea boots outfits we suggest you change things up depending on the style and colour you opt for. Here we will explore what to wear Chelsea boots with depending on your choice. This way, your style is well-fitted to the clean or soft lines of your boot. 

What to wear with leather Chelsea boots

As aforementioned, leather Chelsea boots are one of the most easily adapted styles as their elegant leather construction can be partnered with both casual and formal ensembles.

Black leather Chelsea boots blend perfectly with dark, tight-fitting jeans, a white loose button-down shirt and a black leather biker jacket for a grungy street style. Brown leather Chelsea boots, however, pair better with lighter jeans, chinos or upscale trousers. 

Whether it’s a formal suit or a simple jean and t-shirt combo it’s important your trousers are fitted to the clean lines of your boot. What we mean is you don’t want baggy access material flapping at your legs. So if your jeans are a little gapy, we would suggest giving them an upturn. 

Black Chelsea Boots


What to wear with suede Chelsea boots

If you want to ooze sophistication with ease, then suede Chelsea boots make the best option. Suede boots provide an urban appeal and partner perfectly with skinny distressed jeans and earthy toned overcoats. They can be transformed to night with a blazer or cashmere sweater. 

Due to their varied colour options, suede boots allow you to experiment with different shades with darker colours like deep chocolate and khaki being more popular during the cooler seasons and tan and pearl-grey alternatives working their magic better come spring. 

What to wear with brown Chelsea boots

The rugged aesthetic of men’s brown Chelsea boots is sure to take your sleek casual wear up a level. Showcase an outdoorsy look with a sheepskin or Barbour style jacket over a layered flannel shirt and t-shirt.

Brown Chelsea boots were made for layered outfits. We love them paired with jean jackets, bombers and utility shirts. The important tip to remember is to keep your trousers slim to match the lines of your boot. 

As brown Chelsea boots come in a variety of shades, we’ve got some colour advice to share: 

Taupe brown – Pair with grey, maroon and shades of red.

Honey brown – Pair with yellow, beige and other earth shades. 

Mens Brown Ankle Boot


What to wear with black Chelsea boots 

No wardrobe is complete without a stylish pair of men’s black Chelsea boots. A footwear trend to never go out of fashion, you can combine them with chinos and an Oxford button-down or smart jumper for an office ensemble that can be showcased come evening too. 

Classic and ultra-cool, black Chelsea boots complement dark slim-fit jeans perfectly. Team up with a scoop-neck t-shirt or fitted turtleneck, depending on the temperature.

Adding a contemporary feel to a well-tailored three-piece, you can even throw on your black Chelsea boots for all those formal occasions in your diary. 

How to style Chelsea boots

Casual Chelsea boot outfits

For date night 

Pair tan suede Chelsea boots with distressed or washed out jeans, a cashmere sweater and a printed scarf for a unique fashionable finish.

For weekend vibes 

Partner brown suede Chelsea boots with skinny denim jeans, an oversized white t-shirt and khaki bomber jacket and loose beanie hat.

For lunch out 

Slip-on grey suede Chelsea boots with distressed jeans, a black roll neck jumper and overcoat. Finish with a smart wristwatch.

Smart casual Chelsea boot outfits 


Combine brown leather Chelsea boots with slim-fit jeans, a fitted dark jumper and a well-structured light-coloured overcoat. 

Drinks with friends 

Style out tan leather Chelsea boots with light jeans, a light cotton button-down shirt and a khaki or camel coloured sweater over the top.

Work attire

Wear black Chelsea boots with dark grey jeans, a turtle-neck shirt and textured style blazer.

Formal Chelsea boot outfits 

That special occasion 

Show up in black leather Chelsea boots and a well-polished three-piece black suit. Compliment with a shirt, tie and pocket square in matching hues.

Upcoming job interview 

Show off black Chelsea boots with well-tailored grey trousers, a slim-fitting dressy shirt, and a black leather belt on show.

Weekly business meeting 

Step in with black leather Chelsea boots, slim-fit chinos, a slim grey blazer and a button-down white shirt.

As well as offering undeniable style, Rieker’s anti-stress boot soles can be found in all Rieker men’s Chelsea boots, so you can enjoy incredible comfort and foot support while looking great. The easy slip-on fit means they are easy to pull on and off when you’ve got limited time – a great everyday choice for a busy man.

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