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Home / What to Wear With Chelsea Boots

What to Wear with Chelsea Boots

Chelsea boots have a classic, clean style that complements any man’s wardrobe. Their versatility may lead some to question, what can be worn with Chelsea boots?  Chelsea boots can fit with a variety of looks, depending on your personal style and environment.


Chelsea Boots Design

Chelsea boots grew to popularity in the 60’s in England, partially due to the Beatles donning them as a signature look. Their sleek look remains popular to this day. Chelsea boots have no laces and are roughly ankle high. They have an elastic panel on the side that enables them to be pulled on while remaining close-fitting.

Chelsea boots are typically made of either leather or suede. Leather is the more formal option, while suede is seen as more casual. However, current trends often twist this convention, allowing for even more versatility.

They come in several different toe styles, such as round or pointed. Pointed toe Chelsea boots are typically worn in more formal occasions, however they may have a place in a casual environment when styled with the right attire.


What can I Wear with Chelsea Boots?

The clean design of Chelsea boots suits a variety of styles, both in and out of the office.


Casual Chelsea Boot Attire

Chelsea boots automatically elevate any casual look. While suede Chelsea boots will provide a more relaxed appearance, leather can be appropriate as well.

Chelsea boots pair well with jeans and a T-shirt for a casual weekend look. When pairing Chelsea boots with jeans, try a slim cut, but not skinny jeans. The jeans need to sit comfortably over the top of the Chelsea boots. Skinny jeans will need to stretch to fit around the jeans, squishing the boot and the hem.

For a smart casual look, pair leather Chelsea boots with black jeans and a sweater. The leather boot will provide a sleeker look, without leaving the realm of casual attire. While black leather is the most classic, brown leather provides a less serious look that maintains the same level of class.


Chelsea Boots in the Office

Chelsea boots also have a place in many office or formal environments.

For business casual office environments, leather or suede Chelsea boots are appropriate. However, avoid patent leather, as it can look overly formal in a business casual office.

Chelsea boots pair well with blazers and chinos for a polished look. Choose slim cut chinos if they can fit comfortably over the upper of the boot and are not too tight in the calves.

When paired with a suit, Chelsea boots can be a great alternative to loafers or other dress shoes. Choose a Chelsea boot made with leather and a structured upper. Black Chelsea boots will always look the most formal, but brown may pair well with certain suit colors and patterns.

Choosing a Chelsea Boot


Chelsea Boots


When deciding on a Chelsea boot, think of your personal style and wear habits. Will you be wearing your Chelsea boots to the office, or will they only leave your closet on the weekends?

A Chelsea boot in a classic black or brown leather are versatile, as they can easily transition between formal and casual attire. However, if you’re looking for a shoe that is more unique or fun, try on a Chelsea boot in a color that complements other items in your closet.


Regardless of your personal style, the Chelsea boot is a solid boot to add to your wardrobe. This classic style is sure to be a fixture in your closet for years to come.

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