Best Chelsea Boots For Men 2020

Chelsea boots will make any outfit you wear more stylish and classy.

Even the simplest of outfits like black jeans and a white t-shirt will look amazing and have a whole new vibe to it by replacing sneakers with a sleek pair of Chelsea boots.

In this guide I will help you:

  • Choose the right pair of Chelsea boots
  • Tips on how to best wear them and show you example outfits
  • Advice on getting the best Chelsea boots for men on the market

The Best Chelsea Boots

For Men

(Discounts For All Chelsea Boots Here)

What You Pay is What You Get

What you pay for is what you get when it comes to quality Chelsea boots.

Chelsea boots thrive on materials and construction. If you want a pair of boots that will last you a long time, invest in a high-quality pair that won’t deteriorate after a few months.

If you only care about achieving the sleek stylish look of Chelsea boots, even the most inexpensive brands will help you achieve this, but if you want quality – top of the line materials, construction, and quality control, it’s wise to invest in a high-quality pair of Chelsea boots.

Chelsea boots are an investment piece, they’ll always have a place in your wardrobe (they’ve been in style for 100+ years) – a high-quality pair will last you for years to come and even mold itself with age to create a unique look that is specific to you (like a pair of raw denim jeans).

Leather Vs Suede

Suede Chelsea boots look more luxurious and are extremely in style in 2016. Suede works great with casual outfits and will add the touch of class you’re looking for.

Leather Chelsea boots are on the menswear, formal attire side of men’s fashion, leather will look amazing when wearing a suit.

Pro tip: Suede will break down faster in harsher climates such as snow and slush, so be mindful of the environment you’ll be wearing them in before making a definite decision on which type of Chelsea boot you’ll be buying.

How to Wear Chelsea Boots Style Guide

Chelsea boots are designed to be slim so pair them with a slimmer fitting pair of jeans, this creates a streamlined look of the lower body which looks amazing.

You can wear Chelsea boots in a streetwear outfit, a formal outfit or with just a regular t-shirt and jeans outfit. That’s the great thing about Chelsea boots, you can work them into any type of outfit and it will give a whole new perspective on that outfit.

Below I’ve put together some styles for inspiration.

Dressed up

This is the classic rockstar chic pushed by Saint Laurent Paris. Leather jackets, Blazers, Button ups. Think Harry Styles.

chelsea boots leather jacket
chelsea boots all black outfit
harry styles chelsea boots


There are so many ways to rock Chelsea boots with this style. Flannel, Button ups, Hoodies even knit cardigans can all look great.

flannel chelsea boots

grey-ripped-jeans-chocolate-brown-chelsea-boots distressed-jeans-oversized-sweater-chelsea-boots all-black-outfit-with-chelsea-boots

Fall & Winter

Chelsea boots look amazing in a fall outfit. Overcoats make the perfect combination with a pair of sleek boots.