How To Wear Chelsea Boots: The Daniel Man Style Guide - Daniel Footwear BlogDaniel Footwear Blog How To Wear Chelsea Boots: The Daniel Man Style Guide - Daniel Footwear Blog
15% Off First Full Price Order FP15
How To Latest Trends

How To Wear Chelsea Boots: The Daniel Man Style Guide

Over 150 years of popularity just can’t be wrong, the Chelsea boot is a fashion staple. Men’s Chelsea boots have become incredibly varied in style, meaning you can wear them for a whole host of different occasions. But if this is your first time ditching the trainers and shoes for this more interesting style, you’ll likely be looking for tips on how to wear Chelsea boots and get the best out of them.


You’re in the right place. We’ve put together a straight-talking style guide to help you style up your Chelsea boots and get fully on board with this timeless footwear trend.


First, let’s run through some of the main Chelsea boot styles:


Leather Chelsea Boots

The most well-known, classic style of Chelsea boot is the plain leather style. Simple, sleek and no-fuss, perfect for smart-casual occasions.

Suede Chelsea Boots

The classic Chelsea boot’s casual cousin, the suede style is great for weekends and informal occasions.


Brogue Chelsea Boots

The more dressed-up version of the classic Chelsea style, the Brogue Chelsea boot makes a fantastic day-to-evening all-rounder.


Lace-Up Chelsea Boots

As close to casual as it gets without wearing trainers, the lace-up Chelsea ankle boot style is the jeans’ best friend.


Now you’ve seen the styles, it’s time to style them up:


Casual: How to Wear Chelsea Boots With Jeans


Starting with the casual end of the scale, Chelsea boots and jeans are a classic combo that will never go out of style or season. But which jeans should you wear them with?


Slim Fit Jeans: These are the jeans most commonly worn with Chelsea boots because the leg-hugging fit and tapered shape allows the hem of the jeans to sit naturally on top of your boots.  


Tapered Jeans: Much like slim fit jeans, tapered jeans are another Chelsea-worthy style for the same reason as above. The slimmer fit towards the ankle accentuates the boot and allows the hem to sit just right over the top of the boot.


Skinny Jeans: Good news if you’re a fan of skinny fit jeans, these also work very well with Chelsea boots, especially if you’re looking to create a more alternative, rock-esque vibe.


The Golden Rule: Whichever pair of jeans you style your boots with, make sure the hem of your jeans sits just over the top of them, or somewhere higher up. Pay attention to the leg length, as anything too long won’t look as good and will cover up too much of your stylish new boots.


Smart: How to Wear Chelsea Boots With a Suit


You may be slightly hesitant about switching out traditional formal shoes for Chelsea boots when it comes to your suits, but it really does work.


Black Suit: If you’re going for a black suit we would advise you opt for a pair of black Chelsea boots to keep the look streamlined and smart. Pointed toe styles are great for an extra sharp look, but you can soften it with a rounded toe if you’re not keen. If you’re wearing your suit to work, try and choose a plain, simple boot design to keep things professional. Your suit trousers should sit neatly over the tops of your boots, not flapping around the ankles.


Grey Suit: With a grey suit you can branch out to tan Chelsea boots if you’re looking to take things a tiny bit more casual, but black boots work just as well here. The grey suit and Chelsea boot combo is perfect for all formal and smart casual occasions from the office to weddings, and is perfect for guys who want to give the classic gentleman’s look a slightly more contemporary twist. You can also get away with a little brogue detailing here if you want something a little more exciting.


Navy Suit: Navy suits look great when paired with black, grey or tan Chelsea boots. The colour of boot you choose will dictate how smart the overall look will be, with black boots working best for the office and other colours working well for formal events and weddings.You could also break out the suede Chelsea boots with a navy suit, as the colour is softer and lends itself more easily to casual looks.


Chelsea Boot Styles: Top Tips to Remember


Pants and jeans should always sit over top of boots – but only just, we don’t want to hide too much of the boot itself.


Never tuck your trousers or jeans into the boots – it’s just not a good look.


Straight/Slim fit jeans are best  – perfect if you’re just testing the Chelsea boot waters


Avoid bootcut or loose fitting jeans – they will hide too much of your boot and the stylish effect will be lost


Try rolling up the hem of your jeans – this works especially well with tapered jeans and puts extra focus on the boot


Look after them – leather and suede should be kept brushed and polished for a long and happy life together


Now you know how to style them properly, it’s time to go shopping. Check out our range of men’s Chelsea boots here at Daniel Footwear and find your new favourite style.

You Might Also Like