The Ever Popular Chelsea Boots

Written by Robert | 04/10/2014

One of the most sartorially astute decisions a man can make this winter is to incorporating a pair of evergreen Chelsea boots into his wardrobe, ready to wear them with a whole host of everyday staple items.

There is a foreboding sense that winter has arrived as the weather cools dramatically and the first day of autumn officially passed a couple of weeks back. But swapping lighter and brighter summer clothing for more substantial darker items doesn’t have to be all doom and gloom. A fresh batch of the season’s must-have Chelsea boots are here at Mainline Menswear in a range of colours, prices and brands to suit all tastes. View the whole collection here.


Fashion Savvy males will have been sporting classic variations of this shoe for many a year now but it looks like 2014/15 could be the transitional period where these designs really snowball and make it into the upper echelons of mainstream men’s fashion. Chelsea boots are loved by their fans for perceived elegance and versatility more than anything else but it is the sort of shoe which- if bought from a quality brand- will last a lifetime of wear and tear. Most top brands will even now offer leather and heel re-conditioning services to replenish the appearance and comfort of any shoes that have seen better days, a much cheaper alternative to replacing them.

This said, it isn’t perhaps the shoe for every man. If you want to make this style work you shouldn’t be scared of the odd bit of polish to keep their appearance in-check and if you feel most at home wearing t-shirt jeans then this isn’t going to become your new go-to trainer.


They might be most famously associated with rockers like Pete Doherty in recent culture but it’s clear the boot has gone through a stage of evolution whereby you don’t have to wear skinny jeans or shirt and blazer combination to pull them off convincingly- now, you can do so with a variety of different styles in mind.

Also known by names such as the Paddock boot, Dealer boots and even Jodhpur boots, the Chelsea boots are always characterised by a close fitting, ankle high fit, which will be finished with an elastic side panel. The design itself is years old and actually harks back to the Victorian era in Britain, proving that this is one of fashion’s rare timeless commodities.

For a truly authentic look it is advisable to stick to a black polished leather but it can look just as natty in shades of tan and brown. This is a quintessentially English item of clothing so it is always going to sit well if you keep this theme for the rest of your ensemble with the likes of a pea coat, a crisp shirt or perhaps a pork pie hat or scarf.


Despite being created centuries back they are perhaps most famously associated with mod culture of the 1960’s and part of the reason for the boot’s renaissance this year could have something to do with the alleged mod revival which has been reverberating through fashion in the past year or two. Brands like Fred Perry are always closely associated to this movement and more recently Pretty Green and Dr Martens have become identifiable with avid mod fans.

It is guessed that originally the boot was created in around 1850 for horse riding purposes but this soon became a symbol of exclusivity and young “city slickers” began wearing them in the early part of the 20th century. Perhaps their most famous wearers are the Beatles who helped develop the reputation even further to become a permanent fixture in urban outfits.

Below: pop stars new and old have embraced the Chelsea Boot


It is quite a cliché to describe a fashion trend as versatile, but this item is a true example of just that, you only need to look at the brands who have decided to feature the silhouette this time around. H by Hudson offer the style in both brown and black and their smart casual style is perfect for those wanting to team their boots with jeans. Dr Martens air cushioned sole versions are not only the most affordable, they are an ideal choice for a creating a mod look, combine these with a Fred Perry polo and a Harrington jacket and you’re good to go. Finally, for a touch of class take Oliver Sweeney’s version and pair it with any smart or formal attire to devastating effect.

What did you think of this post?


Thumbs up review image


Average review image

Not for me!

Thumbs down review image