At this moment, as I sit here at my desk (not in my pants for once) and the sun is shining. It would appear that our quirky British summer is squeezing out one last hurrah; which is excellent. A fact I appreciated very much last weekend whilst falling over a lot at Bestival.

But irrespective of this late summer bounty, our wardrobes must always be looking forward. We must anticipate the dreary, grey, damp, dullness of the months to come and prepare for the freezing, wet, blowy and miserable winter that we will inevitably have to endure.

You will often hear that preparation is the key to success – with our wardrobes, preparation is everything. Being able to pull out the appropriate clothes for the conditions at the drop of a hat is one of the easiest ways to stay ahead in the style game and ensure you aren’t still walking around in lightweight chinos and loafers when the snow comes falling.

When we think of autumn/winter footwear, there are certain staples that always spring to mind: brogues, brogue boots, military boots, worker boots etc. They form the backbone of nearly every winter wardrobe and we are all quick to suggest them to anyone who might be in need of advice. However, while these silhouettes rightly deserve their place in our homes and on our feet, our reliance on them can lead us to forget about other types of shoe; styles that might equally protect our feet from the cold and could in fact help elevate our overall aesthetic another notch.

The Chelsea Boot

With roots in the equestrian field and designed for practicality the Chelsea boot is the perfect shoe for the colder months. If you opt for one with a chunkier, rubberised sole you can even tackle the ice and snow we are occasionally blessed with, so it is definitely worth your consideration.

With its clean and simple lines, the Chelsea boot can be just as versatile as our other footwear and without any pesky laces to tackle, much more practical.

How To Wear: Chelsea Boots
Chelsea Boots Lookbook

Men's Chelsea Boots Lookbook

Wear Them With: Heritage

With heritage holding onto its place as the top AW12 trend (at least here at FashionBeans) it’s a good job that the Chelsea boot can slide right in without any great fuss.

Heritage is about simplicity; the clothes aren’t fussy, the materials they are made of are practical and durable, the designs, colours, cuts and shapes aren’t complex and the purpose is beautifully direct; jumpers keep you warm, coats keep you warm, shoes keep you on your feet and accessories are meant to be both essential and hardwearing. It isn’t a style that needs much thought or construction, it should just be thrown on.

The careful matching of colours and cuts in the Italian Riviera outfits of summer just don’t relate. Take things back to basics, heed Matt Allinson’s advice and keep fashion simple. Slim jeans, crisp shirts and autumn appropriate outerwear.

  • Burberry London Gingham Check Cotton ShirtBurberry London Gingham Check Cotton Shirt
  • Barbour Olive Lobster Clip Hurst JacketBarbour Olive Lobster Clip Hurst Jacket
  • Reiss Mississippi Clean Raw Denim IndigoReiss Mississippi Clean Raw Denim Indigo
  • Vesty Kurt Geiger LondonVesty Kurt Geiger London
Wear Them With: Tailoring

The Chelsea boot is a great addition to your work wear wardrobe. Their smooth, unfussy lines make them ideal for use with tailored trousers or slim cut suits, with the familiar elasticised side panel adding a unique touch rather than making a bold statement.

If you want to use Chelsea boots in your smart-casual or formal wear then I would stick to black versions, this will ensure the elastic detailing doesn’t stick out too much and that the colour contrast between clothing and footwear is not too stark. A slim navy suit, crisp white shirt and perhaps a red or green tie, with a pair of black Chelsea boots will be a winning combination in any work place.

In a less formal setting you have more flexibility with colour but you will find that black, more often than not, will be the most appropriate and easy to wear. Chelsea boots were a big feature of Mod culture so you could also look to infuse a touch of the 60s with a buttoned up polo and a pair of tweed or herringbone trousers. Alternatively, make things a little more modern with a collar bar shirt.

  • Reiss Boston Wide Stripe Collar Bar Shirt BlueReiss Boston Wide Stripe Collar Bar Shirt Blue
  • Topman Grey Vargas Herringbone Heritage Suit JacketTopman Grey Vargas Herringbone Heritage Suit Jacket
  • Topman Grey Vargas Herringbone Skinny Suit TrousersTopman Grey Vargas Herringbone Skinny Suit Trousers
  • Grenson Declan Leather Chelsea BootsGrenson Declan Leather Chelsea Boots
Tackling The Rockstar

The Indie rocker image, much championed by the likes of Alex Turner, Miles Kane, Julian Casablancas and that guy from One Night Only, has a special place in many a man’s heart. The lackadaisical approach to dressing, minimal layers and somehow both fussy and uncomplicated details had us yearning for it and repulsed by it.

The problem is, whilst this look makes excellent use of menswear staples – black jeans, black jacket, basic tees etc. – it can often come across as somewhat immature. Whether it is a ridiculous mess of hair, unnecessary accessories, ripped, torn and super tight jeans or hideous printed t-shirts, there is always something there that removes a certain level of refinement.

With just a little refinement, the rocker look can still be rocked, we just need to be more sensible with our clothing choices. Stick to skinny or slim cut black jeans – anything wider just won’t work – and also bear in mind that the wider the leg, the chunkier the boot can be. I would suggest that you use either a biker or bomber jacket. If you crave a little more structure, switch out the tee for a shirt.

A final piece of advice would be to avoid winkle pickers. In my opinion, pointy shoes have had their day, stick to those that are slightly more rounded and you have something much more classic and timeless.

  • James Perse Long-sleeved Cotton Henley T-shirtJames Perse Long-sleeved Cotton Henley T-shirt
  • Asos Leather Biker JacketAsos Leather Biker Jacket
  • Asos Skinny Black JeansAsos Skinny Black Jeans
  • Peters Kg Kurt GeigerPeters Kg Kurt Geiger
Men’s Chelsea Boots
  • Ted Baker Enapay Chelsea BootsTed Baker Enapay Chelsea Boots
  • Topman Hudson Moran Chelsea BootTopman Hudson Moran Chelsea Boot
  • Ted Baker Aleant – Leather Chelsea BootTed Baker Aleant - Leather Chelsea Boot
  • Loake Thirsk Leather Brogue Chelsea BootsLoake Thirsk Leather Brogue Chelsea Boots
  • Topman Hudson Bekker Zip BootsTopman Hudson Bekker Zip Boots
  • Allsaints Buckley Chelsea BootAllsaints Buckley Chelsea Boot
  • Belstaff Tourmaster Black Brown BootsBelstaff Tourmaster Black Brown Boots
  • Paul Smith Shoes Chocolate Leather Otter Chelsea BootsPaul Smith Shoes Chocolate Leather Otter Chelsea Boots
  • Boss Black Brunet Chelsea BootsBoss Black Brunet Chelsea Boots
  • Cluedo Mr KgCluedo Mr Kg
  • Barker Eskdale Chelsea BootsBarker Eskdale Chelsea Boots
  • Lanvin Leather Chelsea BootsLanvin Leather Chelsea Boots
Final Word

So there we have a brief round up of the Chelsea boot, a worthy addition to any man’s wardrobe. With the world and all his mates coming around to the brogue (which still is no bad thing) the race is on to find something that will make you once again stand out from the crowd, and this humble boot could help to do just that.

But how do you feel about them?

  • Are you a fan of the Chelsea Boot?
  • Have you ever thought about them before?
  • Have you been put off them by certain stereotypes?
  • Might you consider them now?
  • Are you already a wearer? How do you wear them?

Let me know in the comments below.