Essential Chelsea Boots for Winter

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Keep your feet dry and your style razor-sharp with a pair of Chelsea boots this winter.

Asia’s winters don’t tend to get very cold, but they can be quite damp, which means that you might have to leave your drivers in the wardrobe for a few months and turn to something equally stylish but a little more robust.

The Chelsea boot is the answer. Created by J. Sparkes-Hall, shoemaker to her majesty Queen Victoria, these savvy ankle-height boots were originally a simplistic alternative to cumbersome riding boots but quickly became de rigueur among the gentry, and for good reason: easy to maintain, even easier to put on or slip off, these boots had all the durability of leather riding boots but also the cut-down style that was slowly being adopted across the United Kingdom.

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If Chelsea boots ever had a renaissance it’s now as they have become a vital component to the skin-tight jeans and shirt look that dominates Instagram. Pair them with your favourite denim and a decent overcoat and you’re set for the street, or add them to urban armour for a sophisticated bespoke suit and spit-shine leather look. With their renewed popularity also comes plenty of variation on the theme, meaning a couple of pairs set you up for not only the chilly months but the whole year’s look.

However, there are some caveats. Because they’re relatively simplistic, you need to ensure you get a pair of Chelsea boots you can maintain well and keep ship-shape – there’s nothing worse than a boot covered in scratches and scuffs! Suede can help with that but then you need to be a bit more careful where you step. You also need the right shape, with an elegant raise and a low profile sole that ensures a seamless line from foot to face.

As we prepare for Asia’s fleeting winter, here are a few of our favourite Chelsea boots for the winter ahead.

Wyatt Leather Chelsea Boot

Wyatt Leather Chelsea Boot

Iconic French brand Saint Laurent has stayed classic with the revisit of its Wyatt boot in black calf leather. Made in Italy with elasticated side panels and are set on Cuban heels, these boots are dying to be polished to a shine and matched with dark denim.

Caractère Capri Leather Boot

Caractère Capri Leather Boot

Another company that does a nice Chelsea boot is Berluti and its Capri boot is one of its best sellers. Sleek, stylish and timeless, this modern take on the classic Chelsea boot is the perfect transition shoe – the tobacco version especially lends itself to dark blue or tan suits, and yet looks just as good with a pair of jeans or short-cut chinos.

Le Cambre Chelsea Boot

Le Cambre Chelsea Boot

A slightly more utilitarian take on the Chelsea boot, the Le Cambre from JM Weston is urban ready. With 100 per cent calfskin outers and interior lining, the boot is as comfortable as a bucket of butter and can handle a little of the rough stuff without losing its appeal.

Chelsea Boot in Suede

Common Projects’ take on this classic boot is presented in tan, ensuring a more casual look that still sends out the message “I care how I look”. With a crepe outsole and suede uppers, the Italian-made boot features a heel pull tab, elasticated panels at the sides, and the brand’s signature gold foil style code.

Character – Brown Chelsea Boot

Character – Brown Chelsea Boot

Dune is another boot guru brand and offers its take on the Chelsea boot in a wide variety of hues and cuts. We love the Brown Character Boot, with its soft rubber soles (yes, not as plush as leather but arguably more durable), flat heel, and deep coffee colour. Perfect with brown, blue or tan suits as well as jeans and chinos, the Duna boot is a bit more affordable than those above, but still strikes the right balance between work and play.

Dunhill Chelsea boot

Dunhill Chelsea Boot

Another classic boot from a brand that knows a thing or two about men’s style, the chocolate brown Chelsea Boot from Dunhill is made in Italy using Blake construction, which allows for greater flexibility. With elastic sides, matte soles, and leather lining, these stunning boots will cost you a pretty bob but it just might be worth it.

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Alpha Men Asia is the region's ultimate destination for today's modern gentlemen, covering everything from travel and style, to grooming, fashion, dating, wines and spirits, and the movers and shakers defining our scene.

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