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Winter Style: Winter Footwear Guide

When faced with the elements, your footwear choice determines whether you make it through the daily commute to work dry or with a sodden step. Whilst it might be wet at (most) times, you can also be assured that it will be cold during the winter months too. Armed with the knowledge that you’ll need to battle the seasons – not just in the fashion sense – it’s time to dress for the weather forecast.

DiscerningGent.com has you covered as the footwear stakes rise during the months where practicalities match up, if not exceed, the style needs when the weather turns. Remember, the thing that is keeping your feet dry from the wet streets is your footwear and what it’s made from. A leather sole might look good but is prone to absorbing water, therefore rubber is a more practical choice and can still look as stylish depending on the type of footwear. Conversely, a leather upper is far more durable and weatherproof than canvas or fabric uppers when the weather get wet.

With these aspects in mind, let’s take a look at the options available to discerning gents in the winter months.

Chelsea Boots

The slick styling of Chelsea boots – the detail free leather with elasticated opening – means they have the versatility to work smart and casual look. The more winter-proof versions will have rubber on the soles, either throughout or in parts to provide the extra grip needed when the streets get slippery. The key to keeping a Chelsea boot looking good is plenty of regular polishing for smartness but also for the practical benefit of keeping out the rain. (Pictured: Loake Ascot Chelsea Boot in brown leather)

Chunky Brogues  

Whilst brogues offer year-round style and weather-proof functionality in equal measure, opting for a chunkier style of brogue – the kind with a thicker sole – providing more distance between your feet and the wet floors. Chunky brogues can be paired up with suits and give a touch more presence than a derby style and easily works with jeans or chinos for the smart-casual look. (Pictured: Ted Baker Rauri Toe Cap in tan)

Chukka Boots

Where in the summer the desert shoe is a staple style pick, in the winter months you’ll call on the heftier brother that is the Chukka book. Forget suede when it’s wet and cold, instead opt for wipe-clean leather and a gripper rubber sole. Chukka boots work the same in the style stakes as its summer suede brother – pair with chinos, dark denim or tailored wool trousers. (Pictured: Barbour Readhead Chukka Boots in chocolate)

Hiking Boots

There are times in the city – where weather and pavement terrain conditions – that warrant the need for footwear fit for the hills. Yes, we’re taking about above-the-ankle boots made a premium leather fitted with D-rings for lace fastening and likely waterproofed throughout. Perhaps more the casual look than smart, the key to not overdoing it with a pair of these in the style stakes is to make sure they aren’t covered in Gore-Tex and bright colours – think more along the lines of tan or brown/dark-brown leather. These pair well with jeans, flannel shirts and chunkier coats. (Pictured: Timberland Heritage Eurohiker Boots in brown smooth leather)

Winter Trainers

Is there such a thing as a pair of winter trainers? In a word, yes! The same principles apply about material – they need to be made of leather or any other waterproof material rather than canvas, lighter fabrics or suede. Colour is also a consideration in the style stakes – tones like black, navy, greens and darker browns. These darker colours are less likely to show up dirt and grime compared to lighter tones. (Pictured: Adidas Originals Jeans in black)

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