It’s that time of year again: we’re clearing out our summer wardrobes, and seeking items of clothing and footwear which are going to set us up for the cold months ahead. For me, autumn and winter are seasons I deeply love for this very reason: I can’t get enough of the muted tones, thicker materials and perfect balance of practicality and style that the end of the year demand – and that’s the essence of winter style; having that perfect harmony between footwear that will keep your toes warm, while ensuring you’re looking your absolute best.

When it comes to footwear, every refined gentleman should keep his options open, and ensure that he has shoes aplenty to cover a variety of occasions and conditions. It wouldn’t do, for example, to wear the same kind of shoes you’d take on a wintry walk in the park at a social function… no matter how heavy the weather may be! With this in mind, we’ve taken a look at the hottest autumn and winter men’s footwear styles for 2017, and are proud to present you with our six favourites. Each of these has been chosen for their appearance as much as for their quality and practicality, meaning you’ll be stepping out with the confidence your status deserves.

High-top Sneakers

Autumn Winter Footwear

Now that the mercury has plummeted in our thermometers, the season of light trainers and tennis shoes is over. Never mind – there is a wealth of options out there for gentlemen looking to keep things cool, stylish and casual in the latter half of the year.

There has been a massive rise in popularity when it comes to chunky, high-top sneakers, which pack in plenty of retro charm, while also making anyone who wears them look ready to hit the streets and dance the night away. The ‘fatter’ the better – just make sure you don’t make the principal error of pairing them with a set of skinny jeans (or heaven forbid a pair of those ‘super skinny’ jeans retailers seem determined to push onto us). You’ll only end up looking like a kid who’s borrowed his big brother’s sneakers. Keep it in proportion with a well-cut pair of straight leg or slim jeans, and you’ll be bouncing along like it’s 1989.

Stylish and Practical Hiking Boots

Autumn Winter Footwear

I can’t be alone in loving a great autumn hike through the forest – it’s a beautiful and evocative time of year when the natural world really gets a chance to show off its colours at their very best. However, if you’re going to brave the elements while heading out into the wilderness, then a sturdy pair of walking boots are going to be necessary, to say the very least.

However, there’s no need for hiking boots to be the ugly, unwielding things they once were. Many of the world’s top men’s footwear designers have poured plenty of effort into meeting the needs of today’s fashion-conscious outdoorsy gent, and the results have been exciting, to say the least. In fact, many of our favourite hiking boots this year wouldn’t look out of place if worn in the city, and there’s that great comfort of knowing that such shoes are capable of taking on whatever challenge you face them with! Well worth the investment, these are items of footwear you’re not going to regret buying and will set you up for many more winters to come!

21st Century Chelsea Boots

Autumn Winter Footwear

Do you want to know one of my favourite things about this time of year? Aside from the falling autumn leaves, the wine harvest season and the fact that most pubs where I live bring out their seasonal ales and light up their wood fires, I also get to pull on my favourite Chelsea boots.

These versatile and stylish shoes are perfect for gentlemen who see themselves as modern flaneurs, happiest when pounding the pavements of European capitals and looking casual yet suave at the same time. Easy to wear, devilishly comfortable and undeniably cool, they bring a bohemian rock ‘n’ roll sensibility to any outfit, and when paired with a pea coat or classic trench, a slim-cut suit or pair of black jeans, you just know you look charming, chilled and timelessly stylish when stepping out in them!

A Sturdy, Heavy-Soled Derby

Autumn Winter Footwear

At this time of year, what you really want is a pair of shoes that you can shine up and wear with your stylish woollen suit, and yet which are also heavy and sturdy enough to deal with those cold winter days. What could be better, then, than a pair of solid-soled Derby shoes? Perfect for both formal engagements and nights out with your friends, they look great when worn with a double-breasted jacket or full-length overcoat.

A Pair of Military Stomping Boots

Autumn Winter Footwear

When winter rolls around, there’s no time for messing about. If you want to hit the town or the countryside, you need a pair of heavy-duty boots that are as cool as they are durable. The recent trend for military-style clothing and footwear is seemingly unstoppable, and we love the fact that big, bold military stomping boots are bang on trend at present.

The great thing about these shoes is that they bring a devil-may-care attitude to both casual and formal clothing. Wear with your everyday shirt-and-jeans combo, and you look like a man ready for action at any time. Wear with your suit and tie, and you’re showing the world that you’re the kind of man who thinks outside the box and embraces his own unique fashion sense. No winter wardrobe should be without a pair!

Velvet Loafers

Autumn Winter Footwear

If you’re looking for some seriously elegant, decadent evening shoes with a seasonal difference, why not take a sideways approach this winter, and opt for velvet over leather? Sure, these aren’t the kind of shoes you’d want to take outside in the wind and rain… but when spending your evenings in with a glass of wine and some beautiful company by your side, a pair of velvet loafers will make you feel like the lord of the manor. Alternative, opulent and more than a little flash (in the best possible sense), these really are going to steal the show!

Benjamin Norris

Benjamin Mitrofan-Norris is an author and journalist from Bristol, England, specialises in luxury lifestyle writing and wine reviews. He is a lover of life's finer things and has a particular fondness for Alsatian and Eastern European wines, which he fell in love with during his three years working in Budapest.
Benjamin Norris

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