Dressing As A Classy Gentleman For All Winter Occasions

winter, men, style fashion, boots, tie, jacket, blazer, hat, coat

Winter is coming, and that means that a whole host of new style decisions are available to be made. If you’re looking to upgrade your wardrobe, why not take this winter opportunity to sort it for good? The winter is often the best place to experiment with new styles, because the layering and general ‘classiness’ of the colder seasons affords greater risks. Despite all the streetwear brands gaining popularity and rightly so, middle aged gentlemanly wear is taking off, and there’s no better time to update your look in this way. Classy is back and it’s bigger than ever.

Here are a few tips to dress like the gentleman you know you are, without overdoing it or trying ‘too’ hard.


Dressing well in the winter season doesn’t always mean purchasing new coats and thick waistcoats. Sometimes, adapting your current wardrobe to the present state of your body can work wonders. After all, bodies change, and so why should we lose out on the money we have already invested in our wardrobe? It’s likely you have a few items from winter’s past you still love and that are still in good condition. However, the difference between wearing these well and poorly lies in how well they fit. Consider bringing all the clothes that matter to a tailor and having them refitted. This can often rival the cost of acquiring new items well.


We mentioned that layers are the best way to dress to impress in the winter season, and not only that, they’ll help you keep warm. Middle aged men will look sharp in a comfortable woolen blazer, preferably adhering to a darker or light brown aesthetic. This can help any dress or denim shirts stand out depending on which color you match it with. If you can, adding a little flair with a darker lapel and blazer pocket header can help the piece stand out in itself. Try to go for around three to four buttons, and make sure they fit with the darker oak tones of the blazer itself. Not only will this piece function as a warm and stylish alternative to a sweater, but it will often go with a variety of outfits, enough to become a staple piece in your wardrobe.


Hats keep your head warm, but they can also be very stylish. It can feel hard to pull a hat off well, and depending on your face shape different styles will work for you. The standard length beanie can work well for people with round faces, as angular or flat hats will work against and emphasise the roundness of your cheeks and jaw. Believe it or not, beanies can look classy as long as the style fits, and you’re opting for a small casual look. Oblong faces will do well with hats such as flat tops, or at least those with a wide brim. Try and opt for darker tones here, as a hat should be an accessory to your outfit, and never become the focal point. Those with a humorous desire can opt for a helicopter rotor on the top of a baseball cap, but unfortunately we wouldn’t recommend that if pursuing class.


How often do you purchase new ties, and where do you purchase them from? To round off your business suit, you may have taken to wearing ‘novelty’ tries, or cheap ties that ultimately degrade your outfit. Of course, no one could blame you for a quick and easy solution during your daily work, but if you really want to squeeze the most out of your formal outfit, consider going for a grenadine tie. These are woven from Italian silk instead of the simple knitted ties you can find elsewhere.

While a tie might not initially be considered as the main piece of an outfit, you’d be surprised as to how these can upgrade and bring together a suit from mediocre to great. Opt for warm, earthy tones. If you like, or are attending a social event, this is a great place to play with color. You might choose to opt for maroons or light pinks. Just be sure it fits with the theming of your outfit and you’re sure to feel excellent wearing it.


A great overcoat is the staple of the mens winter wardrobe. You should make this purchasing decision with longevity in mind. Spending highly here for something that will last, as opposed to something cheap to get you through the season is key. A great coat can last for a decade, while a cheap coat for a few months. If you can, choose thickset heavy woollen coats, or if choosing a more social garment, consider an easy but stylish parka. While we’ve often emphasised how darker tones work best in winter, beige or even dark cream jackets can work well for a guy here, and lend some lightness that might otherwise be lacking from the man’s wardrobe.


When walking on wintery roads and pavements, the need for a sturdy grip is high. Who says you should sacrifice looking good for this? Getting some faux leather boots with sturdy grips that conform to your ankle will give you the walking flexibility and foothold you truly need, while helping you look great. Winter sneakers can be bought, but often the conditions outside are too adverse to use them unless you live in a very urban city. A great pair of boots can last a man a long time, but be sure to polish them and fit them with moisture protection otherwise you may need to have them repaired more often than you think. There aren’t many color options that work here outside of darker hues. Darkest brown or black will work wonders, and help your outfit conform to the same style no matter what clothes you choose to wear. Strike a decent balance between comfort and style, because we all know that some boots can feel difficult to walk in. What fun is fashion if you hate wearing it? Some shoe specialists can conform boots to the shape and size of your feet. If you can afford this, this can be a wonderful way to craft something which works for you, something you know is customized and will give you plenty of walking and stylish pleasure.

With these tips, you’re sure to become the classy gentleman winter was just waiting to help you uncover.

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