7 ways to master winter style a guide for men

3 minutes read

Winter has arrived, and it’s time for men to bundle up and showcase their style prowess even in the chilly weather. Don’t let the cold cramp your fashion game! From layering techniques to must-have accessories, here at Alexandra Wood, we will walk you through some fun and fashionable tips on how to dress for winter like a pro.

1. Layer Up, Gents!

Embrace the art of layering to not only stay warm but also create a stylish ensemble. Start with a lightweight, pure cotton base layer to keep sweat away and to keep your skin cool at the core. A classic wel fitted T-shirt is ideal and an item I advocate buying in multiples as your daily go to. Add a flannel overshirt (My new personal fave for looking stylishly casual) or a chunky sweater for warmth, and top it off with a tailored jacket or stylish overcoat. The layering technique not only keeps you comfortable but also allows you to adjust your outfit as temperatures fluctuate throughout the day.

2. Invest in Quality Outerwear

Winter is the perfect excuse to splurge on that stylish and functional coat you’ve had your eye on. A classic wool overcoat, a tailored pea coat, or a sleek trench coat can instantly elevate your winter look. Opt for neutral colors like navy, charcoal, or camel to ensure versatility and easy pairing with various outfits. If you want to be a little more adventurous, try textures like a wide herringbone and don’t forget to pop your collar to look stylishly nonchalant. 

Overoats no longer need to be strictly worn with a suit and are a great way to sharpen up a casual look. Wear with tailored jeans, knitwear and chunky boots or chinos, smart sneakers and T-shirt. The trick is to pair unobvious items together, to give them a subtle edge.

3. Accessorise with Purpose

Accessories aren’t just for aesthetics – they can also keep you warm and stylish. Don’t forget to rock a stylish beanie, wool cap or a gatsby to protect your head from the cold. Scarves are not only practical but also a great way to add a pop of color to your outfit. Invest in a good pair of leather gloves to keep your hands toasty, and don’t shy away from statement socks that can peek out from your boots. For you classic gents, this is a perfect area to let your inner style god run wild. 

4. Boot Up for Success

Speaking of boots, they’re a winter wardrobe essential. Opt for waterproof and insulated boots that can handle wet and snowy conditions. Classic choices like leather chukkas or rugged work boots can seamlessly transition from casual outings to more dressed-up occasions. My personal favourites are Barkers Mansfield boots, well priced, stylish and they also come in several colours.

5. Jeans and Trousers: Keep ‘Em Warm

When it comes to trousers, it’s time to swap out your lightweight summer fabrics for thicker options. Consider wearing flannel which looks uber chic worn with chunky boots and chunky knit, or wear dressed smartly with a chambray shirt and tailored sports jacket. Flannel trousers in a grey, chocolate brown, navy and olive (I know, it sounds terrifying) but they all work perfectly for your key Autumn/Winter, Always the classic, invest in dark wash jeans that are slim cut (Please, no heavy orange stitching or any sign of fading) Jeans are always versatile and can be paired with various combinations, making them a winter staple.

6. Embrace the Power of Sweaters

 Sweaters are the epitome of winter comfort and style. Chunky cable-knit sweaters add texture and warmth to your outfit, while thinner cashmere or merino wool sweaters are perfect for layering under blazers or jackets. Experiment with different necklines – such as crew necks, quarter zips and polo styles– for varying looks that range between casual and smart casual. Just always choose pure fabrics and knitwear with shape.

7. Say Yes to Plaid

Plaid patterns are synonymous with fall and winter fashion. Incorporate plaid shirts or even plaid blazers into your wardrobe to add a touch of seasonal flair. They’re perfect for both casual outings and slightly more formal gatherings. This needn’t mean heavy weight, stuffy tweeds, it can be playful and fun. Windowpane checks work really well with roll necks and merino wool polo tops underneath, 


Winter dressing doesn’t mean sacrificing style for warmth. With the right combination of layering, outerwear, accessories, and attention to detail, you can rock a fashionable and comfortable look all season long. So, gentlemen, it’s time to conquer the cold with confidence and showcase your winter style like a true fashion aficionado! Still have no idea how to put your combinations together or which invesment pieces to start with. That’s where we come in. Book a call with us here. 

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