Article was written by Chloe Holt

The winter season can be both challenging and fun for stylish guys. On the one hand there are always new trends, and it can be a little tricky at times to balance fashion and the need to stay warm. On the other hand, the need to wear layers and use accessories means more opportunity to show off your personal look. It’s a mixed bag.

Like with anything fashion-related though, a little bit of initiative and creativity will do the trick. So we’ve put together a list of tips – some abstract and some relating to specific style – that can help you stay fashionable and warm all winter. Give it a look, and good luck with the season ahead.

Here are the tips:


1) Stay Fit

Guys should be honest about this: wearing layers and heavy clothing isn’t very comfortable with much extra weight on the body. And unfortunately, extra weight is pretty easy to accumulate during the winter. This is one of the reasons it’s more important to exercise in the winter, even though there’s no “beach season” around the corner.

It’s very easy to slip up, even if that just means adding a few pounds, and that makes it harder to fit into the pants you want to wear, and makes it a little more constricting to put on heavy outerwear. So before you even think about style trends or your next attempt to upgrade your closet, it’s a good idea to put together a plan to stay fit.


2) Start With Shoes

There are three reasons to start any reshuffling of winter fashion with shoes. One is that there are almost always new trends in this category, and it’s good to keep your options freshly updated. Another is that your shoes set the tone for your outfit, more during the winter than during the summer when half of the suitable offerings amount to slip-ons in one form or another.

And the third is that an uncomfortable shoe can mess up your whole day – so you don’t want to wait to have the rest of your clothes planned and then have limited, possibly uncomfortable options for matching shoes.

3) Take A Cue From Celebrities Who Get Out

If you care a lot about your style, you’re probably used to take a cue from a celebrity now and then. But usually that means a look from a magazine or public appearance, or a movie. Those places don’t usually involve bulky outerwear or winter fashion. So instead try to keep an eye on sources that show celebrities who get out and about, and see what they wear when it’s cold out. As for what that means, it depends on your interests.

Guys like 50 Cent, and Floyd Mayweather have been known to hit the tables, which means you might see glimpses of them in their everyday lives heading to casinos or hotels. Celebrities like LeBron James, Jay Z, and so on are known baseball fanatics and might be seen bundling up at frigid October baseball games. The examples could go on and on, but you get the idea. Seeing celebrities out and about in winter can give you a good grasp of cold weather styles.


4) Get Some Stylish Outerwear

Maybe this is an obvious tip, but a lot of guys settle for less-than-stylish outerwear on a regular basis, at least in casual settings. Pullover hoodies with big sports logos on them, jackets you’ve been wearing for three or four years, ski coats that look a little weird away from the slopes….

These are all options that can keep you warm, and which are easy to go with once the weather cools off. More often than not though they’re a little lacking in terms of general stylishness. So make this the year you splurge a bit on some stylish outerwear. Look to the trends, skip huge logos and team apparel, and find something that will be versatile when it comes to matching and layering.

5) Skew Away From Ordinary Colors

We’ve tried to avoid simply pointing to fashion magazines here and provide a less recycled list of ideas. However, it’s always good to know what people are wearing from a color standpoint, and for this we looked to Fashion United. They did a write-up on men’s color on the catwalks, and what we noticed is that all of the trendy shades are just to the side of ordinary.

For instance “black navy” won out over black, mangosteen was listed instead of the occasional recommendation to go maroon in the winter, and caramel was showcased instead of camel. No one should feel the need to adhere to these directly or completely, but it’s an interesting overall picture of slightly off-center winter shades for the season.


With these simple tips you’ll be in good shape!

H Bashir
H Bashir

I write about black men's style, and menswear in general, at Follow us on IG @welldressedbrother