Winter Denim Guide For Men

Photography: Aart Verrips | Styling: Akim Jardine

Denim. Pretty simple, right? Hahaha. Wrong. Jeans are in constant flux, where one minute Jeremy Clarkson jeans are a punchline and the next they’re trending their way down a runway and worn with fashionably fugly shoes. Fortunately, some things never change. Like fit, and the fact that boot cut jeans are still not cool... 

The Way of Us put together this menswear denim guide so that you can simply shop Superbalist for your next pair of jeans. These are the three fits, two tops and one look you need for all your winter denim needs. 

It can take years to earn the type of whiskering, fading and distress that a worn-in look requires. Along with designers coming up with new ways to dress up jeans, we’re pleased to see that they’re also figuring out new ways to beat them up. You may not have patience, but you can get ripped and repaired denim. 

Stylist's tip: Avoid excessive embellishments and anything that looks inauthentic. A ripped knee, patched up thigh and frayed hem are good. Something that looks as if it's gone through a lawnmower isn’t.

These very forgiving jeans are cut the same way all the way down – meaning that if you have fairly standard-issue legs, this cut will be tight around your thighs and will then loosen up as they go down to the knees and calves. 

Stylist’s tip: If you like your denim straight up, this relaxed, lived-in cut has that classic preppy look, which skaters have helped bring back from the 90s.

This style hugs the legs from the thighs all the way down to the ankles. They’re most flattering when worn by guys with slender frames, but if you’ve got football legs and want to rock the skinny then dark washes will always look better than light.

Stylist’s tip: Balance things out by wearing something sizier on top. 

We already told you in our series on military menswear that the overshirt is the ideal layering piece. The versatile necessity is an under-utilised asset and once you invest in one you’ll find yourself wearing it throughout the year. 

Stylist’s tip: Worn over a T-shirt, with a pair of slim black jeans and your freshest kicks it’s casual. Button the shirt all the way to the top, switch out the sneakers for lace-ups and you’re smart.

A hard-working wardrobe staple like the denim jacket deserves a place in every man’s wardrobe. Wearing one is easy – and like everything else on this page, can be flipped from casual to smart with the simplest of adjustments. 

Stylists tip: A great layering item, this jacket can help you get through the coldest of days when worn in-between a hoodie and a bomber jacket, and will substitute your thicker coat when spring has sprung.

The slim-fit style hugs the thighs, knees and calves and then loosens up at the ankle. Finish off the look with a simple puffer jacket and matching black sneakers that break up the blue hues.

Stylist’s tip: Trod-on pants look sloppy. Cuff your jeans so that they don’t hang over your shoes. Which cuff? Check out our feature on How To Cuff Your Jeans.