Sharpen up for winter

How to dress like a grown-ass man, courtesy of the colder weather

By Hugh Upsher

Another summer of slops and boardies has come to an end, and the time is right to start whipping out the type of threads that give off an air of maturity. It’s amazing how much more you'll respect someone once their hairy toes are hidden from view. Winter is the best time to sail the sophistication boat and fool everyone into thinking you’ve finally got your life together.

Quality over quantity

The great thing about winter is you can get away with wearing the same two or three things over and over and over again. Even though coats and jackets are pricier items, they make up for it with their sophistication and versatility during the colder months. No one will ever call you out for wearing the same jersey three times in one week, but apparently it's frowned upon to do the same thing with a T-shirt.


Winter is the great equaliser when it comes to body types. No matter what size or shape you are, if you layer right, you’ll find a way to look good. Whether you’ve got a bit of a boep, a small frame or sloped shoulders, there’s a way to compensate by utilising your winter wardrobe wisely. There are blazers to broaden, jerseys to buff up and jackets to straighten up in.


In an age where the Richard Bransons and Mark Zuckerbergs of the world lean heavily on the casual side of life, the devil is now in the detail. You no longer need to be wearing a million bucks worth of clothing to look like a million bucks. A dude can go from looking like a semi-pro skim boarder to the CEO of a tech start-up by simply picking up the right pair of jeans and a nondescript top. 

Going Dark

There is something eternally stylish about wearing black. Its mature, slimming nature and sophistication all come together to make up a colour that eats other colours for breakfast. Winter is the season for darker shades that will make you appear brooding and complex, even though you’re probably closer to anxious and tired. No need to overdo it and head into full-goth territory, although it can be a cool phase to go through at least once in your life.

Wearing more clothes means more opportunities to sharpen up. Use this opportunity to figure out a few solid looks that you can rotate for the next few months. Looking good will not automatically get you that promotion you want, but it may make people take you more seriously, at the appropriate time, if your track record is also on point...