A gentleman’s checklist for a new year of dressing

a to z

Words: Nhlanhla Masemola | Styling: Akim Jardine | Photography: Jonathan Kope + Ian Engelbrecht

We hate to say it, but the holidays are officially over. Pack away the camp chairs and beach umbrellas and get into gear for the brand new year ahead. Back to work, back to reality. We know it’s no easy transition, but we’ve left negative energy squarely in 2019 and penned a few style notes to help you get back to business. The new decade brings a host of brand-spanking new, office-friendly essentials to make the return to your desk a bit easier – and, more importantly, make a polished impression.


First things first, remember to alter your clothes to fit you well. Sometimes all you need to show everyone you mean business in your new workwear wardrobe is a little bit of alteration. Struggling to find your sartorial footing? Brogues are your best bet. And style extends to the way you smell, which says a lot about you. Think about what you’d like your signature scent to express as soon as you walk into a room. Are you active and sporty, traditional and woody or mysterious and musky? Pick the cologne that suits your temperament and skin. On a tight schedule? Stay ahead of time (and the style game) with a dress watch. Known for its leather strap and small face, it’s the sharpest way to keep you from missing out on all those important meetings. Need a holiday from the holiday? Your eyes may be the windows to your soul, but no one needs to know how much sleep you have – or haven’t – gotten. Banish dark circles with a simple dab of eye cream.


There’s a time and place for dad sneakers, but some occasions need a little versatility. For something more subtle and functional, the formal sneaker is a smart addition to your workwear closet. Next up, the golf shirt. Is it the way the soft collar and short sleeves bridge the gap between smart and casual? Or maybe it’s the long line of sport icons who have worn it? Whatever it may be, this is your workwear classic for any age. Looking for something a bit more distinctive? The Harrington jacket is a lightweight style icon that looks good on pilots, managers and artists alike. But no matter the workwear essential that strikes your fancy, it’s important to invest in it. Quality over quantity is the name of the game. As you take your time making your workwear purchase, we suggest adding a jersey knit to layer over your shirts and keep away that summer chill.


There’s arguably no colour as hardworking as khaki when it comes to workwear. Whether you’re into its brown or green versions, the military colour exudes discipline and works well for casual jackets and chinos. Need to adjust the fit of your trousers? Get a stylish leather belt, which doubles up as an accessory, too. Did you pay enough attention to your nails last year? There’s no time like the present to up your grooming game: manicures are a must. When it comes to list-making, nothing beats pen and paper. A solid notebook is handy and always a good idea. As are overcoats. Make sure to keep a reliable one close so that all your style bases are covered. See what we did there?


It would be thoughtless not to mention the chino – the pleated chino, more specifically, to keep things retro and refined. If your workwear wardrobe needs a piece that’s equally practical and stylish, look no further than the quilted jacket. Next up, keep abreast of technology as the world of work is increasingly shaped by it. Your plug? An insightful podcast about the changing world of tech called Reset, hosted by Arielle Duhaime-Ross. But back to style. Get a satchel to ensure that your bag works as hard as you do. And don’t underestimate tapered jeans: this denim workhorse that’s slimmer at the bottom than the top suits smart-casual environments especially well.


Take it back to the basics and start with a great undershirt if you’re still not sure what to wear. Got vents? Remember to snip away all the sewn vents of your tailored jackets and pockets. The stitches are there to help garments retain their shape but once bought, they’re no longer needed. No workwear checklist is complete without a classic white shirt. Want to earn top marks in the fashion department? You need that X factor, be it a traditional tie from your partner, a standout vintage blazer or your lucky pen. Stick to your workplace dress code and have fun with it wherever possible. And remember to take care of yourself, too. Tried some late-night yoga to get into the habit of decompressing after work? Afterwards, you'll be refreshed and well-rested enough to zip up to the top of the work ladder with a polished leather boot. Now you know your workwear ABCs!

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