6 classic shoes to nail every event

The smart shoes you need to see you through

smart shoes

Words: Nhlanhla Masemola | Images: Nick Gordon

All shoes were not made equal. As much as we’d like to think that wearing our one pair of favourite sneakers is a versatile and perfectly functional excuse to work, visit the in-laws or go on a date — it’s just not appropriate. The ease and proliferation of sportswear have brought with it some marvellous things: joggers outside of the gym and luxury skatewear, for example. But being a grown-up means that we need to embrace dressing as one and sportswear does not always age well. Sport-oriented fashion has the excitement and sheen of a trend, but what do we wear when said trend has inevitably left us? In those times, investing in timeless essentials becomes a sartorial act of survival. Here are a few classic shoes to select when circumstances demand it.



Dressing for any trip warrants comfortable shoes, but comfort doesn't have to mean style has to suffer. The loafer is the optimum shoe when you’re looking for something that looks fresh, but is still simple to slip into. The beauty of the loafer is in its versatility — a laceless, slip-on shoe that can easily be adapted to a business-casual setting with the right trouser or socks. It's an essential.

monk strap


Undeniably formal, the monk strap is ranked high on the "I’m an elegant gent" list of what shoes to wear. It's sleek and cool, but can take you beyond formal settings in the right tan of leather. Show that you’re the only option for the job you’re applying for by ensuring you're leaving a good impression. A shoe with personality that’s here for business is the smart choice.

ankle boot


Gentlemen who want the sophistication of a work brogue and the streetwear cool of a high-top should look to the ankle boot. A tougher shoe to pull off, the ankle boot is similar in silhouette to the Chelsea boot, but features different closings to ensure a secure fit around the ankle. This ingenious, casual shoe is dressed up enough to be worn with a suit and laid back enough to be worn under rolled denims or slim corduroy trousers.



Making the rocky transition from sneakers to formal shoes? The Chelsea boot is your new best friend. Toeing the line between casual and business casual, the Chelsea boot is an option to go blow off some steam after work at your favourite joint. Ooze authority and ease while disarming your co-workers by wearing with black jeans or slim chinos.



There's nothing more traditional or refined than the derby, which shouldn't be confused with the more formal Oxford (FYI, they're two different shoes with completely different lacing systems). When a more sophisticated look is required for an occasion (think weddings), the Derby is your man. When styled correctly, however, the Derby also suits a variety of occasions, including business-casual dress codes. For work, pick a derby or pair of Oxfords in brown leather and avoid patent designs. A brogue and/or wing detail on the toe technically makes the shoe more casual, but who’s paying attention these days, anyway? They make the shoe look classy and add buckets of personality to your look.

formal sneaker


All that manic swiping right has finally paid off. Congratulations – now you have a date. Confidence is key to any date and it shows from head to toe. First dates can be nerve-racking and one way to keep your cool is to keep things understated and relaxed (not advised for dinner proposals). You want to look approachable yet personable, right? Do that through a formal sneaker. Leave the derbys at home this round and go for dark jeans, a navy bomber, crisp shirt and squeaky-clean sneakers.

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