Best Winter Shoes

Need to know what shoes to wear in winter? Look down

Words: Dylan Muhlenberg | Photography: Rudi Geyser

Shoes are a telltale indicator of style, and a guy wearing fresh duds with dud kicks is not someone anyone would want to be associated with, ever. Comfort is obviously key, however, you’ll need your shoes to do more than this in order to meet the challenges of life. And since shoes, like underwear, should never be worn two days in a row, a man needs to own enough pairs so that he’s always at his best.  

Look at building versatility into your closet by keeping a few different styles that can stand up to whatever life throws at you. Also consider what you’ll be wearing and then match accordingly. To help with this we invited two men of distinction to shop Superbalist and style our footwear in their own particular way.  

You may have heard the name Imraan Christian during last year’s #FeesMustFall student protests, where shooting from the frontlines the UCT student had insider access that other photojournalists could only dream of. Fixated on the frame from a young age, Imraan is a storyteller looking to make time stand still, and says, “I’m happy to be a young creative in South Africa right now. My peers are elevating things to insane levels and breaking barriers. I’m just really inspired and grateful to be a part of this.”

Don’t call Rusty Beukes a ‘stylist’, he hates the term, and as a fashion editor who does fashion writing, consulting and, yes, styling, the term is somewhat limiting. Starting out in womenswear at Elle Magazine, Rusty now works at Mr. Doveton where he specializes in menswear, and not one to follow trends or subscribe to a specific style, he’s all about practicality, saying: “If I can work in it I’ll wear it. I don’t like stuff that constricts me. You have to get down and dirty in this field.”

Here’s how to invest in a proper arsenal of footwear and then build your look from the feet up.


Dressy yet casual, the elastic side panel and tab on the back of the ankle allows the boot to be slipped on and off easily and with none of the fussiness of laces. Part of the uniform worn by the Rolling Stones, The Beatles and Russell Brand, the Chelsea Boot is synonymous with swinging London, but can be worn anywhere. The streamlined, polished look goes nicely with narrow trousers and formal tailoring, and if you treat yours right you’ll be able to wear the same pair year-on-year because there’s no reason why they won’t be in fashion for another 60-something years.

Imraan: All black errthang. I wear all black when I need to ground myself. When I’m either creating a concept or writing a script and I’m in a crazy headspace. Art takes me into the mad side of things and all black brings me back.

Rusty: A big misconception with the Chelsea Boot is that you have to dress it up. I don’t like to dress too formal so I paired them with black denims, a polo neck and a casual jacket. I like the clean lines, it’s very modern, plus it’s simple and practical. I went for suede instead of leather because it adds a bit of texture to the outfit. I’d wear this everywhere. I think the key to dressing practically is that you can then wear an outfit anywhere.


Fools wears flip-flops and Rambo wears boots, and that’s because boots aren’t just shoes, they’re tools. Forget the statement socks for a minute and opt for thick wool that will insulate your boots properly. Boots are worn for warmth after all. The American working boot went full fashion in the early nineties – along with England’s equivalent, Doc Martens – but their proletarian origins ensure comfort and security in whatever conditions and have been stomping on everything else ever since.

Imraan: This look I’d definitely wear in nature. I like to fit into the colour palette and blend in with the autumn leaves and the trees and that. The idea of tonality is important to me. These different shades of brown and tan… And these boots are just cool, man. I can hike properly in these. Go bundu-bashing and not worry about my shoes.

Rusty: Paired these boots with distressed denims, a worn in denim jacket and a T-shirt. This is another monochrome look that keeps things simple and clean. This particular boot is especially rugged and is made from canvas with a tyre sole and matches up nicely with the hardwearing denim.


The antithesis of the heritage look that’s spurred a revival for classics like the Stan Smith, ever since Nike introduced Flyknit in 2012 it would seem that more and more dudes have turned to the most head-turning colourways and technological advancements they could find. A $55 billion a year industry, the big brands answered back and are all about coming up with sneakers that promise to make us jump higher, run faster and look more flash, marketing the type of innovations usually only applicable to athletes to us regular Joes who can appreciate the science behind this innovative new footwear silhouette.

Imraan: Tracksuit mafia! It’s kind of a movement, and really big in the UK right now. Skepta! Stormzy! I think it will be big in SA. This look is inspired by that. I wore the Tubular with this, which is very space age, but also very robust. You can run away from the police easily in this. The pigs are crazy in this city. The federales are everywhere.

Rusty: I wore these with a cropped trouser, shirt and jacket. It’s more modern than just throwing on a pair of jeans. The shoe isn’t a high top and not a low cut, but somewhere inbetween, so you can roll your jeans up for a preppy look. I sometimes find high tops difficult because they can bunch up your jeans and don’t look as good, so this mid-cut makes more sense. The technology is great and a neoprene sock is perfect for winter because it’s so warm and waterproof. A great winter shoe.


For a while now fashion forward men have made the monochromatic sneaker a staple on runways and red carpets, replacing dress shoes with sharp-looking sneakers.The late Steve Jobs helped set the tone for the new work uniform in the late ’90s when he mounted his “Think Different” campaign in grey New Balance. But save your cross-trainers for the gym and rock your most low-tech sneakers with tailored outfits for a smart-casual look that can go places.

Imraan: I love my Vans. I’m a skater. I won’t keep these white though, it’s important to scuff them up and allow them to become what they were meant to be. It’s about memories. There are no memories with a white shoe, but when it’s scuffed up you know it’s seen the world. So these white Vans are part of my skate outfit. It’s important to look swerving when you’re skating. You must always look clean and pretty. Probably time to get that boat so I can sail around Monaco.

Rusty: This is the classic tennis sneaker. All white normcore that I’ve paired with denim on denim on denim. That’s jeans, denim shirt and a denim jacket. The shirt was customized with safari pockets that make it really cool, but also give a rugged look to the very clean sneakers. I’m not actually too worried about keeping white sneakers white, especially with this look I’m doing here. I’d want a more worn in look.


Don’t be intimidated. Dress shoes are easy, understated and tasteful if you choose right, so man up. Given the dressing down we’re seeing in menswear, if you up the style factor people are sure to notice. Whether you go for something black, polished and luxurious, or prefer a traditional brogue in a shade of brown, you need something to slip on the next time you have a wedding or a funeral. Spend as much as you can possibly afford and then wear them whenever you need a little pick-me-up or want to stand taller. In a world where every guy is wearing sneakers with his suit it’s the guy in dress shoes who will stand out.

Imraan: I’d wear these formal brushed suede shoes for clubbing with man dem. Not that we’d normally frequent places that care about what shoes you wear… Maybe Eid. There we go. This is my Eid outfit. Got to impress my grandma. She’s going to be so stoked.

Rusty: Even though I wouldn’t get too many opportunities to wear them, I’m still a big fan of the monk-straps. Here I’m doing a cropped trouser, polo shirt that’s buttoned to the top, and a puffer jacket. There’s an element of sporty style mixed up with formal style that makes it more ‘every day’ and not like you’re walking around with a suit on. The whole thing for me is dressing down formal shoes because then you can go anywhere in them and wear them to a lot of different places.