By Tanlume Enyatseng. Photos by Giancarlo Calaméo LaGuerta

GROWING UP, I WAS NEVER A FORMAL KIND OF GUY. As early as ten, I preferred to wear neon green, latex tights with a tie-dye T-shirt and flip flops – usually with
disastrous results. I envied the more put-together boys, effortless in their tailored pants dressed up with crisp golf shirts. But at heart, I was a hipster, always rooting through bargain bags at flea markets for, say, a snakeskin vest, which for some reason I just had to own.

There was never a point when I wasn’t experimenting with clothes, hence a certain photo of me as a two-year- old in a garish, ill-fitting 80s prom dress, yes, DRESS! My mother was complicit in that stunt; she loved dressing up my older sisters and me in a variety of ridiculous get-ups. I believe she hadn’t come to terms with having a son. Not until my younger brother was born.

I honestly think there have been times when my sanity may have abandoned me completely. Allow me to take you on a brief tour of my fashion disasters….

By 1999, I was a carefree, Spice Girls-obsessed eleven year-old. Was there ever a time when knee-high Nike logo socks looked good with denim shorts and a pink Lacoste polo? I may have been satisfied with myself, but in a photo taken at the time, I’m skinny and awkward. My hair is in a Shaft-style Afro, my newly adolescent face is oily, and my stick legs bow out at bizarre angles, sort of like Bambi’s when she first learned to walk.

Two years later, I was making my ascent up the hellish mountain that is teenagedom. In other words, I was a total dick. My clothing reflected this. I was also transitioning from private to public school, and the alpha guys at my new school were rigorous in their enforcement of the social pecking order. If you weren’t big and brawny, you were a target. You were an outcast confined to the dark recesses of the lunchroom – or worse.

Somehow I managed to slip through the cracks and avoid both being teased and being labelled a nerd. With the fear of being bullied gone — and no ambitions to be popular – I explored my sartorial whims in the fashion department.

My style references now were Kwaito music videos, and this brief period prowling the Manyora subculture had an interesting effect on my style. Gone were the checked shorts and Nike accessories. In their place arrived the Dickies two-piece ensembles, Converse high-tops, and bucket hats. I was that guy that “kind of overdid it a little” and was trying to get attention through his clothes. I mean, I wore a silk robe and torn sneakers (a la Trompies) to school once.

Thankfully, I soon moved on to experimenting with a more toned-down look. By around 18, I was alternating between mod and hippie (inspired by a new obsession with new wave French cinema). It was a schizophrenic approach to dressing that ended up yielding some fairly fashion-forward looks and often required ransacking my mum’s
closet for the perfect vintage sweater or floral shirt. I really thought I was Serge Gainsbourg.

But in 2008, Gossip Girl was the new shit. This spawned my metrosexual phase – and another era of bad fashion. When my friend Tshepiso and I woke up one morning in Johannesburg clad in matching baby-blue skinny jeans and polka dot bowties, I realized we’d taken the joke way too far. “Damn that Mother Chucker!” Last year, I discovered fashion blogging and the wonders of sharing my writing on the World Wide Web. My style began to reflect the lifestyle I (thought I) was leading. Just not in a good way.

I overdid the skinny jeans, boat shoes and Amish hat look. I wanted to be so cool so bad. I cringe whenever I come across a photo from that period. It got to the point where I thought I could start a range of Third World Hipster dashikis.

Now I have ditched the everyday-is- a street-style- shoot vibe and focus on comfort, taking key looks from whichever era interests me and working them around my own style and body size. Sure, I may look like a total idiot at times, and to the delight of many, some of those moments have been “immortalized” on film. But fashion should be funny and silly, joyful and irreverent. So when I look at those priceless photographs, I can’t help but smile too.