My teenage years were not stylish.
I grew up in a small village in Surrey called Fetcham, just outside the M25. It was a pretty standard adolescence: Piano lessons on a Tuesday night, bottles of Lambrini in the park on Thursdays, Chicago Town pizzas on Fridays if I was lucky. The first album I ever bought was the Spice Girls (though I now pretend it was The Verve) and my favourite television program was Buffy the Vampire Slayer.
My taste in clothing, at the time, was not much better. An early growth spurt combined with a penchant for packets of Hula Hoops and Trio bars meant that I had to buy most things in a size XL – a point which, for some perverse reason, my Dad took great pride in. I can only assume that for him, having a son with a 17-inch collar and 36-inch waist was a seal of genetic approval - as if by spawning a planet he had proved his virility to all those in my orbit.
There's one particularly awful photo of me which exists somewhere in my mum's house. I'm wearing a short-sleeved black shirt with red dragons on the front (no doubt picked up on one of my monthly visits to TK Maxx in Woking). I'm also sporting train track braces with natty purple elastics and attempting to play the saxophone. I look like a Shaolin monastery melting onto an ear horn.
Though style wasn't present in my early life, creativity was. I remember visiting the local library with my mum when I was about 11 and borrowing Vivienne Westwood's autobiography. Impressed by the clothes she produced (those platforms – very Geri), I went through a period of designing my own clothes, primarily for women. I have several portfolios at home stuffed with half finished sketches of scarily angular ladies wearing not very much.
Luckily for the women of the world my design ambitions dried up when I was 13 or so, but it was also at around that time that my best friend David and I started reading Esquire. I remember desperately wanting a pair of Gucci loafers I'd seen in one of the first issues, but Surrey didn't seem to stock them, so I turned my attention to London.
And so, during my first visit to Knightsbridge in early January 2002, I went to the Gucci store and picked out a pair of boat-like, size 13 white suede loafers in the sale, mainly because at £70 they were the only things I could afford. It didn't matter that I was closer to a size 11, or that at 15 years of age I had nowhere to wear my new shoes, what mattered was that they were loafer-shaped symbols of possibility, a pair of wearable tickets to a new world.
In the years that followed the skater jeans and oversized T-shirts were gradually replaced with logoed sweaters from DKNY, polo shirts from Ralph Lauren and twisted jeans from Levi's (obvs). Then came University, a cider and THC-induced blur through which I somehow managed to dress myself in H&M basics and old lady cardigans from charity shops. The vibe in Leeds was all about looking insouciant and starved, so I lost a few stone and spent three years resembling a strung out Thora Hird.
Things have changed a bit since then. Nowadays in my role at Esquire I spend my days breakfasting, lunching and dinnering with people from all corners of the fashion world, hopping between press days and fashion shows and travelling the globe with the glamorous brands I once lusted after in those old copies of Esquire.
One thing that hasn't changed, however, is my ability to make startlingly bad wardrobe errors. I regularly turn up to events and realise that I've dropped some red wine down my front, for instance, and there have been several occasions where my trousers have split – most notably when I attended the Polo with a major watch brand and my new silk sweatpants ripped from waistband to crotch.
Perhaps the worst and most recent faux pas came to pass in my first few weeks at Esquire in 2010. The then editor Jeremy Langmead had called me in for a one-on-one features meeting – my first – and I'd gone in both nervous and armed with a notebook of ideas.
A week prior to the meeting I had drunkenly jumped onto my bed and knocked my front tooth out on a radiator. In lieu of a permanent replacement my dentist had supplied me with a temporary filling, which sat, loosely, in the gap left by my departed tooth.
At one point in our meeting, just as I was reaching full flow, I noticed Jeremy's face drop. It took me a while to realise that my filling had fallen onto the table (and with it a little puddle of drool), and that I was sat facing my new editor looking like a snaggle-toothed pirate. Mortified, I stuffed the filling back in my mouth and ran out of the room.
I was contributing editor at that point, and today – 6 years later – I've somehow made it to style director. As Churchill once said: "success is the ability to go from one failure to another with no loss of enthusiasm." I'd say that's as true when it comes to dressing well as it is anything else.