Age inappropriate

From skinny jeans to high tops, when is it time to put a look to bed?

First, let's get one thing clear: I'm of the opinion that people should wear whatever the hell they like. The taking of risks, even – nay, especially – those that tend toward the ridiculous, should be applauded. While, on the flipside, it ought to be recognised that trackies teamed with a singlet and thongs is not so much a weekend wardrobe option as a national costume that will hopefully one day be regarded as such by the good people at UNESCO.

Personally, as one of those lazy work-from-home types, my daywear is like that of a male Helena Bonham Carter; a decidedly haphazard look I wish I had the presence to pull off if I dared sport it farther than the corner store. So I say, if it's comfortable and makes you feel confident, who is anyone to tell you otherwise?

However, there is one glaring exception to this wonderfully egalitarian fashion philosophy. And that's if you're going to blindly follow the trends and wear something solely because you think it'll up your social worth, it's best to follow some simple guidelines to ensure you don't end up coming off like a total tool.

If modelling yourself after a Terry Richardson photo shoot of yore (well, the ones containing clothes anyway) is something you really want to do, you need to realise that eventually - whether it's due to age, the fickle nature of fashion or general douchebaggery - there'll come a time when you need to put the look to bed.

Skinny jeans

First out of the gate is one of the most controversial fashion revivals of our time, the humble skinny jean. On one hand, they look killer on geriatric rockers who've been championing them since their youth – think Iggy Pop and Mick Jagger – as well as modern-day legends like Russell Brand. But for every Ramone or Patti Smith you now have one hundred Pete Wentzes and Avril Lavignes. And who wants to be lumped in with that mess?

If you've succumbed to the ravages of your mid-thirties and beyond and don't have a guitar in your hand or the measurements of a young David Bowie it might well be time to give yourself a little more room to move. However, if you're convinced no one will consider your choice reminiscent of Fall Out and Sk8tr Bois everywhere and decide to keep on keeping on remember: once you go black, you never go back.

American Apparel underpants


For years any nosy friends who decided to snoop through my underwear drawer while I was in the shower would have been confronted by a frightfully obsessive selection of rolled up American Apparel undies sorted according to colour. Something about the simple, old-school design coupled with the lack of logo really appealed. You know what didn't? Having my junk packed so flat that I resembled a neutered Ken doll. You could have the manly measurements of Ron Jeremy and still run into problems. So gents, if you want to give off that hung-like-a-mosquito vibe while ensuring your long-term sterility by all means go ahead. For the rest of us, a less trend-based option is in order. Besides, now the full extent of egomaniacal AA head honcho Dov Charney's misogyny has come to light, the company has lost much of its street cred.


Now, no one's denying that White Men Can't Jump is awesome movie. I've always been quietly appalled that Rosie Perez never received an Oscar for her portrayal of the shrill, Jeopardy-obsessed Gloria, but I digress. Just because a movie is great doesn't mean you still have to sport the footwear further popularised by its principal actors decades later. When was the last time you saw anyone wearing Uma Thurman's yellow Kill Bill-inspired Onitsuka Tigers? Exactly. It's no longer the derivative mid-2000s, so unless you're Jay-Z or Samantha Ronson you might want to rethink this look. Converse high-tops will forever be exempt because they're timeless and not solely the preferred footwear of tedious second-wave hipsters.

Bicycle caps

Speaking of hipsters, we have arrived at bicycle caps. While I'm aware that the only thing more eye-roll inducing than masses of poseurs attempting to stand apart by fitting in are people commenting on how irritating they find them, I'm willing to throw my non-cycling hat in the ring on this one. Since the competitive cycling community introduced compulsory helmets, these caps – or casquettes – are now normally only worn in team colours on the winner's podium. Outside that realm they're now seen exclusively on the heads of fixie riders and inner-city bartenders everywhere. Where they'll inevitably be emblazoned with the word “Brooklyn” to signal said wearers affiliation with the New York borough he spent that week in back in 2007. Though often falling under the same category, I'm willing to let actual bicycle couriers off with a warning on this one. For the rest of you however it's probably safe to say you look like a bit of a dickhead.