Why I hate Y-fronts

It was a cold day on 19 January 1935 – actually, it was a blizzard – when Chicago department store Marshall Field & Co displayed the first-ever pair of Y-fronts in its window. Soon afterwards management asked that they were taken down as they were inappropriate for such a frosty morning in the windy city, but before that could happen 600 pairs of these Jockey-branded briefs had already been sold. Thirty thousand pairs flew off the shelves in the following three months; pants had changed for ever.

Jockey’s Y-fronts were inspired by a postcard from the south of France showing a young man in a revealing swimsuit. Out of the heady, carefree days between the wars, following on from the decadent jazz bars of Weimar Berlin and the drunken literary salons of 20s Paris, came the Y-fronted underground of 30s Chicago. In the years after the great depression, these tight pants were far more economical with cotton than the wasteful long johns of yore. They were supportive, they were sexy, they were bright icons of modernity.

This Christmas they’re celebrating their 80th birthday, but the world – like so much dirty underwear – has changed. I don’t like Y-fronts at all. I haven’t worn a pair since I was a child, and most likely I never will again. For me they symbolise discomfort, while soft cotton boxers symbolise loose-fitting freedom, a space to express yourself. I just cannot trust a man in Y-fronts, or take him seriously. Cristiano Ronaldo favours a ridiculously tight pair – he even designs them for his CR7 fashion house. But David Beckham prefers a tight boxer, and he knows best, especially since he’s thought to be branching into menswear himself.

Of course, Y-fronts still have their pros: they show off your bulge; they make you look like a superhero; their Y-fronting looks like a peace sign emblazoned between your legs; they offer support.

But they also come with so many cons. They’re just not that comfortable, and some of the more showy models actually offer too much support. One of my old colleagues at i-D magazine bought a pair of Dolce & Gabbana briefs that were moulded around the crotch, and instantly made him appear very well-endowed; however, when he walked out of the house he found they were far too tight, constantly grasping at his manhood like a waxy, cotton octopus. His day at work turned into a traumatic one.

That’s not all: if you’re out of shape, they’re not very flattering; if you’re a flocculent chap, you may need a bikini wax of some sort; and let’s not forget, too-tight Y-fronts have been scientifically proven to decrease your sperm count. Over the years they’ve lost their cool, their inter-war bohemian wonder, and now they’re most associated with Homer Simpson eating donuts and drinking beer on the couch.

Also there’s something sinister about the Y-front, something ungodly; think of Alan Partridge in his leather-posing pouch, lap-dancing for the commissioner of the BBC in a recurring nightmare. In the words of the Urban Dictionary, they are an undergarment characterised by “a ‘Y’ shaped penis-flap at the front, which allows easy access for BJs or golden showers”. It’s all rather seedy. Wearing them, well, you’re only one step away from a thong or, worse, the Towie demi-thong, which wraps gently around your crotch like a crescent moon hiding its dark side.

There’s not much sexy about the Y-front any more, and ever since Calvin Klein’s black-and-white moment in the 90s the underwear world’s fantasies have focused upon tight boxers. Last night, backstage at the Victoria’s Secret fashion show in Earl’s Court, I asked supermodel Doutzen Kroes what sort of look she enjoys on a man and she suggested jogging bottoms, boxers showing above the waistband, and no top at all. So there you go – even multi-millionaire Dutch lingerie models don’t find Y-fronts sexy any more.

Having said all that, if you do wish to indulge yourself in some, why not? Here are three of the more luxurious options for unleashing your inner Adonis.

If I must:

Y-fronts, £18 for 3, by Jockey

Y-fronts, £20 for 2, David Gandy for M&S

Y-fronts, £20 each, by Cristiano Ronaldo