Why we love ‘woman repelling’ menswear

Tweed jackets? Absolutely. Cargo pants? You do it brother. Socks and sandals? If you must…

There comes a time in every man’s life, when he unfortunately and unexpectedly becomes single.

In my case, that happened about two years ago, and on re-entering the dating scene I realised pretty quickly that most of the eligible women I met weren’t entirely sold on my loud three-piece suits, pin-collar shirts and ties, finished with a pocket hanky and a pocket watch. Yes, that’s how I used to dress – every day.

What followed was an 18 month journey exploring the world of casual menswear. I changed jobs (and joined The Jackal, of course), so was no longer required to wear punchy tailoring all the time. I also joined several dating apps, and faced up to the fact that while my ex had known me long enough to indulge my passion for retro suits, women meeting me for the first time (with no prior experience of my sparkling wit and repartee) might struggle to see beyond the mafioso-inspired wardrobe.

‘Clothes are a means of self-expression. There’s a real pleasure to rocking off-the-wall pieces from time to time’

I was talking to some friends who work in menswear about this a few weeks back, and it made me realise that the way many men dress (whether heterosexual or homosexual) is almost entirely dictated by the desire to attract or retain a partner. Many of us have pieces in our wardrobe that we’re passionate about, but that sadly seldom see the light of day for fear of being written off by prospective love interests.

Which is a shame, because getting into clothes – even weird and wonderful clothes – is a form personal expression, and there’s a real pleasure to be found in rocking off-the-wall pieces from time to time. Lucas Nicholson, manager of Drakes’ esteemed haberdashery on Clifford Street, knows this only too well. ‘I’ve always had a “varied” interest in clothes. Right now, my favourite things are my pair of Paraboot lace-ups covered in mink. They’re affectionately known as my “furry boys”. Other items that cause my other half to groan include a novelty cap I picked up in Spain celebrating the town that invented the submarine, and proper fisherman’s sandals in tan leather. I’m also into super-baggy chinos right now. And yes, I’m immune to the eye rolls.’

Mr Tony Madsen-Sylvester, another of London’s finest menswear aficionados lives within the bond of holy wedlock, and even in a loving relationship as he is, seldom lets certain items surface from the lonely depths of his closet. ‘I enjoy the brinksmanship of dressing just on the cusp of good taste,’ he tells The Jackal, ‘often to my wife’s chagrin. Especially when it comes to what can only be described as “old man style”.

‘I enjoy the brinksmanship of dressing just on the cusp of good taste, often to my wife’s chagrin’

‘There’s actually a list of ‘banned’ items I am not allowed to own until I am at least 50-years-old which is hotly debated and then either begrudgingly adopted by me or even-more-begrudgingly adopted by the missus. Half moon glasses, for example, are a no-no. The most memorable time I had to concede defeat was over a pair of second hand Hogans scored off eBay. After an initial ‘What the f*ck are those?’ from my better half, there were tears. A lot of tears.

‘I gave them up the next day – one thing I have learned is that the key to a successful marriage is in knowing how to pick your sartorial battles.’

Wise words from Mr Madsen-Sylvester. Esteemed men’s and street style photographer Jamie Ferguson is in the same boat. ‘I love high-rise trousers, but my other half says I look like Simon Cowell when I wear them. Even so, they’re more comfortable to wear than low-rise trousers, I think they look better beneath a jacket, and best of all I can crouch down to take a photograph without my butt hanging out.’ Yet, tragically, Ferguson’s collection of high-waisted, elegantly tailored trews attracts only the moths in his closet, so afraid is he that pulling them on will provoke a period of full-blown banishment to the spare room.

So, what follows is a rallying cry to all men out there who enjoy their clothes. If you want to wear your favourite vintage tweed Norfolk jacket with cargo shorts and ugly trainers, you do it. If you want to wear an acid yellow tencel camp shirt with olive green high-waisted trousers and a neckerchief, go right ahead. If you want to rock a ‘70s brown suit with a silk shirt, lots of man-jewellery and Cuban heels, who is anyone to stop you? Your clothes are there for you, not anyone else. You go right ahead and enjoy them – spare room or no spare room.

Unless of course you’re single and dating. In which case it’s unispired chinos and t-shirts all the way…