-Benjamin May

On my penultimate day as a 29 year old, I had a meltdown. Posting pictures of myself on social media, hashtagging nonsense about how fantastic my twenties had been reminiscing and pining after my youth. Endless summers of debauchery and stupidity, winters packed with idiocy and fun. Bouncing back from every weekend bender like I had been at a day spa rather than a squat rave. Take me back. That’s all I could think.


Little did I know that not only comes responsibility as a man in his thirties but a much harder cross to bear. No-one warns you of it, it just happens one morning and you have to come to terms with it quietly, in your own head. Alone. All men know it. All men deal with it. All men live it. 

It happened to me in the summer of my 30th year. One morning whilst I was getting dressed, I pulled on my skinny jeans, added a t-shirt and then some trainers. I looked in the mirror, and there HE was! The older man trying to look cool, trying to dress like a young man. Desperately hanging on to his youth with disastrous, devastating side effects. My jeans too tight, my t-shirt too oversized. My ankles were exposed and looked lost. The nikes on my feet too battered. The rips in my knees…..THE RIPS IN MY KNEES! Why on earth were they there? Who was I kidding? What was I attempting to achieve? Whatever it was, I was failing.


With this apparent new turn of events I decided a change was needed. Topman was obviously not my market and ASOS had to be taken more seriously. No more longline, no more skinny jeans. No more old me. In with the new. Where do I shop? Do I go to Burtons, River Island and Zara? Is that the natural progression for a man…? I had been so used to what I knew that I had no idea how to break out of the cycle. I was unsure of how to dress and where to buy it. I was entering a new world with no guidance. No web forums for me to talk to people about my confusion. How could I bring it up with Martyn (my friend Martyn is from Burnley and refuses to acknowledge anything I say unless sport related) on Sunday whilst watching football that I had lost the ability to dress? He would cast me aside. Given he was still 29 at the time he had no idea of his own fate. Where are men meant to go?


I decided to start looking in places I had been before, but this time looking for normal length t-shirts and tailored trousers. I found ASOS to be a revelation. An extensive range of trousers, nicely tailored and at a reasonable price. I upgraded my trainers and dusted off my faithful collection of Dr Martens (7 different pairs to be exact). I threw out most of my skinny jeans and replaced them with a wider legged denim. I bought a few shirts, only this time not Hawaiian. In truth, I completely changed the way I looked...sort of.

Dressing as a man in his thirties is harder than you think. Fashion is a torturous trap for a man. Though many don’t admit the issues they have we all go through it. I speak with guys all day every day, and we all have moments in life where we question our fashion choices and where we should be buying from. It’s not uncommon.


Sadly for me now though I am fighting a new fashion issue. With 90s style creeping back in I am struggling to keep it out. My dad lived in tracksuits, my brother still does and now the chav in me is desperately trying to resurface. So if you see me in 1Rebel trying to pair Adidas bottoms with DM boots, just remember, I can’t help it. It’s not my fault... 

Ben's Tips

Accessories: I always find ASOS to be great for these sorts of things. A marketplace for many brands and an easy to navigate website which is mobile friendly!


T-shirts, jumpers and shirts: H&M is always great for these pieces. Recently they brought out a new men’s line which is slightly more expensive, but is a much higher quality and shape. The Oxford Street store houses most of the collection and is definitely worth checking out. BUY HERE.


Jeans, trousers and trackie b’s: For jeans I head to the stables in Camden market. They have lots of reclaimed denim and mostly under £30 a pair. For trousers try ASOS and again H&M. BUY HERE. Topman (I know I know) do have some looser fitted lines these days to match with the wide legged current trends. For trackies try Nike, Adidas and Urban Outfitters….or JD Sports! TRY THESE. Or for a more sporty look BUY HERE.


Jackets and coats: I’m a big fan of vintage or second hand. If you’d rather not look so dishevelled then try Zara. They have such a great collection of men’s coats and jackets and far better fitting then most high street stores.


Shoes and trainers: I’m a big Dr Martens fan. Huge in fact. Around £120 a shoe and just about any style and shape you can think of! How can you not!? BUY HERE. For trainers I’m a Nike and Vans kinda guy. Comfortable, reliable and classic. BUY HERE.


So, in short, if you’d like to avoid looking like a hipster chav with serious style issues just give the above a miss. 

Follow Ben's style journey HERE.