Wry Society: The dress-down dilemma

How will a formerly suited-and-booted banker cut it sartorially with the Shoreditch hipsters in his new job as a dotcom starter-upper?

Image: phildisley.com

It was Josh’s 43rd birthday and he hadn’t a clue what to wear. “You’d think I’d have worked out who I am by now,” he said to his wife, Thea, who was calmly making a soya milk latte while he ran around the kitchen in his boxer shorts, a large helium balloon – a present from their eight-year-old twins – still knotted to his wrist. Josh had made all the obligatory midlife alterations. He’d signed up for next year’s London Marathon, taken up being mindful and, last year, in the wake of his father’s death and a rather unsettling heart murmur incident of his own, he’d finally taken the leap and made the transition from banker to young, edgy and socially conscious internet startupper.

So it was out with a large mahogany desk in a glass box in Ludgate Hill and in with no desk at all in a converted bus shed in Shoreditch. Meetings – of which there seemed to be many with people whose names he didn’t know but who all had beards – turned out to be very moveable feasts. Quite literally. In the course of his first week, he had made crucial decisions about the financial future of the company from beside the water dispenser, in the downward dog position during a lunchtime yoga class in the Zen room, and perched on the edge of the pool table, craft beer in hand.

Thea was delighted with her new husband who looked years younger now that he wasn’t dressed like Mr Banks from Mary Poppins every day. “I think I’m just going to wear my old suit,” he mumbled, as he sifted through the laundry basket for a pair of socks.

“No you are NOT!”

“But I like wearing a suit…”

“And I like being married to someone who doesn’t look 27 years older than he actually is.” 


What Josh couldn’t bring himself to tell Thea was that while she might find his new look refreshing, it wasn’t going down so well in the office. Indeed, after several months of trying to crack the dotcom dress code he had finally been brought to his knees. At first, it was terribly freeing, loafing into work in jeans and a cashmere jumper. But then someone had told him that cashmere was no longer ethically responsible. For a while, during the winter, he had got away with wearing his Canada Goose parka for most of the day. This after a crushing incident when, encouraged by one of the Sunday style supplements, he had dug out his old navy blue Puffa gilet from 1998, only to be sniggered at and told he looked “very Marty McFly”. 

But it was the cropped-above-the-ankle trouser that had finished him off. He had bought a pair when he started the job – from Dolce & Gabbana no less – and then chickened out of wearing them when he couldn’t work out how to wear socks with them without looking like a Tudor knave.

With the coming of spring, he decided to try again, this time with no socks, in an attempt to channel the European gentleman look. “Think cappuccinos in a square in Rome,” he said to Thea as he walked gingerly out of the house sockless in brogues. But no sooner had he stepped off his very expensive gentleman’s bike than he was crippled by blisters. As he staggereed past the café next to his office, the moustachioed nods of approval he usually got out of respect for the bike gave way to smirks. Undeterred, he bought himself some secret socks. Which was all well and good until it started to get much warmer and his colleagues had started wearing Birkenstocks with their short trousers. But he was a man in his prime and really did have to draw the line at dressing like a geology student.

Having been forbidden by Thea to wear his faithful old Gieves & Hawkes suit (not even if it was his birthday), he trundled into work in jeans and a T-shirt – nondescript but harmless, he mused. As he walked into the office, Ewan – a former menswear buyer at Harvey Nichols in Edinburgh-turned-content strategist – looked up and, from the look on his face, Josh knew he’d got it wrong. Again.  

“Won’t do?” Josh said feebly, looking down at himself. 

Ewan winced kindly. “Well, normcore is a bit 2014 … But – you know what, Josh? – I’ve been having a think, and I reckon that, by your age – you’re in your mid-40s right? – a man should really be thinking about hanging up his on-trend boots and investing in a well cut…” 


“Suit?” said Josh, his heart silently leaping.

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