Try the new packing order and outsource your holiday wardrobe

The sartorial civilisation of British men doesn’t seem to have eased our basic clothes anxiety. Previously, blokes hated making decisions about what to wear because they didn’t know the difference between a good outfit and a humiliating one. Now they own better clothes and know the difference — but because everyone else does too the bar has been raised. A few years ago, it was considered thoughtful if you avoided black brogues when wearing jeans. Now such questions as the length of a pair of shorts and the pros and cons of V-neck versus round-neck T-shirts are in play. And packing a holiday bag forces the moment to its crisis.

Since my fashion-buyer friend moved into our flat a few months ago, I’ve learned that these calls are not marginal and the answers are absolute. Owing to my shape, some styles of T-shirt make me look like a minor gym-based character in The Only Way Is Essex. Combining shorts, a T-shirt and flip-flops when venturing out to London Fields on the weekend sends out uni rugby tour signals. These personal rules were not clear to me before but now they are scriptural.

Packing an away bag is the moment when these judgments and decisions have to be made at scale, so it’s not surprising that a company has come in, promising to avert disaster, or just remove the hassle of choosing the right items. For a certain type of man, nothing so ruins the prospect of travel like working out what kind of clothes are right for a meeting in Barcelona or judging clubbing clothes for New York. The Chapar — named after the indefatigable couriers of the Persian Empire — offers an expensive version of a fashion-conscious flatmate. Men who can’t face picking out clothes for a trip entrust the job to an experienced adviser, who assesses their personal style in a short consultation (either in person or on the phone) and then sends a box with a few outfits to try (people tend to buy about a third of them). When it launched in 2012, The Chapar might have seemed gimmicky but 3,000 clients and counting (ranging from 25 to 55, and averaging somewhere in the middle) points to strong demand — an unmet need among London’s well-heeled to have these decisions made for them. In recent years Louis Vuitton has employed a “packing artist” at its Maison on New Bond Street while MrPorter.com has a team of style advisers who talk you through the merits of particular items as you browse their site.

“Mostly it’s guys in the City who have the money but don’t have the time and want to look good or say they are a bit nervous about choosing,” says Hannah Newman, the stylist who called me when the Standard’s fashion editor suggested we challenge The Chapar to provide me with an outfit for Glastonbury. Our 15-minute conversation highlighted an additional fashion problem for blokes choosing clothes — that most of us who don’t read fashion and celebrity magazines don’t have the sophisticated vocabulary of dress required to describe clothes.

I couldn’t tell you what “sports luxe” really meant, let alone “modern exec”. What she sent was probably a bit too safe — slim-fit Levi’s (the company The Chapar’s co-founder, Joe Middleton, used to work for), a wine red Scotch & Soda T-shirt, a Ben Sherman bottle-green fleck shirt and a Woolrich McKinley beany — but on reflection staple items such as jeans and simple shirts are exactly the kind of items I get wrong, perhaps because they offer even more bewildering category choices than modern coffee shops.

Packing your bag with the help of a service such as The Chapar will set you back hundreds if not thousands of pounds, so it’s not for most of us. But their success points to the new anxieties of male dressing — more elevated and complex but no less terrifying than before.