What To Wear On A Date

Link Copied


What To Wear On A Date

Words by Mr Dan Rookwood | Photography by Mr Mark Shearwood | Styling by Ms Otter Hatchett

7 July 2016

How to make a good (offline) first impression, without going over the top. Here's the top, trousers and sneakers to get things going.

We all know that, in the realms of romance, first impressions are important. But could it be that, these days, they’re even more important than ever? We’re referring of course to the popular phenomenon of dating apps such as Tinder, Bumble, happn and their ilk, and the fact that, as often as not in the contemporary world, your first date with someone is likely to be the first time you ever come properly face to face with them (in real space, anyway). Oh, for the days of phone numbers scribbled out on soggy drinks receipts, handed coyly across grimy bar countertops. Actually, on reflection, we’re not sure that the old way was any better. In any case, should you find yourself scheduling one of these awkward, do-I-even-like-you meet-and-greets in the near future, the following guide to what to wear should put you in good stead. The key is to be impressive, but not too impressive. In this cynical digital age, no one likes a date that tries too hard.

Yes, you probably look your smartest and most respectable in that Boglioli hopsack blazer you picked up from MR PORTER and have since worn assiduously. But there’s a real risk on a first date of coming across as someone who doesn’t know how to enjoy their downtime – tailoring is not recommended, unless you happen to be going to a glamorous awards ceremony, polo match or VIP booth at some other flashy event (in which case, are you sure you need to be on Tinder?). Demonstrate that you understand style, without being a slave to it, with an understated jacket from Parisian brand Ami – a modern master of this kind of dressed-up casualwear.

Approachable, built to last, relaxed and comfortable – a pair of worn-in denim jeans has all the qualities that you, as a date, should also aspire to possess. So wear them. Just make sure you opt for those with a flattering, slim fit as in this pair from Sandro, to avoid being instantly written off as a dishevelled man-child. As far as footwear is concerned, this can be a tricky, judgement-filled territory – but it would be hard to object to a pair of cream Converse Chuck Taylors, given the fact that they’ve been around since the late 1910s, and show no sign of going anywhere.

Again, in terms of your final flourishes, less is more when it comes to meeting a prospective partner for the first time. Save your vintage Rolex for date number two (or even three) and instead show a commitment to tasteful minimalism with the above timepiece from Uniform Wares. Sunglasses are permitted, but – NB hopeful romantics – only if it’s actually sunny. A dazzled squint is never very attractive, but neither is someone who, on a grey day, can’t look you in the eye.