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Heart Dissection

What To Wear On A First Date

Is a prom dress too much for the local pub? Dating guru and style aficionado Charlie Teasdale helps you navigate the universal dilemma that is the first date wardrobe


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charlie teasdale

BURO. dating guru


From constructing outfits to deconstructing DMs, there are few things more burdensome than stressing about the minutiae of modern dating. BURO.columnist Charlie Teasdale is our source of sage advice. He’s had his fair share of real life and hinge-assisted connections, and, as Esquire’s Style Director, he also happens to be an authority on how to put an outfit together.

So Charlie, please dissect the first date outfit. Are we really justified in agonising over what to wear?

Monochrome Molly

There is something inherently Parisian and, therefore, inherently unnerving (for us British men) about women who only wear black. Your date will think you are cool and cultured and possibly a bit mean, which is perfect if you are neither cool, nor cultured, and struggle to project conviction. Black is flattering, too, I’m told. All-white is cooler though, right? It doesn’t shout so loud. Not billowy all-white like you had a breakdown and moved to Ubud, but scruffy all-white, like you’re in an electro band from Tottenham Hale. Tattered tee tucked into tattered jeans with tattered Converse peeking out at the bottom. Gets my vote every time. Unless you’re in Paris, obvs.

The Sexpot

My pal, a serial dater throughout his Twenties, would occasionally turn up to meet girls with his top off. Just walk into Pizza Express or Vue or wherever with his shirt in his hand and simply not mention it, by way of an ice-breaker. But that much flesh on a date is weirdly unsexy. (Especially in his pallid hue.) Call me a young Tory, but early dates are about conversation and mystique and eye contact and little frissons of stuff, so getting the girls out for the boys (or as good as) seems unnecessary. Your assets, wherever they are on your body, are yours to wield however you see fit. But they’ll still be attached to you on date four when you’ve decided if the person is deserving of an audience.


The Man Repeller

This one begins on Hinge. Oh, so rather than five pictures of you smiling, doing fun stuff, hanging out with pals and generally demonstrating your interests and vibe, you’ve got a screenshot of The Rugrats, a shot of an old man on a park bench, one of you from 16 feet away at a Boiler Room gig, an extreme close up of your eyebrow and another shot of the old man from a slightly different angle. We get it, you’re cool. And lord be hecked if you’re going to play by the rules. Carrying that energy into a date by insisting on a Lars Von Trier marathon, bringing your own small batch sake and wearing a leotard over dungarees is big energy, but beware, your date might understand you, and that would be awful.


I have an aversion to Alice bands. Sorry, I know few hair-holding things are as effective, but they’re so dully pragmatic. Even the wacky ones with diamante and glitter speak of someone who still has every Disney film on VHS. I briefly dated a girl that wore one every time we met. She was smart and pretty and fun, there just wasn’t a vibe. But there was an Alice band. If it’s something your gran might wear – cardigans, petticoats, those curious quilted coats that go all the way to the floor – know that you might just remind your date of their gran. I’m sure some grandmothers are sexy, but never one’s own.

The prom queen

A friend of a friend had managed to get all the way to university without ever going on a date. When the opportunity finally arose, she had no experience in dressing for the occasion, but her guess, like the debutante she was, was that it was a formal affair. So she wore her prom dress. To the pub. You scoff, but it’s nice to make a bit of an effort – unless it’s all-white scruff, of course – and a decade later and they are married with a kid. Therefore, it could be time to dig out the Sixth Form velvet. (And the Crosse Keys Wetherspoons in the City feels a bit like a ball room, so that’s the venue sorted. I look forward to the wedding.)

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