We asked total strangers to tell us what to wear on a Tinder date

Mashable's resident paper doll hunk gets dressed for his date with destiny.
 By 
Rachel Thompson
 on 
Original image replaced with Mashable logo
Original image has been replaced. Credit: Mashable

LONDON -- If you're lucky enough to nab yourself a date through a dating app, then first of all, congrats! Now comes tough part: What on earth are you going to wear? 

Seriously though, choosing an outfit for that all-important first date is really tricky. Should you don all your glad rags, or should you play it mega cool and casual. 

First impressions count, and one wrong move could mean the difference between dreamboat and disaster. 


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We took to the streets of London during men's fashion week and asked total strangers to dress up dress up Ashley — Mashable's resident paper hunk — for his date with destiny.

Here's what they came up with.

iLLAMADi, musician 

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Original image has been replaced. Credit: Mashable

“This outfit is different and it will get people to take notice. Everybody can wear trousers; how many people can wear a kilt with green crocs? It’s just out there. Someone is going to take notice, whether they like it or not!”

Tom Rasmussen, freelance writer

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Original image has been replaced. Credit: Mashable

"I want a man who will express himself though his dress. And, also I think gender is fake, so it’s nice to have him in a skirt. I chose that because it’s what felt right. And, I love those boots. I want them, but they don’t make the double soled Doc Martens anymore.”

Jai'me Jan, fashion writer and blogger

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Original image has been replaced. Credit: Mashable

“I don’t like anything too formal, and not too trendy either. I think this outfit looks really cool; a little bit different.”

Ronan Summers, menswear fashion blogger 

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Original image has been replaced. Credit: Mashable

“I think denim jackets are cool at the moment for spring/summer, and I think you get all the girls!” 

Dylan Ross, magazine assistant 

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Original image has been replaced. Credit: Mashable

“I just picked up a leather coat yesterday and I was going to wear it today. And, the kilt just looks a bit more interesting and more free, out of the selection anyway.” 

Erwin Trinidad, nurse and menswear blogger 

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Original image has been replaced. Credit: Mashable

"I’m into smart casual and I like light blue. It’s very cool and nice and works regardless of the weather.” 


Alex, PR  

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Original image has been replaced. Credit: Mashable

“It’s classic.”

Christopher Clarke, design assistant at TOPMAN

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Original image has been replaced. Credit: Mashable

“I just thought why not dress him a bit like a TOPMAN? Something a bit classic.” 

Craig Hammond, blogger at That Dapper Chap

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Original image has been replaced. Credit: Mashable

“It’s a casual look, but the brogues make it a little bit more formal, just to show the other person that he’s dating that he has thought about things, taken it slightly seriously.”


Darrel Hunter, photographer 

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Original image has been replaced. Credit: Mashable

“For me, it’s normally black that I'd wear on a first date. It’s a staple thing and, of course, with a leather jacket you can’t really go wrong.”

Tony Tran, fashion blogger for Fashitects

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Original image has been replaced. Credit: Mashable

“It’s cool and casual.”

Robert Railton, visual artist

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Original image has been replaced. Credit: Mashable

“I chose this because it’s new puritan, which is a kind of simplicity. It goes back to basics -- stripes -- reviving the modernist 1960s look."

Xuanming Xu, student 

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Original image has been replaced. Credit: Mashable

“Black is always right for pants. I would have chosen another type of sneakers, but I couldn't find my favourites.”

Illustrations by Bob Al-Greene 
Additional reporting by Lindsay Davis
Photography by Andrew Cowie

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Rachel Thompson, sits wearing a dress with yellow florals and black background.
Rachel Thompson
Features Editor

Rachel Thompson is the Features Editor at Mashable. Rachel's second non-fiction book The Love Fix: Reclaiming Intimacy in a Disconnected World is out now, published by Penguin Random House in Jan. 2025. The Love Fix explores why dating feels so hard right now, why we experience difficult emotions in the realm of love, and how we can change our dating culture for the better.

A leading sex and dating writer in the UK, Rachel has written for GQ, The Guardian, The Sunday Times Style, The Telegraph, Cosmopolitan, Glamour, Stylist, ELLE, The i Paper, Refinery29, and many more.

Rachel's first book Rough: How Violence Has Found Its Way Into the Bedroom And What We Can Do About It, a non-fiction investigation into sexual violence was published by Penguin Random House in 2021.

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