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

SEE ALSO: We asked total strangers which fashion trends they would snog, marry or avoid

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

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Alex, PR  

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“It’s classic.”

Christopher Clarke, design assistant at TOPMAN

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“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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“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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“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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“It’s cool and casual.”

Robert Railton, visual artist

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“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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“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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