'If you wear that on a first date, you'll look like you've got low self-esteem,' my housemate said to me as I held up a short, strappy black playsuit, trying to work out what would be a suitable outfit for a drink in the local with a guy I'd been chatting to on Tinder. Ditto an Alexander Wang slip dress I have in a bright tomato shade. 'You can't wear a red dress on a date. You'll look like you're trying to act out a rom-com,' she scorned.
But what do you wear that will help you live up to your posed and filtered profile pictures, but equally, as my frank friend suggests, doesn't make you look a bit desperate? Because admit it, these days you probably go on more dates with people you know via a headshot and a few messages than those you've met IRL.
Of course, once the first impression is over, and you get down to the nitty gritty of whether or not you hate Morrissey and if either of you have encountered any Tinder horrors yet, what your wearing pretty much means fuck all. But in the first instance it matters – even if it’s only for the sake of your confidence.
So we asked some of our favourite fashionable women, with their fair share of experience of swiping right, what works for them on a date to try and decode this sexy style enigma.
For the record, I'm currently trotting out a combo of black jeans, flat, pointy ankle boots, a biker jacket and a black silk camisole. It's a perfectly casual and straight-forward look that still shows a bit of bare arm and shoulder. Because as Cher Horowitz said: 'Sometimes you have to show a little skin. This reminds boys of being naked, and then they think of sex.’ Which when it comes down to it, is basically the point.
Dolly Alderton, writer and TV producer
My go-to date outfit is normally Margaret Thatcher waist up, Julia Roberts in Pretty Woman waist down. I'll team a polo neck or a silk shirt with a mini skirt or leather trousers. I always used to wear flats because I'm very tall and I didn't want to emasculate the guy or scare him off, but recently I've come to realise that any man who is emasculated by a tall woman is no man at all, so now I wear a gorgeous pair of big heels and see how he reacts. I feel sexy in heels and it's a good way to sort the wheat from the chaff at entry level. I also always spray perfume in my hair as my grandma told me it's the way to make a man fall in love with you. I think that's probably a load of old guff and I'd also prefer him to fall in love with me for my Mick Jagger facts and readiness to pun, but it's quite a sweet and optimistic ritual anyhow.
Lynn Enright, sex, relationships and fashion writer
I try to feign sexy nonchalance on a first date. Or nerdy sexiness, if that's not too much of an oxymoron. Legs and drinks. I think those are often key to good first dates. Think skirts (pencil skirts or above-the-knee) and sweatshirts or T-shirts are a good choice. On my first date with my current boyfriend, I wore a yellow wool A-line COS skirt, a white shirt with black polka dots, black opaque tights and high leather Topshop boots. It wasn't very sexy, it was more cute really.
Laura Galligan, creative producer at ASOS
If the weather's not hot, I'll always go for a ripped skinny jean – tight, so your bum is out, or if it's warm out, a little skort that shows some leg. I'll wear either with a T-shirt and trainers which makes it casual enough not to look like you've turned up in a wedding dress. It's not slaggy because you're in a trainer, but at the same time you're putting it out there that you have legs. Plus, if you wear a good trainer, that always impresses them.
Anna Hart, writer, and contributing travel editor at Stylist
My go-to date outfit for years has been the same: a short Urban Outfitters dress, with my battered brown leather jacket over it. Guys can be freakishly literal in their interpretation of women's clothes - wear something pink and fluffy, and they'll think you're Baby Spice, even if you're swearing like a sailor and talking about Butthole Surfers albums. Wear a tailored jacket and they'll think you're a corporate boss-woman, even if you're a yoga teacher. So, based on years of experience, my date outfit rules are: If the skirt is short, wear flat shoes. If high heels make you feel uncomfortable and trussed up, this is the opposite of sexy. Bright colours stand out, but pink will make him think of Barbie. Don't go too extreme in any direction. Balance a feminine dress with a leather jacket/boots, or pretty, girly vintage clogs with denim. I guess a well-rounded wardrobe indicates a well-rounded woman. THE GOLDEN RULE: dress for you, not for him.
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Picture: Sophie Davidson
This article originally appeared on The Debrief.