I remember what I wore on my first date with my husband because I remember the moment I realized I hadn’t put any thought into it. I was leaving work to meet him for dinner on a Saturday six years ago and it occurred to me that I maybe should have worn something hotter than a pair of vintage men’s corduroys. Obviously, it worked out in the end, but I can’t help but feel that I am not alone in never fully understanding what one should wear on a first date.

This week, writer Riley Scarlett Wells does some hard hitting anthropological research and reports back to us at STAR⟡MAIL just what the first daters are wearing.

Fashion and First Dates

Writer Riley Scarlett Wells is a UK based music critic and poet. Her debut pamphlet 'portrait of the artist as a dying star' out now Tall Finger Press. You can read more from Wells on her Substack, Wire Mother.

It’s the month of love, which in my university town means a few things. One: the local supermarket is inundated with pink and red heart-shaped memorabilia – candles, throw blankets, popcorn bowls. Two: everyone I know is posting photos of their partners on their Instagram stories set to Labi Siffre or Lana Del Rey. Three: this week, I went on my first ‘first date’ since October (or at least, I think that’s what it was). I spent days agonising over my outfit, frantically messaging the group chat timeless classics like ‘omg im gonna throw up’ and ‘what if i secretly have an awful personality and no one’s told me yet!!!’ Somehow, I made it through. I wore a dress I loved, followed a makeup tutorial I found online about how to look like Gillian Anderson in The X Files, and listened to some cheesy 2000s pop to complete the atmosphere. Once the heart palpitations and nausea had subsided, I got to thinking: what’s everyone else wearing on their first dates these days?

As a single woman in my early twenties, I’ve been on a few first dates of – to put it diplomatically – varying quality. I take great pride in the ritual of dressing up, taking time to do my makeup rather than the usual 15-minute look I’ve got going on, and to be honest, even if the man sitting opposite me at the bar is incredibly boring, I can have a reasonably good time. At the risk of thinking about myself too much, I tend to have a mythology about myself as a ‘strange and unusual’ person in the vein of Lydia Deetz, someone operating on a slightly different wavelength than my peers. I grew up a ‘weird girl’ (derogatory) but as I’ve developed my interests and personal style this has become ‘weird girl’ (complimentary), and it's especially represented in the way I dress. My wardrobe is littered with all sorts of one-of-a-kind vintage pieces, the most recent purchase being a gorgeous emerald green velvet waistcoat dress with a paisley pattern all over the back panel. In romantic situations, I like to think of my eclectic fashion sense as performing a double-filtering function – it weeds out the people who don’t get it, and the ones who do get it like me more for it. It’s like if a poisonous frog used Pinterest to work out which brightly coloured spots it should wear as a warning signal.

In a world where internet dating has become the norm, you can carry out a weeks- or months-long fling with someone two miles away from you entirely over text. When none of us make the effort to impress our dates in person, the clothing we choose to showcase in our dating app profiles and our social media can sometimes be someone’s only point of reference for our personalities. There are countless guides online titled endless variations of ‘What To Wear In Your Dating App Photos So That People Actually Like You And Don’t Think You’re A Disgusting Sewer Rat,’ which seem to have noble intentions, except the advice they are offering is genuinely awful. Many of the guides I found seem to emphasise the importance of ‘being yourself’ in one breath before listing an extremely long and restrictive set of fashion rules in the next. Don’t wear clothes that are too form-fitting – you’ll give the wrong impression. Don’t wear clothes that are too baggy – you’ll look like a slob. Don’t wear too much jewellery – it distracts from the person underneath. You should only wear red or black on first dates as they increase your perceived attractiveness. Embrace your personal style – but only if you have the right kind!

I’m not entirely convinced these guides are written by anyone who’s actually been on a first date in the last five years, so I conducted some very serious and unbiased research using a world-renowned method: asking people I know. My main questions were ‘what do you tend to wear on first dates?’ and ‘when you have been in longer-term relationships, how has your partner influenced your fashion sense?’ To my surprise (and relief), everyone had very different perspectives on the topic, and there was a clear gender divide in the answers I received. The men I queried tended to opt for functionality over form. Sometimes there are specific pieces they opt for to give them a bit of ‘X factor’ – a well-fitting leather jacket, polished shoes – but generally they don’t dress any differently to how they do in their day-to-day lives. On the topic of dating apps, one of my male friends explained his approach. ‘It’s about presenting a unified image of yourself,’ he said, ‘my best matches have been due to obscure references one of us has made in our profile.’ On the other end of the spectrum, one of the people I spoke to described a violent shift in their fashion choices in the early stages of dating their partner: ‘I think “should I dress in this kind of way because [it’s] how I should look as the partner of this kind of man?”’ The same person also stressed the need for authenticity. As a nonbinary person, they try to dress true to their gender expression so that people come to terms with their identity early on, and don’t mistake them for a woman.

Overwhelmingly, the majority of women I spoke to in long-term relationships said that dating has allowed them to embrace their ‘true’ style, whether it’s more feminine, eclectic or goth. When they’ve tried to dress up for special occasions in outfits that conform more to the male gaze, their partners have been less responsive because it hasn’t been true to them. It was really refreshing to hear this perspective, because I feel like it’s so easy to be swallowed by the idea of who you think your partner should be with, rather than who you actually are.

All of these experiences seem to contrast greatly from the life of my mother, who spent her early twenties in central London in the late 1980s and early ‘90s. Without the immediacy of smartphones and dating apps, it wasn’t so unusual to go out and meet someone at a concert or through friends, though that world seems to be getting further and further away now. Not only was there less immediate access to Hot Singles In Your Area, but there was also no fast fashion. If people wanted to be stylish, they had to seek out clothes that felt authentic to them, rather than following microtrends and buying everything they saw on TikTok Shop. My mother described her style in her early 20s as ‘all black’ – big sweatshirts, leggings, lots of bangles that clinked when she moved, topped with a leather jacket that ‘protected [her] through London life and gave her an attitude.’ There was also mention of printed tights with a map of the world pattern.

I spoke to both my mother and one of her university friends about their experiences in London, and both of them said dating as we know it today wasn’t really ‘a thing,’ at least not in their scene. People went out to pubs or concerts in groups and got to know each other’s friends, or they held house parties and invited everyone they’d ever met. In that regard, if they did date someone, it was probably easier because they got a sense of how that person moved in the world, rather than just one-on-one. She also pointed out that because it was harder to stay in contact with people, when they made plans they were more pressured to stick to them. It wasn’t possible to call people every night for weeks on end without meeting up in person, because that would send your phone bill through the roof. If you were on the move, you couldn’t just phone someone up to cancel plans last minute.

Although it wasn’t that long ago, this world sounds unrecognisable from the trials and tribulations single people go through today just to get one meeting. Maybe these women are looking at the past with rose-tinted glasses, and no one’s memory is perfect, but the world they described to me sounds so much freer than the one we live in now. Personal style was something actually personal, and dating was something that happened with intention, rather than a conversation struck up with a stranger over the internet because you’re bored.

My incredibly serious research over the last week has led me to three distinct conclusions. One, I need to cut my wardrobe in half. Two, I need to sit on purchases for at least two weeks before I impulsively spend money on something I saw online. Three, I need to switch to a flip phone. But before I do any of those, I have to get ready for a date.

The Molehill’s first date formula coverage is perfection:

I emphatically disagree with just about every ranking here: