First date fashion for forty something singletons

When Rosie Green, 45 and a mother of two, started online dating after the end of her marriage this year, she had no idea what to expect. It wasn’t the shortage of men that was the problem …

My name is Rosie Green, I’m 45 years old and until this summer I had never been on a date.
I met the man that was to be my husband at eighteen. Our relationship was fuelled by multiple snakebites at Crystal’s nightclub and then progressed slowly in the usual student way. (Think awkwardly loitering around each other’s halls of residence rooms on the pretence of borrowing highlighters/bread). A few more drunken nights out and we were ‘going out’ with each other by default.
Before that I had experienced nothing that would constitute a date. The courtship with my teenage boyfriend had followed a pattern pretty similar to above.
I did once go on a group date to see Mannequin at the cinema (which then became a Thunderbird drinking session in the park when we didn’t pass for the requisite fifteen).
Fast-forward three decades and I am popping my dating virginity.
Well last year, after fifteen pretty happy years, my marriage imploded.
I didn’t see it coming. I was shattered. I existed for six months in a maelstrom of grief and anxiety. Lost two stone in as many months. And my sense of self entirely. I crawled through each day, barely able to keep it together for my two children.
Now, a year later, I am (almost) back to the old me. And ready to meet someone.
But my worries are manifold. Will they fancy me? Will I fancy them? Can I still flirt? What to order so you don’t end up with black bits in your teeth? Have the kids given me nits? Do you split the bill?
Oh and what will I wear???
It’s a concern shared by many. Google ‘what to wear on a first date?’ and you get 1030000000 results. Which is three times more than ‘what is the backstop?’
I didn’t imagine I’d ever be Googling this.
Sartorially I’m pretty confident. I’ve worked in women’s magazine’s my entire life. I’ve been a beauty journalist for twenty years. I know how to do no-make-up make-up. I sussed a long time ago how to get glowing, come hither skin and artfully mussed up hair.
And as for clothes? I’ve dressed the most celebrated fashionistas there are – think a-listers like Sarah Jessica Parker for Christ sakes. (Let’s ignore the fact I gaffer taped her tits up. Rookie error).
But with my self-esteem shattered in a million shards, I was questioning my ability to nail first date chic.
My first date, with cute, age -inappropriate photographer Chris (35) was a good starting point. (He slid into my DM’s – how very millennial). It was good practice ground. Not too much riding on it. It was only ever going to be fun.
I generally don’t take more than sixty seconds to decide on an outfit, but for this date I’d say the time taken hovered around ten minutes. I wanted form fitting, but not so tight the lace on my knickers would show through. I wanted cool, but not so cool as to be off putting. (Verging into Man Repeller territory would not be good – I think brogues and socks, puffa jackets that require extra wide doors, even one of those turban headbands might be a leap too far for most guys).
I wanted to vibe relaxed, confident, and artfully stylish.
In the end I chose a form fitting denim skirt with a v necked Isabel Marant t tucked in and some flats. (At 5ft 10 height is always a consideration).
I may or may not have worn a ‘two size bigger’ promise bra from M & S….
I then waxed, buffed, bronzed, tinted, tonged..
It felt good. It went well. We went on a second and third date.
My mates who have been on the dating treadmill a while longer, and are thus a bit more skeptical than me, feel more cynical about investing in their prep time.
After a recent disappointing date (he didn’t take off his sunglasses and they were… indoors) my friend Lucy, 46, an events manager, was less peeved with the waste of three of her evening hours and more annoyed with the money she’d wasted on a new skirt and blow dry.
It was one of a string of one-and-done dates she’s been on. And after ten years or so in the game she’s definitely got dating ennui…
Perhaps because of online apps, multiple dating is on the rise. There’s an endless carousel of people to like and message with. You could go on dates seven nights a week if you wanted. (I’m currently on about one a week – as a single mother, with two guinea pigs, lots of friends and a full on career that’s about as much as I can manage).
Multiple dating has lots of positives. It undoubtedly helps stop future projecting i.e. Googling wedding venues. But on the flip side it also means a lot of outfit planning and grooming.
According to on line dating service Plenty of Fish’s research, the average dates cost £106.06, but that’s not factoring in the £74 and £53 men and women respectively spend on clothes and grooming.
So how, I wondered, do I strike it right? To make sure they’re not going to be straight back to swiping/scrolling in the taxi on the way home?
I realise this is all sounding a bit 1950’s, -you know, how to lure your man in with apple pie scent and a kittenish demeanour. For me it’s not about that –I want to look cool and confident so I will then feel cool and confident.
I made a rookie error on an early date. The dress was perfect (fitted, spaghetti straps, but with a relaxed sundress vibe) but the straps were too long. Which meant I was constantly adjusting so as not to show my embonpoint. Adjusting is not sexy. Neither is the word embonpoint.
Then there is how revealing/form fitting to go?
Ironically I dress less sexily on a date than I do for dinner with my girl friends.
Which, after talking to former dates and male friends who are dating, sounds like the right choice.
Bert, a 43-year-old liberal civil servant who, like me is new to the dating scene, says ‘super booby’ is not great because ‘you don’t know where to look.’ He feels midriff is also de-trop for dinner.
Cleaning company MD James (45) says, somewhat controversially, that ‘the amount of sex in an outfit will have consequences on his behaviour. ‘I realise a woman wearing a short shirt doesn’t mean they want to shag you, but it probably means I’ll want to shag them. Lots of flesh revs me up and make me push for more (sexually) than I might have done otherwise. And sex too early almost always takes things off kilter.’
Clothes are also an indicator of tribe right? When I think back to my teenage days this was essential in determining a person’s compatibility. Your clothes marked out if you were a raver, an indie kid, a mod, a townie, a preppie,
Chris the photographer – boarding school, Home Counties boy now resident in London – tells me he has some sartorial rules. No penciled on brows (note to Chris everyone has penciled brows, it’s just some are more subtle than others), no lip fillers and no bandage dresses.
Bert would be put off by ‘Boden-esque Balham’ outfits. Neither does he like flashy labels. He’s also not really into the charity shop vibe. ‘I know it’s a look’ he says ‘but sometimes that look is just shit.’ He debates shoes for a while. Trainers can be cool, but sometimes a bit too scruffy. Skyscraper stilettos a bit too try hard. He eventually settles on… boots.
I’ve also noticed men notice watches. Joking with one date that an outfit of mine verged on ‘escort’ he said ‘escorts wouldn’t wear a Cartier Tank.’ Another potential guy had a quote on his Instagram that said ‘You say you are not like all the other girls, but your Michael Kors watch is telling me otherwise.’
There’s another area that appears to be a big turn off for men. Faking it. “It only works in the short term’ laughs Chris. Artifice has long been hated by both the sexes. It taps into a basic fear of being duped.
Ovid, the Roman poet, said of the painted faces of senoritas ‘no man can say I love you, for you are not what he loves.’ Another Roman, Martial, wrote ‘you are but a composition of lies. Two thirds of your person are locked up in boxes at night.’
Apart from the two sizes bigger bra I’ve tried to limit the fakery. And the getting overly dressed up. ‘Too done equals too keen’ says Bert. If I’m wearing high heels I’ll try and offset that with jeans. Ditto a sequinned or silk top.
There are obvious winners in the dating game. Sheer fabrics, tactile materials. I love cashmere (Wyse is my go to label). Ditto silk tops. High heels feel sexy. And I’ve found the French mid market brands like Ba&sh, Rixo and Sandro always turn out clothes that have both elegance and edge.
I’ve also massively upped my underwear game. Think lace, colour coordinated (I know right?) and pretty not porny. Even if I don’t plan on revealing it too soon (I’m a long way from Fleabag in that regard) it feels good to be prepped. When I was a smug married I wore knickers older than the Tory government. Just saying.
And I now lavish more attention on my body too. No more dusty shins. Smooth, moisturised limbs are a non negotiable.
But back to the clothes.
In actual fact, I now find date dressing is relatively simple. It’s just wearing what you wear normally, but with twenty percent more effort. Oh and I may have worn the same first date outfit out a few times.
But what about men?
It’s a sartorial minefield for them too.
General rule? Anything too Simon Cowell is a no. Bootcut jeans. Ditto slashed-to-there shirts. Ewww.
My friend N tells the story of meeting a guy at a fancy dress party where he was James Bond and in a slick tux.
They agreed to rendez vous in Covent Garden a few days later.
He showed up in his civvies. Padded (!) cycling shorts, a hand knitted sweater with a South American vibe and an earflap hat.
‘Think a grown up version of Nicholas Holt in About A Boy,’ she grimaces.
‘A bad outfit can kill lust in a heartbeat.’
Isn’t that the truth…

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