A recent conversation we had with a few friends turned to the subject of what everyone wore on a first date. Some of us were long married, but we still had fresh memories (as had our partners) of what we wore. Others had dates the previous week.
Strikingly, everyone wore basically the same thing: blue jeans, a navy knit, chukka boots or tennis shoes. Sometimes the knit was a shawl-collar cardigan, sometimes it was worn with a blue oxford and sometimes a white tee, but that was about it.
Why had we all worn the same thing? Probably because consciously or not, we all had the same goal in mind: appear nicely dressed but not flashy, approachable and relaxed, in clothes that flattered us but would not become the focus of attention.
The exact clothes someone might wear on a first date will of course vary hugely by age and culture. But they probably often have similar principles in common: to seem comfortable and congenial, confident but not look like you’re trying too hard. It’s perhaps a good way to think about such a situation.
And actually, it was interesting that our little group varied quite a bit by age, from mid-twenties to mid-forties. The same kind of standard menswear blues that I wore 20 years ago were the same ones a 30-year-old friend wore last week. (Although mine were oversized Gap back then.)
“I was told by my wife that I did a good job on our first date, basically wearing what’s pictured here,” says Lucas. He and his wife have been together for seven years. “The navy knit and blue jeans was simple and safe, with little things like my rope bracelet betraying a bit of personality.
“I was also told I did a good job with grooming: neat and subtly fragranced. I can’t tell you what the fragrance was – that’s a secret – but that doesn’t really matter. The point is it was noticeable but not overpowering.”
In fact it’s striking that this kind of approach is basically what women usually say they want when asked: men that appear confident, honest and open. The opposite of the flashy, showy look that’s supposed to portray confidence, but often seems aggressive and insecure.
“I’d summarise it as, only show them the craziness gradually,” says our friend Matt Coles. “Start simply and easy, with a brown-suede shoe perhaps. Wait until the third date – when they already like you – before bringing out the pony-skin Michaels.”
Matt has a particular predilection for leather clothing, which his lovely wife tolerates and also applies a natural limit on (we all know the feeling). But he wouldn’t wear that on a first date – because then that would be the centre of attention, rather than him.
In the interests of widening this group, I reached out to a few friends in different parts of the world. A friend in his 50s in New York said he would always wear a shirt and jacket to a date (though not a tie). But his aim was similar – for him a shirt and jacket seemed the most likely to seem respectful, yet approachable.
A very cool friend in his 20s, in Paris, said he wouldn’t dream of a navy knit and jeans – it would be way too dull and old. But then he said he usually wears a simple black T-shirt, dark indigo jeans and black boots.
Note that most of these first dates were presumed to be a drink or coffee – not dinner – which definitely puts the emphasis on the casual.
In an attempt to illustrate this article, Lucas and I wore different versions of that safe, easy outfit.
Lucas is in the classic navy-knit-and-blue-jeans, although the collar of his knit is quite unusual. “It’s ‘lamora’, a mix of lambswool and angora that’s really soft. Basically cashmere on a shetland budget,” he says. Apparently his wife remembers how soft the jumper was to the touch (above).
I’m in an easy alternative: T-shirt rather than shirt, grey not navy, dark jeans rather than light (below). The T-shirt makes it much more casual of course, but then I’m often afraid of overdressing (given I wear tailoring so much). The shawl cardigan is slightly risky – to some it looks too much like a dressing gown – but I also know it’s flattering on me.
Of course there’s a risk that two menswear guys turn up on a date and are wearing almost exactly the same thing (as I’m now realising it looks like Lucas and I are!). But then, what a good ice breaker – and you realise early that’s there’s nothing the two of you like to talk about more than clothes.
So what do you, or did you, wear a first date?
Again, I’m very aware the recommendations here are culturally specific, so let’s spread the net as far as the Permanent Style readership will go. From our surveys over the years, I certainly know the age runs from 17 to 70, so that’s a good start.
Clothes pictured:
Simon:
- Drake’s shawl-collar cardigan
- Permanent Style T-shirt
- Bryceland’s 133S jeans
- Edward Green ‘Shanklin’ boots
Lucas:
- Johnston’s of Elgin jumper
- Jake’s shirt in Permanent Style oxford cloth
- Levi’s jeans
- Moonstar trainers
