'Should've Worn a Skirt,' He Said on the First Date. He Was Serious.

Two weeks ago I went on a date with a lawyer at Goldman Sachs. He was 49 years old, “not handsome in the classical sense, more Jimmy Cagney than Cary Grant” as he so charitably described himself and preferred Italian suits over Savile Row’s. His magniloquent and crassly funny e-mails had made me curious, so I’d accepted his invitation to have dinner at Bond Street.

The conversation was a little awkward at the beginning, as would be expected when you meet a perfect stranger, but after three cocktails we found common ground and got chatty. From politics – we discussed the icky subject of racism in Belgium – we jumped to traveling – I asked him twice where he grew up (eek!) – to our professional lives – I now know how to bail out an entire country.

I also told Mr. Lawyer that I had great trouble getting dressed for our date. This might surprise you but it’s really quite simple an equation. You see, I’m not used to dressing for straight men. I work in fashion for pete’s sake. Everyone’s either gay or a woman! And the rare straight man who does loiter around in the colorful corridors of the fashion industry chases models for sport. So I dress for myself and for other girls. It’s become somewhat of a job these days and the majority of thought goes into whether the outfit is inspiring, unique and well, Me. I never really have to think about any romantically enticing hem- or neckline, because I’m either in front of a gay street style photographer or a seasoned fashion maven at an office. So when the odd date does come around I am left helpless and desperate to please. Everything and anything I put on is either too sexy or too fashionable. I constantly have to remind myself that men are simple creatures, including Mr. Lawyer, who told me “there’s no ambiguity, just black and white.”

And so he found no better way to say it then to just be brutally honest: “You should have worn a skirt!” This wasn’t meant as a joke. He was quite sure of this and continued to complain about my lack of skin until we left the restaurant. Mind you, I was wearing a tiny Peter Pilotto shirt that bared my arms and shoulders quite generously, and really, isn’t that the only thing you can see when you’re across from someone at a table? “I would have dropped my napkin a few times to get a peek!” he retorted. OK, this was a joke, but I had to defend myself nonetheless. For one, it was freezing outside. I wasn’t going to run around in a summer dress, or dig up my tights again neither. Secondly, I didn’t want to come across as some ditzy fashionista – the bastard googled me – who’s got nothing but a body as ammunition. (Though I don’t have any tits, nor ass to speak of…) Thirdly, didn’t he already see my legs on-line? “Yes, they are very nice!” he said. “I even told my friend, she’s got nice gams.” So why make such a big deal out of it?

It got me thinking, what is the appropriate attire for a first date? Was I wrong to wear pants? Was I wrong to assume I would come off as slutty or too eager if I wore a short skirt? According to Mr. Lawyer it’s the only way to tell if the guy is a “James Bond”. If he can keep his cool while you’re sitting there flaunting your goods, he’s a real man. Plus, he assured me that “9 out of 10, no, 99 percent of men would say they prefer a skirt over pants.” So I did a little survey this weekend. I put on the outfit again, stopped a few guys around the West Village and asked them if it was suitable for a first date. Or if they would have preferred to see a skirt instead. And the answers were all in my favor, though mildly. Some didn’t understand the top because of the ruffle – it’s too fashion, I admit it. But what it all came down to was that none of them said they preferred a skirt. According to the preppy guy, “jeans is the uniform” so I hit the nail right on the head. So what’s up with Mr. Lawyer, really?

This piece originally appeared on Tales of Endearment. Republished with permission.