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Skirting around the Issue

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 than 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 dart around in a summer dress, nor dig up my tights again either. 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?

Black blazer by Roberto Cavalli; Dark denim cigarette pants by Mih Jeans; Ruffle cut-out top by Peter Pilotto; Purple suede pumps by Casadei; “Modern Retro” sunglasses by Toms; Cotton, nautical clutch by Max Mara.

Photos by Milton Arellano.

 

Leave a Comment

11 Responses to “Skirting around the Issue”

  1. avatar

    I love your outfit, and I especially adore the top! so lovely! But I am a girl…I know you are probably trying to go with the “relaxed, casual and not trying too hard yet feminine look”, but I can somehow tell from a guy’s perspective that your outfit is not “romantic” enough. You don’t necessarily have to wear a skirt-this dude you met, he sounded a bit horn dog, but I do think the jeans&black blazer combo is not a good idea for a first date.

  2. avatar

    This outfit is super cute and yet smart and sexy.. also that pop of color on the shoes made it for me..love love love it! this is an outfit of a independent free thinker and the fact that he preferred Italian suits over Savile Row’s. which is a deeper commentary in and of it’s self for me.

  3. avatar

    First off, “dressing for”? I thought people were supposed to deny every dressing for someone.

    Anyway, as a straight male, it is my opinion that you can never go wrong with a pencil skirt. It is the perfect balance and no respectable guy will question it on a first date.

  4. avatar
    Janissa Brown - Reply

    I think your choice was fine as well, but I do agree with what lawyer date said in wearing something alluring is a good way to tell if the man is a real man who can be respectful, treat you like a lady, and behave. Meaning, not assuming because you wore the skirt or dress or even revealing shirt,that you ready to do the horizontal dance. :) Men are definitely visual when it comes to beauty. Some more than others. I believe as a women we must always leave a man with some sort of mystery, but show him the goods are just that… the goods lol First time reading your blog. I like it very much.

  5. avatar
    Janissa Brown - Reply

    I think your choice was fine. But was it a day to early evening date, or night time date? I do agree however with lawyer date, that wearing something alluring on a first date is a good way to tell what kind of man you are dealing with. Can he be respectful, treat you like a lady, and behave? ( especially if you already find him attractive. but if not ???) That is certainly important. Men are very visual when it come to beauty as you know this. As women, I do believe in leaving a bit of mystery and not revealing all. BUT, we certainly (for ourselves and our dates) Must look absolutely fab. In which you did. But clearly he expected what he had googled. Oh well his bad. the other thing, I did not see what you did to your hair. when you do blazer and Jeans with that fab top the hair ( I hope ) was wispy and flowy. If not straight and long, then wavy would have complimented the outfit. And yes those pumps and blouse AWESOME!!!

  6. avatar

    I feel there’s too much consideration for what the date thinks. And, as LyLynn has indicated above, he sounded a little bit sleazy.
    You clearly have impeccable taste – leave it at that.

    This was the post that drew me to your blog, btw. I look forward to reading through your other posts on Dating.

    Best Luck !

  7. avatar

    FYI, you look fabulous. Your outfit is great for a date, especially a top. You need to stop seeing/dating guys with mental problems and start seeing someone that appreciates you. You are great. Please don’t forget that.

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