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First Date Sartorialist: What to Wear??

Last week, I asked the guy I’ve been seeing lately if he remembered what I wore on our first date (about 8 weeks ago).  “Ummm …” he paused, contemplating. “I don’t really know?  I just remember I could see your legs.  And they looked hot.”


All the hours I spent doing the typical First Date anxiety dance of “AHH-what-should-I-wear?!,” all the carefully considered questions, were for naught.  If I dress up will he think I’m stuffy?  If I dress down will I look cute enough?  If I cover up will he be turned off?  If I show some T&A, will he think I’m a slut?  Should I wear the heels or the flats?  The dress or the jeans?  The push up bra or au natural?  Hoops or pearls?   Black or pink?  And on.  And on.  And on.

All of that was reduced to “I just remember I could see your legs”???

The irony is that I think that’s a perfect glimpse inside 96% of heterosexual male minds when contemplating fashion.

They say that women dress for other women – that is, except when they’re dressing for First Dates.  In that case they’re most definitely dressing for men, except that they tend to forget men, uh, well, aren’t women.  The rules are completely different.

But what ARE the rules?  Check out this week's Time Out column, all about First Date Fashion.  I'll give you a hint: if it's remotely fashionable, guys probably don't "get" it.  Save yourself, your credit card and your date the trouble - just go naked.