Poorly Dressed Men and the Women Who Tolerate Them

30 July 2008

Whether walking along the streets of hipster neighborhoods or drinking in the random pub/bar/restaurant/lounge it is a common sight: nicely dressed women and their proletariatly attired gentleman date.  Cute and coiffed ladies with men whose attire is more appropriate for a casual picnic than a night on the town are a far too frequent sight.  My general disdain for khakis (garanamals for people who wear adult sizes) shorts (for all men over the age of 14, never appropriate unless athletic activity is involved) and flip-flops (not the political variety but those that may be worn for running errands, beach frolicking, or when sick) is a bit of an aside.  This is a question of balance, and one that I have never understood.


For the longest time I had dismissed this phenomenon as being as relevant to me as Facebook, Late Night Shots, and Abercombie & Fitch – trappings of youth about which I refuse to care.  And then I saw My Favorite Redhead last night.  She walked into our mutual watering hole and was simply stunning in her black and white summer dress and shoes that would have inspired LivLuv’s envy.  She was about to have a birthday dinner with her boyfriend – significant mostly because she is not a woman prone to having boyfriends or other long term romantic entanglements.  Between me and our other friends in the room, she surely received scores of compliments on her hotness in general and the hotness of the dress in specific.


Later in the evening, after her dinner had concluded, she and her beau strolled down the street as I was outside having a cigarette conversation with my crush de jour.  I was gobsmacked by the contrast.  She was dressed in a manner where she could have entered the finest of restaurants, and he looked like an extra in a Gap commercial – cargo shorts and polo shirt but thank the baby Jesus his collar wasn’t popped.


MFR is brilliant, accomplished, funny, an all around terrific woman, and my age – mid 30s.  Yet she, from outward appearances at least, was accepting of her boyfriend having dinner at a nice restaurant in shorts and flip flops while she was dressed to the proverbial nines.


Does it no longer matter to women how their partners and paramours attire themselves?  Has the collective man behaved so badly for so long that treating a woman well excuses poor attire?  Do women simply no longer consider a gentleman’s attire relevant?  Am I so hopelessly old-school, prim, proper, and fashion addicted that I am wrong-headed on this matter?

Feel free to answer those questions in the comments.  I will still follow the only fashion rule I have considered for the better part of two decades – if Cary Grant wouldn’t wear it neither will I.


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