Dressing dilemmas

For a fashion editor, or maybe because I am one, I am mighty indecisive about what to wear. I need to feel comfortable and together before I leave the house, otherwise I twitch all evening, regarding other women who've got it right with envy tinged with a little venom. If I get it right I never think about my outfit again.

I also have a terrible habit of only wearing one or two looks for a month or so, convinced that nothing else in my wardrobe works. Then I get bored and start putting together the next great go anywhere outfit.

At the moment I'm wedded to very, very short, cuffed hem flannel shorts from Gap of all places, in charcoal grey & in black. I wear the grey ones with patent platform Mary Janes in burgundy with paler grey wool Levante tights and an oversized grey/blue cashmere V neck cardi, or purple tights and the same shoes in French Navy, with a poloka dot chiffon blouse underneath the cardi. The black ones go with opaque black Wolfords, black suede & patent ankle boots and an oversized tux.

I have a date tonight, so I'm thinking the grey shorts - lots & lots of leg, but minimal cleavage (I have a lot going on up there, so even a peek is an eyeful). Only thing is that I have a plan B lined up for tonight if I get to the point where I wld rather stick pins in my eyes from boredom/horror/disgust than stay a moment longer on the date: the Whitney Biennial and a drink after at The Carlyle with my girlfriends. This outing requires less sassy and more sexy, ideally a cocktail frock & stilettos. I suppose I cld shove the frock & heels in a bag just in case, but it's a right pain to have to lug a spare outfit around with me.

Goodness, dating is complicated.