Summer Dilemma

Though it's been 6 years since I left the dating game (and almost 3 since my wedding), I still enjoy weighing in when it comes to outfitting for such an occasion. My dear friend Jane L. has been dipping a toe in the dating tide recently after a brief hiatus, and through her varied forays into fabulous (and not so fabulous) rendezvous, I've gotten to revisit some of my favorite rules of dressing.

Sunday brunch at Limani in Roslyn. No high heels on a sunday. Wedges are fine, (this Maribeth espadrille is a perfect choice) a peep toe, a sling back, a flat strappy number, all okay. And no denim. Never blue denim in the summer (thats more a rule of logic than a principal of fashion, but important nonetheless). Anthropologie Sundress, gauzey scarf, light colored skirt and top, keep it casual.

Friday night dinner at One if By Land Two if By Sea in the West Village (venue says a lot about the potential suitor- this one is good so far). Heels are good for a Friday, but nothing too formal. No black dresses (unless there's a pop of color at the neck, like this Bubble from J.Crew). Stick to straight cut ankle length pants, and a silk top. An no boots. Boots go back in the closet after March 31st, and must stay there until mid September.

Saturday drinks at PJ Clarke's, midtown. (A better choice for an afterwork night, and date number 1 or 2, not such a great 3rd date). Jeans would be a yes if this were May, but the white jean is an acceptible alternative for June. No flat sandals on Saturday night. And a large bangle is a nice touch. I love a few large bracelets jangling together as one sips a vodka gimlet (or two, if hes a keeper at this point. And if he's not, the 2nd one may temporarily alleviate the sting of disappointment).