Deep Thoughts: Hanging Outfits

Many ill-fated nights begin between these walls.

Inspired by a good friend's musings on first date outfits (and okay, a little miffed I wasn't consulted to weigh in on the subject) I set about conducting a serious scientific survey of my own, appeased by said friend's promises that when she writes her 'what to wear to make out in an alley' post, I'll be her first call.

Since I adhere to a strict anti-dating regime, many of my hang-outs happen spontaneously so I don't have the benefit of knowing when I'll run into friends who also happen to be boys. This week, however, I found myself in unfamiliar territory, panicked and stressed, not only because I had committed to an actual time and place but because all I really knew about the boy I was meeting was his seriously stylish aesthetics quite possibly surpassed my own. A text from my fashion advisor/life coach reassured me that showing up in anything other than my usual sartorial masterpieces would feel wrong, so I settled on a variation of my daily uniform: boots, dark denim, loose layered tanks, an oversized cardigan and 3 or 4 necklaces.

The responses from friends confirmed that the only thing to remember when selecting "hang out" attire is to wear what you love. I assumed the input from my fashionable circle would lead to the magical culmination of the perfect date ensemble, a veritable 'nothing can possibly go wrong if you wear the following', checklist. But tragically, all but one of the friends surveyed have been off the market for some time and I was forced to make do with what they donned for the first date with their now beaus. Phenomenal and reassuring, their answers solidified that it really doesn't matter what you wear! Or at least it didn't in these cases. Names are omitted to protect the fashionable.

• "Bop Basics dress with the ACNE Dolores top under it, leggings and boots because it fits really well and it's not too scandalous."


• "Well we were both bartenders so either black pants or a skirt and a Pokegama polo or white shirt."


• "I don't know, it was super ugly. I think a long white prairie skirt with a brown camisole I got in London. I can't remember which shoes exactly, but they were flat sandals. Gold I think."

Which then brings me to the friend who graciously supplied almost a powerpoint presentation including (but not limited to) a numbered list detailing where and when she purchased all items. Did I mention this date happened in 1995?

• "Black ribbed merino turtleneck sweater from Club Monaco, vintage Levi's bellbottoms, de rigueur chunky black boots, an ill-fitting vintage velvet peacoat from Cheap Jacks and a Prada knockoff black nylon bag from French Connection."

Obviously, we're desperately in need of a brush up on date dressing, so please help us! What are your go-to pieces?