It's not like in my head I don't know what I'm supposed to wear: cool jeans, a white tee and slouchy blazer with killer knee-high boots and funky necklace, but my body is more Joan from Mad Men and less Miranda Kerr unfortunately, so I sometime looks like I came out of Talbots (I own nothing form Talbots). Being, ahem, blessed, with a larger chest I think is not good for a first date either. Anything that is remotely low-cut has me looking like Jessica Rabbit. It's a lose-lose. Unless it's summer, I can rock a cute summer dress any day.
I once described an outfit of mine before a date and my friend said "What your describing reminds me of that Jessica Simpson pic with the bad jeans." No, I did not wear a leopard belt! I did wear trouser jeans though.
Also, another time I was getting my hair blown out, and was talking to the guy about my date (it was my second date with Jay). He was getting into my dating stories and asked, "So....what are you going to wear??" Um, I was wearing what I was going to wear! I thought jeans, a tank and a little cardigan were cute, granted a bit 8th grade. I was embarrassed so I lied to him and said I am changing at home. My hair looked fabulous, but obviously when you have to lie to a gay about what you are wearing on a date, you know you've made a fashion fatality.
In sum, this post is mostly meant to solicit feedback. What would you wear on a first date in the freezing city of Manhattan in the winter?
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