Couture for Cocktails

Q: When it comes to a first date, I have no idea what to wear. Are there any rules of thumb if I am taking a woman out for dinner or drinks?

When it comes to dating, you only have one chance to make a first impression, so every little detail counts. No matter where you plan on wining or dining, don't even think about wearing white socks with black, wingtip shoes are the most severe fashion crime ever to be committed. Stick to solid black socks (absolutely no argyle) and black loafers (Jon Varvatos and Banana Republic make stylish pairs that are worthy every penny).

Also, forgo the pleated beige Dockers and frayed jeans you wore during your fraternity days. Instead, opt for a sleek straight legged pant with subtle pin stripes, paired with a solid white button-down shirt. And make sure to tuck in your shirt and add a black leather belt or you'll look like a total schlep. Lastly, stay away from shocking shades like fuchsia, orange and busy floral prints or you'll definitely ruin your chances of scoring a second date.

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