Fit

Ludlow Two-Button Blazer
Buy It Now at J. Crew, $365 

Slim Secret Wash Shirt in Faded Gingham
Buy It Now at J. Crew, $65 

We prefer some mystery where size and shape is concerned, but just like guys, girls want some idea of what we're getting into. It’s great if you have a six pack, but if we can see its outline, your shirt is too tight, and the same goes for your other, um, assets. We get a little nervous when our date’s jeans are tighter than ours. On the opposite spectrum, an ill-fitting blazer and an oversized shirt makes you look sloppy. Just make sure you look comfortable, but still put together.