The Boyfriend shape is everything you love about a man's shirt, cut slimmer to flatter a woman. It has a slightly oversized collar and cuffs, longer tail and front pocket for receipts, bobby pins, or an emergency breath mint. Tuck it in or don't — we love it worn out with the hem out over trousers, jeans of all kinds, short skirts, or cutoff shorts. This one is made up in our go-to Italian poplin that's crisp and silky at the same time. A well-cut black shirt is as chic as it comes and dresses up nicely for nighttime.