Night: Add a tailored blazer, switch to pointy-toe heels, and stack on some jewelry for a sophisticated evening outfit. Why It Works: A great pair of jeans and a standout top is the ultimate easy win.

Zach sent the video to his date after the man had asked to see his outfit over text. But his date responded to the video saying: 'Hey! You're very attractive and I'm not opposed to grabbing a ...