Say goodbye to the baggy bibs of the '90s — the modern iteration is fitted, slim and slightly cropped above the ankle. Look for them in chic black, a dark denim wash or charcoal gray. And yes, wear with heels! Overalls, $80, and shirt, $25, gap.com. Heels, $119, and bag, $198, vincecamuto.com. Sunglasses, $139, toms.com. On location: Coppersmith Sidle up to the DIY Bloody Mary Bar at this restaurant, then enjoy your creation — and take in killer city views — at the rooftop space.