Key Piece: Vest
WHO: Rachel Snyder, 25, attorney
THE INVESTMENT: Isabel Marant vest, $4,140 (212-219-2284).
WHY IT'S WORTH IT: It's the perfect finishing touch to any ensemble, and it has staying power: It can be layered over a knit sweater for work or top off a tank and shorts to last throughout the summer.
Play up the vest's laid-back Bohemian vibe with a pin-tucked, floor-length white skirt and simple tank.
Flat motorcycle boots in python add texture and tone down the look's innocence.