With your college years firmly behind you, step into the working world in a chic pair of pointed toe pumps. Classic Manolos worn with a pencil skirt and silk blouse is a style trifecta that'll impress even the curmudgeon-iest of bosses.
Splurge On: Manolo Blahnik BB Pointed Toe Pump, $595, bergdorfgoodman.com
Quarter-life crisis on the horizon? Retail therapy to the rescue! Buy yourself that spendy tote you'll love for the next 50 years. Go for something classic that you can carry forever—and then pass on.
Splurge On: Hermes Kelly Bag, $20,399, farfetch.com