Loafers
OK - so your boyfriend's loafers would probably be a bit roomy, to say the least, but how about boyfriend-inspired loafers made for women? They're definitely more comfortable than heels, and they're super trendy right now, too. Wear with high-waisted shorts to show off your "new" kicks, a simple tucked-in top, and awesome retro sunglasses for a look that's the perfect combo of feminine and masculine.
Gucci 1953 Horsebit Loafer in Leather, $640
ModCloth Nautical High Waist Sailorette the Seas Shorts, $50
Exclusive For Intermix Sleeveless Poplin Button Down, $198
Ray-Ban RB3447 Round Metal Sunglasses, $164.95