The gladiator boot is an interesting animal. Half sandal, half boot, and totally bohemian in a sexy, Free People kind of way—we were surprised to see it on this young, straight-laced New Yorker. Chanel handbag? Check. Pinstriped poplin shirt? Check. Clean white miniskirt? Check… Who would have guessed that these preppy staples would keep company with the ultimate hippie-chic sandal? Do you think it works? We’re thinking—against all odds—it actually might. Maybe it’s the neutral color that almost disappears against her skin. Or maybe it’s the perfect pedicure.