Like the riding boot, the stiletto boot is a classic. Even when you’re trudging around in the slush, this boot manages to exude a sexy aura. “The stiletto says ‘I’m fearless, and mysterious,'” says Rose. And even though they might not be the most comfortable, Bloch says it’s worth the pain since they always look amazing, whether over a pair of skinny jeans or with a pencil skirt.

Buy:



Jessica Simpson Khlaen Platform Dress Boots, $210

Calvin Klein Rosa Tall High Heel Dress Boot, $129