Best Bet: Cheap Monday’s Convertible Dress


This Cheap Monday dress goes from day to night, while steering clear of the awkward proportions so many "convertible" clothes seem to have. The black jersey frock is accented with three subtle rows of hook-and-eye closures, so you can wear it loose during hot summer days, and then cinched for a more figure-flattering fit should the occasion arise. No accessory-swapping necessary.

Jenna Dress, $65 online.