5. The Midi Dress — We still love a good maxi dress, but this season, the midi dress is moving into prime position. Less boho and more '40s-inspired, the midi offers a nod to designers like Marc Jacobs and Prada who have long appreciated its quirkier quality. And, depending on the length, this dress can look equally good with super-high heels and flats — so start experimenting.    

ASOS Pencil Dress, $64.46, available at ASOS; DVF Zokaya Dress, $475, available at DVF.