As true lovers of cutoffs, we spend most of our Summer dreading the eventual end of its wearable season. When the slouchy boyfriend length erupted onto the scene, it was a eureka moment — finally a piece that could eke out a few more weeks of wear once Fall arrives! Koral's midthigh cut ($195) is ready to be worn right this instant with a filmy tank and flat sandals, and then with a layered knit and blazer when temps start to dip.

Wear Now: Collective Concepts Sleeveless Button-Down ($68), Trina Turk Palermo Sandals ($110)

Wear Later: J.Crew Classic Schoolboy Blazer ($198), Acne Lia Mohair Jumper ($260), Bass Penny Loafer ($99)