A hat can add the perfect finishing touch to a Fall outfit — so do yourself a solid and stay toasty in one of our top five choices. The downtown girl can sink her head into a floppy, fedora, or trilby style from Rag & Bone, J.Crew, or La Cerise Sur Le Chapeau, while the uptown lady can don cute cloche cuts from Brooks Brothers or Stella McCartney.

Left to right: Rag & Bone Floppy Fedora ($115), J.Crew Trilby Hat ($150), Stella McCartney Felt Cloche ($345), Brooks Brothers Rabbit Felt Cloche ($298), La Cerise Sur Le Chapeau Fedora ($280)