3. The Ankle Boot — The ankle boot is always a fall essential, but there are so many new, tailored, utterly wantable options out there, we had to sing its praises once again. Our wardrobe suggestion: Wear them with everything and as often as possible to give them that seasoned broken-in feel that only a good rainy festival can replicate. 

A.P.C. Zip Ankle Boot, $515, available at A.P.C.; Zara High-Heel Ankle Boot, $129, available at Zara.