Best Bet: Wren Snake Midi Pleat Skirt

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Midi skirts are typically considered tricky to wear, but as the weather cools, you'll need a bottom that offers a bit more coverage than your standard mini. Chiffon prevents this piece from feeling too heavy, while the snakeskin print transitions nicely from summer to fall. Pair it with a tucked-in tee right now, and next month, toss on a chunky knit.

Wren Snake Midi Pleat Skirt, $250 at Bonadrag