The Very Best of Playboy’s September Covers

From the '50s to today.

Classics September 1, 2026

Summer is coming to a close, and we here at Playboy are feeling nostalgic. It must be something about the impending chill and the changing leaves. Luckily, Playboy nostalgia will always keep us warm. Our archives are full of fiery photos of gorgeous women, and these September covers from past decades are no exception. So, as we enter this new month, check out how Playboy celebrated autumn in days gone by. Here are our best September covers through the years.

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