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The Best October Covers of Playboy

What a treat!

Classics • October 1, 2026
The Best October Covers of Playboy

October is here, but at Playboy, you’ll only find treats—no tricks. Our first treat for you? A look at the best October covers through the decades. From a spooky debut in the ’60s to a fall classic in the ’80s to a reinterpretation of football body paint in the early aughts, these covers are sure to delight you. If nothing else, the ladies on our October covers are perfect inspiration for your next Halloween costume.

S.J. Fellowes by Tom Staebler, October 1980
Jennifer Allan by Richard Fegley, October 1996
Sara Jean Underwood by Arny Freytag, October 2005
Simone Holtznagel by Gavin Bond, October 2015

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