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Resort Evening Wear While the difference between "evening wear" and "elegant casual" can be small, it is real

At a 92nd Street Y event to promote his new book, Cancel Me If You Can, the Barstool Sports founder celebrated his own longevityand appetite for controversy

Or, like in the case of this outfit, I wear fall colors in an outfit that is decidedly summery

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Then we brought our favorites to Wirecutters Long Island City, New York, headquarters, where we compared notes and took mirror selfies (for posterity)