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1. Sunny T-Shirts
A free-spirited graphic T-shirt can take you into autumn, if you opt for a sophisticated, arty optic, like these from Monogram, a Los Angeles-based brand designed by Jeff Halmos and Lisa Mayock. The duo, known for their ’70s-style typefaces, colors and cuts, were “thinking year-round T-shirt weather,” said Ms. Mayock. She wears tees in a more formal way—with a suit, not a bikini—an easy idea to pull off, swimmingly, in the fall. T-shirts, $65, monogramstudio.com
2. Round Sunglasses
Twiggy adopted…