Jackie O loved black and oversized. John Lennon opted for small and round. Elton John has worn every size and shape imaginable. Fit is important but personal taste is often the guiding light in frame selection, especially when it comes to frame size. Find your favored proportion, whether you prefer a perfect circle or an exaggerated CatEye, and you may become a style standout like this month’s Street Seen star Anna Wintour.

–Iris Johnson

Photographed by Stephen Mark Sullivan