The Vintage Sneakers
Credit: Photograph by Greg Broom

"A clean pair of white sneakers with a suit or dress trousers is a perfect mix of casual and tailored," Club Monaco's Levine says. "It has an Ivy League appeal but looks just as sharp and relevant now." Buy vintage-inspired, minimal sneakers, because you can wear them with anything (even a suit). Pair white with light-colored chinos for a clean look and a colorful pair with otherwise neutral tones for pop. [Brooks Heritage Sneakers, Price TBD; brooksrunning.com]