Derrick suggests getting creative with bolder choices, like a streamlined sneaker, as well as circling back and modernizing the classics.
“The classic tassel loafer is having a bit of a ‘moment’ again,” says Derrick. “But today's tassel loafer has a higher vamp—the front and center part of a shoe that covers the top of the foot—so when you’re trying on a pair of loafers, look down at your feet. If you see a lot of sock showing, your vamp is too short.”
To try out the sneaker trend during your 9-to-5 shift, Derrick suggests a clean, polished calf sneaker or trainer (as modeled above by our own associate market editor, Moti Ankari, in To Boot's Farley sneaker). “Suede sneakers speak more to weekend wear,” he says.
But he stresses, “Know your audience, too. For instance, a trial lawyer appearing in court in a suit and tie does not need to be experimenting with a clean sneaker. Instead, wear a classic, straight-tip cap toe or wingtip and look the part.”