Michael Bastian on layering
Credit: Getty Images

For Michael Bastian, layering is a lifestyle. "I personally would rather layer up than put on a big, heavy coat," says the upstate New York native, whose namesake label has become a must-have for legions of men that appreciate his preppy but lived-in aesthetic. "When you live in a city where you're always in and out of a car or a building, I feel it's . . . better to treat a heavier, tweedier sport coat almost as you would outerwear."

Bastian has spent a lot of time figuring out how to build an outfit up toward a heavier sport coat. His advice is simple enough: Tuck in your shirt and work from the bottom up. "I prefer simpler shirts like a solid oxford or pinstripe, and with a solid cashmere crewneck or V-neck," says Bastian. "And then with the sport coat, have that be your pattern à la glen plaid or houndstooth." It then makes it easier to mix in accessories and play around with color more. "The coat is what everything spins off of and ties it all together," says Bastian. "If you wear a solid sport coat the way I'm describing, it kind of throws the whole look off. The key to this is the jacket is one of those heavier, tweedier jackets – and by heavy [I mean] they look like they have depth to the fabric and not like the old days when tweed was almost bulletproof."

If your mobility is compromised, there are too many layers. If you've got the Michelin Man thing going on, there are too many layers. "If everything is a little baggy, then everything will look sloppy when you layer one piece on top of another," he offers. "Your sport coat should easily fit over a shirt and a fine-gauge sweater." Take your cues from JFK, Jr., who was often spotted on his bike going to work clad in a sport coat and dress pants with a hand-knit cap or down vest.

"That is very inspiring to me," says Bastian of that offhanded way of dressing. "It was like he grabbed the things he really loved and, depending on how cold it was, added another piece."