When it comes to staples, Michael says, "if it's totally, totally familiar it's a big bore." So instead of plain navy or black, he suggests buying an embellished or mixed-media blazer like this one. It has all the versatility of the classics—but none of the blandness.
faux-leather-sleeve tweed shimmery blazer, $225, michael michael kors, michaelkors.com
Wear Your Clutch in Daytime, Too
"You can wear a metallic clutch bag with everything," says Michael. An oversized envelope shape is especially transitional. It'll jolt a little energy into a daytime jeans-and-sweater combo or a nighttime cocktail dress without overwhelming either outfit.
"I always love the idea of a girl looking like she's swiped something from her boyfriend, like his watch. It's very sexy," says Michael. Plus, it's an easy way to add a bit of attitude to an outfit in two seconds flat.
"In today's world, since weather is so upside-down crazy, you need outerwear that can kinda span the seasons," says Michael. With its layering capabilities, a great fur vest—real or faux—might be the easiest way to do that. Over a filmy silk dress or under a thick trenchcoat, it's an outfit-maker that's customizable to any climate.
To shake things up after spring's splashy statement pant craze, Michael suggests reaching for a pair of gray flannel trousers. But "instead of wearing them in a conservative way," he recommends "choosing ones with a slim silhouette" with details that give them a "whole different attitude," like these zippered skinny pants. Coupled with shiny aviators, they're about as badass as flannel can get.
"I love the idea of sweaters as coats," says Michael, adding, "knits move with your body in this very sexy way." Pairing swingy, cozy toppers like this one with sleek pants just enhances the effect, creating a flirty silhouette that doesn't look too try-hard.