When it comes to style, guys have been trying to walk in Steve McQueen’s shoes for more than 50 years. White jeans. Baracuta jackets. You know the drill. What many don’t know is that it’s still possible to get the chukka shoes that were key to his look. (Google: “McQueen chukka sports car.”) Sanders, shoemakers in the U.K. since 1873, still makes its unbeatable “polo snuff” suede boot, which comes with a distinctive crêpe sole. Its extra height protects the shoe—and you—from puddles and snow. (Not that a tough guy like you worries about little things like that … ) ($250, sanders-uk.com)

Don’t even think about pairing these with a pastel twinset, demure pencil skirt, and sensible heels. Fallon’s crystal-and-rhodium bow earrings might, at first glance, seem perfectly sweet, but, like most of designer Dana Lorenz’s jewelry, they’re ironic, subversive, perhaps even a bit naughty. Imagine their dazzling effect on a lean sheath dress, an all-business blazer, or even Levi’s and the proverbial perfect white T-shirt. (We’re still hunting for that one, rest assured.) ($190, modaoperandi.com)

If you were to stumble into Air Mail headquarters on any particular workday—and we truly hope you do, provided you’ve made an appointment—you will likely spot at least one of our editors wearing Ulla Johnson’s Lottie dress. After style editor Ashley Baker picked up the red version earlier this summer, at Johnson’s sparkling new boutique in Amagansett, chief marketing officer Emily Davis ordered the blue version, and the domino effect has continued. Someone at the office thought they spotted Graydon browsing the Internet for one. The Lottie owes its popularity to a charming floral print, a breezy cotton-voile blend, and an exceptionally appealing silhouette that can be dressed up or down at a wearer’s whim. If you’re so inclined to join the club, make sure to tag @airmailweekly when you take yours out on the town. ($425, net-a-porter.com)

The term “elastic waist” tends to give us pause. We happily make an exception, however, for these Gretchen Scott pants. Discovered in Southampton by the ever stylish Anna Scott Carter (no relation), these slightly cropped Capris have become an integral part of her wardrobe. “They fit well, come in lots of different colors, and are a total problem solver—as well as being dead cheap at the end of the summer, when the store is on sale,” says Carter. They’re an ideal pant for those harried weekend days that include everything from running errands to meeting friends for lunch, to chaperoning a playdate. Luckily, for those who can’t quite get to Southampton, they can be procured online. ($98, gretchenscottdesigns.com)

Newly-minted creative director Riccardo Tisci has enlisted this monogram print—inspired by one found in the brand’s archive—in all sorts of interesting ways. It’s especially impactful in this boxy leather wallet. Thanks to a detachable gold chain, it can be worn as a cross-body—a gentle suggestion that you leave your phone behind, for a change. Because if you aren’t doing that during these final days of Summer, then what is the meaning of life? ($490, matchesfashion.com)