Welcome to What to Wear Now, GQ’s recurring recap of the need-to-know menswear hitting stores imminently—plus our shrewdest insights into pulling it off right.
Back in February, Terrence O’Connor says, he found out he was going to the Grammys about 15 minutes before the car arrived to pick him up. “Luckily, I had my Saint Laurent suit,” he says, laughing. “I ended up being on the broadcast so much that night.”
That’s not unusual for the creative director, whose behind-the-scenes work with pop phenoms—like the lo-fi “What Was That” music video he directed for Lorde, or the visual strategy he cooked up for Haim’s I Quit—tends to ricochet across the internet at supersonic speed. “I’m always on the cusp of potentially having to go to the awards show or the fashion show or what have you,” O’Connor says. “So you kind of have to be prepared to serve if you need to.” When you’re that in demand, you quickly learn how to pack on demand.
In the summer months, O’Connor sometimes finds himself away from his home in Los Angeles for 60 days at a stretch. “Traveling’s exhausting,” the 32-year-old says, “but if I’m in LA for four straight weeks, then I get really antsy.” How does he stay healthy and sane bouncing across time zones for months on end? “Wake up with the sun, hit the gym, do breakfast no matter how little sleep I’ve gotten,” he says. “It reminds me of a Taylor Swift quote that I think about all the time: ‘Jet lag is a choice.’ ”
Even on your laziest afternoons, when the only thing on your to-do list is napping under a palm tree, it’s still possible to look supremely fly.
1. In 2026, the most versatile travel shirts all look like something your dad would’ve worn on his honeymoon: slouchy, striped, and enviably lived-in.
Louis Vuitton
Striped Long-Sleeved Shirt
2. Call it “vacation commando”: Those swim trunks of yours look even fresher layered under a bigger, baggier pair of shorts.
18 East
Emery Pleated Big Shorts
3. No accessory says “out of office” quite like an anklet—or two, if you’re really in beach mode.