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 …