On Monday night, The Devil Wears Prada 2 premiered in New York. As you might expect, the red carpet was awash with plenty of spectacular fashion—Meryl’s Givenchy cape!—but the menswear on display was, well, just fine. Stanley Tucci, who’s returning in the sequel as Nigel Kipling, looked sharp as ever in a form-fitting velvet sport coat and charcoal slacks, but that was, ultimately, the only highlight. (TDWP, after all, is the rare blockbuster franchise not aimed squarely at a male audience.) But it did have us looking back with a little yearning at the simple, sexy looks worn by men on the original film’s press circuit in 2006.
Back in that era, before celebrity styling had grown into the high-stakes game of chess it is today, there was far more room for spontaneity, personal taste, and plain old fun on the red carpet. Take Adrian Grenier, for example, who played Andy’s much-maligned boyfriend Nate in the first movie (and is not, to the cheers of many fans, back for the follow-up). At the movie’s New York premiere in June 2006, the actor, then 29, sported a charmingly simple semiformal look: a slim, single-breasted, black suit with a striped button-up shirt and a silky grape-colored tie, all punctuated with a boyish mess of curls.
A week later, when the movie opened at the Los Angeles Film Festival, Grenier opted for a darker, moodier look—a boxy pinstriped charcoal paired with an inky, unbuttoned, dress shirt. Later that same day, he was spotted in the same shirt with a pair of dark-wash jeans.
It’s the kind of natural, loose, uncalculated panache that so many of today’s younger celebrities are chasing: Grenier’s suits are, all things considered, pretty simple and straightforward, especially when compared to some of the flashy, full-runway ensembles we see on red carpets in 2026. Combined with his laid-back grooming and finishing touches—tousled locks, a tugged-at tie, that 5 o’clock shadow—and you’ve got yourself two looks that are far more worthy of praise than Grenier’s whiny character in the movie.