Justin Theroux
Actor, 49
The past couple years have seen an upending of the tight, tailored approach to dressing that dominated the decade prior. Unless you’re Justin Theroux, who still wears skinny jeans and trim blazers like it’s 2011—and looks damn good doing it. This is a guy who knows what works for him, dialed it in years ago, and is absolutely intent on sticking with it. It’s something to aspire to.