There are two kinds of boys in this world: boys who have good style, and boys who have bad style. I don’t need to say much about the boys who have good style. That’s the point of GQ! But within the other category, bad-style boys, there are two subcategories: 1) boys who try really hard to have good style, but it just doesn’t work (yikes), and 2) boys who just do not care about what they wear at all, and look like shit, but in a way that is hot. Usually, this is because they are already hot.
For most of my adult life, I have dated men in subcategory two. I have showed up to a date in a Comme des Garçons miniskirt, freshly polished loafers, and a cute little vintage blouse, while a boyfriend of mine has showed up in…a stretched-out blue shirt, a pair of jeans that are four sizes too big but not in an on-purpose way, and Nikes with a hole in the sole. I have one ex-boyfriend who almost exclusively wore button up shirts from the brand The Territory Ahead, which you can only buy from eBay storefronts based in the armpit of Vermont; it made him look like he was in a jug band circa indie rock’s “hey ho” era. I am obsessed with these types of boys. I love it when a man dresses like an orphan or like he sleeps on top of a newspaper or used to be an actual crust punk, violent dog and everything, but now sort of has a job. Cameron Winter is one of these types of boys. He has, terrible, terrible style.
Cameron Winter, in a fitted cap and loose Calvin Klein tank top, onstage in March, performing with Geese in Berlin.
Pedro Becerra/Getty Images
By this point, we’ve all seen the photo from the other week—there’s Cameron Winter and Olivia Rodrigo. They’re walking down a Los Angeles street. Twenty-three-year-old Rodrigo’s wearing an adorable red cardigan, a straight-legged jean, and ballet flats. Next to her is the Geese frontman, 24, who is dressed like he is going to participate in a math olympiad: a black XL Champion T-shirt, dark blue jeans that are too big on him and also could use a hem. I can’t really make out his shoes, but they appear to be busted-looking Nikes, which he has been known to wear. He is wearing the uniform of bad-style boys who don’t care that they have bad style. The ensemble has a horseshoe-theory effect, where if at one end is literally not caring (in an unconsidered way) and the other end is looking effortless (in a considered way), he manages to do both. Winter’s style is that of someone who isn’t trying very hard, which is why he looks so good. Earlier this month, at the music festival known as “Coachella,” Winter wore two other iconic bad-style outfits: a T-shirt for the stoner doom-metal band Sleep with baggy black jeans on one weekend, and a stretched-out ribbed cotton tank top with a different pair of baggy black jeans the next. Two outfits that are not so much low effort as they are no effort at all.
