Someone sat next to me at work last week named Desmond. He sent me a text on our way to the airport before a business trip to Miami last week asking, “what sunglasses are popular for guys rn, gotta get something before the flight.” Not “what should I buy,” not “what do you typically wear,” but “popular.” Like out trending and someone somewhere sat down on a Tuesday and said these are popular now. I stared at his question more than I should have because it is how you guarantee yourself buying sunglasses you’ll wear four times and immediately feel self-conscious about, same as asking “what stocks are trending rn” will get you invested in whatever’s about to crash.
The actual problem with that question, and I say this as someone who maintains a “cost per wear” spreadsheet for clothing his girlfriend has seen and legitimately judged me for keeping: popular is doing a lot of rhetorical heavy lifting to mean “what companies are pushing this season.” There are, at most, four actual silhouette shapes that sunglasses come in that actually matter (aviator, wayfarer, round, square) and the entire internet dedicated to menswear spends time cycling through which one reporters get to say is “back in a fresh way this season” while tacitly agreeing that you probably own three of the others already. Oversized square frames are in right now, and so is a thinner, more architectural wraparound shape that’s basically ski goggles that decided to go to business school and major in leverage. Both styles exist, both are being purchased by real human beings who aren’t just having them styled on top of each other in front of a cement wall for a streetwear blog. They’re just not both popular in the same way.
Thesquatch co-founder Tim Regan explains how to find your best jeans for your body type.
Forbes; Getty
The news cycle isn’t lying to you, it’s just uniquely refusing to answer the question you want
I’ll grant the news cycle its due.

Square frames do something for my particular face shape that I didn’t realize I needed until they were back en masse. Square jaw, wider than it is long. Like could’ve looked really great in some of the tiny metal framed jobs everyone was wearing ten years ago, but would have looked absolutely terrifying in when I tried them on. Bought a pair of those tiny round Jackets in in 2019 because they “were popular” showed them up to dinner twice, and got asked “where did you get those? )” and then told “they look like a substitute teacher costume” not horribly by a friend. Went untouched until 2021 when I gifted them to my brother who does not have my face shape and can actually wear them without issue. Trend isn’t “wrong.” Wearers was just.
So when I say that the wraparound resurgence is popular right now I mean in the same way that stocks being “popular on reddit” is popular: true, it is happening, yes people are buying them, but that doesn’t mean it’s the right investment for your face or your lifestyle. If you spend eight hours a day in an office with fluorescent lighting and your commute to said office is a fifteen minute walk, that wraparound is grandma glasses the second you step inside, same as they did when they were being marketed to women that actually ski. I wore a pair for three weeks trying this angle specifically, wore them on the subway to and from, wore them casually walking to lunch with colleagues and what I genuinely found was they took attractive photos, sure, but I felt like getting hypocritically judged every single time I put them on for doing something I wasn’t actually wearing them to. My cost per wear on those ended up being around $14 uses before I just admitted to myself I wasn’t using them and put them away, by my luxury watch I’m making a bad investment and created the whole spreadsheet to help me identify these when they happened.
The strategy that actually matters once you learn not to ask that question
The style that has held constant for me for as long as I’ve actually cared about these things and passed every test I actually care about: does it look like I can wear it twice before it loses any shape sunglasses sit funny on my face when they’ve been in my pocket? Does it actually block out sunshine, or just make everything uniformly darker? Does it look like I got this for a reason, or like I saw it featured on one of the blogs above.

Smile?s last sentence but it truly is the thesis of this whole project. The wraparounds made me feel like I saw them on Hypebeast. Wayfarers, through three summers of testing, still feel like I just wore them because I wanted to, not because someone told me to.
I won’t say I’ve eliminated the cycle influencing my buying decisions at all. Every March I open up a google tab, almost put_stock_newsletter,. Every March I scroll through four shapes of sunglasses and think about it like I’m rotating capital in my portfolio. Then end up buying the same black wayfarer shape that I know, I have in another minor lens tint and telling myself the decision is different enough to matter. It isn’t. But if I ever do work out how to break that train of thought for good, I promise you it’ll be better explained than thatand that’s a lesson popular learned years ago.
Ade works in finance in the City and treats his wardrobe like a portfolio, which he admits is a slightly mad way to think about a blazer. He writes about office clothes that survive twelve hour days, back to back meetings and the odd video call.



