Understand your body.
Reporting live from menswear’s trendless present: We have good news for you. You don’t have to wear skinny jeans. In fact, most guys don’t look good in skinny jeans, tight bulging shirts, or barely hanging-on sports jackets. One of the most important lessons to learn while developing your style is understanding what looks good on your body. I’m proud of you for committing yourself to leg day, but the cling of your jeans doesn’t need to make that point. —CW
Don’t be snobby about band T-shirts.
Band tees were once a badge of honor, attesting not only to your taste in music, but your commitment to leaving the house to hear it in person. Now, of course, you can pick up a Nirvana shirt at Old Navy. But instead of asking high school students to name three songs, as some TikTok jokers like to do, we should embrace the democratization of music merch. Streaming pays pennies and touring is less profitable than it once was. When I discover an artist I like, I might buy their album on Bandcamp or pick up a concert ticket. I’ll also search to see if they sell a cool-looking T-shirt in my size, and then I will order it and wear it around the house and on weekends, or under a button-down shirt at the office. And yes, when I wear my Gulch shirt, I feel cool as hell. —Nick Catucci
Pack light—it forces you to be creative.
You’re not a sommelier—don’t pack a ‘capsule wardrobe’ of basics you think will pair nicely together. Stuff the clothes you love most into a carry-on and figure it out once you’re there. Necessity is the mother of invention, and limiting your choices will inspire the type of gloriously unmeditated fits you usually see at the bodega. —AG
Take stock of what you have.
Every few months, Hanif Abdurraqib—the acclaimed cultural critic and poet—goes into his sneaker room and surveys his entire 230-pair collection. “I’ll pick out the 20 or so pairs that I’ll rotate through for the season,” he says. That tight edit allows him to get dressed every morning without feeling overwhelmed by the sheer number of options available to him. “It’s mostly based on color palette: In the fall and winter, I’m wearing mostly black, which gives me a lot more flexibility in the sneakers that I can wear.” While he’s sorting through his shoes, though, Abdurraqib also picks out the pairs he hasn’t worn in a while to give away. “There’s a culture, particularly around sneakers, that revolves around how much you have, how much you’ve attained, and how much you can hold on to. But to me, none of that serves the questions of: What are you actually wearing? What feels good on your feet? And who can benefit from me being honest with myself about what I don’t need anymore?”
Wearing a shirt? Tuck it in.
Tees, tanks, sweaters, button-ups—they all looked better tucked. Your legs look longer, and the rest of you looks leaner, when your pants constitute two-thirds of your outfit. —AG
Buy a fancy tuxedo.
Even if you only wear it a couple times a year, it’s worth splurging on a fancy tuxedo. Nothing is more memorable than a dreadful boxy rental tux. —SH
Never wear flip-flops outside of the beach or pool.
Are you gazing out at a blue-green ocean right now? About to mosey over to the pool bar for another tequila soda? Financially dependent on getting featured on wikiFeet Men? No? Then you, my brother in fits, should not be wearing flip flops. As a resident of New York, I’m spiritually dismayed whenever I see someone strolling around a city in thong sandals, their feet barely supported and exposed to all manners of grit and grime. And don’t even get me started on what they look like—“flop” is in the name. Do us and your soles a favor and save the flip flops for your beach vacation. And while you’re at it, explore the wonderful world of huaraches, espadrilles, and slides. All exponentially better styles, requiring the same amount of extremely low effort. —Gabriella Paiella