Can you dress cool if you never leave your house?

Goats need to graze. Plus how to keep a relationship healthy, and is there a non-cooked way for people over the age of 16 to rock streetwear?

Aug 05, 2025

Our interviews with Nathan Fielder, Brendan from Turnstile, Adam Sandler, MJ Lenderman, Steven Yeun, Mac DeMarco, Bon Iver, Seth Rogen, Kim Gordon, André 3000, 100 gecs, Danielle Haim, Matty Matheson, Laraaji, Sandy Liang, Tyler, The Creator, John C. Reilly, Maya Hawke, Camiel Fortgens, Rashida Jones, Father John Misty, Kate Berlant, Clairo, Conner O’Malley and more are here.

Mach 3+ city intel for traveling the entire planet is here.

Did you hear that Cool Dudes have been joining other Cool People in buying Cool Ceramics? We’ve been writing about them since Spyplane Year One — check the ceramics section of our Home Goods Index for a rundown.

Life — people want to know how to live it.

So every now and then we put out an open call for reader questions about living, loving, and the slapper sciences, and then we answer them correctly.

Case in point—

“How to properly style streetwear at 40+?” —kbarbour22

First, let’s establish what we’re talking about, because “streetwear” is an elastic term. Here at HQ we take it to basically refer to graphics-heavy tees, sweats, trackpants, windbreakers, hoodies, caps, bags, etc., whose essential function is to carry and spread the swag pathogens known as brand logos through the world.

We’re ambivalent about this category. The best case to be made for streetwear, as we see it, is as an entry point — both for young people first getting into clothes and also for young designers trying to break into the business, who find that printing a graphic on a blank is a lot easier than learning how to cut patterns and getting cut-and-sew collections produced.

By definition, an entry point is something you eventually move past. And so — even though Blackbird Spyplane is a non-doctrinaire sletter that operates with peace, love and open-mindedness — we think the best way to style streetwear if you’re over 16, much less over 40, is to wash every piece you own, fold it neatly in a box and then donate it to Goodwill. Parents of people younger than 16 should feel free to encourage them to wear other, cooler, logo-free clothes, too.

The lines can get blurry, to be sure. Not all graphics-driven garments register as streetwear, and while we definitely felt Spyfriend MJ Lenderman when he told us that “recently I don’t wanna wear anything that says anything on it at all,” Erin and I will never entirely abandon our love for the graphic slapper writ large. We have far too deep an appreciation for vibey merch, souvenir garments, band tees, the occasional bootleg movie tribute, and other miscellaneous curios to ever repudiate them wholesale.

But we do believe that, statistically speaking, all clothes with designer logos are cheesy, and streetwear represents a particularly youth-coded subset of that cheesy category.

Are there exceptions? Of course. One that springs readily to mind is the great skater and San Jose legend Jerry Hsu…

Jerry Hsu, photographed by Justin Crawford for the Nine Club, left, and skating in Merrells on the September 2025 cover of *Thrasher*, right

Hsu is 43, seems very cool, clips up in dope flambéed Merrell Moabs and dresses well in a chill, understated way — even as he mixes in graphics-forward pieces from his own Sci-Fi Fantasy line, which he designs, and whose cleverness and appeal we can appreciate even if it’s not really the kind of thing either of us wears. It also bears noting that, as with some other skate brands, when you rock a piece from a line like Sci-Fi Fantasy, you’re also repping for a team of cool and gifted skaters in a way that starts to scramble the distinction between streetwear and team apparel…

The main takeaways here, for those of us who are not Jerry Hsu but refuse to totally eliminate streetwear from our wardrobes, are:

Mixing one or possibly two non-stupid streetwearish pieces into an otherwise chill, logo-free fit is what’s up, as opposed to rocking a gang of the s--t head to toe cacophonously, and
When it comes to box-fresh 2025 streetwear, the Moving-Goofy Fuccboi Quotient is dangerously high, so it helps a ton if we’re talking about old streetwear pieces you’ve owned for ages, worn a lot, made memories in, and therefore made more personally meaningful and more visibly yours.

As it happens, the garment I’ve owned longer than any other is a Stüssy tee I copped with allowance money when I was in middle school 👴💅 30+ years ago 👴💅, which I wrote about earlier this year, here. When I wear it, I tend to do so with things like old jeans and a beat-up cap, as opposed to some cooked high-low approach where I try to weave it into a “dressier” fit.

Next up —

“Best advice for maintaining a healthy and sustainable relationship?” —water.damage.watches

Minimize the time it takes to get from fighting about dumb s--t, which is inevitable, to making each other laugh.

This can be hard sometimes. But you can help things along tremendously by 1) reminding yourself, even in moments of heat and tension, that you both love each other and that we are extremely fortunate to find love in this hard and lonely world, and — crucially — 2) by remaining ready, able and willing to laugh at yourself.

We explored some more of the secrets to swaggy relationships here.

Finally —

“How do you replicate the feeling of putting on a nice fit and going outside while WFH?” — shrimpsandwitch

Some people might reply, “Put that s--t on, then take a fit pic and share it to IG / a fashion Discord you’re part of / a group chat you’re on with clothes-minded friends.”

Not us, though. This is a perfectly fine thing to do, but we have to reject the fundamental premise of this question, because there is no remotely commensurate replacement for going outside, much for less wearing cool clothes while you do.

As much as contemporary life virtualizes, no one will ever be able to engineer away the intrinsic social and physical components of taking pleasure in clothes. This is because clothes are meant to be worn by a body as it moves through space and time, not compressed into a 2-D .jpeg or video for consumption on phone screens. Moreover, putting together a fit is a form of communication, i.e. it is about engaging in a kind of conversation with others — not chattering to yourself at the cribbo with nary a soul around.

With that said, we do have a great answer for this reader. It involves something that all Real Life Enjoyers share, whether they work from home, at an office, part time, or have no job: An expansive love of lunch.

As Spyfriend Lauren Collins put it a couple weeks ago in a fantastic Lunch Rhapsody in The New Yorker, lunch “is the only meal that, for many months of the year, reliably allows the person eating it to simultaneously experience the pleasures of food and light. With the day stretching out ahead of you, lunch can feel less transactional and slotted in than other meals. It’s a moment out of time — the August of the day.”

Amen. In college, I ate long a-- lunches with friends whenever I could, lingering over empty plates in the cozy smoking section of the 👨🏻‍🎨Bard🤹 cafeteria well into the afternoon, even though I didn’t smoke. When I graduated and started working an office job, I took as many opportunities as I could to enjoy long, luxurious lunches, too, whether they were with coworkers, friends or by myself. And by luxurious, I don’t mean big ticket: Bringing a pack lunch or takeout to, say, a park bench or picnic blanket and posting up for an hour or two is, IMO, the height of luxury. The more trees in the park, the better for cell regeneration.

I still love long lunches, even as manifold social, cultural and economic pressures combine to make “scarfing a salad at your computer” seem like the increasingly default choice. Recently, a friend and I instituted a standing weekly lunch at a macrobiotic spot equidistant from our homes. If that’s remotely plausible as relates to your schedule, I can’t recommend it enough. If you are single and have vision and swag, you could even experiment with the wild frontier that is asking someone out on a date… to get lunch.

What I’m talking about here is simple, but deep, too. People, alienated and made lonesome by the fragmenting forces of modernity, are, as Lauren wrote, “turning to religion as a source of connection. God is great, but sometimes fellowship — a certain kind of existing in social space — can be as simple as a tuna sandwich.” Or a plate of lentils, garbanzos, steamed squash and brown rice.

So: Put on a great fit in the morning. Look down at yourself admiringly. Dance to some music in your living room with that s--t on. Post a fit pic if you wish. But be sure to get outside. Rock the fit on a 10 a.m. coffee run, rock it to some cool event in the evening, and in between? Do yourself a favor and rock it to lunch.

Can you dress cool if you never leave your house?

Goats need to graze. Plus how to keep a relationship healthy, and is there a non-cooked way for people over the age of 16 to rock streetwear?

Discussion about this post