Yes you should dress your age
Stunting on Father Time, achieving advanced swag... the based, blessed, non-oppressive way
Welcome to Blackbird Spyplane.
Our roundup of the Best Pants Out is here.
Mach 3+ city intel for traveling the entire planet is here.
The B.L.I.S.S. List — a comprehensive index of Beautiful Life-Improving Spyplane Staples — is here.
There’s a few Spyplane tees and totes in the Spy Store.
— Jonah & Erin
What does it mean to “dress your age?” This question connects directly to one of the thorniest issues in modern self-presentation: What it means — and whether you should or shouldn’t want — to look your age.
It’s an issue shot through with so many cultural prejudices, canards, and pathologies, it’s hard to know where to start. And the pathologies are only accumulating by the day. Our society has long been image- and youth-obsessed, but when the front-facing camera BUSSED onto the scene? Those obsessions went into hyperdrive.
Clothes, of course, are one of the oldest, simplest & most prevalent forms of “body-modification technology” — around long before fillers, contouring tutorials, Facetuning apps and Looksmaxxing regimens — and they follow their own unique laws of physics and swag semiotics. So it’s no surprise that we recently got several Personal Spyplane questions on the topic of age as it relates to sauce, including:
“Dress your age? Or dress however you want?” — junkinthetrunkbrooklyn
“I’m trying to maintain a sense of whimsy in my closet, but also trying to mature into adulthood. What to do?” — gesamtkunstwerkinprogress
Today we’re going to explore the AGE ~ SAUCE continuum, Spyplane Style, and serve up powerful, definitive truths.
I. PERFORM PERIODIC STRESS-TESTS OF YOUR SWAG
One night when I (Jonah) was like 29 I went out rocking a button-down shirt overdyed a bright banana yellow. It was part of a Band of Outsiders x Opening Ceremony capsule where all the colors had a “Lego” theme. I’d worn it a bunch and felt fully at home in it. But this evening an acquaintance from college was in the mix and feeling a touch ~sPiCy~: He raised an eyebrow at the shirt and said, “Can you see what color that is??”
Bruv’s question “got into my head” — in a good way. Because it truly hadn’t even occurred to me that there could be anything potentially outré about my clothes-loving-a** wearing a bright yellow shirt. Spiciness notwithstanding, I welcomed this invitation to examine my assumptions. Was I out of pocket for pushing 30 in a jawn the same hue as Lego skin??
I concluded that of course I wasn’t. This self-deputized Shirt Cop wasn’t going to clip my wings that easily. But what stayed with me was a broader realization of how easy it can be to “stop seeing yourself” over time — to develop a certain self-conception, build a style vocabulary around it that feels appropriate, and then lock it all in and put it all entirely out of mind, “set it and forget it” style. Kind of like how you stop seeing the furniture in a room after a while…
And you are not a room, you are a human, in FLUX !
I don’t believe there’s an age limit on wearing, e.g., a yellow shirt. But there is a broad (Western?) cultural norm whereby we’re “supposed” to dress in more subdued hues the further we get into adulthood. This is not a two-way street. A younger person visibly “trying to dress older” might look a little silly (you’re in middle school, chill with the three-piece suit and ascot). But they also might look swag (those big tweed pants and cardigan you thrifted over Winter Break are gas, lil player). Whereas an older person visibly “trying to dress younger” just tends to bum people out. Now, the word visibly there is doing a lot of work, and there are plenty exceptions, BUT what I’m getting at is that, fairly or not, it’s regarded as “ungraceful” and “undignified” to dress in nakedly “attention-seeking” ways the older you get. (See also: the scorn, typically aimed at women, for “showing too much skin” past a certain age. Young women also routinely get s**t for “showing too much skin,” but for opposite reasons.)
Again — this is an attitude that can and should be interrogated. But it’s also a norm. And when the Mach 3+ clothes-rocker bucks convention, I think they generally want to be aware they’re doing so, even if they decide the norm is hogwash, on the principle of “know the rules, then break them.”
To stick with the yellow shirt example, over time I might decide that a jawn the color of a d*mn SCHOOL BUS is too loud relative to where my style has gotten. Or I might commit to a long happy life as a “screaming colors guy” and decide that society simply needs to deal with the fact that I smoke too tough, my swag too different and my b*tch is too bad, chromatically speaking. In order to feel sufficiently confident in that decision, however, I’d want to perform periodic stress tests on my whole gestalt, to make sure it still feels right, the way structural engineers check in on suspension bridges to make sure they haven’t aged out of service and don’t need to be condemned!! (See also: the embarrassing risks of middle-aged dudes wearing loud graphic tees with bubbly fonts and cartoony drawings on them that 16-year-olds also wear.)
Reading a recent T Magazine profile of the avant-garde master Rick Owens, I was intrigued to discover that he feels similarly and discusses it openly. At 62, Owens is preoccupied with getting older as it alters his relationship to outré clothes. “‘At some point, I’m going to have to make a choice: Am I going to accept or resist? Am I going to pull back or become even more extreme?’” he says. Owens is talking about his designs, but he’s also talking about an age-based reckoning with his own swag. In Lucy Sante’s new memoir, she writes about taking a similarly clear-eyed sauce inventory as a 69-year-old trans woman, in a passage quoted here.
Because a lack of self-consciousness is cool and liberatory to a point. But if you forego all self-consciousness, you risk getting dressed with an outdated image of yourself in mind. Over time, you might start looking funny in a way that, if you weren’t oblivious to it, would bother you. Like when you get salad stuck in your teeth but don’t catch it for hours and it just perches there, f**king up your smile unbeknownst to you.
Check in on those pearly whites in the mirror every so often. Slosh some water around and keep things circulating!!
This is important, because —
II. WHEN YOUR INTERNAL COMPASS IS OUT OF ALIGNMENT, YOUR FITS LOOK MAD NERVOUS, AND HOWEVER UNFAIRLY, THAT NERVOUS VIBE “HITS DIFFERENT” THE OLDER YOU GET.
The upshot of the Yellow Shirt Allegory is that sometimes an aesthetic that once felt thoroughly correct can reach an expiration date — thanks not only to shifting trends but, yes, to your own shifting age.
This rightness or wrongness is partially up to you, but it’s partially up to other people, too, because “style” is not just an accretion of individual personal choices. Style is also, inescapably, a social creation.
That said, society get all kinds of things wrong. And the herd instinct can lead you off the based path and have you rocking some goofy s**t, no doubt. What this means is that the better-calibrated your internal compass is — and the better you are at checking in with it during those periodic swag-integrity tests — the better you will look in clothes.
There’s no one way your compass has to point you. Some compasses will lead people to dress more conservatively with age — not the most exciting decision from our POV, but we can respect it. Other people’s compasses will lead them to get way looser and way more daring with age — the kind of inspiring, harder-to-pull-off maneuver we thrill to, baby!!
In either case, it’s a Core Spyplane Conviction that
Life is about change and the self, like the flesh, is not fixed. No!! The self is exhilaratingly protean — and to paraphrase the brilliant shapeshifter Bob Dylan, “He not busy freaking jawns is busy dying.”
And yet!
There’s a difference between experimentation and self-reinvention (which is tight) and unconvincing, incompetent, vain FLAILING (which you hate to see).
When you look comfortable in your clothes, whatever those clothes are, you look more convincingly like yourself in them.
Obviously we all have off days. And as a pro-experimentation sletter we gotta acknowledge that some experiments simply go sideways. So, while Blackbird Spyplane commends “big swings,” here’s a small handful of illustrative cases where you can see the results of a 40+ guy “raging against the dying of the light & refusing to go gentle into that good fit”…
Zero disrespect to Spyplane Hero Daniel Day-Lewis above left, who has earned the right to a “swing and a miss” with his brilliant acting career and a strong track record of putting on dope s**t. And zero disrespect to Bradley Cooper, who once took me for a sunrise walk on the beach in Malibu for an interview and then made me a great omelet at his cribbo and was very kind, thoughtful and chill throughout. No disrespect either to Spyfriend Salehe Bembury’s big-gas Crocs, pictured above in an otherwise eyesore fit on the music-biz legend Lou Adler, 90, yet dressed like a teenage f**cboi Smurf. And by the way, if Adler was rocking some standard-issue “we made it” Cucinelli rich-guy ensemble or whatever, that would be safer but it wouldn’t necessarily be saucier — looking rich is not the same thing as having style!!
To be clear, these are all bad fits* that no one of any age would look good wearing. But when you’re 40+, the badness “hits different.” The older an outlandish fit-bricker gets, the less forgiving onlookers become, because — again, fairly or not — society casts youth as a “time to make mistakes,” after which “you should know better”….
Think of it this way: Clothes are a language, and we admire proficient speakers. We expect babies and toddlers to babble nonsense. We expect kids and young adults to make grammatical mistakes or overuse big words because they think it makes them sound smarter. They’re young, it’s cool, that’s part of the process!
But when a grown MF is talking wild gibberish and saying s**t like “utilize” and “orthogonal” every other sentence? It reveals the underlying incoherence, chaos, and meaninglessness of the universe — and is disturbing to behold.
*It’s worth flagging that dude above bottom left — a reality-TV producer who helped inspire Benny Safdie’s character in The Curse — has committed so thoroughly to his “blasting Halen from my T-bird on the Sunset Strip” look that we probably gotta salute him for going F.I.E.R.I. Mode (Focus Inward and Embrace Resilient Idiosyncracy).
And that’s a crucial point to conclude with, because —
III. “DIGNITY” CAN BE AN AGENT OF OPPRESSIVE CONFORMITY. AND WHEN ELDERS COOK?? THEY CAN ACHIEVE STATES OF PROFOUNDLY INSPIRING DOPENESS
This is the note we wanna go out on. The reader above who wants to maintain “whimsy” in their wardrobe as they mature shares our instincts: The mandate to look dignified in narrowly conventional terms can be a cudgel of conformity, deployed to iron out whimsy and suffocate the sui generis misfit souls of real ones…
In this sense, the command to “dress your age” is scoldy and washed, like the sartorial version of when you’re talking about politics with defeated or corrupted people and they tell you to “grow up” and renounce your “naive youthful ideals” — you should treat such people with skepticism !!
Above are 8 stylish older fellskis, resolutely freaking these unlikely patterns, colors, accessories, juxtapositions and proportions. Rather than looking like tryhards or goofies, they convey vitality, balance, harmony and SPIRIT!
Ditto these ladies: 83-year-old Annikki rocking head-to-toe Vuokko; an unnamed swagstress on the subway in Daniel Arnold’s Pickpocket; Katharine Hepburn rocking the black turtleneck, roomy split-hem trousers and some PAN-SEARED Nike runners; and of course Spyplane Style North Star Georgia O’Keeffe shot by Doris Bry in 1973 —
Each and every one of these elders radiates dignity, but on their own swagged-out 🎸funky🎸 terms.
One practical takeaway here is to hold on to cherished slappers: Older people’s fits often look phenomenal in large part because they have owned and worn and washed the clothes for so long that they rock them with an effortless, lived-in, low-key PANACHE you can’t fake. That’s true no matter how “outré” the jawns are in isolation, like ma’s clear wraparound frames above right.
But also?? They’ve had a lifetime to develop their internal compasses, so if they choose to experiment, their success rates are higher and they’re good at picking compelling experiments in the first place.
So no, you should not “dress however you want” with zero consideration of your age. Dress your age!!
But do it in the most blessed and non-doctrinaire sense of the term, and in the knowledge that your age is a cool, beautiful, meaningful part of your whole MF gestalt, to be celebrated & worked with — not denied or struggled against.
Blackbird Spyplane is subscriber supported, so we count on readers to keep us Mach 3+. Join our Classified Tier today, if you haven’t, to enjoy the full Spyplane experience.
Our newest Home-Goods Guide is here.
Peep our list of the world’s 35 slappiest shops, where Spyfriends have added a ton of gems in the comments.
The SpyTalk Chat Room, where Spyfriends trade elite intel, is here.
Molly Ringwald and Erin recently discussed the often-asinine pressure to “dress your age” as a woman here.
Nice article on dressing your age. I completely agree that finding one's own style is an essential ingredient of being well-dressed, at any age. As one of your 75-year-old (she) readers, I thought it might be useful to append a few observations from the loftier end of the age spectrum. First, I do think that whatever one's age, it's important when one thinks one has finished dressing to take a cold, hard look in the mirror in good light, ignore what you THOUGHT you were putting together, and consider the result. If your knees no longer look good in that dress, change/don't buy it--why show off something that's not so attractive? (You wanna draw attention to your best features, not your worst.) If the two greys clash, change one of them. Etc. Often I see people (sometimes me in a shop window--OUCH!) wearing some ill-conceived idea they have about what would look good, instead of something that's actually comfortable and attractive. Second, though, for those of us who are older the challenges of an aging body may lead us to make hard choices about what to wear as a function of comfort and health. I do love boots, very much, and would prefer to wear them, rather than some form of sneaker, with many of my pants and dresses. BUT, my feet are poorly, my back hates standing on hard surfaces, and so I have to choose sneakers 9 times out of 10 before I hit the NYC sidewalks. Not only do I want my poor old body to keep going for a few more years, but when one is uncomfortable or in pain one looks awkward and unattractive. So gritting your teeth to bear the pain of high heels because you think they're attractive doesn't really work. Finally, on hip, swaggy looks that are a little outre'e: Many of these subtley make fun of nerdy-ness or age. That's fine, I get a kick out of seeing that on hip young people, where it has a significance I can enjoy. But when one is actually nerdy or old, that joke falls flat. For example, in the past couple years many of the young designers I enjoy have been offering dresses that remind me of the granny dresses of 60s and 70s hippiedom: high collars, fussy sleeves, trim, etc. Fine if you like that sort of thing. But I don't wanna look like a granny signalling that she's a granny. All these things are subtle, but clothes do carry meanings. . . Keep up the good work.
What a fantastic article in the New York Times, Jonah! I loved every word. Seems appropriate to comment about it on this thread because age was mentioned in the article. Agree with you about useless style advice like "Wear what you love" or the "Having confidence is all you need to be stylish." Well, there are plenty of people out there who couldn't care less about what they're wearing and are happy enough, but safe to say I wouldn't turn to them for wardrobe guidance, confidence be darned. Having said this, I'm sure the people bring interviewed about style are absolutely terrified about saying the wrong thing and having their heads taken off, so they opt for safety and churn out these unhelpful statements.