42 Comments

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.

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Mar 4Liked by Blackbird Spyplane

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.

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Mar 2·edited Mar 2Liked by Blackbird Spyplane

A few days late to the party here but reading this post further encourages me to rock the Man-tle yellow pants in great style given that I am a guy in my late 50's. I mostly wear muted stuff but when I do bring out my color jawns I often get more compliments than I handle haha. To each their own I say and for this- out come my pinks, peaches, bright purples, orange and now soon to be yellow outfits! Peace to ya'll and if you see me on the street somewhere, please dont give me sh*t as I wont care a rats ass anyways hahahha.

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Mar 1·edited Mar 1Liked by Blackbird Spyplane

As a 60+ subscriber, I agree with the advice to ‘hold on to cherished slappers’! I’m pleased to have a few 1990s Italian and Japanese treasures still in my wardrobe, and slightly regret selling some or giving them to charity over the years. Yes, many of these 90s clothes can be found second-hand, but without the attached memories.

Quality does seem to stand up to a lot of wear. According to the Guardian it’s harder to find now: https://www.theguardian.com/lifeandstyle/2023/sep/19/garment-quality-not-the-same-why-closet-clinic

You may find, as I have, that your body shape changes in later life. A good tailor can work wonders adjusting your older garments. Bigger waistline I understand, but have my legs really got shorter???

Obviously, styles that once looked outdated can make a comeback (wide pants!). I might wear a tie once or twice a year, but with a collection of about 20, I’m still waiting for the great tie revival.

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Feb 29Liked by Blackbird Spyplane

I'm an older subscriber, over 50, and I personally find it helpful/interesting to hear about styles or items of clothing you (or others whose opinions I respect) don't much care for. Helps me to narrow down my shopping options. Dione Davis and Amy Smilovic openly discuss their disdain for items like cropped jeans, wedges and cork-soled shoes - interesting information! If I completely disagree and feel extremely confident in doing so, then I'll ignore these opinions. I own many of the jeans/trousers Erin and Jonah have suggested, which I think are keeping me out of frump territory.

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Feb 29Liked by Blackbird Spyplane

As an older (50+) subscriber I would suggest you interview some older people who you consider stylish (I know this term dates me but…) as I suspect that like me, their style has gone through some evolution (honestly as it must) and hearing how they navigated that would be interesting—there can be no doubt it’s been intentional if it’s successful. It takes a fair amount of skill and thoughtfulness that I’m pretty sure would be edifying to the group, no matter the age.

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I really hope you revisit this topic because I don’t think I’m understanding your message and it’s interesting to think about. What does it mean to dress your age? If it’s a conversation between your own whims and sense of self and society at large, what is that message at every age? Every women’s magazine has taken on that subject as naseum and I’m not sure how your message is different. The examples with the text seem to say, take risks, but only tasteful muted risks, because you’re old and we would feel sorry for you if you really followed your heart and wore color or a certain silhouette or mixed patterns. That’s reserved for the young. Your mens examples are all soooo muted (except for the man knitting) as are the women--and at least two of them are long gone. It seems to say, be invisible, except maybe wink with a cool shoe or the way you tuck your sweater. Anyhoo, food for thought. Looking forward to part 2 if you get into it.

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“Orthogonal” users are cursed

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Feb 28Liked by Blackbird Spyplane

beautiful writing as always

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Lots to consider but hard disagree re that nonagerian in yellow - pa is killing it.

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Feb 27Liked by Blackbird Spyplane

Lets not forget this lord Hironobu.

https://www.instagram.com/hokanobunobu/

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Feb 27Liked by Blackbird Spyplane

I'd like to think that with age, I've grown a good bullshit radar on fits - my own, and other people's (miss me with celebs trying to manufacture a 'candid street style' fashion moment with the really obvious help of a stylist or a whole team of them).

A lot of the advice for women about dressing your age seems to basically be 'don't dress too much like the youths' and a lot of feedback from those who 'find their style' seems to involve active regret over having dressed a certain way that's now out of trend, when they were younger. The latter makes me sad tbh, like sure maybe you think your style is fully cooked at 40 or 45 or 50 and you would never dress the way you did in your teens and twenties, BUT your twentysomething or younger self didn't need to be dressing like you do at age 30 or 40 or 50 or whatever, yk? The journey is a thing, and all parts were necessary, even the cringe ones.

I agree with Amy about self-confidence, it's correct that we expect elders to have a certain level of internal equilibrium and for their clothes to reflect it in some way, and when they reflect the opposite it's kind of sad.

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Feb 27Liked by Blackbird Spyplane

key in your piece for me was the part about self consciousness, and related to that, self-confidence. BUT i think what it is about the first set of photos is not just shaming "bad fits on older people" but rather the fact that when older people exude a lack of self-confidence it makes us feel esp sad for them... because we'd hope they'd know better by now... because we hope we will become more awesome with age ourselves. SO, your point, BBSP, that "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." does NOT ring true to me for the first set of photos because they in fact don't look like people who lack self-consciousness; rather, they look like a bunch of really self-conscious people who are trying hard to fit in. the second set of photos look like older people who have in fact forgone self-consciousness because they know they are fly as hell!

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Feb 27Liked by Blackbird Spyplane

One of my fav posts (…to date)! I made the wise & adorable call in 6th grade to buy my first pair of high waisted, disco-and Style Wars-ready, pocket-less, 1970s Levi’s with a little flare kick at the bottom suitable for sk8ing and Delia’s platforms. Now 40, I still eff with them at least once a week in some form of hyper feminine or tomboy expression. Having the quintessential staples that become your personal *Classic Looks* to dress up/down/accessorize/theme-out over different decades of life is fun and becomes a legit part of both your fashion and poetic life story.

Two indulgent side notes tho — 1) I thought the anonymous Sunset Blvd producer (?) guy was Cedric Zavala from At the Drive In and it immediately made me question if I was actually super down for his wacky look after all too, and 2) the street style cameos felt completely illustrative and didn’t feel harsh or hurtfully “not tender” at all! I’m actually a little distracted by that critique in most of the comments. My best friend and I have a recurring text update on Bradley Cooper’s latest sartorial missteps bc for real, the advice to just take a beat and gaze in the mirror before forcing the public to free-pass a garishly confused and existentially “lost Jamiroqui” look will only have negative ripple effects on non-celebrities too… You captured this take with a humane, philosophic, and smize-based approach — i.e. ultimately quite empathetic and wise at the end of the day, and I was v. down! ✌🏼🧸🎯

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Feb 27Liked by Blackbird Spyplane

Loved the set of photos at the end, nice to see older folks doing their thing and looking great!

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founding
Feb 27Liked by Blackbird Spyplane

Where the hell is Jeff Goldblum in your photos, the man just gets it right every single time. As an older Spyplane enthusiast (54) and a woman, I’m leaning into embracing the things I was too self conscious to wear in my younger days…a leather harness ( Ārdēo Studios is my go to), sequins during the day (they add so much joy) and “ugly”shoes, I need comfort and my size 11/41 feet mean I often just buy men’s shoes. Lovely GenZ is always giving me compliments on my outfits, so I figure I must be doing something right but people my age tend to give me the side eye - which makes me laugh. Have fun with your style and do what makes you happy!

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