The crowd you want to attract does matter. If i were on the market (and I’m not looking for a romantic/sexual partner, but I’m social enough that I’m often interested in making new friends, so in some sense i am) i would be trying to attract nerds, not just anyone.
So i do put some thought into my appearance. “Sharp”? I doubt it. But there is usually something there to spark the interest of fellow nerds.
It’s a little important. I don’t need to be all GQ and “suit up” all the time but I like to look put together or at least “deliberate” in my attire, even if it’s just a T-shirt and shorts. Like clothes should fit and be in flattering colors.
I believe something that makes people appear “old” is to not give a shit about their appearance. Like they reach some threshold where they don’t care about their physical appearance so they no longer care about their dress. Which then leads to a downward spiral of not taking care of their physical appearance.
Although looking around these days, even in NYC, I don’t see anyone really dressing in any what that I would consider a coherent “style”.
But what if you never gave a shit to begin with? I dress now, at 50, not dissimilarly to how I dressed in my 20s. In fact, I may even have some of the same clothes! My favorite flannel dates back to 1997. I think people who care will continue to care; people who don’t will continue to not. The older people in my neighborhood are sharper dressers, in my opinion, than the younger ones. I think I just grew up in a time where casualwear was more acceptable, and, to me, old people look old to me because they wear old-timey/overly formal clothes, not so much that they look like they don’t care. I mean, it’s not that clean-cut, but that’s my impression.
Back when i was in my 40s and could pass as younger than that, i made sure to always change out of my business suit and into jeans and a tee shirt before dancing with college students, so as not to emphasize how old i was. I definitely looked older in the suit.
Never gave much of a crap about style, but I used to clean up nice when I wanted or needed to. Now that I’m old, long married, and WFH since the pandemic, I wear a t-shirt and cargo shorts in the Summer and t-shirt, flannel, and long cargo pants in colder months. When the occasional wedding or funeral comes around, I have to scrounge through my closet to find a decent combo of collared shirt, jacket and dress pants that still fit and are in decent shape.
I own several antique cars, so I do at least drive around in style.
But I definitely do not dress in style. I don’t even own dress clothes or dress shoes at this point. It’s either jeans or sweats, and a T-shirt or sweatshirt depending on the weather. I have a fairly high tolerance for cold, so my “winter coat” is just a light hoodie. And my shoes are just sneakers. Nothing fancy.
At work a few years ago, we were having some big-wigs in and our CEO specifically singled me out and told me that I had to wear dress clothes. So I had to go out and buy dress clothes. One of the managers from a different department saw me and exclaimed “you’re wearing dress pants!” like it was something worth notifying the media about. And then she told me to stand up, and when I did she took my picture.
So apparently, me dressing in style is some sort of newsworthy-level event. 
Something I notice loud and clear is a lot of people are equating “style” with “formal”. As if for a man, only a suit or tuxedo could be “stylish”.
IMO that’s not so, not even remotely.
Hehehe, that might be true. I am often complimented on my selection of odd T-shirts, after all. Right now I’m wearing one of a cat wearing a 1950s style space helmet. I don’t know if plaid pajama pants are stylish, though.
That would be great! I’d only need five outfits
In the city: formal morning wear:
(That cad in the middle is wearing a stroller. Pay him no mind)
Formal evening:
In the country: riding whipcord and rambling tweeds.
And #5: some of those newfangled pyjamas from the Hindus
I’m not a very stylish person, but the aesthetics of my environment are pretty important to me.
I dress as basic as you can imagine the vast majority of the time. I have some nice t-shirts from Universal Standard and some other solid color shirts from LL Bean and that’s basically my whole vibe. These are not cheap clothes but they are very casual and will last me years. I don’t even use product in my hair. I have no idea about a personal sense of style; clothes are primarily functional in my life. As far as cars, I mean… We drive Hondas. Once in my life I’d like to buy a Cadillac but it’s not happening anytime soon.
I have a tendency, however, to want nice things. I have some high quality furniture which we’ve acquired over the years whenever we get a windfall. We put about 90% of it into savings and investments and then spend the rest on stuff we want for our house. We recently splurged on a custom-made Amish wooden kitchen table and I have zero regrets. It’s going to last at least 20 years. So I’d rather have something fancy that I only have to buy once that brings me pleasure for decades.
Having this stuff around, clean and simple design with minimal clutter, truly makes a difference in how I feel every day. I recently (finally) found the perfect duvet cover for our comforter and I swear every time I walk into my bedroom I feel good about it. I know you’re not supposed to care about stuff, but I really care about a lot of my stuff. But I think another way of putting it is, I appreciate it.
I do, too. Although i prefer clutter to the arid look of my grandmother’s house, where everything was in the right place.
I think the difference is in my 20s I had to spend a lot more time to look like I didn’t give a crap about my appearance! 
There is nothing wrong with caring about your stuff and anyone who tries to tell you differently is a judgemental asshole trying to make themselves feel superior to you.
This is a bit of a sore point with me because of my particular family situation. I think it’s ok to care about “stuff” that legitimately has utilitarian, financial, or nostalgic value. And I respect finding good deals on things you actually use or wear. But my wife and her family have such a distorted view on the value of the junk cluttering up their living space it literally drives me insane. To me, all that clutter is just useless junk that represents some actual economic cost to acquire it, plus it occupies emotional, cognitive, and literally physical space in trying to figure out what all this shit is, do we actually need it, and where it should actually go.
I really hate clutter, but it’s a function of having ADHD. I find it overwhelming. Several years ago I went through my house and got rid of at least half of the stuff I owned. It’s never been easier to find, organize and clean up my stuff. Ever since then I’ve been utterly ruthless about getting rid of stuff I don’t really use. I have a handful of very sentimental knick-knack things but I’m all the time looking at stuff like that and deciding I don’t need it that badly.
I even downsized to three craft/hobbies with a low footprint. Jigsaw puzzles (under the bed), crossword puzzles, and cross stitch. I decided I really don’t need any more physical hobbies than that. I have plenty of digital hobbies, not to mention whatever writing fiction is.
Different people are different i find a certain amount of clutter to be comforting. And i feel really uncomfortable in barren rooms.
My husband and I were discussing his wardrobe this morning. He’s shed significant poundage in the last 6 months and even the last 5 pairs of jeans he has are on the baggy side. Most of his button shirts are far too large. He has 3 suit jackets, but no pants to go with them, and I doubt that any of them fit anyway. I think the last time he donned a suit was when our daughter married in 2004, and that was rented. He may or may not need one when my mom dies - I’m sure he’ll be tapped as a pall bearer. But we’ll deal with that when the time comes.
He’s much more style conscious than I am and he always has been. To the point that he would weigh in on all of my clothing choices for occasions. He does have good taste (he married me, after all! 
) and a good eye for style and color. Not that it matters much now - jeans is jeans and t-shirts is t-shirts! We’re retired lay-abouts!
When my wife and I watch BBC or BritBox shows, we often comment on how poor some men must be when they can’t afford the extra material for a comfortable (i.e., loose fit) jacket or shirt. So…nope. If being stylish means tight-fitting, close-cut clothes, they can count me out. Big, baggy, and loose-fitting is my style when I have to put on a suit, jacket, or dress shirt.
I, on the other hand, am a registered fashion risk. Flight attendants in first class, maitre de’s at restaurants, and concierges at even cheap hotels look at me with disdain. I haven’t reached the point of sweat pants worn so thin that one can see through them, like one gentleman in Anchorage that we used to see at concerts who was usually sans underwear, but likely not far off.
There’s a common refrain for women: beauty is pain.
I decided pretty early in life, I’m gonna pass on the pain, thanks. Even if it makes me less “beautiful.”
I refuse to wear heels even for formal occasions. I wear makeup occasionally, but I’m not tweezing my eyebrows or getting a wax any time soon. My vibe is quality casual. I dress up a little for work, in dark pants and a blouse, but that’s about it.
Periodically (too often), I am required to attend large formal events with my husband’s family and so I have to wear an evening gown, and I’ll get into it a little bit, I’ll curl my hair and wear my grandmother’s jewelry and have a little fancy clutch purse, but my best efforts cannot compare to some of the wealthy and attractive women who show up to those events and I don’t even try. These are women who were raised to look pretty, it’s inherent to their identity. Whereas my goal at such events is just to avoid notice.