Was there some way you used to (or recently) dressed or wore your hair until you saw someone else sporting the same “look” and it was so bad, you gave it up?
I’m in a rush right now but will be back to post my own examples.
No, for a couple of reasons:
- I’m pretty basic when it comes to clothes and hair, even when I do care what others think about my attire (mostly at work)
- I have a wife and 2 grown daughters who would likely give me good council before I committed to something new
I have a neighbor, a woman in her mid-fifties, who does lots of animal rescue stuff around the area. Consequently, she usually runs around in kind of grubby jeans and t-shirts, hair loose and messy–perfectly appropriate for this kind of activity. Nuttin’ wrong with that. But she will wear gorgeous, exquisitely arty, sculptural (usually) silver earrings when she’s running around like this. I do understand that thinking-- “I’m not really a homeless person or a sanitation worker. I have taste and a little money.” (Yeah, that sounds snobby…) It just looks ridiculous to me. I used to do that until I got a good look at her. A middle-aged woman in grubby clothes wearing REALLY nice, clearly expensive earrings that would be appropriate at at the opera in Santa Fe-- nah, looks dumb. So I stopped doing it.
Also, a good friend of mine shaves his head (a great look on him and on many men these days). I asked him why and he said that he used to wear his hair really long and bushy (in the 70s) and eventually in a pony tail. As he gradually went bald, the pony tail got longer and he kind of liked what he thought was a professorial/counter-culture look. Until one day he saw another middle-aged man who was bald on top, with a fringe of hair around the side, and a long pony tail. He said it looked so ridiculous that he immediately went home and shaved his whole head.
These are not exactly indictments of how other people dress and think they look–some people can carry this stuff off. I’m talking about that “aha” moment when you realize you are not someone who can carry it off.
For women, it sometimes happens when you realize you can no longer wear skirts as short as you once did, either because of weight gain or because you don’t want to be seen as “mutton dressed as lamb.”
Maybe this only happens to me…
My theory is that many men are so hyper-conscious of this potential problem that we decide to “head it off at the pass” by wearing a lowest-common-denominator boring style that no one could find fault with - except for the boringness itself, which I feign to cultivate as a pseudo-virtue. 
I used to wear overalls around the place. They were always too big and too short ( long legs). Sometimes I would run to town in them for a quick pick up. One time a checkout girl called me Farmer girl. I never wore them again. Well, I take it back, I wore them when we did some painting a few years ago. Never off the place again, though.
It used to bother me when people reacted badly to my having a little panache.
Now I feel sorry for them for being so dull.
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Not sure if this is exactly what you mean. Way back when my son first started college, he put on my blazer with the shoulder pads, took a picture posing like a football player and sent it to me. I got rid of all my '80s clothes after that.
I would agree with this. For many men, the decision making is “what will cause the least trouble?” If it’s a modest dark suit, then that is what to wear. If it’s khaki’s and a plaid button shirt, then that is what to wear. If it’s jeans and a t-shirt…
Fitting in and reducing conflict are strong motivators.
Yeah, this is the sort of thing I’m talking about. Ugh, when I think of the foam shoulder pads I used to stick inside a regular t-shirt! :smack: Big hair, big jewelry, and big shoulder pads-- the 80s were a bad fashion decade.
I used to be fine wearing pants from Target and Costco. I also used to train various martial arts in street clothes, so having pants with a little room in them made sense, so I’d buy them a little big. Then I started seeing middle-aged guys in baggy Target or Kirkland pants and realized that’s really not a good look…
For some reason I always wore white sneakers (this was years ago), until we had a trip to London and noticed how out-of-place they looked when everyone else was wearing black or brown shoes. Now I can’t wear white shoes since they “flash” when I walk.
In high school I stopped wearing my yellow denim leisure suit, floral print polyester shirt, and platform shoes when I started noticing that a lot of 40 year olds were wearing the same outfit. They looked like schmucks. Of course, I looked cool, but you don’t want to be mistaken for a schmuck at a distance…
For years I wore the same model of white sneakers (New Balance 609) and crew length white athletic socks as my default casual footwear. Did a trip to London and Paris, but was forewarned that wearing sneakers (“trainers”) would mark me as an American tourist. Switched to dark (brown and black) trail shoes and hiking socks and never went back. Now I am trying to dump the hiking socks (unless actually hiking) in favor of dark low-cut (anklet?) socks.
I dress like a bag lady, but if it is a contest between how I look to others and whether I’m not getting strangled and poked or scratched or annoyed in any way, I pick my baggy tracky dacks and my soft cotton ancient t-shirt.
In the 1980s, I was overseas. I was wearing my ancient levi jeans around and about. They had torn across the knees, but they were really comfortable because the denim was lovely and soft so I loved them. One day, the owner of the cafe where I hung out looked at me, shook his head, tsk tsk tsked and said “tomorrow, I buy you new trousers”. Even though he was an old(er) guy and I was young, I realised the time had come to say goodbye to my old faithfuls.
In my mid-40’s I was presented with a picture of myself when I was 17 … I was wearing the exactly same thing at the time (think Al Borland from Tool Time) … I’ve been varying my clothing purchases since …
+1 on the middle-age man with a pony-tail … I wear mine down as often as I can now-a-days …
For a while I fell into the habit of wearing certain ugly, baggy dresses, figuring I’d outlived my attractive years, so why not be comfortable. Then one day I noticed a lot of crazy right-wing evangelical women dressed this way, and that’s the last thing I want to be mistaken for. So I had the idea of finding different comfortable baggy dresses, all in black. Now people ask if I’m a witch or an artist. I’m just trying to be comfortable and blend into the shadows.
Sort of? Some years back, I was getting sloppy with trimming my moustache, and realized that it was growing into the Hulk Hogan style. And as soon as I noticed that, I started being more vigilant about my shaving.
Well, I hadn’t before, but now …
Really, though, I’m more prone to thinking, 'Well, at least I’m not making that mistake." I am very, very boring.
You’re dressed ridiculous right now. So am I. To prove it, put on your best, and/or coolest clothes. Take a selfie and look at it again in 10 years or so. You look ridiculous.
Closest I’ve had was seeing this image shared on the Dope and deciding I need to throw out any baggy clothes I have.