Interesting thread, but I guess I never look/notice/care what others (or me) are wearing. When we are leaving the house to go somewhere together, my gf will occasionally ask me to do her a favor. “Anything” is my standard reply. She’ll then ask me to change to a different shirt/pants/whatever. I never understand why, I just do as she asks.
Meh, I had the same experience around my son’s 21st birthday. The wife was looking at some of his infant pictures and showed me one holding him as a newborn and wearing the same polo shirt that I had on that day. The shirt was literally older than my adult son. It made me laugh a the sheer coincidence, but didn’t make me change my “style”. If jeans, polo/tee and sneakers ever goes out of style, I’ll go with them. I’m truly a function over form kind of guy.
The salient factor in my OP was changing because you realized you looked ridiculous. Something being simply old doesn’t qualify.
I stopped wearing my batman T-shirt (and most other printed Ts) when I hit my 40s because everybody else wearing them was a child or looked like a dweeb.
There’s a lot of terrible looking dudes wearing the ubiquitous t-shirt, cargo shorts, tennis shoes combo in the summer, but that’s not going to stop me. Too damn comfortable and utilitarian.
One day I saw a guy walking into my office building with brand-new khakis. So new were the pants that the sticker with the size on it was still attached to the backside of one of the pant legs. I thought he looked like the typical, generic cubicle-dwelling office drone. I then realized that all I wore to work was khakis, so decided to ditch them in favor of blue jeans (company policy allowed it) and non-tuck shirts with no tie.
I am still a cubicle-dwelling office drone myself, but at least I don’t look like it.
I wore cargo pants to work virtually every day until one day I noticed that another worker did the same and it gave off, to me, a negative vibe. I have not worn them since.
Still wear cargo shorts, though.
mmm
Hmmm…
I used to wear different outfits to work, mixing and matching colors and styles. Then, about 30 years ago, I just decided to simplify my life by going business casual with pleated khaki pants and long-sleeved, light blue, button-down shirts. It made my life much easier. In fact, I wear exactly the same thing on weekends and for all occasions except funerals and weddings (when I add a tie and a jacket).
I may look like an office drone 24/7, but I’ve never regretted it.
Well…maybe when I was in France. They did not like that outfit.
The husband of a girlfriend of mine is an accountant and this was his daily uniform at work: khaki pants and a light blue button-down shirt. When she threw a 50th birthday party for him she instructed all the guests (male and female) to come dressed in khaki pants and a light blue button-down shirt. I wasn’t there, but she told him it took him a while to notice… 
I have an image of you guys in your one outfit and your wardrobes with everything hanging the same distance apart… (I’ve been re-watching my Monk DVDs.)
Sorry, my point was that watchwolf saw “old” and thought “ridiculous” where I saw “old” and thought - well, nothing. Didn’t mean to violate the spirit of the thread.
My daughter and I both like to dress a little fancier than is strictly necessary. Occasionally this can cross a line to where we look as if we’re wearing a costume. I can recall an outfit I used to wear all the time which was a long tight black skirt, and a tailored blazer with long tight sleeves and lace draped cuffs. Basically, Morticia. I still think it was an awesome outfit, but not really appropriate for my office job!
Not at all. Some old stuff does look ridiculous, like the ginormous shoulders of the 80s, and I’m talkin’ about the women. Some old things are classics, like the little black dress. Polo shirts being in the latter group IMHO.
At the beginning of the year I started watching a YouTube channel called Gentleman’s Gazette, I don’t really know how or why it appeared on my suggested videos. I started to go through some of the videos and even though it’s just too elegant for my taste it got me thinking. Then, I saw this guy at the supermarket, my age, with a t-shrit, some bermuda shorts and flip-fliops and it just clicked.
I’ve been transitioning from my “dressing the same for the last 25 years” style to more shoes, shirts, polo shirts, and stuff like that.
Not me. Even my suits each have their own dresser drawer.
That is a fascinating web site! Love it.
Bolero jean jackets: Bolero Denim Jacket | Shop Old Jackets at Papaya Clothing
I don’t think these abominations look good on ANY woman. The jacket looks like there was a dryer shrinkage accident – skinny women look like they raided Barber’s closet, on average-to-fluffy women it has a Hulk-like effect (Bruce Banner’s Hulk).
My BFF wore one to work once and asked if I liked it. I replied honestly and she was a bit miffed. Later that day we ran into a colleague wearing one; BFF ripped hers off the moment we were back at her office, informing me I was entirely correct about the jacket.
I dress very nicely for work, I’ve invested a lot in career clothing. Otherwise I’m in ripped jeans/shorts, logo t-shirts, ballcap, and old sneakers – like an 18yo boy, more or less. I’m sure it’s not a particularly flattering look but it’s comfortable and I don’t care.