I did have a polo which had the two-collar look, but it was actually just a single garment. (I’m female, though, so our clothes are always bizarre)
I remember the polos and popped collars being more of an early-80s thing- think Ted McGinley in “Revenge of the Nerds”.
Tight rolled jeans were a few years later, after popped collars had somewhat faded.
I don’t recall people wearing two polos simultaneously though…
Then again, I was in elementary, middle school AND high school in the 80s, so my perception of the earlier half may be somewhat skewed.
I assume that the three shirts is absurdist exaggeration on the part of the show, based on the existence of layering two shirts.
According to some posts in this thread, there have actually been single polo shirts with double collars for this very purpose.
Black on black on black–so chic!
I went to a Pittsburgh-area prep school in the early Eighties and rarely saw it there. More common were turtlenecks, or polo shirts with collar popped, worn under button-down shirts.
I graduated in 1985 and it was definitely a thing while I was in high school. I’m fairly certain I recall multiple contemporaneous depiction in popular culture at the time. I’ll gladly re-watch Repo Man and The Decline of Western Civilization and Suburbia, etc. for them.
TV Party!
Yeah, you just jump on that grenade why don’t cha? 
Graduated HS in 87. I definitely remember the popped polo collar and the two polo fad. I did the popped polo collar but never the two polos. I think anything more than 2 is probably a more modern joke on the trend.
Why did we wear multiple layers like that? I was watching The Goonies the other day and cringed at the gym shorts over sweat pants but I remember wearing that. Same with two pairs of shorts, usually jams, at the same time. Just… why?!?
Graduated HS in the 80s, yes it was a thing. It had to be an alligator Izod shirt also. In the case of my local HS, it was very much a display of affluence. The kids that wore them had the parents that could afford to buy many multiples. Woe to us poorer kids that tried to replicate the look with JC Penney knock-offs.
A few years ago, I was in Macy’s or Nordstrom and saw a table of Izod alligator polo shirts in the men’s department, at something like $60-80 each. I looked carefully at them to see if the construction was noticeably better than the ones from the Gap or Lands End or wherever, that cost $20-30. I really couldn’t see anything better in the Izod ones, aside from the alligator logo.
So yes, wearing the alligator shirts definitely seemed about flaunting your wealth.
Just FYI, I believe that the alligator logo actually belongs to Lacoste, not Izod.
French tennis player Rene Lacoste invented what we now call the polo shirt for tennis in the 1920s. He made the collar soft so it could be easily flipped up as needed to protect the back of his neck from direct sunlight. So popping the collar was part of the original design.
In the 1980s, Lacoste licensed the alligator trademark to Izod, but I believe that agreement ended a while ago. So if you are looking for a genuine alligator shirt today, you won’t get it from Izod.
As with all fashion trends, the preppie polos had their adversaries. In one case: Croc o’ Shirt
FWIIW Rene Lacoste was nicknamed the Crocodile, so while everyone calls them alligator shirts I think the logo is a crocodile
The logo does look more like a crocodile than an alligator, to me. Though its head is mostly in profile.
There’s also a Chinese company that does a similar logo, to much legal dispute. They date to 1952, so it not your typical “knockoff.”
Turtlenecks under button down shirts continued into the nineties here, because we used to wear them that way in high school.
I don’t remember the multi-polos, but then I was just a kid in the 80s. I DO remember French-rolled jeans, although we called it “pegging”. (Yes, seriously)
I was a youth in the 80s and I remember it well. I also remember they also came out with some double collar polos. Do a search, you’ll see plenty.
I remember this in the 2000s as a throwback homage type thing to preps of the 80s, but I didn’t know the multiple shirt thing was actually a thing in the 80s.
Heh. I once had a gag necktie with polo players riding crocodiles.
This is also my admittedly dim memory of things.