We’re watching the 6th anniversary show from 1988 (so good) and he’s doing the suit/sneakers thing (it looked cool then too). Was he the first to do it? I googled around and only found a mention of Ellen Degeneris in 96.
I did that for the first time around 1970, so no. Unless you mean the first person on TV. But you might have to check the Disney movie The Computer Wore Tennis Shoes, I’m not sure he’s wearing a suit, but maybe a jacket and tie with sneakers. Unless you mean the first talk show host and them maybe it’s Letterman.
I was thinking “who first popularized the look”- but it sounds like it may have originated with you 
I’m chuckling, thinking of all the guys wearing nice suits but over tennis shoes and a t-shirt. One comedian said “You guys think you look like Don Johnson on Miami Vice. But you know who started that look? Jed Clampett.”
I had a prof in college, very British (knighted, even). He’d just gotten back from an exclusive party in NYC where someone had worn “trainers at a black tie event… excuse me, sneeeekers”.
He was horrified: “WHAT is NEXT? Swim fins? Are we going to start going all out and wearing Halloween outfits to upscale restaurants?”
Watching that clip of Irwin Corey reminded me of how much I miss that super laid back style of the earlier Letterman show. I remember when he put on the Alka-Seltzer suit and before being immersed, an audience member yelled out, “Bye, Dave!” We get so little of that kind of casual stuff today.
My friend Kareem in high school wore black Converse high-tops with a Tuxedo to an event. Got mentioned in the paper with some sort of “being his own man” sort of thing, but the fact was, he had a foot injury, and they were the only shoes he had that he could wear. At least they were black. This was about 1982.
That anniversary show was really fun to watch. It was at Radio City Music Hall. (It’s on YouTube)
The audience was full of natural young goofy energy - on their feet constantly and reveling in the absurdity. Felt less…orchestrated than these days.
I remember a sketch on Spike Jones’ TV show in the 1950s . It featured the very short actor Billy Barty parodying Liberace. His outfit consisted of a tux, and black and white ‘Chuckies’ sneakers. I thought that would be the earliest, but Professor Corey predates it.
Nah, as you can see from posts above I was actually late to the game. I did know that Chucks were the proper sneakers to wear with a suit though.
Well, don’t forget, it’s “Black Chucks After Labor Day”…
Ah do declare, we all still recall the time Beauchamps Armistead, of the Buena Vista Armisteads, you know, showed up at the Club’s annual Lowbrow Luau in black tie and a pair of off-off-white Chucks. Everyone turned to stare, you could’ve heard a prime rate drop.
I wore them to my brother’s wedding in 1970. Red sneakers at that. Dennis
Jews have been doing it for decades- no, really. Way back when, before the coming of sneakers and off the rack, Jewish culture viewed leather shoes as luxurious and especially comfortable. So there were certain times you weren’t supposed to wear them- when you were in mourning and on Yom Kippor (the Day Of Atonement). So on Yom Kippor you should up in your finest suit- and sneakers. The first time I followed this tradition, I felt very nervous until I saw the rabbi was also wearing sneakers!
When in mourning for my Father (may his memory be a blessing), my mother, sister and myself wore formal attire and went shoeless at home when receiving guests.
PeeWee Herman hasn’t been mentioned yet.
The 10th Doctor did it, and he’s a time lord so he could have popped back in time to do it before sneakers were invented. (The 6th Doctor may have worn sneakers, but I think that was a cricket uniform, not really a suit.)
I don’t remember if I ever did that. On the other hand, I did wear sandals a lot back then – so much that the school principal threatened to not let me graduate if I showed up to graduation in sandals. While I don’t recollect wearing sandals with a suit, I am pretty certain that I did that frequently.
My preferred footwear with a suit, though, is cowboy boots.
Tucked into the top, like Roy Rogers, right?
I don’t know who the first to do it was, but I remember seeing photos of Woody Allen wearing sneakers with his suits (and people commenting about it) in the 1970s, if not earlier. That certainly beats Letterman
I always think of Billy Joel 52nd Street when I think about that look. That must have been 77-78 or so.
Interesting. That album is available in paperback…