Before you say anything. Here’s the picture from this GQ article. Breathe and hear me out.

I know what you see. MC Hammer made chinos, right? And pleats and that one pair of shoes look like what was on Neil Armstrong during a famous walk he made.
But look closer. See those canvas sneakers? Might they be classic Converse? Are those brown suede Adidas. I KNOW that is a letterman jacket. And that looks like an untucked oxford (I might be finishing someone else’s sentence here but maybe not. The palate? Appropriate khaki colors.
I’m not saying that a man of my age could or should wear them. In fact, I am not saying that a man of any age could or should wear these. But I am also not saying they shouldn’t. If a modification to Ivy opens the gate a little, then by all means perform You Can’t Touch This in the second from the left pants.
Let me put it in Ivy terms. You cannot expect a freshman to know what a senior knows. And if you berate the level of deftness with which the Ivy freshman dresses, they are gonna drop out.
And, as my teenage daughter would say, “Bee-Tee-Dubs” there are legit players in this wide khaki game. J. Crew. Lauren. L.L. Bean.

That bucket hat looks more like a pilgrim bonnet. Somewhat more seriously, these pants are also a step away from tight fitting daughter pants. That too is progress.
I’m a twentysomething Dartmouth student (huge IS fan as well!) and I wouldn’t be caught dead wearing most of this
Welcome Keanu!
I could probably make the Gap 90s work. I’d cuff ‘em, press ‘em, and wear ‘em with loafers and a BOCBD. And I’d love a pair of All-Stars, to wear with 501s and a white Izod.
What other pants can you wear with a Polo shirt, a rugby shirt, or an OCBD (tie and blazer optional), and look good with any of them?
wide-wale corduroys
Grey flannels!
I actually tried that shirt on at the Gap the other day (it’s on sale now too if anyone’s interested) and it’s a twill fabric. Not an oxford.
Here it is if anyone is curious
https://www.gap.com/browse/product.do?pid=488612032&cid=15043&pcid=15043&vid=1&nav=hamnav%3AMen%3ACategories%3AShirts%20&cpos=1&cexp=2859&kcid=CategoryIDs%3D15043&cvar=25416&ctype=Listing&cpid=res23022523116908949854275
Bucket hat: check
Pleated, relaxed fit khakis: check
Untucked OCBD: check
Suede shoes: check
Grandpacore in full effect!
The extremely baggy pants are an overreaction but, as whiskeydent notes above, at least a move away from the short, tight Pee Wee Herman look.
The Oxford bags of the 1920s were similarly wide-legged, and the bellbottoms of the 70s likewise oversized in length and width at the hem. There was a similar fad for baggy clothes in the late 80s and early 90s, with European designers leading the way, but I still recall Ivy holding its own in that era, at least in NY and DC. The Bond movies, from Roger Moore’s ground-brushing bells, through Timothy Dalton’s droopy shouldered suits, to the skinny suits of Daniel Craig, give a pretty good glimpse of the various extremes. I wish fashion would hit a well-fitting medium between too big and too tight and stay there, but I suppose that is the difference between chasing trends and developing a style.