The pant roll is just a really dumb #menswear thing in my opinion.
I don't appreciate #menswear very much—and the discussions that surround it often come off as "this is what's Masculine and therefore Good"—but I'll respect the fact that some people's taste happens to line up with that aesthetic. Extended thoughts on #menswear(Click to show)
The pant-roll is just like any of the many idiosyncrasies in #menswear (I kind of want to shoot myself for writing something with a hashtag in earnest but whatever I suppose): it'll look flair-y or contrived if you don't dig that look; otherwise it'll seem as "smart" and "casual" as #menswear enthusiasts sincerely believe these things to be. Really this isn't any different than your average Joe looking at a photo of someone Rick'd out and thinking something along the lines of "wow, that is overdone and far too self-serious." A lot of my friends like the #menswear stuff, and I don't really begrudge them for it. It's a popular look right now, and it's really nothing more than inoffensive appreciation for (though frequently a fixation on) a glorified "adult" costume. The funny thing is that, as much as we on SF might mock #menswear enthusiasts' belief in buzzwords like "classic," "clever," "flair," "casual," etc., we do something similar with the terms we (explicitly and implicitly) throw around with varying degrees of irony: "slutty," "outré," "romantic," "dark," "baller," "clean" (or, conversely, "messy-in-a-cool-notcontrived-way"). I think what I'm trying to get at is the fact that this backlash against #menswear reminds me of seventh graders arguing about taste in music as if there's a "right answer," or a superior way to appreciate aesthetics. This isn't to say that one shouldn't say "I don't like that," or "X bothers me about that aesthetic"; but it's the air of superiority—as if there is some inherent value in one's entirely contingent taste—that forecloses plurality in taste. And that's kind of a shame.