A "go-to-hell high roll in the (shirt) collar." What does this mean?

In the novel I Am Charlotte Simmons, author Tom Wolfe writes of a basketball coach who wore custom-tailored suits with shirts featuring “some kind of go-to-hell high roll in the collar.” Usually I can easily understand Wolfe’s elaborate sartorical dissertations on menswear, but this sentence confuses me somewhat.

I can only guess that he is saying the roll in the collar is in some way extremely exaggerated and that the wearer figures that if people don’t like it, they can “go to hell.” Am I totally overanalyzing this? It’s really the only possible meaning I can discern.

I picture an 1800s protestant minister wearing something like this.

I remember The Official Preppy Handbook defining go-to-hell pants as slacks in some non-corporate color, to be worn on weekends. IOW, let it all go to hell; you’re wearing salmon-colored slacks, next comes the apocalypse. There was some other item that could be go-to-hell, but “There is not a go-to-hell shirt.” As for the collar, the book said that wearing it up starts in childhood; perhaps the roll is something more elaborate, and thus, go-to-hell. At least that’s what I remember; I don’t have my copy to hand.

That sounds plausible (that the definition Wolfe is using was copped from the Preppy Handbook) - however, does anyone else want to take a shot at this question? I’m a little baffled as to just how far you can take a shirt collar. What exactly do you do with it to make it “go-to-hell”?

Wear it for so long that the collar gets loose and floppy, and the top quarter inch naturally rolls over? I’ve seen hardcore golfers with shirts they wear season to season, and if they’re polos, that’s exactly what happens.

Judging by how Wolfe dresses vs. how 99.999% of the straight male world dresses, I would say it doesn’t mean a damn thing.

Yeah, based on the description in the OP, I pictured a really high collar not unlike the one Wolfe himself usually wears.

And the go-to-hell part just means he doesn’t give a damn whether it’s in style or not, and anyone who’s worried about that can go to hell.

(I think the phrase being in the Preppy Handbook is coincidental and unrelated.)

If you’ve actually read Wolfe’s writing, you’d know that although he himself dresses oddly, he is able to describe with extreme detail the fine points of all sorts of traditional men’s fashion. He clearly knows a lot about suits.

I saw an old Looney Tunes on Cartoon Network this last morning and it reminded me of this thread, It was very memorable because I believe it was one of among the first, or prototypical cartoons, of Bugs Bunny and Elmer Fudd. Bugs was drawn differently and voiced by someone other than the classical voice actor, or this was before his Flatbush accent. But the point is that Elmer Fudd is dressed in a typical “flipped up” collar, with tie, and bowler, perhaps reminiscent of the classical “Accounting Clarks” of A Christmas Carol. It reminded me of this description and must have some particular popular cultural ennui inherent to the late thirties early forties.

I guess maybe Fudd was dressed a bit like Chaplin, but he reminded me of a clerk?