Thare yur britches.
I’d say, if you use the word “trousers,” then you are probably way beyond worrying about being modern and cool. At least in the US.
That said, I only roll them if they’re too long. Young hipster types like doing it severely, or more likely they buy dreaded near man capris.
I associate that with Tintin. But he wore breeches.
I was thinking of John Cleese on Monty Python. Not sure if the pants were rolled up though. But I think it would work for the OP.
No, Chris.
Yes. And part your hair behind.
Only if they’re white flannel trousers.
Of course, in Cabin Boy! 
I was going to craft a witty reply…
I was going to write a reference-laden and melancholy reply.
But how should I presume?
And I thank you for that. Really. sniff
Specifically Mr. Gumby (Michael Palin, but who keeps track anymore). Who would put a tax on all people who stand in water. … OOOH!
I knew exactly what you meant when you said it. And got stared at for giggling.
ETA: Ok, maybe all of 'em at some point.
Now that’s how I’ll imagine Leo looking like.
You should wear white flannel trousers and walk upon the beach.
Oh you sweet and aged dear
Gumming out your love song here.
You know the women of today
Ne’er “Michaelangelo” would say.
It would not ever pass their lips
So roll your trousers to your hips
And part your hair behind your head
It matters not; you’re nearly dead.
Just make sure that one leg is always rolled much higher than the other, with a half-eaten sandwich hanging out of your pocket.
And make sure you wear an onion on your belt, as that’s the style of the time.
Yes, and two world wars followed shortly after, not to mention all the ensuing mayhem. <shakes head> Don’t do it.
Really, the major question here is: would you describe yourself as an easy tool?
If not, I say you should go for it.
That is not it at all, that is not what I meant, at all.
What the hell is wrong with capris or culottes? Which, by the way, are called pedal pushers…
:dubious:
Or clam diggers.
Capris are slim pants that end just at the ankle. Laura Petrie wore them. With ballet flats.
Culottes are something else… a skirt disguised as pants and vice versa.
[QUOTE=Tom Waits]
See that little Jersey girl in the see-through top
With the peddle pushers, sucking on a soda pop
Well I bet she’s still a virgin but it’s only twenty-five 'til nine
You can see a million of 'em on Heartattack and Vine
[/QUOTE]
Unless Leo Bloom is a little Jersey girl, I say avoid peddle pushers.