Just went to Jcrew on Broadway yesterday in the freezing cold, saw so many frate boy and frat girls in santa outfits getting drunk and acting dumb

.
So common now, hate what NY has become.
But anyway just brought these. Bowery Tartan Pants.
2 questions.
how high should i get the break on the bottom, one of the girls in the store said I should get it just above the top of the shoe. but I always feel like when I sit down my pants rise up too high and I ain't with the high waters.
next question I'm trying to rock it british rocker style like get some t shirts and nice looking boots and rock them like they do in Europe.
What goes with blackwatch besides a blazer?
Also does ironing the front take the pleat out?