irishguy202 saidI guess that is a good problem to have.
One could have worse. But when men's dress trousers were looser than today, a tailor could make alterations that would give one leg a little more room than the other at the crotch, so you wouldn't have an obvious bulge hanging down. You do know most men always hang to one side or the other, and it's the opposite to which hand is dominant? So a right-handed guy hangs to the left, and vice versa.
In the summer 1963 I was 14, and my Father took me to his own tailor to have some suits and jackets fitted as I began my first year of prep school. A big deal for me, because until then only my Mother had taken me shopping for my clothes at children's stores. It was a sign of my entering the adult male world.
I was having my trousers measured, standing on a little carpeted platform, full-length mirrors all around, and my Father sitting nearby. As the tailor ran his tape measure up my inseam he pressed it against my stuff, and asked me: "On which side do you dress, sir?"
On which side do I WHAT? I'd never been asked that before in fittings. What does "dress" mean? I briefly hesitated as my mind raced to figure out the meaning, and thinking I had the answer, replied: "Neither, I wear Jockey shorts."
The tailor replied: "Very good sir, I'll make both legs equal." I was relieved I had apparently gotten it right. Nowadays I only wear boxers with baggy cargo shorts & pants, with lots of room to hang free, and still wear snug briefs under my dress trousers. So a tailor never has to worry how to "dress" me, though I'll still get asked the question in better shops.