Hey Jacob Fred,
I've had my ileostomy for 11 years, and wear a dress shirt/pants to work. What works for me is :
First, pull your shorts/underwear up over the top edge of the pouch ( I had to switch to boxers ), shirt on, then pants on last. Tuck the shirt in carefully while you pull basically your pants up over the shirt. Keeping your shorts pulled over the edge of the pouch helps protect the flange and pouch from belt wear etc, especially if you are mobile at work.
Be careful of the old pre ostomy method of quickly shoving the shirt down in the pants, ya might catch the edge of the pouch and rip it off...which sucks when you are getting ready for work in your nice clean clothes ! :)
And yeah, no way I can wear my pants as tight as I used to, need a bit of room at the waist now. :)