Mostly throughout the game I wore the black suit with the red tie and the black dress shoes, but after I beat the game I decided to go ack to Niko's roots and I put back on the original brown jacket and track pants he started in. I'm in those clothes to this day.
I wear my suit when I go out on dates, any suit actually, with a tie or without. I like wearing the breasted jacket although I rarely wear it. I usually wear the blue jacket, from the Russian Shop I think? Maybe Modo. I like wearing Claude's clothing, but with different pants and shoes.