steve_w: For me, I never really got into the hip-hop and baggy stuff. I grew up in the lage 80's and early 90's, during the "transition" period. That was when the tight jeans went out, and the baggy look with the underwear hanging over the top came in.
I never really got into why people liked that baggy look at all, and I stuck with my "metalhead" look even to this day. For me, I am a rather skinny person, at 5 ft 9 inches, and 130 pounds, with a 28 inch waist, and a 42 inch chest. I've gained a whopping 20 pounds since high school, but it's all been in muscle. It's obvious that I am in good physical condition today, but I was rather skinny as a high school kid.
I have never really liked pants that the inseam does not meet my crotch, or any pant for that matter that has a ton of excess fabric in the legs slopping around. For shirts, I like the sholders of the shirt to be on top of my sholders. I am an active person, I walk quite a few miles in a day, and I have a fast pace that few people can keep up with. My job requires me to climb ladders and crawl into equipment cabinets. Because of this, I don't want to worry about pants falling down as I do my job. Not to mention, I want the material hanging off of me to be under control and not slopping aroun all over the place. I don't wear skin tight clothing, but do wear a much closer fit than what is typically in style today.
THen there's the showing off part. Yes, I am in good physical condition. Why should I hide my body's shape with baggy sloppy clothing. I think that when the butt of the pants meets the natural shape of the person's butt that it's much more attractive than having a bunch of excess, loose material hanging around that person's thighs...it's just unattractive, and unprofessional no matter how much you paid for that suit...GO TO A TAILOR, OR BUY THE CORRECT SIZE!!!
One can wear clothing that fits and still be comfortable...in fact for me, wearing clothing that is not excessively baggy is in fact more comfortable