I remember when I was younger I used to wear my pants about 3 inches too big. I actually had to keep my pants from falling when I went through the security line at the airport.
I also wore my sports jackets about 2 sizes too big. I probably could have fit a sweater, tie and vest underneath it without having any problems walking around.
But now that I am older and wiser, I realized that wearing clothes too big just isn’t very flattering for anybody. Sure, wearing oversized clothes is cool when you are young and casual, but when you want to be taken seriously you really should know your size and wear clothes that fit perfectly. This is what most of the men’s fashion magazines do anyway when they re-style dudes on the street.
If you don’t want to spend a ton of money replacing all your gear, don’t worry – there are these people called “tailors” that can help you out. For a couple of bucks they can make any necessary adjustments to the clothes you have.
Some great examples for this case would be Diddy and Jay-Z. When they are wearing casual clothing, the clothes are loose, baggy and oozing with street cred. When they are in suits, the suits are perfectly tailored and they are still oozing with street cred.