I am 30 and usually dress in a wide range of styles from "skater/snowboarder punk" through "outdoorsey hippie type" to "metro".
When I am wearing cargo shorts (usually from AE) with deep pockets, I usually carry using a cheap Uncle Mikes Pocket Holster containing one of the following:
NAA Mini Revolver in .22 Mag
S&W Model 60 in .38 Special
Makarov in 9x18 mak
Springfield 3" Micro Compact GI in .45 ACP
I use a blue bandana folded over the top of the holster to block the guns view from prying eyes.
When wearing tight low rise jeans, I carry the NAA in a front pocket using the Uncle Mikes Holster with out the bandana. I am looking at a Kel-Tec P32 or P3AT to fill this purpose with a bigger caliber.
In Colorado, our CCW permit law is very accomidating, and very few places are legally off-limits (schools, secured gov't buildings, controlled access federal property). Unless they are running full metal detection stations with contolled access, private property owners have little abiltity to restrict your CCW, regardless of posted signs. If your weapon is discovered, they MUST first ask you to leave the premisis. If you remain on the property after this request, ONLY THEN have you comitted a criminal violation (tresspassing). This is similar to going barefoot at McDonalds or wearing a vulgar t-shirt in a fancy restaurant. I frequently attend rock concerts in Denver, and some of the venues are not in the best parts of town (Colfax, Broadway, etc.). I order to get through the half-hearted "pat downs" at the door, I carry my NAA in a homemade "crotch holster". There is NO WAY that security types are going to "pat" that area. I usually don't have any concerns about the crowd inside the concert venue, its the several block walk back to my car at 12:30 am that gives me the willies.
During cool temerperatures, I usually carry one of the above metioned guns in an Uncle Mikes Belt Holster under my Quicksilver or Volcom sweatshirt.
I spent too much time in the Army to wear "tactical" clothing, so no BDU pants or other "tacticool" clothing for me.
Hunter