VIDEO HERE (9:28 minutes)
*****
I've always maintained that you have to dress for success when carrying a handgun.
My normal wear is Wranglers and a loose fitting button down shirt, and that's just fine for me to carry a 1911 shorty in a strong side holster - but that's with my build and posture. Your mileage may vary.
I also need to add that's with a belt holster that hugs my body tightly. While a paddle holster is more comfortable, it's not nearly as concealable.
One thing I have never done is the photographer's vest mentioned in the video. Nothing screams 'Concealed Weapon!' like a loose vest on a middle aged guy, particularly on a hot summer day, whereas a loose fitting shirt is perfectly normal for most men during that season. It's also one less layer of clothing I have to work around when drawing the weapon.
I do have different holsters for different occasions. If I want to carry completely concealed, I wear my 45 in the 5 o'clock position in a Galco Jak-Slide, positioned over my right hip pocket. It works so well that I test drove that holster by wearing a gun into the police station, and I'm not fucking kidding about that - the ultimate go/no go test.
Most of the time though, it's on my strong side at the 3 o'clock position and that works fine. You might be able to see the gun printing occasionally, but that's if you're looking for it and I honestly think that most folks assume it's a cell phone. Luckily, I live in a State where a gun printing is not that big a deal, unlike California where it's a big legal no-no.