I have carried many handguns in a variety of ways and have settled on several configurations I like based on what I am doing and how I dress. For suits, I carry an Officer's 1911 in a shoulder holster but in a SOB holster if intending to take off the jacket. For hiking and hunting, a Smith & Wesson 329 (Scandium featherweight) 44 magnum in a cross draw, a Saharah rig if wearing a bulky jacket, and a fanny back if in shorts (We live in bear and mountain lion country). For flying, a shoulder holster and an Officer's 1911. For casual shorts and jeans, SOB Officer's 1911. For backups I often carry a smaller pistol in a pants or coat pocket, but always in the same pant pocket or jacket pocket for easy memory, things happen FAST when needing to draw. There is no time to remember where I put the pistol. For women, the same applies for holsters but they also get the option of a purse. There are lots of options in purses, I know, the wife has them all. :) For purses, buy them with cables in the straps to prevent cutting (Purse snatchers cut the straps and run away with the purse), and forget velcro closures as it can be a pain to get through when needing the gun. Good gun purses have great gun pockets that allow instant access while keeping the gun secure. Usually they have a simple mechanical clasp or spring closure with an internal holster to keep the gun hidden and secure from being dropped.
Also, a side topic about concealed carry.
Armed Citzens Legal Defense Network
We joined this network for $135 for the family as it provides $10,000 immediately to a lawyer so the lawyer can immediately engage in your defense if you ever have a shooting event. They also send out hours of DVDs from various experts on the subject of concealed carry and shooting. Click the link and check them out for yourself. We also maintain a lawyer on retainer for genral legal work but that costs $2,500 up front and a monthly maintenance fee, so that ACLDN $10,000 up front retainer can be real handy for many people.