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I wouldn't look at a shoulder holster for concealed carry. The firearms moves arounds too much bending over as well as other range of movements. I know a guy that uses a concealed chest holster like this one ULTRA Model Concealed Carry Deep Conceal, LLC Holster Review | YouCanCarry.com and most on the time you can't tell if he is carrying or not. I use my shoulder holsters while I'm hunting/fishing but I would'nt use them for CC. As for the size of the firearms you plan to CC it all depends on how you dress and your body type. I've found that I prefer a leather IWB holster for CC but that's just me. The best thing for you would be to go to a gun shop and try a few holsters on with your firearm and the clothes you plan on wearing while your CC'ing.
 
If you cannot go IWB, consider a pocket holster (if you are a relatively large male). DeSantis holsters work well.

Pocket holsters have clear drawbacks (there must absolutely be nothing else in that pocket, it does not work well when you are sitting, ...), as well as a few advantages (you can grab your weapon, flip the safety off and get ready to fire without drawing any attention).
 
I have a shoulder holster, rarely wear it. One thing i can say is, the smaller the pistol the (possibly) more difficult it is to get at/pull out. If its too light/small your shoulder holster is going to come with it. Bigger Medium/Full sized are easier to draw. It's also harder to find uni shoulder holsters for smaller frames.
 
I carry my Shield with an IWB holster custom made for a CT laser from Ted Blocker holsters, couldn't be happier with Don & Shelly's service and quality.

Took a while though as flat as it layed, thought everyone could see it lol
 
Shoulder holsters are niche holsters. Why shoulder holster? Why not AIWB? The Shield is a very concealable gun.

Well, when I carry (p239) I normally ride it at 4 to 5 o'clock. I don't really like sitting or driving with it on my hip for extended periods. I've been thinking about the idea of wearing a holster under a button down shirt where I can go "superman" and tear open the shirt when necessary. I've been thinking of cutting 10 oz from the p239 and going with a shield or a .380. Since host holsters start at $80, it is big investment to make with out getting advice.

So, I should have been more clear. Thanks everyone for the advice.
 

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