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To reiterate a point brought up by others -- find clothes to wear around the gun, not otherway around.

Having said that, here are some thoughts to consider...

I find the flatter the gun, the more concealable it is for me. I carry a Browning Hi Power in a CompTac C-TAC IWB holster, and I find that works very well, even under just a tucked in polo shirt. 1911 would probably work for the same reason, altho I think the Hi Power is a bit trimmer. Sounds like you would definitely have to go up a size in jeans. Also, you might find a shoulder holster would work. Might be tougher to get to if you wear polo or t-shirts, tho.

If you decide to try to fit the pistol to the clothes, then perhaps go for a Rohrbaugh R-9 (I think there is one for sale on this forum right now). I do not have any personal experience with them, but I hear they are well-made and reliable. They had better be for the price! Not cheapest gun, around $1000 last time I looked. Kel-Tec's newest 9mm might be a possibility too.

If you go the .380 route, I would recommend finding the smallest pistol that you can shoot a .380 with. Choosing a .380 that is as big as one of the small 9mms doesn't compute with me, unless you just plain can't shoot the smallest versions of 9mm and .380. (Note that a Kahr PM 9 is shorter, slimmer, and lighter than a Sig p-232, and with the slightly extended magazine, carries the same number of rounds in a significantly more helpful caliber.)

A Kel-Tec P-3AT or the Ruger LCP would fit very nicely in the back pocket of your jeans, and you can even get a neck holster to wear under your shirt. Also they would fit easily IWB if you wear your shirt untucked. Heck, for the size and cost, you could buy two and wear them both. As for ammo for a .380, I've never shot anybody with one, but I respect John Farnam's opinion highly, and he highly recommends the Cor-bon DPX ammo. Good penetration and expansion for what it is. It is what is in my wife's P-3AT.

And of course the j-frame revolvers are usually pretty handy to hide away. I carry one as a BUG in either a front or back pants pocket, depending on the pants (and I will slowly be weeding out the pants that do not have deep enough back pockets.) The alloy frame ones are pretty light and comfortable to carry.

Good luck with your decisions. (I use the plural, because whatever you choose initially, you'll probably at least modify it some down the road. takes awhile to figure out what works best for you.)

elb