What sort of wardrobe are we talking about here? I'm not the biggest fan of off-body carry, so I'd be looking for deep concealment options, or wardrobe modifications first, rather than committing to carrying off-body. There are lots of trustworthy small 9mm's out there now, but the difficulty with slide racking is a significant limitation. As others have mentioned, the Shield EZ and Walther CCP were designed with this in mind, but neither are really small. The Beretta Tomcat gets rid of the slide racking concern entirely, and is small, but at the expense of only being a .32. Beretta also used to make a .380 with a tip-up barrel, it was the model 86. I'm not sure if they still make or import them. They're not small by today's standards, but again, no slide racking required.
Maybe ask in the Women's Shooters sub-forum. You might get some good advice from women who have experienced the same wardrobe challenges.