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Just wanting to know about a comfortable IWB Holster or do you just get used to it?

Mailed in all my info today. I am looking for small frame, pocket size, .380 or 9mm. I work outdoors & wear jeans in winter & IWB holster just sounds uncomfortabe. I don't want to buy too many before I find one I like. I never tried one on so I don't know what to expect. Any place in Beaumont Or Houston area to try one on before I but many? My other thought was to carry a small compact in my jeans pocket, that may not be too comfortable either. I am sure I have many other questions but just one at a time for now. I have really enjoyed reading this site , Thanks