I was a big kydex guy and thought leather was for "old timers" until I tried a Milt Sparks holster. I was sold immediately. I still have some kydex holsters around (just picked up a CTAC for my M&P) but as far as comfort and conceal-ability goes leather takes the cake.
As far as wear goes I don't think it matters either way. I do caution that in the humid summers the leather seems to hold moisture so when it gets hot out I usually wear my CTACs.
I prefer leather. Leather conforms to your body better; and leather is more comfortable for me. I do have a couple kydex holsters I'm trying though. I bought a kydex OWB for competition; and I'm getting ready to try a Fist IWB.
I have had both and to me they both have advantages. I had a Comp-tac Gurkha that I used with my Glock G27. I really liked the holder. I now have a very nice leather holster for my little Kel-tec P3AT that I got from http://kdholsters.com/ . I will probably get a CTAC from Comp-tac for my new M&P .40 Compact and already have a Cochise Defender ( http://kdholsters.com/basefile/iwb-defend.html ) on order from K&D.
The kydex holsters are nice in that they are fast and retain the gun very well. Reholstering is also very nice with a kydex holster. This Cochise Defender will be my first leather holster for a larger gun, but I am sure that I am going to like it a lot. I think it is going to be very comfortable. K&D does awesome work!!
I love my CTACs, and I have several. But I must admit that I don't like the factory stock CTACs and I have to add my personal touch to make them work for me. With the end result being the perfect carry rig for me I don't mind it at all. I have been known to personalize/customize my pistols as well. Maybe its an OCD thing with me.
With some of my CTACs, I found the edges of the kydex to be a little rough so I take care of that by sanding it down a little. Then I add moleskin to the top backside of the holster body, behind the rivets on the leather tabs, and around the edges of the leather tabs as well. I also do >>this<<. I have even more plans, but I'm letting them marinate in my head before I take the plunge.
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