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I carried leather for many years, switched to nylon with the velcro inner belt as described below, and never looked back.

I bought the best quality belt and stuff holders (a mix of brands but mostly Bianchi Accumold) and never had to replace anything. I've always found this approach to be cheaper in the long run. Buying 2 crummy ones of anything is more expensive than buying one good one, and after the second purchase, you still have a crummy one. I also didn't have to put up with the "it's kinda torn and falling apart, but can I live with it for another few months to save money?" situation.

Dirt came off with a damp cloth, or soap on a wet cloth, or soap and a stiff brush, and in the worst cases Gigag04's touch of shoe polished brought back the professional look.

When I worked marine patrol I wore this rig without keepers in case I had to ditch it to stay above water if everything went really wrong. On land I used the keepers for a "belt and suspenders" approach.

For a holster I went with the Blackhawk Serpa Level III for my 1911 for road work and warrants, and a Level II Serpa for my Springfield XD for the boats. They were light, secure, had versatile positioning (with various Blackhawk adapters) and fast.