Shoes and winter jackets are some of the few things that I've found are really worth spending more on to buy quality. I don't think I need to explain to all you Mustachians that I'm not talking about "luxury" shoes here, since luxury != quality.
For instance, I bought a pair of leather/suede shoes 4 years ago that I still wear daily. They're unbelievably comfortable, they're still in great shape, and I'm planning on keeping them for as long as they last. They cost me $160, so I'm looking at $40 per year, so far. I think they'll last another few years, so that will drop.
I don't bike to work (I car pool or bus it), but I do bike a lot for fun, and I do have clipless pedals. My ride of choice is off-road mountain biking, and I can't really see how it can be done without clipless shoes. That said, I've had the same pair of mountain biking shoes since I've bought my bike in '98.
The other shoes I own are sneakers that I buy once year. I'm not a fan of barefoot running/walking, so I have to put something on. Fortunately, I buy last year's fashions on sale, so I get them at a pretty good discount.
Finally, I have two pairs of dress shoes. These are very cheap, since I only used them a few times a year when I need to put on a suit and my regular daily shoes just wouldn't work.
I'm definitely not the most Mustachian when it comes to clothes. But I am more frugal that most regular people, and I'm extremely happy with my footwear situation. both in terms of selection and price paid.