The question of whether or not to speak to women about what they are wearing has been discussed quite a bit. I've had a couple of interactions recently that went really well.
There is a woman at work who I know only slightly. We've spoken occasionally over the years about casual things. One day she was wearing a dress with a very cute pair of heels. I couldn't help but say "cute shoes!" when she walked by. After a moment she started telling me they were only an inexpensive pair from Payless. I complimented her again on how great they looked. We talked about how awesome DSW is. It was a really nice talk. I didn't say exactly that I like *wearing* heels, but let her know how much I like the way they look.
Since that conversation I've noticed that she has started wearing heels almost ever day!
In a similar situation, I stopped in a convenience store to get a drink. There was a really cute girl there wearing a nice dress and a killer pair of heels. Again, I couldn't resist complimenting her on the shoes. As soon as I did, she just opened up and started telling me about where she got them, how much she likes them, etc. I was really surprised by how open she was to talking with me about it.
In both situations, I started by saying something along the lines of "Cute shoes - Someone has been shopping at DSW!" They both momentarily seemed a little unsure how to respond to the compliment. What is funny is that saying "DSW" is what seemed to open the floodgates.
Maybe a simple compliment seems like an attempted pick-up line? Then, mentioning a shoe store makes the compliment seem less personal, and more like casual conversation?
Anyway, I guess it can work out OK so long as you can manage to avoid coming off "creepy"