My shoe dilemma:

The shoes are black closed-toe high-heeled sandals. They are intended to be work with skirts or dresses in situations where I don't want to show my toes. Their wearability with pants is not priority, although, as always, flexibility is preferable. They aren't for daily wear, they're for sitting in my closet and being worn a couple of times a year.

Pair 1: Leather (ie. preferable shoe material), more casual (could not wear it with a formal dress, but could wear it with jeans if I were inclined to do so), heels more difficult to walk in, but heel shape more attractive. $40

Pair 2: Fabric/artificial material (ie. less preferable shoe material), being fabric might make it look a bit funny against black pants (mixing too much black fabric), makes my feet a bit sweaty, dressier (ie. could not wear it with jeans, would look quite nice with a formal dress), easier to walk in, less attractive heel shape. $30.

Both are reasonably comfortable, but still need some definite breaking in. I can't walk fast in either. Both have aspects that make them likely to go out of style: Pair 1 has white stitching, peekabo detailing on the toes, and a slight platform under the toes. Pair 2 has a fabric flower on the toes (reasonable enough to wear now, but might look silly in the future) and one of those heels that looks skinny in profile and chunky from the back. In all other aspects they are virtually identical.

And yes, I hate myself for being the kind of person who has shoe dilemmas.