Originally Posted by
cooker
You need a fairly smooth sole that you can pull out quickly. Note that the toe clip (and presumably, strap) will wear a bit on your shoe, so don't use too fancy a shoe. I used to use toe clips with Sperry boat or dock shoes but they would wear out along the stitching from the friction of using toe clips with straps.
Thats the hard part about using toe clips with anything other than running/cross training shoes. Converse/Puma/Adidas shell toes were great for getting in and out of the clips, but the soles were too thin and flexy to make them comfortable for more than a couple miles.
I have used my lace-up Shimano clipless shoes with the little rubber cleat cover/sole piece that they came with (the piece that comes bolted on where the cleat should be) before with toe cages and it worked pretty well. My particular shoes actually kinda look like running/cross training shoes, so they aren't too out of place with casual attire either. The downside is that walking is a bit stiff though, since the sole is so firm, and they certainly aren't appropriate for business attire. Most loafers I tried had too wide of a toe to fit in the cage properly, and most dress shoes have too pointy of a toe to get a good foot placement on the pedals.
Do you have a locker or someplace you can stash shoes at work? That was eventually the best solution for me - wear running shoes on the bike, then change when I got to work.