Shoes

Assuming you're on the road you can't really go wrong with Look pedals - simple technology and they last forever.

For shoes I can only recommend one brand - SIDI. I've got road and mountain shoes and they are simply the best: simple, light & very durable. If the clips wear out you can buy replacements too. My MTB shoes have gone through 9 years of abuse and are still used every weekend.

Agree with MBL - can't go wrong with Look. PP357's are a good buy, and so are the A3's. I would also suggest that, if you go with Look, you get the "red" cleats rather than the "black" ones. The reds allow for more float i.e. your foot has more lateral movement. The Red Delta Cleats allow for 9 degrees of float in all non Free Arc pedals, and can adjust from 0, to 3, 6, or 9 degrees on all Free Arc pedals. Black Delta Cleats can only be used on non Free Arc pedals, and provide a fixed, no float position. You'll get a pair of red cleats by default anyway, but just to bring to your attention that there are different cleats that can be used with your pedals.

I'd try the DMT anatomic fitting shoes. I find they fit me like Cinderella's glass slipper. I almost feel like the pedal is part of my foot.

I am debating whether or not to get Shimano's ultegra pedals vs Look's PP357's. Does anybody have any input or preference regarding these two pedals?

I have a few pairs of look pedals. The better ones pp396 are no longer able to have float as the dial on the back fell off. They all seem to squeek at different times (especialy in the rain). The cleats are plastic and wear out pretty quick, even though I dont walk around in my bike shoes. The right one wears heeps faster as this is the one I clip out at lights or when I stop etc. A few friends have dura ace pedals (very simmilar to the ultegras) and they love them. I think they secretly laugh at me and my bulky look pedals😉