Alert! I need your fashion help!

This is the "Hot or Not?" portion of my blog. I'm going to post pictures of three pairs of shoes and I'm hoping you'll tell me that I'm on the right track as far as what to do...

The background is this: I leave for NYC in less than 24 hours (there are stops on the way, but I digress). I would like to look stylish while maintaining my comfort in the big apple. So, in a fit of indecision, I purchased three pairs of shoes yesterday. I will share them now with my comments, and I'm hoping you'll share your comments as well.

The shoes are meant to be worn with black leggings and long sweaters - so all are black shoes.

First up, a test shot with my Thanksgiving turkey socks.

Okay, now I'm serious. The first pair of shoes is the cushiest. They've got the highest heel and seem to be pretty comfortable, although it's difficult to know for the long haul. I think they're pretty cute.

Next we have suede slouchy boots. These always look funny to me. Even on other people, I start thinking about Robin Hood, or something. But, they don't look that bad in these pictures. The only issue is they have ZERO cushion. If you vote for these, and know of a good insole - please share that info, because I'm pretty sure that's the only way these are viable.

Finally, my personal favorites - but they're still not quite perfect... These are kind of cowboy, kind of motorcycle. I'm thinking these would be good, with another pair (or two) for variation for the toes. Again, it's the long haul that I'm a bit worried about.

So, there is my dilemma, in black and black. Speak words of wisdom to me, friends of electronic assistance!

I suppose a fourth option would be to shop when I get there... ;)