I am at work, waiting for my shift to start, so I don't have time to respons individually at the moment.
It just occurred to me, though, as I was coming to work: sometimes I miss my bus. and choose to walk home. It's about 5 kilometres. Which ones would be best for that?
OK--given all I have heard, it is between the eccos and the pettys. I, personally, love the Clarke's, too. So hard!

I like the SE Pettys and the Eccos best. They are 10s if they past the comfort test.

I agree with Angie on the Pettys and Eccos for looks. Both are so versatile and will go with the outfits you posted. I also agree with you, Alana, that the buckle detail on the Clarks is very cool. Those would go with your outfits, too, though I think they look a little more casual and the buckle might be a little more limiting style-wise. Still, I think you really can't go wrong with any of these three. You could go back to the store with your leggings and tunic on and see which ones you like best for looks and fit.

I like the Pettys best.
I'm also going to be a spanner and say that I actually love the Cobb Hills on you as well. I adore that height and shape in a lace-up boot. I am also someone who has skinny ankles relative to the rest of my legs, and sometimes I like the more balanced look something that covers up my knobby ankles gives. I'd actually lace them just a little looser at the top to give them just a bit of flare there. Just a little bit of a different persepective.

My least favorite are the Clarke's and the Steve Maddens. I think something more sleek is a better choice for you. And I prefer a black heel. I have a soft spot for lace up styles so I do like those. But I think one of the others- Ecco or one of the SE styles- could be more versatile. Any of them would work well. Which is most comfortable?

I like the Eccos, but I do not yet own Pettys so have not drunk that Koolaid yet. And it still could happen.