A couple of weeks ago, I asked for help choosing a chelsea boot. I have a pair that I really like but had problems with my little toes if I was going to be walking for more than 3000+ steps. Since I have a couple of trips coming up, I decided to look for another pair to wear when walking in cities, museums, airports, etc. I ordered five pair and thought I'd let you know how they worked out.
#1 Naturalizer Aster: Really cute and comfortable but the back of the shoes rubbed against the back of my legs.
#2 Cole Hann Newburg: I liked this pair a lot too, but the toe box was too narrow for my foot.
#3 Blundstone 1671: Another really cute pair of boots but I had a really hard time getting them on and then DH had to help pull them off.
#4: Timberland Sutherlin Bay: These were my second favorite. I wish they were a bit wider in the toe box.
#5 Born Lenni: They were easy to get on and off, had plenty of room to wiggle my toes, and were comfortable. They weren't the most stylish but they felt good on my feet.

Result: I'm keeping the Born boots for long walks.