Marc Fisher LTD Yale Chelsea Boots ($179-$200)
"When it comes to walking around NYC, my first concern is comfort, but I'd be lying if I didn't also want to look cute. I own these Marc Fisher booties in multiple colours and I wear them with just about everything. While I am transitioning to Fall but it's still warm, I wear them with shorts or a dress; once it's colder I still pair them with jeans, or leather pants and a chunky sweater. I can wear them all day long without complaining of blisters or pain, so these are a total fashion win!" — AM