Neither. Wear shoes. With that said, I bought a pair of Clarks desert boots in the fall. They're nice, but I find them a bit too bulky and not as form-fitting as I thought they might be.
I was waiting or hockeyinsider to weigh in on this one. He had the same question a few months ago.
I vote on the AE for what you want. If you buy the Clark's you will run out of things to do with them quickly or spill salad dressing on them and end up buying a smooth leather chukka anyway. That said, consider hockeyinsider's comment. The man just went through this and votes "shoes."
Chukkas are awesome if you really like chukkas or intend to use them as they were intended--which is as a boot that can be donned and removed easily. If you travel a lot and need a shoe that dresses up or can function as a boot and that needs to get on and off your feet quickly at the airport, a chukka in smooth leather with a Danite or commando sole is the answer.
I wouldn't experiment with the Alden chukka because it is a $600 experiment, and shell cordovan is not weather friendly. If you are going to spend that much, go to your local riding academy and have a Dehner chukka made bespoke or contact goodman Richard at Shoehealer and get a pair of Tricker's Winston's MTO in your exact color and sole specs.
