Hmmm... Looking at those leaves a lot of questions for me...
I think your caution is well placed. AE usually has a "View with pants" section on the far right side of the various views of the shoes. In this case it is noticeably absent. It gives one the feeling that they might not have a good suggestion what pants would go with this shoe. I think it is safe to say jeans, shorts, and khakis. I don't think I could pull off any other combinations.
I've been wearing mine with shorts and light-colored chinos. I alternate them with the AE driving shoes (e.g., Ventura Highway, Interstate 90, Daytona). Great summer shoe and super comfy.
The Sherwood is casual, almost "boat shoe" in appearance. The front is an apron style 3 eyelet moccasin with padded insole and lugged rubber sole. Not sure of the leather other than it is "soft" with a padded collar. There is contrast stitching, so I would recommend using leather lotion for cleaning and neutral for any polishing you contemplate.
The Bergland is also a comfort shoe with padded insole and rubber outsole. This blucher cap-toe is made of antibes leather and came in black and brown. Both were discontinued in 2007 and you can use condition/cleaner on them.