I would pick out a few guns in the price range that you mentioned, then I would go to the local gunshop and see which one fits you the best. If it was me looking for an auto that fits your needs (with good looks) it would be a Benelli Legacy. If it was an over under I would take a look at the CZ line of shotguns, Citoris, and Berettas. All would fit the bill nicely.

I currently shoot a sporting clays league (we are in the championship this week), and I shoot a Benelli M1 Super 90 with a 24" barrel and a camo stock, last week I shot 48 out of 50 with that gun. I am looking at buying a Benelli Legacy or some sort of O/U for a pretty gun to shoot/carry while guiding pheasant hunters and busting clays.

Another option would be the Ruger Red Label.