Often considered the brand for high school kids who want giant logos on their clothing, American Eagle is actually a great resource for classic, branding-less essentials. Especially when you can get them on deep discount! Here is an outfit I've put together with clearance items, all of which have most sizes at the time of writing.
You can check out the full 60% off clearance sale here, where you can find more deals like cheap tees, henleys, and button up shirts for under $20.
Update: Looks like the boots have increased from $50 to $89.