Dressy Casual Discuss this oxymoron in the comments below. cat never understood when restaurants and such said they had a ‘dressy casual’ atmosphere. like, its either one or the other. in my world anyways. 😛 Learn More About Dressy Casual Wear a dressy top and a casual bottom? The phrase Dressy Casual exists to fill a certain need. It exists to describe something that is not at either extreme of either Dressy or Casual, but rather to describe something that is a happy medium. Ramona Dressy Casual? Never heard of it before today. I’ve heard of Casually Dressed or Dress(ed) Casually, but never Dressy Casual. Maybe it’s a regional thing.