One of the easiest ways to look dressed up is just wear a dress - you look nice with minimal effort! Part of the reason they are so easy to wear though is because they aren't very versatile - you can throw a cardigan or something over it, but it's pretty much a stand alone piece. I've been meaning to try the "dress as a skirt' thing for a while, and I'm so glad I did because it really felt like having a new piece in my closet, although it wasn't! So now that I've done the dress as a skirt, and a shirt as a scarf, what do I try to re-wear in a new way?
Dress: J.Crew [similar below]
Sweater: J.Crew Factory [similar]
Tights: Target [exact - slimming but not constricting!]
Scarf: H&M [similar]
Boots: Vince Camuto [exact]
Watch: c/o Daniel Wellington [exact]
and a few similar options below (I love the first one!)