This isn't actually my grandpa's sweater, it's my dads, but since he knew that I would never ever let him wear it in public because it would make him look like a grandpa, he gave it to me. It's actually a very versatile sweater; it can take you from day to night and keep you nice and warm from cold weather to colder weather. Wear it belted with a flowy mini and flat boots for day, because you don't really want to be running around pants-less when everyone can clearly see what you're wearing.
(sweater: my dad's closet; belt: Urban Outfitters; bag: my mom's closet; tights: DKNY; boots: Enzo Angiolini)
Then when you want to channel your favorite celebrity who wears shirts as dresses... strip off your skirt, put on some chunky heels, let your hair out and go! I took the belt off my waist and wrapped it around my wrist as a bracelet and took the strap off the bag to make it into a clutch to give the sweater a bit of a fancier look.