Being short (5'2"), I've always felt that maxi dresses were WAY out of my league. Luckily, several retailers have started carrying petite and just more height-appropriate maxi dresses that I'm actually going to give a shot. Paired with a cute denim jacket and sandals (or cowboy boots), these could become a staple in any wardrobe!
Old Navy Petite Maxi Dress
Anthropologie Nautical Dreaming Chemise (really a dress)
Emily Maynard's Maxi Dress from The Bachelor (I'm an addict)