Wearing a dress over jeans is not something I normally do; in fact, this may be the first time I've ever tried it. I've always considered the look to be reserved for tall women, and at 5'8" I don't consider myself to be among the very tall. Why I was inspired to give it a try with this outfit is anyone's guess, but I think it works, although for my proportions I think it would look a bit better if the dress were about an inch shorter.
So why is the dress/jeans combo so successful for the very tall? It's all about playing with proportions, and for taller women this generally means avoiding anything that elongates your already long legs, which in turn makes you look even taller (although why that's a bad thing is a mystery to me -- I'd love to be a full 6 feet, and you can bet I'd still wear towering heels if I were).
In this outfit, the wide belt helps to bring definition to the waist rather than letting the eye get lost in the long expanse of dress pattern. Note how the positioning of the belt divides me into three roughly equal parts: shoulders to waist, waist to bottom of dress, and bottom of dress to the end of the legs. Meanwhile, the jeans define where my legs end, whilst the rounded toes and contrasting color of the shoes keep them from adding length to my legs. The length of the dress is also key; very long or very short hemlines tend to exaggerate height in tall women, whilst a mid-length serves to balance the proportions of the legs to the torso.
Since I'm not actually that tall, I chose 3.5" heels to wear with this, because otherwise I felt like this outfit would have made my legs look stumpy. However, someone who's over 5'9" would probably want to stick with a lower heel to maintain the correct proportions. Unless, of course, you're like me and would welcome with delight an opportunity to tower over your friends and colleagues like a looming giant. In that case I suggest you buy a micro miniskirt and wear it with these:
Dress: Diane von Furstenberg
Hat: San Diego Hat Co.
Belt: Audra Jean
Shoes: Faryl Robin
Looming Giant Fantasy Shoes: John Fluevog