The Rag & Bone silk dress above is really lovely. I think it might look good with a blazer and boots, but it would be too dressy for me. I usually wear my dresses with flat boots, I'm more comfortable that way.
Today I've been wearing an Etoile plaid dress with these Hope boots. It's a casual dress, but somehow I still feel like I'd be too dressed up if I wore it with my IM boots, even though I'm sure it'd look better. How do you feel about dresses and heels?