"When was the last time you wore a dress?"
I have never been a big dress wearer, but only because I've been too afraid to wear one. I thought I wasn't pretty enough or thin enough to wear a dress, so my normal attire for most of my life has been jeans and hoodies.
I love dresses and skirts. And it took me a long time to feel comfortable in them. The last time I wore a dress - for a special occasion - was at my friends wedding last summer. However, I found a cute navy blue summer dress online at Old Navy and I wore that a few weeks ago. I've only worn it twice so far this spring, but I have a feeling I will be wearing it more over the summer. It is incredibly comfortable.