I seldom wear dresses. OK, never, so far. I love skirts, and wear them a lot in the summer. In winter, it's pants. I love how I look in skinny jeans.
Back to dresses, though. I find it's a problem to get something that fits a trans woman's body shape: broad shoulders, small boobs, and narrow hips. I have a couple that didn't look too bad in the store, but I haven't had an occasion where I would feel comfortable wearing them. I just recently found one with a flared skirt. Now, that one looked good, and may be the fist one I wear out "in the wild".