I never thought I'd be trying to give dress advice to anyone, but here goes
I'm answering mostly because I spent many years of my early adulthood being clueless about clothing and feeling very uncomfortable when I'd yet again dressed "wrong".
I'm not very feminine, and being heavyshouldered frills and lace around my neckline tend to look very silly. Anywhere, actually. But dresses are a lot more than that, and I've discovered that "athletic" dresses are my best friend. My favourite at the moment is a loose, black, sleeveless knit dress that stops just above my knees and has a draped shawl-like neckline. It's more comfortable than a bathrobe, I can wear it to work or wear it to a party with a little jewelry and attractive tights.
I never wear shirts, blouses or blazers, since I've never found any that fit my shape. Being tailored and often (always?) in unforgiving fabrics, they have to fit well to look good and not bind. I usually go for lightly fitted clothes with some stretch. All my work clothes are basically some variation over jeans/knee-length skirt/loose linen pants plus a light sweater/thin wool top/simple sleeveless top. Most of this is "dinnerworthy" too.
I second the idea of trying things on at home. Take it all home and just return the things you don't like. Whatever your shape, count on 90 % not fitting. It gets easier once you can spot what you're after
Winter riding is much less about badassery and much more about bundle-uppery. - malkin
1995 Kona Cinder Cone commuterFrankenbike/Selle Italia SLR Lady Gel Flow
2008 white Nakamura Summit Custom mtb/Terry Falcon X
2000 Schwinn Fastback Comp road bike/Specialized Jett