Help me wear my fedora

I bought a black straw fedora. Every time I wear it I look like I'm trying too hard. I don't know why, since it's such a classic piece.
Here are some ways I've worn it:
1. With a solid-color maxi dress to keep the sun out of my eyes. I looked like a preggers Jamie Lynn Spears.
2. With skinny jeans and a tank top. I looked like I should be making you a soy-milk latte with extra foam, whilst examining fondly my new inner-arm tattoo.
3. With a skirt, blouse, pumps, and a trench. I could have stepped off the Casablanca screen.

So clearly I need a little help here. How should I wear my fedora? Design me an outfit!