Polka dotting

We're to that point in Texas where it's generally hot, but then when the sun goes down it gets suddenly cold and lately, very windy! I go to a lot of my boyfriend's sporting events (soccer, flag football) in the evenings, and it's hard to know how to dress in order to stay comfortable. I figure it's a good opportunity to experiment with layering and unique contrasts, which I love anyway!

The modern oversized beanie is little unexpected with a summery outfit, especially one with a retro touch (I also love throwing this cap on with just a simple ribbed tank top and jeans, and it's definitely my go-to accessory on a bad hair day!) I paired this somewhat "dressy" tank top with ripped jeans (another contrast), threw on a leather jacket at the game, and I was good to go!

 What are some things you use to create some unexpected looks??