You know what I like? A good scarf. In the winter it's huge warm scarves, in the summer it's silk scarves and recently I've been into this middle ground option - the bandana scarf. Sure, it's a little Western, but it packs some punch that doesn't necessarily scream 'yee-haw'.
I used to wear a lot more statement necklaces, but since having a kid who is always pulling and tugging at anything when I pick her up, I've found other ways to incorporate a much needed oomph into an otherwise casual outfit. What felt a little dull at first sight, now has a bit of flare!
Honestly, I wear it with a daytime outfit, a work outfit or an evening outfit. I think it looks especially baller with a leather jacket to really take the Americana/moto trend to great lengths. Surprisingly, I've never once looked at someone with a bandana on and thought 'pirate' or 'cowboy'..... it's just really been 'dang, that looks cool' more than anything. I say that to calm your fears that you'll look like Jack Sparrow meets Clint Eastwood.