Id wear a really big Panama hat, my pineapple sunglasses, and my dress that has the neckline that drops to my waist that EVERYONE checks out my rack in.
Not just turquoise (though you might think so as my style gravitates to it), but yeah you're on the right visual track. Odangos represent what hairstyle I identify with the most, it doesn't reflect what you'll find me wearing if you sought me out on a dime. Though it's more reflective, it's similar with everything else, it's the most "me" in a pure sense but different influences might distract my aesthetic sense from that.
Dark gray or navy jeans, charcoal sleeveless tee, black & gray plaid flannel, Docs or Chucks, wallet chain. This is exactly what I wear in real life. Plus a bandana if I don't feel like washing my hair that day.
But honestly I own enough leather jackets to be the bad boy in a cartoon. Put me in a plain T-shirt and jeans and then draw me sweating profusely since it's 100°F where I live.