Love the boy-girl look of a floaty dress with a blazer. I'd definitely ride in this outfit - maybe with polkadot bloomers underneath. If the breeze catches your skirt why not have a hidden surprise that keeps your modesty intact?
Basic white shirt with a nice sweater in grey. Classic but never out of style. Camel coat makes this look more elegant and stylish. Lastly the leather pant and the knee high boots refresh this look. Make it more trending.