If you gravitate towards casual looks, why not try this combination of a white and red vertical striped long sleeve shirt and brown chinos? Perk up your getup with a pair of black leather casual boots. When it comes to dressing for weird fall weather, nothing beats a kick-ass look that transitions easily between seasons. As you're maturing from a kid to a teenager, you probably want to look a little older than your age. That's when looks like this come in handy.