There's a lot going on here. Bit of a four-seasons-in-one-outfit thing, with a spring dress, summer shades, an autumn bag and winter boots, yet it works. More than that - it's flipping fabulous. Mind you, the usual disclaimer applies: it is Victoria's Secret, Pirelli Calendar, etc, etc model Rosie Huntington-Whiteley wearing it. But even though a woman such as her would look intergalactically amazing in any half-decent outfit, when she gets it really right - like here - there are still tips and tricks to be gleaned that work for real people, too.
The thing I would take from this is to make the unique challenges of trans-seasonal dressing work for you. Don't stand in front of your wardrobe with a cartoon question mark over your head. Let the sartorial test inspire you. Have some fun with it.