How do you wear 3-inch-heel, pointy-toed, suede slouch boots; bright blue skinny jeans; and an ice skating penguin sweater without looking like an idiot?" (Unless you think I look like an idiot, in which case you should stop reading this post...)
To get "I meant to do that" and not "I played eenie-meany-miney-mo in my closet," you need a couple of things: tightly coordinated colors and one focal point.
The gray slouch boots repeat the sweater's gray background. The bright blue jeans have the same value and chroma as the red in the sweater - that is to say, they're both bright, clear colors. The white hat and scarf echo the white in the sweater, tying the whole together.
Because the ice skating penguin is so eye-catching, everything else needs to complement and not distract. All of the supporting players are solid colors. In a simpler outfit, the boots could be a focal point in their own, but they are not detailed enough to steal the show from such a distinctive sweater.
There's also a nice mix of textures: the softness of the suede, the nubbly stitches of the hat, the smooth jeans, and a little bit of fuzz in the scarf and sweater.
So the outfit is bold and energetic with strong colors and the unexpected combination of the sophisticated boots and silly sweater, but coordinated color choices and single clear focal point make it coherent.
I hope this helps you choose your own outfits. Here's to those unexpected combinations! Just make sure the colors hang together. Happy hunting in your closet!