One memorable one had a set of parents with 3 daughters and a son. They had decided to all wear green, but their son was at that obstinate age (gotta love 3 year olds!), and insisted on wearing his favorite orange shirt. The mom was very apologetic, but would rather have smiling portraits than tear stained, sullen glares. I laughed and told her it wasn't a problem. We set him in the middle of a loose circle, and did a few other fun things with them. If you're creative, and by what I see on your site, you are indeed, you'll be fine.
There are a few bonuses to using accessories well (as well as layers). One is that changing them up a bit throughout the session can give you multiple looks without having to do many wardrobe changes. They can also be something that the subjects can interact with. A sassy little tip of the hat, holding the ends of a scarf while running and letting it billow behind you, grabbing the lapels of a husbands jacket while pulling him close for a kiss – all these little gestures and ways to interact (and become more comfortable in front of the camera) can be made possible with styling choices. Many of my sessions will feature items used outside their intended use or subject. My girls are often seen in mommy’s hats or scarves (scarves can be used in different ways like wrapped around their shoulders, as a hair piece, etc) and they love to wear my costume jewelry.