Plaid has been a long time favorite of mine. It could be my lingering obsession with Cher-inspired pleated skirts or too much time was spent layering at The Buckle during my youth. Either way, I really can’t get enough of it. This year, it’s back in vogue, but if I’m being completely honest, it is always in for fall. Period. Because, it doesn’t get much more “fall” than plaid.

While it is one of the most cheerful prints, it is not always the most forgiving. Pay attention to the scale of your plaid when picking a piece to wear. A large version can make you appear bigger, which is not on everyone’s wishlist. It is certainly not on mine. Think about which area of your body you’d like to emphasize and go from there. If you’re throwing on a shirt, look for a fitted jacket to put over it.

This month, I wanted to feature an outfit that is completely kid friendly. My plaid shirt is machine washable and doesn’t have to be ironed. My riding boots are comfortable and low heeled. The coat I pulled on is warm for chilly mornings, but can be folded and shoved into a bag when the sun comes out. I still feel pulled together, but can run after an ornery two-year old if needed, which is pretty critical.

Shirt, Banana Republic – old (similar here); Jacket, Jack – old (similar here); Riding Boots, Calvin Klein – old (similar here); and Jeans, J Brand – old (similar here)