I really struggled with this one. I have two plaid items - a long-loan skirt from Cyn that is a tad too big, and a comfy flannel shirt that is a tad too small (how weird, because it used to fit). Decided to make the latter work. Threw around four or five different outfits so that I'll be returning home later to the bedroom clothes bomb. It was too casual, too weird, all of the above. Finally, thought, hey! Let's just give it a plaid touch. So that shirt is now under a white shell and a flouncy skirt.
It all worked out well because two co-workers said to me today (independently), "You look so polished today!" Three-piece anything.
Flannel: J.Crew (similar)
Sweater: J.Crew Factory (similar)
Skirt: Zara (similar)
Shoes: Jeffrey Campbell (similar)
I've had this plaid shirt for four years (I know this because I bought it to wear for my older daughter's FIRST birthday and she is turning FIVE next week... WTF?!), and I always seem to forget I have it and then rediscover it and say "why don't I wear this more?" So when Karen and I had our usual frantic "what are we doing for Wear it Wednesday?" text convo last night, I stared into the depths of my closet looking for inspiration, saw this baby and said "plaid shirt?" Real rocket science there, folks.
Shirt: Old Navy (similar)
Skirt: The Limited (similar)
Shoes: Nine West
Necklace: Towne & Reese (similar-ish)