When entering Kindergarten, we allowed her to make her daily clothing choices. The ladies outside of her school would look forward to her arrival in the mornings to see what kind of outfit she had put together. She often chose colors and prints that never matched. I always made sure her tights were unusual and her shoes, while keeping them inexpensive, were on the trendier side. She adored her headbands and hair bows and was always accessorized. She refused to wear an 'outfit' like the other girls in her class.
Now, she's still the same way. She's changed from tights to leggings. Won't wear an 'outfit' and still chooses to put colors and patterns together that one wouldn't normally choose. We take her shopping and allow her to pick out her own clothes. She has more costume jewelry than one her age should have and plenty of headbands, flower clips and sparkly things for her hair. Her pocketbook holds several chapsticks or girly lipgloss purchased from stores like Libby Liu (I think this is how this is spelled).
While some moms I know think I'm giving my Mad Hatter to much leeway by allowing her to choose her clothes every day and not policing her outfits. As long as the clothes are clean, they fit and she's not inappropriately dressed for the season/activity/outing, I really don't care what she has on. I've taken her to the grocery in her full-on princess dress up including tiara and dress up shoes. She was dressed, clean and had shoes on. She was happy, I was happy, why start a battle over something so trivial?
We are the same way with 4 year old Chunky. He's a little more bull-headed in our direction. He'd rather wear jeans when it's sweltering hot and flip flops all year long. And he'll wear the same favored t-shirt daily if we'd let him.
Shopping with Mad Hatter is exhausting and time consuming. She wants everything but not what I want to buy. We went for new 'fashion' boots and walked out with an outfit as well. I had a coupon and the outfit was mostly on clearance. Chunky, on the other hand, generally wants toys when clothes shopping. And if he's in the mood for clothes shopping, he wants stuff that doesn't come in his size or shoes...which he doesn't need.
Tomorrow is closet and season change cleanout time. In their closets and mine. I'm very scared and what is going to remain. Closets will be as empty as my pocketbook is going to be. Floods and hoochie skirts are not approved in this house.

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