This post and giveaway is Sponsored by Old Navy. Shop the funtastic Kids & Baby Sale, now through February 22nd. Leave a comment below for a chance to win a $500 Old Navy gift card. Thanks, Old Navy!

As you know, Annie has been picking out her own clothes for about five months now. There are still days where I can, um, trick her into wearing what I want, but those days are getting fewer and farther between. In fact, most mornings she wakes up, I pick her up and put her on the changing table for a new diaper, and she’ll say to me, “Mama, want [insert very specific clothing items here].” She will say which shirt, pants, shoes, and sometime which hair accessory she wants. I can’t remember what I wore to my own wedding, and she has her entire wardrobe memorized.

When this picking out her own clothes thing first started, I admitted to you all that my control-freak tendencies were going to make it hard to allow my child to dress herself like a hobo. Then some people wisely pointed out that Annie doesn’t buy the clothes so I just had to make sure I didn’t get her hobo-like clothes. So, I devised a plan and it looks like this: 

a bounty from Old Navy

That right there is five shirts, one cardigan, three pairs of shoes, two pairs of shorts, and three pairs of pants (all birthday gifts to Annie from either me or her friends, all from Old Navy, purchased with our own monies). And they all match. See, look:

blue and white striped tank top, blue cardigan, red twill pants, white flip flops or clear gladiator sandals
Outfit One: blue and white striped tank top, blue cardigan, red twill pants, white flip-flops or clear gladiator sandals

blue and white striped tank top, blue cardigan, white or brown shorts, clear gladiator sandals or white flip flops
Outfit Two: blue and white striped tank top, blue cardigan, white or brown shorts, clear gladiator sandals or white flip-flops

blue cardigan, pink tank top, brown shorts, pink flip flops
Outfit Three: blue cardigan, pink tank top, brown shorts, pink flip-flops

t-shirt, black and white striped pants, clear gladiator sandals
Outfit Four: t-shirt, black and white striped leggings, clear gladiator sandals

t-shirt, white shorts, white flip flops
Outfit Five: t-shirt, white shorts, white flip-flops

I could easily make another dozen outfits with these pieces. Now when Annie wants to dress herself, everything she has goes together and I don’t have to worry about her looking like a toddler hobo.

My shopping tricks:

~When you’re buying your kids their basics, stick to a color palate so everything matches.
~If you find a good item for a good price, buy more than one. And possibly go up a size for longevity.
~Shop in all sections. That boom box “Turn It Up” shirt was from the boys’ section. It’s perfect for Annie.
~Shop during sales. That makes my second tip a lot easier.

Speaking of shopping – who wants to win a five hundred dollar gift card to Old Navy? No one? OK I will keep it. To enter, leave a comment below telling me one of your kid style tips.

One comment per person, please. Sweepstakes starts now and ends on February 15, 2012 at 11:59 p.m. EST. Winner will be chosen by Random.org and announced on February 16. Sweepstakes is open only to legal residents of the fifty (50) United States and the District of Columbia who are at least eighteen (18) years old at the time of entry. Sorry, citizens of Liechtenstein.

You can find a full copy of the official rules here.

Good luck!