I actually loved to dress like a boy, and I still kind of do and try to sneak boy's pieces into my wardrobe. I have Levi's boot cut jeans that actually might be from the boy's department, but I love them. Those jeans and flannel are my favorites. If I could choose anything to wear for the rest of my life, I'd just want a boy's outfit.
Stay simple and true to your gut. If you feel uncomfortable in something, no matter how fashion-forward it is, it's going to look funny. At the end of the day, I don't think it really matters what you're wearing, because if you shine through in that confidence, you really can convince anybody that what you're wearing is great...as long as it doesn't have too many sparkles!
I have an older sister and my mom would dress us up identically, so in all of our pictures, we're in these giant pink, poufy outfits. I remember when I was four or five, we all went to a theme park and I had to go to the bathroom but couldn't hold it in anymore. Let's just say, I had to buy a brand new outfit! But that moment was the first time I remember ever wearing something different from my sister at an event. It was my breakthrough moment when I decided I was never going to match my sister again!
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I always carry around a giant makeup case with about fifteen items in it. I so want to be the girl who just carries lipstick as if that's all I need, but I'm just not that girl. I need my lipstick, but then, just in case my cheeks start to lose their color, I need my blush. Then I'll need my oil pads...so I just take the whole thing. And now I need a full on fashionable backpack for it all!