I have always dressed up so casually. I have always gone for the jeans-and-a-shirt kinda look, because it was always comfort over style for me. I was the practical dresser among my peers, and I never dared to wear clothes which I thought were unflattering for me (turns out I was wrong). I looked plain, boring, and my outfit choices never reflected my true personality.
Lately I have been feeling more body confident. I owe it to my weight loss (not saying that losing weight is the way to feel more confident, but it is for me) because now, I can dare to show more skin and wear figure-hugging dresses. It took me a while to feel more comfortable in my own skin, and I'm actually still getting there, but I have seen the changes in my fashion choices.