So I'm a notorious casual-dresser -- I have well-made, nice clothes, but they're all very basic. I pretty well live in these black high-waist jeans and either a grey t-shirt, pale pinkish cardigan, sheer white camisole... You get the picture. I also always wear boots similar to the ones below, or plain black Vans. Now that I'm losing some weight and starting to like my body a bit more, I'd love to be a little dressier! My friends are always wearing cute little skirts and dresses from stores like Urban Outfitters or Asos, and I feel like the frumpy tomboy any advice on how to start incorporating dressier, chicer items without looking like I'm trying too hard? And I live in Toronto, so no worries about sticking out, fashion-wise! I also wouldn't be opposed to heels.