How to coax myself into dressier clothes?

[SatelliteEyes]

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.

 

[classichic]

I would advice you to see if you find any dresses that you may like and you could still wear your boots with it or a dress that matches your pinkish cardigan. I think that would look cute

 

[Babydoll]

Also, change sneakers or boots for flats (or even heels) once in a while. You don't know how much dressier accessories can change a casual look! Also, try to find accessories like bags, belts or shoes in patent leather (it looks so stylish) and you can make your jeans-and-tee look chicer! Also, starting with a little dress in a solid color, you can wear your Vans or boots and still look girly with an edge!

 

[fatfreefitchick]

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.

THIS ^^^^^^^ Same here. I just can't get myself to take RISKS. ugh.