How can I elevate my wardrobe?

Please excuse the lack of photogenics in the image and poorly worded/broad question. To my friends, I tend to dress older than I actually am (I'm 31) and wear washed out or muted colors that don't compliment my skin tone/complexion.

To give a bit of detail, I like extreme motion or flexible/stretch jeans to move in, and Henley shirts. I'm still trying to decipher what's fitting of me and at one point, I wore nothing but flannels. Shoe-wise, I'm a size 18 so I don't have a lot of options for comfort and style unless I custom order.

I guess my question is based on the photos, what would work for me? What resources and styles should I look into?