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How to look more "expensive"?

I was out shopping in the city and I just felt so frumpy, frazzled and scruffy whereas everyone else just seemed so polished and well styled. I'm not sure if "expensive" is the right word, but the clothes look good quality, classic and well-styled. I already like classic styles and try to emulate that kind of look but I just fail at it. I think I am doing ok until I am in a nice restaurant or out in the city and I see how put-together these other women look.
Today though I was wearing skinny jeans, I chucked on Converse that is looking a little scruffy and worn and just put on my navy blue parka jacket which is ill-fitting and I just felt so frumpy and horrible. It doesn't help that I have some weight to lose which I am working at but I want to feel nice in myself now and not in some distant 3 months+ when I am at my goal weight.
Tomorrow I am going shopping again with a new source of motivation and I want to treat myself to some things to elevate my style. I am a graduate student so I still need to be fairly comfortable and casual but the scruffy coat and Converse have to go. I am also having my haircut next week to freshen it up with some layers.
I have tried to find some photos that show the kind of classic look I mean:




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