Gremmie, when I was much younger I went through phases where I would only wear black (because it was supposed to be slimming) or I wouldn't wear skirts b/c I thought my knees were weird looking. As I got older I decided to try new things - like adding color to my wardrobe. I discovered that I liked color and coordinating colors and balancing with neutrals is pretty easy (I didn't want to look like a color wheel) I started looking at it as a fun challenge to go out and try on clothes that I would never consider buying from looking at them on the racks. It was fun and I would find things that I never dreamed would look good on me - but they did. I think it's like mastering any art. Many people think fashion is stupid or pointless or expensive, or take themselves too seriously to act like they care, but I disagree on all fronts. It's a form of self-expression that can be challenging, creative, technical and fun.
I live in Seattle, a city where the norm is outdoor wear and fleece - I dont' consider these fashion and I only wear fleece and thermals around the house. If you've ever seen the tv show "What Not To Wear" that's the world I live in. Taylored jeans, tasteful colorful tops, a fitted blazer and heels (and handbag and accessories). But I wasn't like this when I was younger. I'm 38 yo now (people say I look early thirties) and it has gotten easier with time. I don't worry about what others think so much anymore and I feel good.
I say just start by going out and try on things you wouldn't normally wear. Eventually you'll find something you love so much you'll have to buy it.
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