In the summer I wear shorts with a bright top and ankle boots or just sandals. I'll add a nice scarf maybe a hat some cool sunglasses. It's all about the accessories.
I used to love to draw. I didn't want to go to art class because I felt that would be too corny when I was young but architectural drafting was the cool thing to do because there was more precision. It taught me a lot about building and structures and doorways and frames and windowsills.
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Look at Scottish guys wearing kilts – you could look at them and laugh but the way they carry themselves how can you? You can wear some of the weirdest things and be cool. If you believe in it that's what makes it cool.