Puzzle with a piece missing

Hmm I completely forgot that I was going to ask the internets an opinion. I have recently been pondering the whole shorts over tights movement. I can't even remember the last time I wore shorts. It may have been year 11, I had these horrible pair of sports shorts for school. The fabric was really harsh and disgusting and I used to complain that they were touching me. At no point in my life have I been known for wearing shorts. I have also never been sure that they look decent on me. I think my legs are too curvy and disproportionate.

What do you think? Could I pull off shorts? I don't mean high waisted high cut type shorts, or knee length shorts, just...shorts. Maybe a nice vintage look with a blouse or cardigan over opaque tights?

Contemplating shorts coming into winter seems a bit odd but really how much cooler are they than wearing a skirt and tights? And shorts don't blow up in the wind...

*EDIT - it's been pointed out that I wore shorts for my 20th. But I made those myself and they are more bloomers than shorts and quite unflattering...oh well here's me in 'shorts.'

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