A reader asked me awhile back about wearing high-waisted black shorts. I'm not really an expert in shorts wearing, but here is what I have come up with.
Various runways have shown shorts and high-waisted is the trend of the moment, so the appeal is clear. Some are slim-fitted, while others are more of a bloomer/baggier style.
Facehunter ladies are also all over the style--they tend to opt for the super tight and the super short (most of them are *tiny* so the look works easily on them, but some of us have to be more careful...).
High-waisted (though tooted as unflattering and difficult) can be worn by anyone--but fit is key. The short needs to hit the smallest part of your waist and make it fitted--not skin tight (clothes should be comfortable, not constrictive). If wearing tights with your shorts opt for a different color or at least sheer black. Contrasting elements are always interesting, so a looser blouse or long cardigan (worn open) with high waisted shorts will look nice. In the end, confidence is key, anyone can pull almost any look with the right sense of adventure and confidence.
I don't own any high-waisted shorts (yet), but here are some shorts I do own. 
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