I am not a big shorts person. For some reason I feel self-conscious wearing shorts, which doesn't make sense because I wear dresses a lot (clearly, see these last few posts here, here & here).
I think it comes down to finding the right pair of shorts. Last summer, I searched for the perfect pair of denim shorts that weren't daisy dukes (I found them at Gap! See here). This year, I wanted to find something that was comfy, but still a little more dressy than jeans.
While browsing Target one day, I found this pair and decided to buy them in 3 different colors. I've only worn the black pair so far, because again I felt self-conscious, but now I think I need to start wearing them more often.
Did I still feel self-conscious in my shorts? Absolutely! But I put on a fun tank top, grabbed this awesome bag I had rented through Rent the Runway, and my favorite pair of summer sandals.
As women we put a lot of pressure on ourselves -- "I won't wear that dress until I lose those last 5 pounds" or "I don't want to show my thighs so I'm never wearing shorts again" or whatever the statement in your head may be.
And while a lot of it does come down to knowing your body type and dressing for it (i.e. I'm pear shaped so I wear a-line dresses, or I have a short torso so I avoid peplum tops), sometimes you just need to through it all out the door.