I never wear shorts, but we're going go Disney this weekend with another couple and their little girl. I figured it might be a good investment.
I managed to find a pair that covered all my gingerbread, but weren't frumpy. I bought them a size too big so I can wear them a bit longer, even if it's just to go to breakfast on the weekends or to the beach.
And all shorts are $15 at Old Navy.