I'm a relative youngster at 65, but I'd say if the venue is appropriate, go for it. In my eyes, the grocery store or the mall are not appropriate places. The seashore is. Picnics with friends are. I guess, I'm thinking casual, social settings with age peers. 25-year-olds do not want to see a 65-year-old in a miniskirt, but 65-year-olds do.