I dress to please me and really don't care what other people may think of me. I like to be comfortable in my clothes.
My favoured style (be it summer or winter) is jeans, trousers or long shorts, longline t-shirts, floaty tops, tunics or jumpers, flat shoes or sandals and no makeup. I have two summer skirts but rarely wear them.
I'm 72, 5'4" and definitely overweight with bulges in all the wrong places, so I never wear leggings, tights, or anything figure hugging. I do have one pair of (real) leather trousers, but they're a classic straight fit and look good even on me. I don't wear high heels (never have done), false eyelashes or artificial nails.
In my youth I wore the shortest mini skirts and hot pants imaginable, but also maxi skirts, afghan coats, thigh length boots etc. I was very slim and had great legs. Those days are gone now, just a happy memory. Our photo albums are a revelation to our AC and GC! 
My grandmother often used the phrase 'Mutton dressed as lamb'. She was a very stylish dresser herself, made a lot of her own clothes, and looked much younger than her years. At 67 she applied for a job and put her age as 40! They believed her and she got the job. Eventually her deception was discovered. Her boss was amazed and paid her cash-in-hand from then on as he didn't want to lose her. She worked until her mid 70s when early dementia became apparent.