What does it mean to dress your age?
First of all, your dress age, is not based on the number of days you have lived but the stage of your mental level. Fashion, after all, is a strong representation of your views on life in general.
Let me explain, fashion is like a fine wine. In the beginning you start out as a seed, then a plant, a flower, fruit, grape juice, and with much time, "hopefully" into an amazing wine.
With fashion, there should also be a level of progression and development. We are an ever changing living creature and our fashion choices should reflect that.
The key rule to remember is, fashion represents your current life views. Therefore, what you wear should represent your current mental state. If a small child is dressed in stiletto heels, a mini skirt, make-up, and purse, what kind of life is this child leading? Perhaps, she is a starlet, who has already grown up to a mini adult, but normally a child, going to school to play in the sandbox, will have no reason for such attire.
Just the same as fashion, your body develops in different stages. A girl goes through puberty, which prepares you for child birth, and then menopause.
In each "physical" change are corresponding life changes, that reflect on what you wear and learn. For example, when you are in your teens, there are rushing hormones during these pubescent years. It is a highly experimental stage of your life, and "usually" your fashion will reflect that. You will make many mistakes, and experiment with crazy fashion, but all of these experiences will enrich your knowledge for the future.
As you fall in love and start a family, your life circumstances once again change, and your fashion preference will again, "evolve".
However, these natural forms of progression are often stunted by the desire to remain forever young. When this happens, some women find themselves in a "fashion period" that no longer corresponds with their life experiences.
Most importantly, there is no right or wrong in fashion as long as you are staying true to your own views. If you are a child that likes to dress in old lady clothes, then do so. If you are an older woman who wants to dress like Madonna then do so. However, never use it as a tool to be someone you are not or pretend to be in a stage of life, that was long gone, years ago.
Fashion is all about reinvention.