I agree with the person who said that being “gray” is different at different times.
Right now, I generally try to fit in with the other moms who are in their 40s-50s like me. That generally means having my hair and makeup done when at the store and wearing nice jeans and a t-shirt. I don’t want to be super-messy and look like a bag lady because that would draw attention. (Watch her, she’s going to steal something.) Nor do I want to be far more dressed up than the other folks around me, because then I’ll also draw attention. (I bet she’s got money in that big purse.)
I try not to go around looking overly tacti-cool, with Army pants, open carry, and a belt full of goodies, although I do have some of these things. I figure it’s better to look like the sweet little mom and then surprise the heck out of someone when I pull out a gun that was concealed in the small of my back if they decided to target me.
It’s tough to get this through to people because Madison Avenue has programmed us to constantly try and look “better” than everyone else. Everyone wants to call attention to themselves and telling them to downplay their looks or their wardrobe or their wealth is not always well-received.