In what ways would you teach your teenager, child, or young adult to dress appropriately for certain situations?

I've heard quite a few times growing up phrases such as "Go change" followed by weeks later "Why don't you look nice?" or "Is that what you're wearing?" "I hope you're not wearing those shorts out!" but without explanation or an "I don't care" mumbled under their breath. It left me confused, frustrated, and upset quite often cause I didn't understand and nothing was explained till later on. But aren't there better ways to teach children of any age how to dress for any situation the right way without those common phrases? I couldn't even wear a dress around my own friends that I grew up with a cause, oh well it's easy to pull off to have sex and you'd be uncomfortable if someone saw you in and tried flirting and stuff with you. And if my friends really wanted to do stuff to me they would've done it by now. I've also heard the constant phrase that i don't care about how I look when that's far from true it's that it bothers me a lot.

In what ways would you teach your teenager, child, or young adult to dress appropriately for certain situations?
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