As a mother it has always been important to me to let my children feel the freedom to express themselves through their clothing.
Sometimes that works in my favour, Adaliah (11) LOVED wearing fancy dresses from the age of 2 till about the last year or so. It was so much fun to find (cheap, used) dresses for her. And since we always got them second hand, she was free to wear them wherever and whenever she wanted. She always looked dressed up and put together..made me feel like my job was easy...hahahaha
Allora (12) has always preferred comfort over style. She loves Amadeus' (16) old t-shirts that have dinosaurs or reptiles on them. She was always clean but not necessarily dressed up.
Adonijah's (5) favourite outfit is a full three piece suit...including fedora. In fact, today as I write this, he has dressed himself in it to attend a drop in play time at the local library. I can guarantee he will be the best dressed 5 year old there.
But sometimes my kids just look dirty and messy...their clothes are stained with the paint they made creations with (anyone else find "washable" paint that is not so washable?!?!), their hair is unbrushed cause I do not feel like fighting with them...lol Sometimes they don't match and sometimes they forget pieces that should be worn (anyone else have kids who forgot to put on underwear? Lol) But I want them to do two things...1) learn what a socially acceptable outfit looks like and 2) be able to move outside that mould, if they choose to.
Is it always easy on a mother (or father or grandparent) if a child chooses outfits we would not pick for them or ourselves? No, it is not. But do I feel it is an important life lesson for them (and me!)? Yes I do.
Now, there are times/certain circumstances where I will/do dictate what they wear (teaching moment of what a socially acceptable outfit looks like). But since these events are few and far between (for us, since we homeschool) I feel it is a nice balance for my kids. They have also all learned that if they do not regularly brush their hair out, it will hurt the next time they get it done....does that mean they do brush it regularly? Nope. But they do think about it more and more as time goes on...and the older they get, the more times they do brush it than not :)
Everyone has to parent the way that works for them. For me, clothes/hair/messy vs always clean, is not the top of my priority list. If my kids are kind and compassionate, loving and honest, respectful and loyalty....those are what really matter to me. That they show those colours to the world. And if they want to add a little sense of "style" so be it...but if they want to dress in two different plaids while helping us get our groceries, this mama will take the kindness over the classy any day :)