To wonder why people with lots of money dress their kids so badly?

It's a class thing not a money thing. Less to prove. My children are pretty scruffy (as am I and DH) and we are pretty solidly middle class. I'd say not truly posh though as they wear lots of second hand clothes from supermarket brands as opposed to high scruffy stuff!

Even if I was very rich I'd not be buying new children's clothes

It’s a class signifier, see also ballet tutu / Princess dress with wellies. Extra points if a little boy with long hair is wearing them.

Better educated so more aware of the environmental impact and irresponsibility of buying new for a toddler. Toddlers don't care if they're wearing the slightly stained pass-ons from the neighbours. Good quality barefoot shoes that aid good bone development don't tend to look as smart as the mini trainers and fancy shoes that damage feet either.

I think they are worried about impressing others though, mostly their upper middle class circles. A child in a matching sweatshirt and leggings and trainers doesn’t match the ‘boho, messy, relaxed mum’ aesthetic they go for.

A few years ago they were the mums who dressed their girls in sparkly party frocks to roll around in the mud at the park, to look whimsical and fun.

This.
If you feel equal to professionals- GP, school teachers etc., you’re not proving anything. It’s a good thing imo.

Yep that was the look when I lived in london- faded boden clothes, wellies and messy hair.

I agree with this. I could afford to dress my four DC in designer clothes but I would think that a waste of money.

They wear whatever they want, so long as it’s appropriate for the weather and activity. One of my DS loves wearing a jumper that has holes at the ends of the sleeves but it’s his favourite so I don’t have a problem with him continuing to wear it.

I was brought up in a wealthy family and my lovely Mum absolutely loved jumble sales . We were always dressed in second hand clothes…really cannot remember caring.
Ironically our school uniform was from Harrods’!

Because people with money have nothing to prove to people like you.

Oh hi, it's me - I'm the problem 😂

Could shop at Jo Jo, get all my kids clothes on vinted or Facebook market place.

Did you know that even 'rich' peoples kids shit through them? And they also get bigger every 6 months? Just caus we have the money doesn't mean we don't think £60 on a kids coat isn't a piss take. I'd rather spend it on my wine THANKS.

A few reasons:

1. if you have more money you tend to buy higher quality children’s clothes to start with they last longer and tend to get passed around between friends and cousins. By the time they reach my youngest the everyday ones have a few stains.
2. you then use these clothes for the activities that don’t matter and your child might get messy at. Like playgroup or going to the park. Best clothes are saved for best.
3. you’re secure in the fact that you have enough money and your children are loved and cared about that who cares that what they are wearing doesn’t match, so long as they are comfortable and warm enough.
4. some hair types and children’s hair just look messy all the time at that age. I have one where I brush their hair and 10 minutes later they look state. If their teeth are brushed and they ate their breakfast, that’s more important.

Either nothing to prove, or the desire to fool people that they’ve got nothing to prove.

Toddlers don't care what they look like and are notoriously messy, so there's not much point in buying them expensive outfits. If you want something to dress up, you can always get a doll.

I wouldn't group a GP with a teacher, a strange one. Or, are you meaning people with jobs have nothing to prove?

i used to buy my toddlers clothing at a big annual consignment sale. I bought good quality items, but they were used. I then resold them the next year as long as they were in decent condition. I had the money to buy new, just like most of the parents shopping there, but why? I could be putting that money into a university fund or into my retirement. They are toddler clothes and are going to be worn a short time and very likely beat up.

In a way I think they are trying to prove something because what the OP describes, is like a middle-class uniform in some wealthy areas of London.

Bonus points if the scruffy DC are wearing knitted striped tank tops.

I bought my kids lots of brightly coloured clothes in natural fibres and let them choose their own outfits so no they rarely matched and/or often went out in fancy dress. I wash and brush their hair often but they both have fine flyaway hair and I don’t use products on it so it didn’t stay looking tidy when they were small and it wasn’t long enough to stay in styles on its own. It’s not something that bothers me, I think it’s nice for little kids to dress like little kids instead of mini adults and have some agency over their outfit choices especially for something relaxed like a toddler group! I wouldn’t take them to a wedding in a random outfit but how neat do you have to be to play with some communal toys in a church hall or a garden somewhere, especially when you are two?

Do you know they are definitely wealthier than the people who dress their kids 'nicely'?

Maybe they've got the same amount of money but spend it on things you wouldn't see at a toddler group, or things that aren't clothing for preschoolers?

I suppose I don't know any upper middle class people who would buy designer labels for their children. Especially not ones with logos. But I am not aware that the wealthy have an aversion to hairbrushes?

I suppose many rich people stay rich by spending wisely and little kids grow out of things and mess them up so much that I guess they don't see it as a good use of their cash.

I’m using them as examples of people parents interact with with their children.

as PP said it’s a cultivated look. Not just not caring. It trying to signify a boho wild carefree fun childhood. The “eccentric” look is also cultivated they do it to fit in. The clothes are probably hand me downs, hand made, second hand and probably very expensive ethical brands.

What do you mean by "match" clothes? Surely that's subjective?

I think it depends what sort of money you’re talking about!

Old money - the aesthetic isn’t showy and they have a kind of bred-in confidence that stops them worrying.

New/professional money - they are just too busy or have too much going on intellectually to spend time on this kind of thing. Again, not worried about others judging them.

Will happily stand corrected but that’s my theory. I was in camp 2.

Perhaps some of the toddlers are permitted to choose their own outfits. My mother allowed us to do that when we were small (much to our horror at the resulting photographs when we were older!) because it was much easier to get us dressed if we were wearing an outfit of our choice. That way, she didn't get, "I'm not wearing THAT!" on a daily basis 😂