How and when to wear wellies?

[wiltingflower]

I have never worn wellies, even as a child. I've always lived an urban life until recently now that I've started running and walking a lot more. I wore wellies for the first time today to walk through a forest and found it enchanting- I could go through mud without worry! This is a huge novelty!

I am keen to keep walking through new green places and now need to know (because I don't have family or friends who I can ask):
When do you personally wear wellies?
When do you definitely not wear wellies?
What do you wear with wellies? (Jeans, leggings, outfit ideas)

I wear mine most days through winter to walk the dog. Get a decent brand with foot support, I also add an insole for extra arch support so they are really comfortable. I have ariat country boots as well, but I much prefer my wellies for wet walks. I wear them with whatever I'm wearing on any given day, jeans, skirts, dresses, as do most women in our village.

I've had my Hunter Wellies for over 10 years and they are really sturdy. I wear them mostly skinny jeans or leggings when I'm doing errands out in the rain or taking DS to the park.

Loving these wellie stories.
Someone who wanted to undermine me at work, once criticised me for seeing a client in my wellies (the rest of me was smartly dressed).
She smirked 'I guess it's a bit like wearing your slippers.'
In fact, I'd just been out for a brisk lunchtime walk - wellies to me mean exercise in the fresh air.
Clients actually used to remember me as 'the lady in the wellies'
Luckily I now work somewhere where my skills are valued over my sartorial choices.

Thank you so much for your help! This is perfect. I now need to get a second shorter pair for commuting/ town wear and am planning on getting better longer wellies once my current ones wear out/ break.

H dear, first the wellies, then the dog.