Dear Cassie - FWIW - southern UK fabber view, who is in love with Scotland (and it's gorgeous weather).
Should I take a waterproof hiking trainer/sneaker like Adidas Terrex Goretex Yes for the reasons below
or will an everyday (not waterproof) trainer/sneaker like Nike or New Balance be okay?
...probably not, because there will be dew and in the morning at Stone Henge and you would be very lucky to get away in Scotland without any rain
That said, there will be a few outdoorsey type shops around, so if you decide not to take waterproof trainers than you could top up
I vote walking boots with stable ankle support - I wear my all year round, in Scotland, in SE uk, in 24 Degrees celsius. I like them because of the ankle stability. I am also wary of stinging nettles and snakes. There aren't so many dangerous snakes, but there are a few non poisonous ones around. Adders etc. I have comfy socks. No one looks out of place in Scotland wearing leather walking boots, shorts and Goretex.
Considering the rain we have in Florida I don't have proper raingear. I don't have proper anything. (see below)
Northface do a fab Gortex jacket for men, lots of rain protection. DS wears mine on occasion and it goes in the wash etc. Failing that, I have a Sweaty Betty one which is shorter, fab and has a good 4 hours of rain protection.
For Edinburgh/London should I bring a light colored maybe waterproof bootie (like Blondo) with a little heel to dress up with blue or white jeans?
Sounds sensible, but Edinburgh needs comfy shoes - because of cobbles and the street called 'the long mile' (I think).
I also plan to bring a white leather tennis shoe like Cole Haan.
I'll try to add the finds soon. Very good plan.
Think about an umbrella and also mosquito stuff (the stuff in the UK is no where near as good as the US / Canadian stuff - is it Deet that is in the US stuff? it is banned here but I got some in Canada years ago and it is v good at quelling itchy bites.
If it helps, I don't feel at all ashamed by admitting I wore 40 denier tights in Scotland in August more than once.