UKH

I'm sure I can't be alone in having so much gear that, at times, it's very hard to choose what to take for a given activity!

Take tonight - I'm helping take a Beavers group canoeing, weather is cool, slightly overcast, minimal chance of rain, probably going to get splashed, unlikely to actually fall in.

And I'm completely overthinking what to wear from my myriad watersports clothing options - and what I'll probably end up in is just a running T-shirt under my PFD

Yes, I’ve been having a purge recently. Far too much stuff, most of which overlaps in purpose and was bought for marginal gains or to try it. I only really use a small core setup with a few tweaks for the weather. Most of it could go, but I always think I might need it later. 
 

often it seems like it’s worth keeping too as the resale value is so low that it’s not really worth it. I am now trying to use every thing until failure and then repair, and only but something else of it offers a new capability

Yep, cycling kits, paddling kits, walking kits, dog walking kits. 

Options for Cool but dry, Cool and wet, warm and wet and warm and dry.

Always over dress especially paddling and walking

These are a thing?

Barbour jacket, checked shirt, plus fours

Blanket, snow booties, matching collar and leash, ...

Isn't that the dress code for those Lebedev parties Boris went to?

Dog walking or dogging?