My winter hiking stack:
Cheap "icers" bought on Amazon. I keep being told that they're not as good as chains, but they've served me well on icy paths in Toronto.
Expensive hiking pants from Fjalraven. I actually don't regret buying them. They've been extremely comfortable, and I haven't needed an under layer because I have a volcano inside me. I don't use any of the extra pockets. Sometimes I hook my cuffs to my shoes, but I usually don't.
T-shirt and a thin sweater (because of the volcano inside me) and my extra-warm parka.
My "Iceland" toque and a the scarf my ex gave me (or which I stole from her, I forget).
My warmer weather hiking stack:
A thin jacket just in case I need an extra layer
T-shirt and cargo shorts
All seasons:
Carhartt hiking shoes that have been quite durable. They are by no means waterproof, though.
Extra socks
Extra t-shirt
Lots of snacks
Usually too much water (weighing me down, though there have been time where two water bottles wasn't enough)
iPhone and charger
Strava and Fog of World
Merlin Bird ID to learn which superior beings are present
Groups I hike with, mainly for safety's sake:
Parkbus (originating from the Toronto Reference Library)
Bruce Trail Conservancy (originating from York Mills Station)
Toronto Outdoor Club (great cheap option to see the ravines of Toronto, originating from subway stations)
Every now and then I'll do a solo hike, but only evern in town and where there's people around. It has always been the free Parkbus shuttle to Rouge National Urban Park.