Living in Ontario and happy to ride all year I had decades of accumulated smorgasbord of gear to cope from the warmer and warmer summers starting even in June and extending to September and then cool and colder into to winter
Couple of helmets, multiple gloves, couple riding pants and several jackets.
Numerous layers underneath.
I'm sorta similar that I have a mix of gear, but not a ton of gear. I buy what I need to stay comfortable in different conditions, and then I use the crap out of it until it's worn out. My current textile riding jacket is going on about 6 years old now and is getting faded, but is still comfortable and warm, so when the zipper broke last summer I spend the money to get it fixed and will continue wearing it.
I bought a set of textile riding pants this past fall, something I'd never bothered with before, but really should have considering how much shoulder season riding I do. One big ride (my IBA back in October) made me realize I should have made that decision years ago - there is no substitute for good gear, and I started and ended that day in near zero degree conditions, so they were glorious. They'll probably be something I'll now wear maybe 5-10 times a season tops, but they'll be appreciated.
For anyone interested in the pants thing like me but doesn't want to spend $250-$300+ for something they might only wear a few times a year,
they were an Amazon purchase, an off brand type thing, but I'm 99% sure they are rebranded Oxford pants - they match my Oxford textile jacket almost perfectly, and the liners even have the identical red piping along the edge. Super happy for $100, suffice to say.
I don't have a ton of extra gear aside from what I'm actually using at any point in time, though. I have a full face that I rarely wear unless it's cold or raining as I enjoy my half helmet far too much, when it's hot I ride without a jacket at all (yeah, I'm not an ATGATT guy, it's a risk I understand and accept), and I do have 3 pairs of gloves depending on the weather, a heated vest, but aside from that, not much. I collect helmets - when my helmets are worn out and reach end of life I hang them on a nail in the rafters just as a memory of the rides they were part of. I'm sure my kids will enjoy throwing all that garbage out when I kick the bucket lol.