I admit it, I generally chase warm weather when I'm traveling long-term; you have all the freedom in the world, so why go somewhere cold?
This is, of course, controversial; you can't control the weather and you can't predict the rain; but you can plan ahead and try to align your travel plans with summer season (i.e. semi-decent weather).. And if you run into a string of bad weather.. you can always buy a small poncho, an umbrella, long-sleeve shirts, gloves, hats, hand-warmers, ear muffs, scarfs, thermal underwear or anything else you might need, if it becomes necessary; you don't need to pack for every season.
That being said, I do (usually) pack a light, compressible jacket, and I travel with a reusable poncho and thermal underwear occasionally. If you know you'll be traveling through arctic tundras but still want pack as light as possible, and you're willing to spend a little extra, check out the High-Tech Minimalist Packing List for cold-weather gear.
Worried about waste? Just remember you're supporting local retailers by purchasing their goods and you can always donate gently used clothes/gear to the hostel or fellow travelers.. Most hostels I've stayed at have had a freebie/donation box where people share or leave things they no longer need.
Check out my Essential Gear post for a list of things I always pack, and my Clothing Optional post for some nice-to-have extras.
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