I tend to buy something good quality then wear it 'til it's past its use by date. Riding through OZ this trip I noticed how faded and threadbare they've all become, but still they're functioning well, though not fashion show examples, however. I reckon you pay a bit more in the beginning and you get the extended life from it. I do care for them, washing with Nikwax Techwash and TX-Direct to retain the waterproofing, for example.
My Shoei X11 and HJC AC12 carbon helmets are eleven and seven years old respectively. My BMW Comfort Shell jacket (best I've ever had) is from '08, my BMW Summer trousers with zip-off leg lowers are the originals from '04, Marsee waterproof trousers I bought in '01, my SIDI On-Road boots have no sole left (but plenty of soul) and are from '02 and yet still fully waterproof. The gloves I wear, of three pairs, are a ten year-old pair of Pro Summer Gore-Tex waterproofs, a Cortech leather/mesh for heat and some Marsee leather perfs, also for heat. For warmth I have a Gerbings heated jacket liner and a newer Powerlet far-infrared carbon fabric heated jacket liner with remote control so there's not a maze of wires dangling from my hip as I'm plugged in to the bike's power with one, single 12V hose.
I recently found a clean, used but discontinued by BMW, Comfort Shell jacket on eBay for $275 (original price was in the US$700 range) and will wear that through another upcoming Seattle Winter (I don't own a car) and picked up a used pair of Pro Summer gloves, one size too large, but perfect for silk liners when the temps dip to freezing, for $25, and another pair of almost-new, old school SIDI On-Road boots for $80. Deals are out there if you know your needs and have a budget. Oh, and the Arai Corsair helmet my former boss handed me two years ago, when I returned to work in the States, is still my helmet of choice for touring and commuting due to its many vents and visibility due to its bright colour scheme.
Cheap bastard, effective gear though old, keep your eyes open for a deal, and I couldn't care less what it looks like as long as it works, though there is a black/grey theme so it
fits whichever bike I'm riding, if that means anything at all. If it fails or doesn't live up to its name then into the deepest recesses of the closet for someone else to use later on or for sale down the track.