Askel, thanks for the opportunity to throw my opinion on the internet.
TLDR - me blabbing about my skiing setup
I won't ever claim that the backcounty skiing I used to do or the downhill resort skiing I do now is mustachian at all. I've tried to do it mostly cheaply though, but that's not the same thing.
I've been through a few pairs of brand new boots, tried choosing myself, tried having an 'experienced' ski shop person help me choose... all pairs tore up my feet. Then I saw an ad for a ski shop selling old rental boots, bought a pair for $15. Holy shit my feet were in heaven! Those boots have been from the Snowbowl in AZ to Switzerland. I finally wore the bottom off and they couldn't clip into skis. :-( But I used the almighty power of the internet to find the exact same old model on eBay so now I'm on my second iteration of heaven. I am sad that when these die, that old model will probably not exist anywhere and I'll have to find a new pair.
I've also gone through multiple sets of skis... I've done telemark and alpine and then regular downhill setups. My current skis cost $20 from goodwill. They match my skiing ability very well, so I'm happy with them. I also know that no one in their right mind would ever steal those old pieces of shit, so that's nice as well. But then again my ski poles cost $120 I think.
And then there's the cost of lift tickets. I've been through some long dry spells when I didn't live near a place to ski. I finally won the skiing lottery though - got stationed in Colorado springs, I get the Epic Pass for $99, which is UNLIMITED visits to all Vail resorts for the whole season. HOLY FUCK! Yeah it's a big deal to me. I got stuck on a broken chairlift a few weeks ago at Vail for maybe 30ish minutes... I get off the lift and they give us all a pair of vouchers for lift tickets. That's pretty cool, but I was more excited about the hot chocolate voucher they gave us too. Until later, I look up these lift tickets, and they're charging $199 per lift ticket for one day. HOLY FUCKING SHIT THAT'S INSANE! And now I look at the other skiers now and wonder if they're paying that mad price to ski. If I had to pay that I'd quit skiing. So I'm obviously very thankful for the circumstances that are allowing me to ski for relatively cheap.
My clothes setup is all over the price map. Bought goggles new with swappable lenses, but a $15 garage sale helmet. I wear mountaineering pants (probably cost $150-$200 in 2010), and a $90 hoodie, under a big $50 Walmart jacket. Mittens maybe $15. I definitely go with what works best, and I've gotten a lot better at looking at shiny expensive new gear and then walking away and finding a better option. I've started to really appreciate it when I have the feeling of the 'perfect' gear/clothes setup as opposed to the newest, cutting-edge technology, most baddassest setup.
I'd say the whole experience of backcountry skiing to a yurt or cabin, using an outhouse with a full moonlit-snow-covered view better than the view that many millionaires have was pretty incredible and hard to beat. But on the other hand the amount of downhill time I can get in a day at a groomed place is pretty incredible. Backcountry skiing was a cool way to travel in winter, but spending hours walking uphill and doing snow checks for avalanche danger just to ski down a 10-20 min run wasn't nearly as fun. More peaceful and magical though.
I saw it mentioned how there may be judgement about having old gear, but I've only noticed it when I used to ski with snowblades. Other than that, I think people may notice, but most don't give a shit. They want to ski/snowboard and that's what they're there for.