First and foremost - it does not have to be brand new top of the line gear. It just has to be the right gear. Look for quality over quantity. Choose gear you want to take on long walks in the woods. Watch sunrises and sunsets with. Make nice fancy freeze dried dinners with it on. Fall asleep looking up at the stars together. Outdoor equipment was made to live a full life of wandering through mountains, hills, streams, canyons, glaciers, and valleys. My favorite gear is patched with duct-tape, smudged with soot, and tattered with holes. For example- my mint green snow pants. They are stained with muskeg, frayed at the cuffs by crampons, and torn at the knees from bushwacking. Mismatched fabric with seam sealer dot their character. They will be adored until the day they die.
Secondly, I highly recommend sleuthery. Look up and ask around about recommended brands and equipment - then sleuth. Visit nearby outdoor consignment stores and thrift shops. Check ebay and amazon regularly. Work a seasonal outdoor job to get hooked in with some pro deals. Ask friends and family to borrow gear. Host a dinner or bake regularly in exchange for donations. Look into rentals. Paint a house and get a payment of a packraft. Raid free stuff boxes. Befriend students with disposable incomes (I once heard a legend of an instructor trading a snickers bar at the end of a ration for a brand new puffy jacket).
It takes a bit more leg work to go the route of sleuthery, but it is so much cheaper than going straight to an outdoor store and buying everything brand new. Also the story of now you met your gear with stay in your heart forever.
Here are recommended places to start your search-
New Gear Websites:
Backcountry: https://www.backcountry.com/ General outdoor equipment.
Coalition Snow: https://www.coalitionsnow.com/ Rad all lady ski shop.
Eastern Mountain Sports: http://www.ems.com/ General outdoor equipment.
Evo: evo.com Skis.
Moose Jaw: http://www.moosejaw.com/ General outdoor equipment.
REI: rei.com General outdoor equipment.
Sierra Trading Post: sierratradingpost.com Another great website- often over 50% off.
Used/Discounted Gear Websites:
Gear Trade: www.geartrade.com is a good site for a lot of general outdoor items. It's like outdoor gear ebay without the auction.
Steep and Cheap: www.steepandcheap.com used to just have one item super discounted but now also has the "gear cache" you could monitor for gear deals on running, skiing, biking, camping, etc.
Ebay/Amazon/Craigslist:ebay.com/amazon.com/https://www.craigslist.org/ good spots for random things.
Mountain Project: http://www.mountainproject.com/v/for-sale--wanted/103989416. Mountain Project is a place for individuals to buy and sell gear - it's used, and you'll only get specific climbing items.
Teton Gravity Research Forums: http://www.tetongravity.com/forums/forumdisplay.php/9-Gear-Swap TRG Forums (gear swap) is just like mountainproject, but specializes in ski gear.
Local Stores: Always try to support local businesses! Here are some favorites gems in Juneau and Southeast Alaska to check out:
Fairweather Ski Works: http://fairweatherskiworks.com/ Skis.
Foggy Mountain: http://www.foggymountainshop.com/ General outdoor equipment.
Nugget Alaskan Outfitters: https://nuggetoutfitter.com/ General outdoor equipment.
Second Wind Sports: http://www.secondwindsportsak.com/ Outdoor consignment shop.
So, in summary - Do your research. Find equipment that is made to last. Do not focus on the latest trendy items. Aim to buy something once. Love it your whole life.