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What's your sc/out/fit? If you're a beginner, I made a guide for you based on a basic casual /fa/ guide but removed unfitting clothes for outdoor activities. Luckily, a lot of /out/fits are also very fashionable and trendy.
Put your money on your outerwear, good jackets and boots will last you forever and keep you warm, they also are very high-tech and have a lot of functions. Read up on possibilities (like waxing the G-1000 fabric on the Fjällräven jacket), so you don't miss anything. I had no idea where to buy them in America though, if anyone knows you can fill in stores that stock these items.