Comment by tbeseda
Under $100: Koss KPH40 Utility On-Ear Headphones. $40 on AMZN right now. Best, minimal headphones. Not my daily driver, but clutch when I just need to plug into my gaming PC or my turntable.
Under $1K: Helly Hansen Alpha Lifaloft Jacket. At ~$600 it's worth every cent in Colorado. No complex layering mechanisms, but works well from 35ºF to -10ºF. Wear it with a t-shirt or a thin down layer. It fits perfect and sits just below my belt. Great pocket layout. etc. etc. It's my go to for everything from snow shoveling to long ski days.