I made the switch a few years ago. I followed the trend that was typical for my age group: briefs until about 7th grade, then boxers through high school. For sports I wore sport trunks. When I got to college and made my own underwear purchasing decisions, I tried boxer briefs, and liked them better than boxers. Why was I stuffing all this extra fabric into jeans anyway? And in hindsight, boxers were terrible at hiding erections common for high schools boys - something form-fitting would have been superior. Not until maybe 5 years ago did I think to try briefs again. I bought a few brands and found pretty much anything is better than Hanes or Fruit of the Loom. I think the support offered is superior to boxer briefs, and honestly, why do my thighs need to be covered? I would try lots of things to see what you like. Bear in mind that are lots of different styles within the briefs genre. Hip briefs have less coverage (2-3" outseam), full-rise have more (8-9" outseam). My personal preference is for something in between, mid-rise with 4-5" of outseam. There are tons of brands out there too. Some of my favorites are calvin klein (but not the classic - anything else), Lacoste briefs are good, Dockers actually makes great briefs, and I love my Champion briefs, but I don't think they make them anymore.