In our society, not wearing underwear is a conscious choice when otherwise clothed. Aside from the personal freedom, it quietly tells others that you are comfortable in your own skin, and perhaps a nudist. For example the guy finishing up in the gym locker room putting on a fitted pair of shorts and a t-shirt often attracts curiosity. Then there's the well dressed business man, fitted dress shirt and tie, but no undershirt. Nice pecs! Or the well tailored suit fitting like a glove, attractive bulge and great butt. Not restricted or re-shaped by underwear. No underwear tells volumes.
As far as benefits of not wearing underwear, I think it's more a personal preference than any real benefits. If you're a full-time nudist, like we are, we are constantly washing towels. Towels we use to dry off with after a shower and towels we sit on. Throwing underwear in a load of laundry isn't that big a deal. Packing for trips, the underwear (panties) my wife wears is so damn tiny, you could hold a weeks' worth in your hand. Doesn't really save any room in the suitcase. Her bralettes, while traveling, are fairly compact as well. Lacy, spaghetti strap bralettes that are only worn to minimize the sway and jiggle in public.
For me, I've always preferred the freeing feel of going commando. Like I stated earlier, I began in HS. I played sports and after practice and showers, I noticed the older guys all slipping on their Levis without underwear. One day I followed suit and hardly ever wore underwear again after that day. My wife and I dated in HS. We had lunch each day together. Sometimes we were in a secluded spot where we could make out. She noticed right away that I was less contained as previous times. She asked, "are you not wearing underwear!?" I told her I wasn't, and she smiled. I took that as she was okay with it and not put off. So, it became the norm.
Doctor visits, I've not worn underwear at doctor visits. GP, Chiro, Dermatologist, dentist, Gastro, Cardio, Endocrinologist. Though all but GP and dermatologist really have any reason to see you naked, our GP and derma, have on several occasions. Both these doctors are female and have examined both my wife and I found that we didn't wear underwear. Our GP asked me if my scrotum ever hurt because I didn't wear underwear. I said, "never." She said, "ok." Our dermatologist couldn't care less. She knows we are nudists and always has us strip completely for the exam.
I suspect that in time, with age, we may have to resort to wearing underwear again at some time. As your body ages, you lose muscle tone and certain muscles restricting residual flow of urine are weakened. For now, we seem to both be in good enough health where that has not been an issue.
I enjoy going commando in many situations but wear boxer briefs a lot. Underwear for work because of the stiffness of pants fabric. I live in a cold climate and the extra layer of fabric between my butt and a cold car seat is just more comfortable. But in summer or casual situations, going commando is great in sweats, shorts, workout clothes, etc.
Going commando in warmer weather is a pleasure, cooling too. Underwear in winter is just warmer, although maybe it's what you get used to.
Was commando over summer as normal a few years ago, was on a camping holiday along the coast. Went to a pop up summer clothes sale and needed to try some shorts on, the sizes were unusual. I was with my sister-in-law, she knew about my summer underwear preference and discretely stood beside me to shield me, she's seen me naked a few times. While that was funny, you can get caught out, it probably was not the ideal place to be seen naked on a side street in a busy coastal town.
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