Curious question--my dad always (and I do mean ALWAYS) wore white briefs, so naturally, I did also. There was never a point when I felt the need to switch to boxers as I became an adult--at age 46, I've got a drawer full of "whitie tighties". Even though I've decided that I like boxers, I don't really see it as a boys-to-men issue. But from what I'm reading, a lot of guys think white briefs are about like pajamas with teddie bears--something little kids wear between diapers and puberty--and they'll tease guys who don't make the change. It seems like lots of guys change over to boxers at some point--and if they don't, they'll change to "boxer briefs" or at least colored briefs. What did the rest of you do? Was there a time when you decided "no more briefs--I'm a big boy now"? Did your dad wear boxers while they bought briefs for you? I don't even know if they make boxers for little boys, but I'm not sure what difference it makes. Was there a time when your folks just quietly started buying you boxers, and didn't make a big deal of it? Or maybe you just kept wearing briefs and didn't think much of it. What gives, guys?

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Go a little wild. Try colored briefs. LOL
I never...NEVER... wore boxers...guy's I'm talking 60 years...I was a dyed in the wool briefs man, until I bought my first pair of Duluth Brand performance boxers. Kinda expensive, but I caught 'em on sale...I'll never wear anything but these undies. Super comfortable and micro-biologically treated to stop odor. Try them....feels like commando style... free-balling to the max!
In my family from my dad to grandfathers to my great grandfathers (Still got 2 around!) they all wore boxers for comfort. I have had always worn boxers till I joined the military and forced to wear ghastly brown government briefs. Not comfortable what so ever! I remember the bands around the legs would ride up and dig in during long ruck marches and no amount of picking would seem to alleviate the situation. Once i was done and allowed to wear civilian clothes again I remember being almost too happy to run to a store and buy some boxer.

I have tried a lot of different boxers and I have to say some of my favorites are the Duluth like Mr.Hunter has stated above. They, like most clothing I got from Duluth are extremely comfortable and last a long time. I have even bought these boxers for my younger cousins to older male members and none have not enjoyed them.
My dad wore boxers. My brothers and I wore boxers. I just recently switched to boxer-briefs. Don't have a clue what my brothers do now-a-days. You "boxer wearers" should try the boxer-briefs. Way more comfortable!
Bruce---was there an age when you and your brothers switched over to boxers? And if so, was it like an "I'm growing up" moment? Or were boxers just what all the boys (and your dad) wore at your house all the time?
Well now that I think about it, I switched around 13 or 14. I guess with puberty. Not sure about the others. I guess they wore whities in the early years too. It's just that most of my memories of our household, include a bunch of guys running around in their boxers. (4 males in my house).
I'm 21 - briefs man all my life.

However, I find the white briefs horridly looking (I know you don't wear them for style, but... cmon! ;-) ).

I wear colored briefs. They're comfy. And nice. I don't think I could switch over.
For most of my 45 years, I've been a tightie whitie guy. Over the last year, with my marriage in terminal decline, I read that women don't really appreciate white briefs or find them all that sexy so I experimented with some black and grey briefs. The ex loved the black briefs (but unfortunately not enough to save the marriage). Since then, I've tried boxer briefs which I love. I wish I had switched years ago. (Like 20 or 30 years ago.)
Tighty-whities (perhaps it's a regional thing, but that's what we called them where I grew up) were part of my childhood. Once I hit about age 12, it was boxers exclusively until age 17. Then I went back to briefs. They're just more comfortable.
I switched to boxers in my rebellious youth of 13-16 because it was "cool."
I have since switched back to briefs. Compartmentalization and support are KEY to comfort!
My dad wore boxers. I wore briefs until I was 17. I then decided it was time for me to buy my own underwear and went with colored briefs and boxers from 17 until married. Then the wife brought home some black boxer briefs after we were married and I really liked them. So now it's only black or grey boxer briefs.
Boxer briefs are the only way to go in my opinion. Except, of course, those times I wear my silk boxers, which the wife just loves the heck out of.

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