How old were you when you switched to boxer briefs from boxer shorts?

32 comments

1. I’m almost 40. I’ll let you know.

2. Probably 25. I’m 40 now.

3. Since I was 14. I like how everything gets arranged.

4. Define overpriced. Last time I bought it was $20 for a 6-pack of Hanes. Unless you’re buying some fancy ones that cost $40 a pair, they are relatively cheap.

5. I’ve always worn briefs. They’re way more comfortable and don’t make me feel like my junk is flying everywhere.

6. I’m 53 and still wear boxer shorts.

7. 35, boxers for life. I’ve tried a few times to do boxer briefs and I just can’t take it. Nothing against them, it just wasn’t comfortable for me despite all the brands I tried.

8. Just go commando. Gotta save money in this recession.

9. I was 19 when I discovered that boxers could provide support and not have to ride up your jeans when you put them on. Boxer shorts are useless and I’ll never go back.

10. I don’t think I ever wore regular boxers.

    The point of underwear is to keep my junk in place, not act as a pair of shorts under my shorts

11. Switched from briefs to boxers in middle school and never looked back. Have considered boxer briefs, but I like the comfort of boxers

12. Boxer briefs are the all round underwear. Briefs are great for athletic non jockstrap situations so your junk doesn’t go flopping around. Boxers are meant to be worn with dress slacks, because they prevent the leg from bunching up and causing wrinkling. It gives the suit / tux a sharper look.

    So it’s not about when did I switch, it’s about wearing the right underwear for the right occasion. I do like Boxer Briefs the best, but know when to wear the others.

13. Several years ago I tried on my first pair of [Saxx](https://www.saxxunderwear.com/). They are $30 US per pair but you would have to torture me to get me to go back to regular underwear. The ballpark pouch is a life changer. No more scrotum sticking to the leg.

14. I did the opposite. I switched from briefs to boxers when I was a little kid. I thought all underwear was just uncomfortable and tight my entire life. Up until that point. Boxer shorts are just so much more comfortable to me. They breathe better too in the summer.

15. Went from briefs to boxer briefs at around 15. Never looked back.

16. I did the opposite – switched from briefs to boxers.

    I wear briefs only if I wear tight fitting pants or something, and don’t want my butt crack to be shown.

17. For me it’s the opposite. Switched to briefs at 15 and switched back to boxers at 25, I’m 29 now.
    I realized I don’t want something so tight around by body specially around my balls, I cannot even wear jeans.

18. Never

19. Why do you think people only switch from one to the other, or that it has to do with age?

20. I wore boxer briefs when I was 15 years old, until now this is what I wear.

21. 55. Wish i had discovered them sooner

22. I think I was 18 or 19, boxer shorts were getting holes here and there and I got a new pair of boxer briefs realized how much more comfy they are and slowly switched my way out

23. About the only time I wear boxer briefs is for athletic stuff, like going on a long jog, or underneath a cup.

    Otherwise, I don’t like them and I stick with boxers.

24. Mid 20s. I still wear boxers on occasion. Boxer briefs/compression shorts are the most common, but I wear legit brief style or basically a jock strap when I’m out of the bike. Much easier to ensure nothing gets caught between myself and the tank during spirited rides.

25. I tried boxer shorts one time, and they always got bunched up throughout the day. I got tired of constantly having to straighten them out. For me, shorts are ok on off days, but it’s briefs only at work.

26. When I was ~24 I was working at a theme park and it was blazing hot. A cop told me about Under Armor’s headgear boxerjocks. I bought a pair and it was clearly better than anything I had worn before. I switched to them exclusively. Their quality went downhill, and they’re expensive, and other companies started making similar, so now I’m not picky about brand. Not really boxers to briefs, but kind of.

27. At home I wear boxer shorts, while going out I wear boxer briefs. Boxer briefs stay tight and good under a pants or jeans. And I love the breezy feeling of boxer shorts at the comfort of my home.

28. I got for boxer briefs because I don’t like how the fabric bunches up with shorts. I go trunks style with shorter legs for the same reason, and also as I get older my shorts get shorter so need the smaller underwear

29. I bought a pair of boxer briefs when I forgot to pack my underwear for an out of town funeral. At first I wasn’t a huge fan until I went to the gym & noticed that they don’t get caught in your crack like boxers. Additionally they don’t roll up when putting jeans on.

    The last thing was how great they made my ass & legs look. The wife initiating sex increased by 300%.

30. Many times its the other way: older guys switch into boxer shorts.

    Personally i went from fruit-of-the-loom tighty-whities as a kid then moved into boxer briefs. Lately ive moved into not wearing any underwear at all. Way cheaper.

31. I switched from shorts to briefs when I was like 19ish. I don’t think I’ll ever switch back.

32. Might not be helpful but, Right up untill I started suffering with severe lower cramps regular, around 23 I went commando one day and stop having the cramps for what ever reason.
    Been doing it since, its not as bad as people imagine it.