WIBTA if I continue wearing boxers as shorts?

So I (22m) have been a runner for about 8 years. I like running shorts and had been looking for casual shorts that length for years. However, the issue is even when I got 5 inch inseams since I am a pretty short dude they didn’t end up looking as short as I wanted (I know that they now make easier to find 3 inch shorts, but this was a few years ago).

Anyway I discovered that if I got boxers a size too big (large instead of medium), they just looked like shorts rhe length I wanted. I started wearing them like other people would wear gym shorts (hanging with friends, going to class, the gym, etc). And genuinely no one has ever noticed. Before anyone asks how:

1. I’m talking baggy boxers, not boxer briefs. The ones that are essentially shorts except for the fly, which I see shut.

2. I wear regular underwear underneath (think v-shaped briefs). Nothing is visible that shouldn’t be.

3. I’m aware boxers are typically underwear. I just have never worn them as such.

4. They are just comfortable. I know I could get other shorts but I like these. I like how they feel and I like all the fun designs you can get.

Anyway I’ve done this for years. No issues.

Last weekend, my brother (23m) invited some of his old college friends to my family’s cabin and invited me along. They’re mostly his friends but I’ve gotten to know them fairly well.

Anyway we were doing a drinking game and a girl got dared to do snow angels outside. When she came in she asked me if she could borrow some dry clothes, since I was closest to her size. I agreed and gave her a sweatshirt and some boxers I use as shorts. I don’t even think of them as underwear anymore so it didn’t cross my mind not to do this.

When she got them she saw the label on the inside and asked why I gave her boxers. I explained to her and the rest of the group everything above. They all looked at me like icwas out of my mind and asked if I’d been hanging out with them in underwear for years. I said technically but explained the distinction. Things got awkward but we moved on.

Anyway the next morning I woke up to a DM from the girl’s boyfriend (not on the trip) who said to stop being a creep and put pants on, that I made his gf uncomfortable. I don’t see the big deal, because if no one had looked at the label no one would have ever know. AITA if I keep wearing rhe boxers?

14 thoughts on “WIBTA if I continue wearing boxers as shorts?”
  1. I hate the underwear as outerwear trend so YTA for that but it’s personal preference.

    However who goes for a weekend in a cabin with no spare clothes? And if they don’t take clothes then why do snow angels? So she’s TA for being disorganised.

  2. Had to recheck you age because your friends seem a bit immature and yep young enough to be immature. lol. Wear whatever you want as long as your bits are covered so nobody has to see them. There is very little difference between underwear and swim suits too. Though I don’t recommend wandering around casually in a speedo.

  3. If you can sew then why not just shorten some proper shorts? I think the issue would be that boxers are made of very thin cotton.

  4. NAH since you’ve been wearing them and no one noticed but yeah, it’s kind of weird that you’re wearing underwear as shorts. No matter how you frame it, you still gave that girl underwear

  5. NTA. I’m a woman and I wear boxers (with the fly sewn shut) as shorts all the time. As long as you’re wearing underwear too, who cares? Women wear bikinis in public all the time and that’s the same thing as underwear with a different fabric.

  6. Two separate situations here IMO.

    NTA for using and continuing to use boxers as shorts.

    Offering *someone else* your boxers to use as shorts, is uncomfortable. I’d say YTA for that situation.

  7. you should have asked someone else to give her clothes after she questioned you on the boxers, it might be your preference but for her it’s probably quite awkward and uncomfortable to be wearing a guy’s boxers when she’s not dating him, even if she’s got underwear on underneath.

  8. I can’t imagine that people don’t notice, I bet they just don’t say anything.

    NTA, but for your own sake buy real clothes. You’re a man now.

  9. I don’t know man. If a girl tried to convince me a bra was the same thing as a top I wouldn’t be convinced but you do you 😂

  10. I don’t think you’d be the asshole, just be careful of what you wear in public, especially places where people might bring their kids, you never know what’ll happen and I don’t know if “but I wear two pairs of underwear at the same time” holds up in court haha

  11. I guess if there’s no open fly, and you’re wearing underwear underneath there’s nothing wrong with it, but I still find it kinda weird. I’m also a short guy that likes shorter shorts, so I feel the struggle of finding shorts at the length I like, but I’d still rather wear actual shorts that are a little long. Also, do you not use your pockets?

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