A Question of Boxers

I’ve never worn boxers before, until this week. At least as undergarments. On a whim I purchased a few “Fruit of the Loom” brand boxers. You only live once, right? At least in this body.

But the ones I have purchased feel baggy and kind of frumpy, like I’m wearing an ultra-thin adult diaper. Not that I know what an ultra-thin adult diaper feels like. Yet.

For those of you who wear boxers, I have a question for you: How exactly are boxers supposed to fit? And what brand(s)/style(s) do you like?

Until next time...

25 thoughts on “A Question of Boxers

  1. My story may assist you. I switched to boxers a few years ago. Size XL. Then last year I lost 80 lbs., but I never got around to downsizing my underwear. Baggy doesn’t begin to describe them. Two weeks ago I went to Kohl’s and bought some size M boxers (32-34 waist) and I’ve been really enjoying underwear that aren’t falling off me. My manparts are still quite free to move around. My advice to you is to buy boxers that are the same size as the shorts you wear.

    1. I’ve purchased mediums, but they just feel “baggy” to me. That could be because I’ve never worn them as undergarments before though. I’ll give them a few weeks to see how it goes.

  2. Slighty baggy is cool cuz it gives ur privates room to breath. I’ve made the mistake of buying some that were too tight once and they kept riding up my balls and sliding down my ass every time I sat or bent forward. One cool thing about boxers is that they come in all sorts of cool colors and designs.

    1. They’re still a little awkward feeling at this point. I’ve not had an issue with bunching or riding up yet. But We’ll see how that progresses. But I have noticed that there’s definitely a lot of options out there.

  3. When I’m in the mood for boxers, my preference is the jersey knit ones because in addition to allowing the guys free range, they stretch a bit if you move around and they are not as scratchy as broadcloth.

  4. I like all cotton boxers and size them like Cubby says to πŸ™‚ My last boyfriend (before the present husband) switched me over, and I have to say, I love them. Love them, LOVE them. My granddads both wore boxers, although my dad is a Munsingwear man. I like the Target store brand ones since they’re snappy and have endless cute patterns. And, yes, I have more than one pair of boxers with red hearts. I’m wearing them now. I like the free hangin’ they gives me.

    1. I’m still attempting to adapt to the whole “free hangin'” thing. That kind of freaks me out a little. I’ve always liked my junk all in one place, so to let them hang free has taken a little adjustment.

  5. I only wear boxers to sleep in. And I’ve stopped doing that and sleep naked. I don’t like the way they seem to bunch up in your pants. I don’t like my boys flopping around. I like the feel of boxer briefs and the longer inseam of boxer briefs vs, briefs. But feel free to model the next brand of boxers you purchase. I like Joe Boxer, they only seem to be sold at K Mart. Their quality is not what is used to be when I first started buy their boxer briefs. Their boxers have fun patterns.

    1. I briefly wore boxer briefs, but it seemed the extra leg bits would always ride up. So I switched backed to regular briefs.

      I’ve always been one that liked my stuff parked in one spot. I’m not used to my junk flopping around, so it’s taken some adjustment. I’ll give it a bit to see how it goes. Worst case: I go back to my briefs. πŸ˜‰

  6. I can’t wear boxers as my thighs are too big (I can’t wear 501s either for the same reason). I wear Jockey midway briefs which conform to my ass, nuts and legs going midway down my thigh – kind of like a pair of bike shorts, but not all lycra-y. Every couple of years I’ll buy a set of boxers only to be disappointed on how poorly they fit my body. If I get them big enough to fit my thighs, they are WAY too big in the waist. Oh…I also like to just wear a jock.

    1. Wow. Those are some nice sized thighs that you’ve got there!

      If the boxer thing doesn’t work for me, I might try those midway briefs of which you speak.

      And I tried the jock thing before, but that just didn’t seem to work out for me. πŸ˜‰

  7. Uh, you got on my britches there, pal. For a comfortable loose fit and feel, boxers are the only way to go.

  8. I wear nothing but boxers
    They are more comfortable and airy and more ready for easy access.

    Seriously, the best brand of boxers is Derek Rose. They really do last much longer than other brands, and they have great masculine colours without being drab or stuffy.

    1. Those are some pretty snazzy boxers. And the stripes even go the correct way! Granted, I don’t know that I could spend that much on underwear. They’d be the most expensive clothing on my body.

      And I think I need elaboration on the phrase “more ready for easy access”.

  9. My father started me off wearing boxers as a kid because he wore them but I absolutely hated them and switched to briefs. Particularly in the hot summer if I perspired the boxers would roll up or bunch in uncomfortable places. And I much prefer the support. I wear Calvin Kleins except for certain occasions when I expect to be getting undressed with someone and then I wear one of the hot little numbers I got on my last trip to Germany.

    1. I’ve always been a “needs support” guy. Not because there’s a lot to support, but because I like my stuff to be parked in one location. So the boxer thing is still freaking me out a little.

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