Is it wrong to gift my boyfriend underwear he doesn't usually wear
May 1, 2015 5:21 AM   Subscribe

My boyfriend wears --- um -- Walter White underwear. It's his birthday, and I would like to give him some spiffy boxers. Is this a wrongheaded idea?

He has never worn a pair of boxers in his life, and I have some worries that boxers will be uncomfortable for his penis. I lack a penis so have no empirical knowledge of how briefs v. boxers impact dangly bits, but I have heard that boxers are sometimes uncomfortable for those who are used to uh -- support. Do penises need support?

If there is a penile support thing, and that's why some men wear briefs, uh how do I put this -- are there briefs out there that are like awesome super briefs? That don't look like what my dad wore around the house?

I do worry I am being Underwear Hitler, so please tell me if I am.

ALSO IMPORTANT: I must get said underwear in my hands by today. There's a Macy's I can hit up, but I can't order online for birthday deadline reasons.
posted by angrycat to Clothing, Beauty, & Fashion (44 answers total) 7 users marked this as a favorite
 
Response by poster: THANK YOU
posted by angrycat at 5:21 AM on May 1, 2015


Best answer: Boxer briefs are the best of both worlds. I speak from experience.
posted by dobi at 5:23 AM on May 1, 2015 [20 favorites]


Best answer: Boxer Briefs are the perfect hybrid. They offer support and they look hot (I'm a woman).

Anything you buy will be great. He's a guy, he's going to be thrilled just knowing that you were thinking about his junk. :)

And no, it's not wrong. Men don't mind being led. It is wrong to demand that he wears it, but you aren't doing that. You are offering up an alternative in a loving way.
posted by myselfasme at 5:25 AM on May 1, 2015 [6 favorites]


Best answer: I think the only problem here is that you're considering an improvement package (heh) as his birthday present. Birthdays are a time for treats, not gifts signaling tacit criticism, even if it comes wrapped in the promise of sexy times. So another time, and perhaps some boxer briefs, which are a hybrid.
posted by carmicha at 5:26 AM on May 1, 2015 [44 favorites]


Best answer: If you really have to get him underwear, then I N-th boxer briefs. Much more appealing than both Y-fronts and boxer shorts. The only thing worse than boxer shorts are... satin boxer shorts.

But I agree with carmicha that this might not be the best idea for a birthday present. Give him better underwear next week, and buy him something that he might have actually wished for for his birthday.
posted by kinddieserzeit at 5:36 AM on May 1, 2015 [4 favorites]


Best answer: I'm with carmicha -- yes to boxer briefs (you can give him a pair of boxers to try out too, if you think he might be open to them), no to giving it as a birthday present. Give him something for him, not for you.
posted by chickenmagazine at 5:37 AM on May 1, 2015 [2 favorites]


Best answer: Frame it as a sexy gift, like "this is really more for me than for you, but you will receive benefit." He'll love it as long as it's not framed as an improvement gift. Men give women sexy gifts of this sort all the time (like lingerie). Men do like to feel sexy and like to receive sexy things as gifts.

It's possible he really prefers tighty-whities, and won't be converted by the boxers or boxer-briefs you buy him. Be ready to accept a future with this guy that amounts to him only wearing your preferred underwear option when he would like to signal sexytimes. There are worse fates.
posted by juniperesque at 5:37 AM on May 1, 2015 [4 favorites]


Best answer: I am pretty much perfect for this question! I used to wear nothing but briefs, and when my significant other suggested that she would find me more attractive in boxers, I tried them but did indeed find them uncomfortable. Then she bought me boxer briefs as a present once, and they are indeed awesome and the best of both worlds.
posted by Cannon Fodder at 5:39 AM on May 1, 2015 [2 favorites]


Best answer: As a proud, tighty-whity wearing man, I gotta say that switching to boxers is nearly impossible. Yes, boys need support.

That said, a nice pair of silk boxers as a gift can be ok if they're intended for sexytimes only. Lack of support can be part of the fun.

But if you're buying him boxers to say "here, you should wear this type of underwear now", it's probably not going to work unless he's been unaware, up until now, that there are alternatives. It's like telling someone to swap their left and right shoe all of a sudden.

Ok, it's official, The Internet now knows everything there is to know about me.
posted by bondcliff at 5:42 AM on May 1, 2015 [5 favorites]


Best answer: I must respectfully disagree with those who do not see this as the perfect--nay, perhaps the highest form of birthday present.

If he's never worn boxers or boxer briefs before, this will be a crazy new experience. I do agree with the idea of boxer briefs, as boxers themselves can be a little saggy and weird, especially if they are cut too loose, and it feels like trying to put your pants on over a miniskirt.

Don't worry too much about cut and fit right this second though, get patterns and colors you like, and let him experience the difference...then his happiness or complaints can guide future purchases.
posted by mittens at 5:45 AM on May 1, 2015


Best answer: If you think he might prefer to stick with briefs, there are some nicer ones out there than the WW's; I'm sure there are a lot of fancy brands but the ones from Ex Oficio are very practical, well made, and might look a lot better to you than the tighties. REI/outdoor stores/travel stores.
posted by ftm at 5:45 AM on May 1, 2015 [1 favorite]


Best answer: Get him some boxer briefs + something small you know he'd like. That way, just in case he's one of the tiny, tiny percentage of men who doesn't love boxer briefs (I am a lady and they are fantastic and hotttttttttttt), he's still got something he'll definitely enjoy.
posted by pretentious illiterate at 5:46 AM on May 1, 2015


Best answer: My husband is a briefs guy so I started buying him the fun brightly colored ones from American Apparel. I think he looks pretty great in them, and apparently he does too because now he seeks out fun colors for himself. And he would kill me if he knew I was telling the internet about this.

There are some good briefs options out there if you want to stick with his comfort preference but jazz it up a bit!
posted by something something at 5:50 AM on May 1, 2015 [4 favorites]


Best answer: Boxer briefs are the way to go.
posted by Dip Flash at 5:54 AM on May 1, 2015


Best answer: Dude here. Respectfully disagreeing about boxer briefs. In a way they are like the worst of both worlds IMO. I eventually grew fond of boxers when I'm lounging around, not expecting to do much walking/working/stair-ascending. Otherwise, briefs are non-negotiable to me.

Anyway, if he likes briefs, I'm confident he doesn't like them for their color. They make a lot of "shapely," non-grampa-ish cuts of briefs in attractive colors these days. AFAIK my Mrs. would agree that I used to have ugly briefs and now I have non-ugly briefs.

So the support of briefs is not mutually exclusive with attractive appearance, and boxers or boxer-variants are not IMO the only path to attractive male undergarmenthood. That said, it may be possible to convert him to wearing boxers in certain circumstances, as I converted myself.
posted by CheesesOfBrazil at 6:00 AM on May 1, 2015 [8 favorites]


Best answer: I totally agree with your boyfriend, but Under Armour Boxer Jocks changed my life.
posted by pjenks at 6:01 AM on May 1, 2015 [1 favorite]


Best answer: Do penises need support?

This is more a question of, "Do penises like support?" It can feel nice, sometimes, in my experience, but -- personally -- not necessary. It might feel "right" in tighter pants, but might make me feel like I'm "swimming" in looser styles (i.e. that my pants don't fit right, when they do). Generally, boxer-boxers are my preferred comfort choice, with the exception of the gym, where all that floppin' leads to chafing. Other guys' mileage may vary.

And yes, if you're trying to split the difference between tighty-whiteys and boxers, boxer-briefs are pretty nice. Whether someone feels comfortable in them may depend on how they feel about their body, though: I think I look better in normal boxers, due to my love handles, while my girlfriend absolutely loves it when I wear boxer-briefs. But there's no accounting for her taste, obviously. The point is, they tend to flatter a guy's butt and legs (and, obviously, penis), while really accentuating any extant muffin-top. A devil's bargain.

But here's the deal: As a general rule, people shouldn't try to direct their SO's dress.

Buying clothes for someone else, as an "improvement" effort, can really backfire. It can send the message that you don't like them for who they are, don't respect their choices/boundaries, and etc. I think it's one thing to request that your man up his game a bit for social reasons, e.g. having a decent suit that fits, for weddings and such, and another to buy him that suit without his input. Practically speaking, this can result in problems like beefy guys wearing rail-thin "trendy" clothes, not things that fit or reflect their personality.

NOTE: Some guys clearly don't mind being dressed by their partners, as it takes care of an area of their life that they'd rather not fuss with. If you already have that sort of arrangement with your fella, then gift away, I guess.
posted by credible hulk at 6:09 AM on May 1, 2015 [2 favorites]


Best answer: Get him some nice young guy briefs. Boxers are really unsexy. Bro, I want to see that you have a butt. Boxer briefs are great, but if he already likes briefs then stick with briefs.

When you walk into a place like Macy's and go through the men's unmentionables department, you'll come across a section where you'll realize, oh, this is where gay men get their underpants. Buy him things from the periphery of that section. You can find briefs in non-saggy-grandpa cuts and they come in about a billion colors. Calvin Klein ones are really nice. Maybe start with some black ones.
posted by phunniemee at 6:10 AM on May 1, 2015 [10 favorites]


Best answer: CheesesOfBrazil: "Dude here. Respectfully disagreeing about boxer briefs. In a way they are like the worst of both worlds IMO."

Cosign 100%. I genuinely do not understand how guys can say they prefer boxer briefs. I sometimes feel like the world is trying to gaslight me about them.

THAT SAID, I think the difference between this being a great gift or a bad one is how much of his underwear preference is intentional. If he just wears briefs because that's what he's always worn, and he just buys whatever brand is on sale, and he's never expressed much of an interest in different types of underwear, then I think it would be really fun to give him a little bit of adventure, to try out something new and different. But if you've had discussions about how he can't stand anything but briefs, or he has one and only one brand that he will buy, and he expresses his preference for briefs strongly, then yeah, it is kind of an "improvement" kind of gift.

THAT SAID, I prefer boxers, and really can't stand boxer briefs, but my wife occasionally buys me a pair of boxer briefs, or even better TRUNKS (which are basically boxer briefs with really short legs), and I wear them quite happily when I know there is a chance sexytime is in the offing.
posted by Rock Steady at 6:18 AM on May 1, 2015 [1 favorite]


Best answer: So I've gotten underwear from my birthday. I've had a partner buy me something he was more excited to see me in than my normal undergarments. I'm also a straight lady. So I don't know that this has to be read as an insult or an "improvement project"--it's like the fun lingerie present, only for your dude, and if you present it in that sense of fun and "I got this because I like to imagine you in underwear more than any other dude" I don't see a problem with this.
posted by blue suede stockings at 6:19 AM on May 1, 2015


Best answer: But here's the deal: As a general rule, people shouldn't try to direct their SO's dress.

Buying clothes for someone else, as an "improvement" effort, can really backfire. It can send the message that you don't like them for who they are, don't respect their choices/boundaries, and etc. I think it's one thing to request that your man up his game a bit for social reasons, e.g. having a decent suit that fits, for weddings and such, and another to buy him that suit without his input. Practically speaking, this can result in problems like beefy guys wearing rail-thin "trendy" clothes, not things that fit or reflect their personality.


I think this is a useful insight. I personally am over the moon when my partner buys me clothes, as my fashion sense is close to non-existent, but am happy to dress better than I did; I developed my dress sense while having no self esteem, so my taste is usually just completely incorrect. But obviously this will depend on what your partner is like. You know him best. That said, I don't think there's anything wrong to buy him special underwear for sexy times, just as there's nothing inherently wrong in a man buying such things for a lady.
posted by Cannon Fodder at 6:20 AM on May 1, 2015


Best answer: I wear boxers, except when I'm working out, I wear boxer briefs for the support. Boxer briefs will provide the support he gets with briefs, and be less dad-like. But I mean, he could try both if you get him some options. It's not like you'd be throwing out his current underwear when he wasn't looking, so you shouldn't really be risking hurt feelings or anything.
posted by J. Wilson at 6:23 AM on May 1, 2015


Best answer: Seconding pjenks' recommendation of Under Armour Boxer Jocks. My husband refuses to wear anything else any more.

You should be able to find them in sporting goods stores near you.
posted by bookdragoness at 6:31 AM on May 1, 2015


Best answer: TLDR: a lot depends on your relationship with him and why he wears briefs.

On whether or not to do it on his birthday - this depends a lot on him. Some guys would view it as a sexy surprise. Some would view it as criticism on a special day. The way it's phrased can make a big difference too. Think of how your female friends would react if they'd never worn a thong in their lives and their boyfriends decided to give them one as a birthday present.

Do penises need support?

It's more the testicles, but yes, some guys prefer form fitting underwear for support/comfort reasons. It's not as extreme, but think of the difference between jogging in a regular bra and a sports bra. Things move around and it's not always comfortable. If he's circumcised, the support can make a difference with the glans rubbing in obnoxious or uncomfortable ways. Both are things that most guys can acclimate to after a switch, but it can feel weird going from support to non-support.

You might offer boxers as more loungewear/PJs and if he wants to try them as underwear too that's up to him.

are there briefs out there that are like awesome super briefs

I like support most of the time and wear about 45% men's bikinis, 45% boxer briefs, 10% boxers. Bikinis are the least trendy, but they provide support while not binding/riding up/getting overly hot in the summer, come in some nice colors and patterns, and I have a slim and relatively athletic body so I and my partners have thought they looked good on me. Boxerbriefs are more forgiving visually but I don't always want that much frabric - think of the difference between wearing a woman's bikini cut and a woman's french or full cut.

There are definitely nicer briefs out there, both in terms of using quality fabric and interesting colors and patterns.
posted by Candleman at 6:31 AM on May 1, 2015 [1 favorite]


Best answer: Depends on the guy. My partner had at one point expressed interest in trying different underwear, so one year I gave him (among other things, not as an only gift!) a big box full of a ton of different styles, colors, patterns, etc. of underwear. We both found it an incredibly amusing gift, and over time he tried on the different kinds and found some new things he liked, so that was a winning present all around. YMMV.
posted by Stacey at 6:37 AM on May 1, 2015 [1 favorite]


Response by poster: Thanks so much for the answers so far. I plan to utilize this great advice and would report as to the results but for the fact that one day the man may come across this thread and read about his underwear choices and SORRY HONEY I DID IT FOR LOVE
posted by angrycat at 6:44 AM on May 1, 2015 [7 favorites]


If you have a Uniqlo near you, I really like their boxer briefs.
posted by smackfu at 6:59 AM on May 1, 2015 [2 favorites]


In my personal opinion traditional boxers are great. Hang loose, I say. It don't mean a thing if you ain't got that swing.
posted by Segundus at 7:07 AM on May 1, 2015


I just wanted to add that even if your BF doesn't end up loving the boxer briefs, you can still find sexy brief-briefs! I recommend checking in stores catering to gay men, honestly. :)
posted by rainbowbrite at 7:08 AM on May 1, 2015


So there is a lot of answers here., but here's mine.

I like hipster briefs more than Boxer Briefs because they are shorter in the leg, so they feel better under trousers.

They are a good alternative to tighty whities.
posted by MarvinJ at 7:11 AM on May 1, 2015 [3 favorites]


Don't ask the internet, ask your man. Penises, like men, vary and they can do so over time. Just ask him. Also, get him something more than underwear for his birthday.
posted by Brandon Blatcher at 7:31 AM on May 1, 2015 [2 favorites]


I wear boxers and have for a couple decades now after switching from briefs. I don't find support to be an issue in normal wear; I prefer the freedom down there, actually. Hard to know with your boyfriend, but it's worth it a try. If he doesn't like 'em, maybe boxer-briefs next time. I agree that his motivation or lack thereof for the wearing the briefs is important as has been mentioned above.

Here's my two-cents. Don't get him something fancy and "sexy" to start with No silk or silklike smooth fabrics. THAT can actually be a problem in wearing boxers, because fabrics like those tend to stimulate the junk as they slide across it in normal wear. That can either lead to actual discomfort or it can lead to embarrassing binder-in-front-of-crotch-in-high-school situations that are also not particularly fun either.

Here's my suggestion based on years of buying all types. Go to Walmart, Target, wherever, and just buy a 5-6 pack of FROOT OF THE LOOM cotton boxers with colors that you like in his waist size. They're comfortable, durable, and they're cheap if he just doesn't take to them. You may ever like wearing them. Froot of the Loom is my unpaid strong recommendation based on my junk's valuable input.

Take things one at a time, obviously, but if he DOES like the boxers, I would generally not recommend them for working out or sports. In those cases, it's probably best to wear a jockstrap (which normal boxers fight like the dickens), and sans jock, he'll want some sort support so he's not flopping around doing exercises. That could be potentially junk-damaging, and that might be where those Under Armour boxer briefs come in. Good luck, and come back and give us a brief on your boxers situation.
posted by KinoAndHermes at 8:01 AM on May 1, 2015


It's not clear to me how underwear became a trend item. Color, sure but having a preference for a type of underwear? Get him some boxers in hella awesome prints. and some boxer briefs, and some basic jockeys in great color/print. Sweetheart, I thought you might enjoy having some options. Then don't make it an issue. it's what inside that counts.
posted by theora55 at 8:38 AM on May 1, 2015


I also wear briefs and yes there is a support thing that boxers do not cut it. Consider getting him some 'sexy' briefs with colors, etc instead of trying to change who he is.
posted by nogero at 8:53 AM on May 1, 2015


Response by poster: to anybody who's worried: underwear (if it happens, maybe it won't) is only part of a sort of funky low-cost present extravaganza. and yeah, thanks for helping me contextualize it as more *sexy present you may enjoy* as opposed to *your fashion choices are inappropriate* thing. I really don't mean it as the latter. As somebody who wears the same sauce-stained t-shirt around the house for days at a time, I am understanding when it comes to the limitations of sartorial criticisms of a loved one.
posted by angrycat at 9:05 AM on May 1, 2015 [1 favorite]


Also, my boyfriend has some briefs (not boxer-briefs) that are gray, black, and navy. Much sexier than the white ones. :) You could buy a pack of those and a pack of boxer briefs.
posted by amaire at 9:16 AM on May 1, 2015


Coming in a member of Team Briefs. And, yeah, it's a junk thing. It is a lot more comfortable for me to keep things in a certain orientation. I have been experimenting with boxer briefs, but the jury is still kind of out on that one.
posted by Samizdata at 9:48 AM on May 1, 2015


I nth the advice above about not wanting to receive underwear as a birthday gift, unless it was like a specific kind that would be fun for sexy-times for you guys. Also nth the advice about differently-colored briefs - you might be partial to black in particular.

As another data point: I wish I could get into boxer briefs, I love them in principle, but they always ride up on my legs such that they fit like briefs but are all bunched up. It's super uncomfortable and awkward. I didn't know this until I tried them out. Changing to another style of underwear can be kind of a big deal mentally.
posted by hootenatty at 10:58 AM on May 1, 2015 [1 favorite]


From having an office in West Hollywood, I can say that a gay-oriented underwear shop will have boxer-briefs that are both more comfortable and more uh accentuating than ones at Macy's. Just FYI.
posted by klangklangston at 11:03 AM on May 1, 2015 [2 favorites]


Response by poster: I want you all to know that since I don't really how he might react -- we're still new at gifting for each other, maybe extremely obviously -- I didn't get the underwear. He is a dear sweet sweet man who is much more likely to enjoy a Better Call Saul t-shirt than some different underwear, and this informed my buying choices.
posted by angrycat at 5:08 PM on May 1, 2015 [3 favorites]


Maybe you can declare some future non-birthday day as Funderpants day and celebrate by both wearing new-to-you-both styles of underwear for each other's amusement.

Tighty whiteys are sad. Don't give up on the dream!
posted by phunniemee at 5:27 PM on May 1, 2015 [2 favorites]


OK didn't read everything, but the support is for the olives, and not the pickle. If he's used to it with tidy whities you may have to wean him off it. You can remind him that the olives need to get some cooling in order to produce maximum potency swimmers, and make it a macho thing, and that ought to be motivation enough.
posted by halhurst at 6:47 PM on May 1, 2015


Don't get them for his birthday, but if he likes technical things and you live near an REI, try ex-officio's boxer briefs. They're very very nice.
posted by phoebus at 7:47 PM on May 1, 2015 [2 favorites]


Don't get them for his birthday, but if he likes technical things and you live near an REI, try ex-officio's boxer briefs. They're very very nice.

Yes! My partner has had a pair of these for over a decade and, aside from some fading, they're still in nearly perfect shape. If you're OK with buying from Amazon, they've been on a pretty good sale lately - around $10 less than you can buy them elsewhere, at least for certain colors. They're easily the most durable underwear I've ever encountered.
posted by dialetheia at 9:11 PM on May 1, 2015


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