Directions To Under...Where? Underwear For The Ages? Swim and Underwear for guys who prefer to point North and can you wear briefs after 40?


It's long overdue for a reader question and answer article so here are my responses to two readers who sent in some detailed requests for advice. I'm not sure if I can own the title of men's underwear expert-it was never my intention-but I appreciate that these readers felt like I had something useful to say regarding their underwear purchasing options. If anything I hope some of this writing is entertaining and maybe it's informative for some of you as well. There are so many more questions that have been sent my way the last month and I'll try to answer more of them soon. If I'm lucky I will be able to post the official 6th edition of Reader Comments and Questions this weekend. Thanks again for reading!

Underwear Guy


Dear Sir, Please help me.

I am trying to find just the right style of bikini for my boyfriend, and you seem quite knowledgeable about them, so...I'm asking for your help. If I may, I'll briefly state the situation.

My boyfriend and I have attended hot tub parties of late with some friends who are gay. The environment is one of 'showing off' one's assets, both men & women. There are three men for each woman, and the guys enjoy wearing brief bikinis that define & emphasize. At the last party, my boyfriend tried on one of those bikinis and everyone, including me, thought he looked great in it. This is where I need your help.

His birthday is coming soon, and I would like to order an outfit, underwear, like this. I know nothing of what brand or what features to ask for, please. The guys outfits are not see-thru, but they define every ridge and valley, so I know they are unlined. Too, they have a built-in pouch and all three parts are supported out front. While they seem to like it pointed downward, my boyfriend, I know, likes to be held upward. Stretch of fabric is, of course, a necessary since coverage under all conditions is important. This said, please tell me what brands, models, etc you recommend for my boyfriend.

Thank you ever so much.

Love, Janet

Hello Janet, thanks for reading and for writing in with your question. The interesting challenge you pose with this question is that in order to create the most prominent “package” through underwear or swimwear, designers typically create patterns for the pouches that assume a guy will be pointing down. This position tends to create the best overall visual size since you are combining all the parts into one shape. In some cases these pouches are cut almost anatomically so the minute you do something different like point up, the pouches suddenly don’t look so great. What can happen with pointing up is that there becomes an excess of material created in the pouch which either wrinkles or flops around and looks like you aren’t rounding things out very well-which is of course the opposite effect you want. So the solution for your boyfriend is to find sexy styles that accent and enhance without assuming the down position.

For underwear, there is one brand that I know of that is specifically designed for guys who want to point upwards: King Style. and are the only online stores that I know of that stock this line. I have not personally tried the King Style brand of underwear so I cannot specifically endorse them as far as fit or how well they accentuate. I think it’s clear from the different product shots that your mileage-or as the case may be inches-varies greatly depending on how well proportioned your guy is down there.

King Style Erector Brief from International Jock
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King Style Bikini Briefs from DealByEthan
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For swimsuits that are revealing you can never go wrong with light colors like white or light blue that tend to get a little sheer when wet. AussieBum sells several nylon swimsuits that are low cut and sporty as well as the swim Wonderjock which has an enhancing pocket to help keep a guy’s assets out in front. Again, I haven’t worn the Aussiebum wonderjock swimwear but based on the underwear which I have worn, I think a guy can wear the brief and still point up without the package result looking odd.

AussieBum Wonderjock Swim Brief
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AussieBum Classic Swim Brief
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Another swimwear and underwear designer that specializes in men’s package enhancing products is California Muscle. A couple of swim items with built-in enhancers are the Elevator Brief and the Colt Brief. I believe the Elevator brief in particular is not cut so extreme in the pouch that it wouldn’t work if you didn’t point down while wearing them. The Colt Brief may be a bit more of a challenge in terms of the package size and pointing upwards but I'm listing them here as a possible option regardless.

California Muscle Elevator Swim Brief
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California Muscle Colt Swim Bikini
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There is also a variety of underwear options from California Muscle that include enhancer rings or pouches including the Levitator Brief, Komodo Brief (I have tried and liked), and the Arrowhead Brief.

California Muscle Levitator Brief
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California Muscle Komodo Brief
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California Muscle Arrowhead Brief
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Last but not least you can always turn to N2N Bodywear for a variety of revealing cuts in both underwear and swimwear. I would advise that because of the way N2N designs most of their pouches they won’t look very flattering if the guy point upwards since they tend to design fairly large pouches requiring everything to point down. The items for underwear from N2N Bodywear that I would recommend are the ones that do not have a pouch but mold to your guy’s shape and thus reveal all the lines and budges. Those choices include the Tropic Boxster and the BT Boxster. I realize those are not bikini cuts but they may fit what you are looking for.

N2N Bodywear Tropic Boxster
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N2N Bodywear BT Boxster
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There are several options for swimwear from N2N Bodywear that would work for an upwards-facing arrangement although do keep in mind that because all of N2N Bodywear's designs are very low rise, in most cases the guy won't really want to be pointing downwards so much as off to an angle-lest the whole story be revealed. Currently almost all N2N Bodywear Swimwear is on sale so now is a great time to try out one of their briefs or bikinis.

N2N Bodywear Ultra Sport Swim Brief
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N2N Bodywear Ultra Competitor Swim Brief
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N2N Bodywear Ultra Rider Swim Brief
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Hello Mensunderwearguy,

First, my congratulations on keeping yourself in great shape.

I came across your site when doing an Internet search. After 10+ years of Calvin Klein boxer briefs (with some pairs losing their elasticity), I decided I need a change. Especially since I'm finding it annoying when the boxer brief legs ride up under slim fit jeans. Anyway, I noticed some guys at my gym wearing interesting underwear styles, so I went to the Internet to check out what was available. I found your site, and now I'm kind of overwhelmed by my style options. But I'm convinced that you are pretty much an expert on the subject. So here's my question. Should men over 50 wear briefs? I read a comment on a Men's Health blog, by their female correspondent, that men over 40 should never wear briefs. Do you agree?

I am in my mid 50s, and I'm in decent shape...short (5'5"), well-muscled, 32" waist. I'm one of those solid, tight, metamorphic guys. You probably know the type. Although I look younger than my years, I have to admit that I look over 40. I work in a creative industry, and there is an expectation that we dress casually and stylishly. So I admittedly dress young, and I look pretty good in athletic cut t-shirts and low rise jeans. But I don't get too style crazy. After all, I'm a senior officer of the company, married guy with two grown kids. So I go for a stylish profile, but make conservative choices within the style.

I'm looking for comfortable everyday underwear. I like a good pouch (hate it when my balls stick to the side of my leg), and I don't like my shorts to stick way out above the waistline of my jeans. So I'm thinking about low rise briefs. (The few pairs of briefs I already own are not low enough.) But at my age, should I go there? I've seen several older guys at the gym -- even some in relatively good shape -- wearing bikini briefs, and I think they look kind of pathetic. That's not the impression I want to make.

I train three times a week and play court volleyball twice a week (yes, even at my short height), so I am changing in a locker room at least five times a week. Whether I like it or not, my everyday underwear can be seen by others. Thus appearances matter.

But I am comfortable enough with who I am to try different brands and looks, so I am up for your suggestions. I am also vain enough to consider styles that will flatter my profile. I may be in my 50s, but still want to look like I "got it going on".

I look forward the hearing your advice,


Hello SQ thanks for writing and I appreciate the detailed question. You raise some very interesting topics that are very broad and in many ways challenging to address. I should start off by saying I’m not a sociological expert by any means so what I have to say should be taken with a grain of salt but I think I have good common sense and an analytical approach to problems so hopefully I have come up with some good reasoning here. Very quick answer: I don’t really like it when anyone lays down a broad rule about fashion so I disagree that men over 40 should only wear boxers. I try to review underwear of all styles, shapes and colors without judgment about what is “right” or “wrong” for any particular individual to wear because I think we’d have a very boring world if we could only wear what others deemed as acceptable for certain ages. We might as well start dictating certain heights, ethnicities, hair color, and personality types for underwear as well. To deconstruct my answer a little more I have included some more general thoughts on age below but if you want to just skip to the recommendations click here.

Let’s be honest, that author’s stated opinion is probably driven at least partly by what she considers sexy and attractive, or conversely, unattractive and non-sexual. At some point in her life she decided that older men could not really be sexy and should cover up more of their bodies lest we turned off by seeing too much. I must admit I first had to evaluate what myself and society as a whole, would consider attractive and whether that quality isn’t possible past a certain age. I think there’s nothing new in the admission that our culture is very youth-obsessed and we deem attractiveness to be associated with the young, under 30 set. I decided to see if I could first find any examples of men over 50 that would be majority-consensus-approved as “attractive”. I must admit it wasn’t an easy search but then of course I remembered Dennis Quaid who recently had a spread in Vanity Fair (Italian) and there was a lot of blog discussion and coverage primarily for how attractive he looked regardless of the number of years he’s got under his belt.
Dennis Quaid
March 2008 Vanity Fair (Italian)
Dennis Quaid
March 2008 Vanity Fair (Italian)

Another example I was able to find was Rick Dinhanian who is also above the 50 year old mark but is in better shape than probably a majority of guys 20 years younger. Interestingly enough, Rick had gotten out of shape up until 5 years ago so he’s proof that one can achieve fitness at any stage of life at any time. You might wonder why I’m bothering to first point out “sexy” men over 50 and the reason is that what we deem fit and attractive tends to affect how much we want to see. So the more fit and attractive a person is the more likely people will accept less clothing, therefore the briefer the cut of underwear is possible. I think by clearly breaking the association that age equates to unfit, we can break the assumption that age = boxers.

Rick Dinihanian Rick Dinihanian
Louis LaSalle Photography

Part of my recommendation factors in that you mentioned you are in excellent shape and I think it’s accepted that there are simply more options the better shape a given individual is in. It tends to go against my philosophy that I should say anyone can or cannot wear a certain type of underwear but I think in public situations like a gym there are “rules” set by society and culture that come into play. It’s just like I’m not going to wear a see-through mesh brief at work but at home I would say “no rules apply”.

I think it is acceptable for you to wear low-rise brief underwear if it is the right style. A good option would be a classic design with an exposed waistband and reinforced, covered elastic on the legs which would be perfectly suitable to wear at the gym without crossing the line of the “unfashionable-for-fifty” mindset. The C-in2 low-rise brief or the 2Xist no show brief would be excellent choices as these both are low-rise (per your original request) but still masculine and attractive for pretty much any age of guy to wear. The 2Xist Bold line as well as the Varsity line would also work well in my opinion. I own all of these briefs and can recommend them for fit and quality.

C-In2 Classic Low Rise Brief 2Xist Classic No Show Brief 2Xist Bold No Show Brief

As far as the “rules” of color go, I had to ask some friends about acceptable choices because I’d hate for my recommendation to be “if you are more mature then you can only wear black, gray or white” and I got some good feedback. Basically darker colors like navy, browns, and olive green to dark forest green seemed to go over well as “reasonable without getting too boring.” It was also determined that too much pattern wouldn’t look “right” but classic, sporty stripes could work if executed in the right combination such as a tone-on-tone approach. Not surprisingly, bright colors were vetoed e.g. pink, orange, red and yellow.

C-In2 Kinetic Mesh Brief in Dark Olive 2Xist Contrast Countour Pouch Brief in Navy 2Xist Varsity No Show Brief in Black

I hope these recommendations are useful for you as well as the general discussion. I would reinforce the fact that freedom of choice is great and to a certain degree I would hope that we all would feel free to wear what we most desired even if it didn’t necessarily fit in with the crowd. This question was really interesting for me because it made me think of how I will age over time and how I wouldn’t want to feel limited in my choices due to age. I think ultimately this has been inspirational for me to continue to adhere to an exercise routine as I see how age doesn’t require becoming inactive, wearing boring underwear or becoming un-sexy. If the readers have any comments about age, attractiveness and underwear please feel free to comment or e-mail. I have also included a poll below if you'd like to quickly share your opinion on men over 40 wearing briefs.



Can a guy over 40 wear briefs?


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