Men’s Underwear 101: A Brief Review of Boxers, Bikinis, etc.

Submitted by SharpMan Editorial Team on Monday 11th October 2010
In this article
  • Tired of looking like a dork in your underwear?
  • What underwear most SharpMen prefer.
  • What SharpWomen think SharpMen should wear.
  • A listing of styles and makes SharpMan-Approved for style, quality and price.
Men’s Underwear 101: A Brief Review of Boxers, Bikinis, etc.

With Republicans and Democrats readying for the upcoming Presidential election, has decided to join the political forum and raise an important issue that that has been largely ignored during the campaign:

The Great Underwear Debate

Sure, any candidate will take a stand on First Amendment rights, education, and balancing the budget, but show us a politician ready to defend his boxers in the public forum and we’ll show you a natural born leader. In the true spirit of democracy, we polled representative SharpMen and SharpWomen on the subject of men’s underwear in hopes of finally putting the boxer/briefs argument to an end. We may have been better off trying to balance the federal budget…

Preliminary Findings

Not only do politicians avoid the topic of their shorts, SharpMen in general don’t like to talk about underwear. It might just be that men really don’t care enough about what goes on down under to have a strong opinion; after all, who among us doesn’t own a pair of "wear" clearly worn past its prime? Either way, when pressed for an answer, SharpMen showed a slight preference for boxers or boxer-briefs over "tighty-whiteys," with bikini briefs coming in dead last — with no votes.

In contrast, SharpWomen polled definitely had strong feelings on the issue, commenting openly (and we mean openly) and extensively on their preferences. The SharpWoman consensus? Well, like any hot issue, there was no clear-cut winner. It turns out underwear is like most things; beauty is in the eye of the beholder. Here’s a quick overview of our findings:

Boxer Shorts

The pros: The loose, relaxed fit is comfortable and flattering to all body types. There are lots of color and patterns to choose from, and everyone loves "wacky" boxers.

The cons: No support, and they can bunch up in tighter-fitting pants.

Thanks to surfers, skaters, and rappers, boxers (worn with at least the waistband exposed) have become the most popular style of underwear with younger SharpMen. Most 30- and 40-somethings agree, but prefer to slip into something with a little more support when it comes to exercising.
Jersey Knit Boxer

What SharpMen say: "It’s boxers or nothing! I’ve slowly let my skivvies die out and I’m down to one pair. Maybe I’ll miss them when they’re gone, but for now I feel free." "Boxers during most waking hours."

What SharpWomen say: "Boxers compliment even the most imperfect of male figures and there’s something adventurous and cool about a guy who’s willing to ‘just hang’ out." "Fat men should stick with boxers — there’s something sexy about that look." "Men with no butts should definitely stick to baggy boxers."

SharpMan-Approved versions: Boxers come in all kinds of styles, but the bottom line comes down to great looks and quality. No SharpMan wants to spend more than necessary on underwear. For our SharpMan-Approved boxer test, we went with quality over quantity, figuring that spending ten bucks once is better than spending ten bucks on a three-pack — every other month.

One of our top-choice lines turned out to be Boxercraft — tough underwear that comes in great SharpStyles. Our favorite styles merged plaid and flannel with the Boxercraft Blackwatch, Stewart and Campell Flannel Boxers— great style and great comfort.

Another favorite was the Jersey Knit Boxer, in black or gray. For us, this was a great combination of jersey comfort and stylish-looking "hang."

Classic Briefs

The pros: They provide good support, especially for exercising and showing off a good gluteus. (Your gluts not lookin’ so hot these days? Check out Want a Great Butt? The Sharp Rearview.)

The cons: Tight fitting, dull, and not very flattering to most builds. Lines can show through thin pants.

Also worthy of note is the fact that wearing underwear that keeps the family jewels so close to the heat of your body may hinder production of sperm. Is this a form of birth control? No way. However, for those SharpMen in the reproductive game, looser-fitting underwear may be your best bet. Also worthy of note is the fact that your chances of conceiving are much better if your SharpWoman isn’t appalled at your underwear selection. According to our survey, if you’re a briefs guy, you better find a briefs girl — otherwise, Sports Center is about the only late-night action you may see.

What SharpMen say: "I wear briefs, although I think women prefer boxers. Don’t tell anyone I helped you." "I wear a banana hammock when I work out (my boys need the support)."

What SharpWomen say: "I love it when my boyfriend wears his tighty-whiteys…his package looks incredibly sexy. It makes me just want to grab him." "Boxer-briefs seem to get all the sexy advertising, but I think it takes a real man to don briefs." "Briefs are never flattering, regardless of the build." "Tighty-whiteys are the biggest disappointment when a man drops his drawers. They say he doesn’t care about how he looks underneath his trousers."

SharpMan-Approved versions: For those of us still devoted to the classic brief, our SharpMan testing called for us to find traditional briefs that looked — well — better to all those SharpWomen who scoffed at our need for comfort.
Rips Crew Brief

We came out with several styles that answer the call for comfort and support, while providing a bit more for SharpWomen to look at. The Rips Crew Brief turned out to be our hands-down favorite. It’s a white brief with a black band that looks cool, while still being a snug enough fit to keep all the essentials in order.

Another favorite was the Rips Drawstring Brief, designed to look like a pair of drawstring gym shorts that are still snug enough to hold the goods where they should be. Super-style for the ladies, great fit for us guys.

For the athletes among us, it was all about the 2xist Sport Brief, a higher-cut version that holds front and back where they should be, with a cool band around the top.

Finally, for the value-conscious guys still looking to please the ladies, we chose the Chereskin Basic Brief — good fit, good feel, nice-looking design and quality. Available in a three-pack.

In the check-out-what-he’s-got department, we couldn’t resist testing out the Contour Brief. These things could make a baby look good! Plus the quality cotton, non-dweeby design and great price don’t hurt either. Best yet, this style is sold in economical three-packs and six-packs. When ordering, please use "SharpMan" in the source code field.

For the more adventurous SharpMen (or SharpWomen) among us, the style above also comes in a mesh version, the Mesh Contour Brief. Also available in value packs. When ordering, please use "SharpMan" in the source code field.


The pros: Style and support. The most universally flattering cut of underwear.

The cons: Complaints of the tight-fitting legs riding up the thigh and bunching under the pants.

Thanks to designers like Calvin Klein and Tommy Hilfiger, boxer-briefs have burst on the scene as a "best-of-both-worlds" solution for many SharpMen. The newest fad in men’s wear, the boxer-brief unites its ancestors in the most harmonious combo since Reese’s crossed chocolate and peanut butter.

What SharpMen say: "They feel great and women seem to like them." "They’re all I wear now." "I don’t like the way they ride up my leg."

What SharpWomen say: "Boxer—briefs are the sexiest, regardless of a man’s build. You know what you’re in for, and yet they cover up!" "It drives me crazy to see the band poking out over a guy’s belt line. I just want to snap it." "They’re a perfect combination of sexy and practical."

SharpMan-Approved versions: In our search for the ultimate boxer briefs, we went looking for quality and the bottom line. Many companies make great-looking versions of boxer-briefs; our mission was to find high-quality briefs below the usual $18-25 mark. Where higher-priced versions were considered, we "let them in" based on an unusual style not found at the local department store. We also found a number of styles designed to enhance the "contour" of the SharpMan wearing them — these were a big hit. Check ‘em out:

In the traditional-looking boxer-briefs, we chose Joe Boxer’s Button Fly Boxer-Brief. Great quality, cool design, plus the button-fly aspect makes the brief a bit more cool and unusual. Nice breathing room inside, while still presenting a nice, overall look from the outside. Finally, unlike many boxer-briefs, we found the leg length slightly shorter — less fabric to bunch up under your slacks.
Mesh Contour Boxer

We also liked the Rips Squarecut Boxer Brief mostly because it was comfortable and unbelievably popular with the SharpWomen polled. Most reactions sounded like this: "mmmmm." This, combined with the high quality of the Rips product line was enough for us to include it. If you’ve ever wanted to look like an underwear model, here’s your chance.

In the "cool" department, we choose the Unico Fitted Boxer, in black, white or dark gray with a white band. Nice quality cotton combined with a shorter boxer style makes this boxer a comfortable choice that will definitely be popular with the crowd you’re trying to please. This, combined with great fit and great support, makes this brief a winner. When ordering, please use "SharpMan" in the source code field.

Finally, our absolute favorite choice for an awesome look and feel. The Mesh Contour Boxer is made of, you guessed it, mesh, and has a great low price (also comes in a three-pack) and a totally designer look. Best yet, it’s made to enhance what you got and add to the stuff you don’t. Our top choice, hands-down. When ordering, please use "SharpMan" in the source code field.


The pros: You’ll fit right in on the French Riviera.

The cons: Everyone will point and laugh at you. Just say no. The only thing everyone agreed on was bikini briefs are a definite deal breaker.

What the SharpMen say: "I wear everything but the bikinis." "No way. You couldn’t pay me to wear those things."

What SharpWomen say: "I dated a French man for a while, and though I could overcome the language barrier, I never got over the bikini underwear."
Ultimate French Contour Brief

SharpMan-Approved versions: Sure, after reviews like that, it was tough for us to begin looking for a "SharpMan-Approved" version of a style no SharpMan or SharpWoman seemed to approve of, but then again, our poll wasn’t anonymous. After all, some athletes swear by this style, and may SharpWomen are happy to stuff these drawers full of singles at those bachelorette parties they all seem to love so much.

Our first pick of this category is conservative — even die-hard boxer fans may take a second look (just picture it in white or black). The Ultimate French Contour Brief is designed to look good, despite its name — and make you look like you’re got it all, despite what you got. Great comfort, great quality cotton. When ordering, please use "SharpMan" in the source code field.

We also chose the Shape Enhancer Brief, a high-comfort design aimed at accentuating the positives at a pretty good designer price. When ordering, please use "SharpMan" in the source code field.

Technically in the "brief" section, but showing enough leg to make it into this one was the Gladiator Brief. Pretty cool design — kind of like a bathing suit — in high-quality cotton and spandex, sold in three- and six-packs. When ordering, please use "SharpMan" in the source code field.

In Conclusion

So, what have we learned? Big or skinny SharpMen are better off in boxers, and as one SharpWoman put it, "Men with great bods can wear whatever they want."

Surprise, surprise.

The most important thing our survey discovered is that no matter what kind of underwear you choose, chances are the current or future SharpWoman in your life probably cares more about it than you do, and as any truly Sharp man can tell you, "Give the lady what she wants and no one gets hurt."

This article last updated on Wednesday 13th October 2010
As you like 'Men’s Underwear 101: A Brief Review of Boxers, Bikinis, etc.' you may also like following Sharp Dating articles . . .

From Breeches to Boxers: The History of Men's Underwear

You slip them on every day, but have you ever stopped to think where they came from? We don’t mean Bloomingdale’s or Marshall Field’s. Those ultra-comfy boxers or briefs —

Great Gifts for Your SharpWoman

It’s that time of year again. Yup, time to break out the old (soon-to-be-much-slimmer) wallet and join the droves of other bedraggled SharpMen prowling the stores for holiday

How to Buy a Great Pair of Shoes

Buying shoes always seems like a no-brainer. You go in, pick a style, and come out with an extra pair and less money in your wallet. Is that it? Hardly. Whether you’re

Tailor-Made Suits for Ultimate Style

Off-the-rack and designer suits can be stylish and of good quality. In fact, off-the-rack suits are perfect for most occasions. But there may be a time when you want a look

Get rid of stuff you don’t wear

Is your closet full of clothing you never wear? Are you saving a "lucky" T-shirt from every event you ever attended? Time to clean up and clean out. Every guy’s got a closet

Why Cool Pens = Women

In today’s technology-driven world, where the latest wireless gadget is supposed to "define the man," it’s easy to lose site of cool "gadgets" that always have. Consider the

Assessing the Value and Quality of a Tie

Why buy a more expensive tie? A SharpMan does not need a closet full of ties. Particularly in today’s world of increasing business casual, a few timeless, high-quality ties

Wedding I DOs for the SharpMan Guest

At work, at home and even in the classroom, it seems as though traditions and customs have become a thing of the past. But rest assured there’s one place where customs and