Underwear Style Guide

There are more men’s underwear styles today than ever before. The types of underwear for men, in fact, are so varied that you could wear a different cut of underwear each day of the week for months. The Underwear Expert’s men’s underwear styles guide breaks down all the types of underwear for men in an easy to read and informative format.

In our expert style guide, you’ll find men’s underwear styles and information including:

Pro’s and con’s of each of the different men’s underwear styles. Where the design of the different types of underwear for men originated. Which of the men’s underwear styles will work best for you, and why.


Perfect for:  Moderate Sports, Everyday, Dressing Up, Going Out

Most guys own a pair of briefs, and for good reason.  They’re your standard, run-of-the mill underwear and come in a variety of different rises, designs and variations.  They cover your entire backside and package, but leave the upper thigh and side of the leg exposed making them comfortable to wear under just about anything. Briefs are perfect for guys who need support or prefer to keep everything in one place but don’t care for the excess fabric found in boxer briefs, boxers or trunks; a well-made brief can even provide a little lift.  They now come in low, medium and high-rise and more than ever, more flavorful cuts that accentuate the profile and back-side.

Boxer Briefs

Perfect for:  Moderate Sports, Everyday

Wear With:  
Workout clothes and gym shorts, jeans, pants.

A true boxer brief will cover about half of your thigh, but many boxer briefs now cover about 1/3.  They offer protection from chaffing during workouts and sports, and often are made with a moderate rise on the waist.  They provide just about the same amount of support as a standard brief, and provide complete coverage.


Perfect for:  Everyday, Dressing Up, Going Out, Moderate Sports

Wear With:  Just about anything.

Trunks are quickly becoming a favorite cut for underwear among men in the know.  Why? A trunk cut is a hybrid of a brief and boxer brief without the heap of fabric (in other words, they’re boxer briefs with short legs and a square cut appearance). If you like briefs but want to try something a little different, you should try trunks.


Perfect for:  Rigorous Sports

Wear With:  Uniforms, Tight Pants, Bike Shorts.

Jockstraps offer complete frontal support and protection, but lack fabric to cover the backside.  They often lift the package up and away from the body resulting in a cooler and dryer wear than basic briefs.  The pouch is harnessed with two leg bands that fall to the sides of the glutes on the upper thigh and connect between the legs to the underside of the pouch.  Cups can be inserted into some jockstraps for protection during rigorous activities like sparring and martial arts.


Perfect for:  Everyday, Going Out

Wear With:  Tight Pants, Bike Shorts, or anything you want.

You want the lift and support of the high-quality cups you’ve grown accustomed to, but want to let it all hang out when I comes to your backside. A thong is the answer, and one that’ll make you feel sexy in your skin like no other. With a tiny, narrow strip of fabric that sits neatly between your butt cheeks, thongs famously make butts look fantastic. Because you’re working with very little fabric back there, you’ll be able to wear tight-fitting pants and shorts without any unseemly underwear lines. Plus, nothing elicits confidence quite like wearing a thong does. Wear this pair under your bike shorts, on a red-hot night out, or to turn up the heat for a sexy night in. Time to let your glutes do the talking.

Other Styles


Perfect for:  Everyday, Casual Sports, Going Out

Boxers are loose-fitting underwear with no support and more breathability than any other undergarment. Many boxer shorts have an open fly allowing the user an exit route with maximum ease. Boxer short styles are varied, spanning from the underwear you may associate with your Grandfather, to trendier, slimmer ones.

Relaxed Fit:  Boxers are traditionally slightly baggy allowing for maximum leg movement.

Wear With:  Baggier Pants, Pajamas, and shorts.

Slim Fit:  Boxer Shorts are now available in a slim fit, which provide for a loose fit, but are able to be worn under slim-cut pants.

Wear With:  Slim-cut pants, tailored dress pants, shorts.


Perfect for:  Everyday, Dressing Up, Going Out, Relaxing
Wear With:  Tight Pants, Shorts, Gym Shorts, Pajamas.

Men’s bikini bottoms, often designed without waistbands and flys, are used mostly for sunbathing and recreation unless, of course, you’re a bodybuilder, in which case they’d be used as a uniform.  With more material than a g-string and jockstrap, bikini bottoms are acceptable in public and are in many cultures preferred to traditional swim trunks.  Gaining popularity among women in the very early part of the 20th century, bikinis are a possible predecessor of the standard brief, originally sold in 1935.  Bikini’s haven’t made much progress in design for most of their history, but Sasha Baron Cohen  recently made a different take on the bikini famous: the mankini.  A sling bikini that stretches to the shoulders and back leaves the hips and butt bare and very well could be the future of swimwear.  Maybe.

Long Underwear

Perfect for:  Cold Weather, Relaxing
Wear With:  Warm weather pants.

Also known as long-johns and thermal underwear, long underwear has an interesting history.  Originally designed for women in the  19th century seeking less restricting garments, long underwear was actually part of a one-piece garment called the unionsuit.  It quickly caught on with men and was used by working men well into the twentieth century.  Popular for its thermal qualities and rear flap, otherwise known as the “access hatch,”  “drop seat,” or “firemen’s flap,” unionsuits quickly evolved into two piece garments that were worn during colder weather.  Now, a staple in men’s and women’s cold weather wardrobes, long underwear comes in form fitting and lightweight fabrics with moisture wicking properties for optimum comfort on the season’s coldest days.  And most importantly, they’re just like, really cute.

Shop Long Underwear

G-String Thongs

Perfect for:  Everyday, Relaxing, Going Out,
Wear With:  Just about anything.

Not for the faint of heart, or for the avid athlete, g-strings are pretty much as bare minimum as underwear comes.  A thin piece of fabric connects a pouch to the waistband in the back leaving the glutes fully exposed.  Perfect for an underwear fetish, or for men that like their jeans extra tight without having to worry about underwear lines or going commando, the g-string is both an erotic and sensible alternative to more… wholesome underwear.

Shop Thongs

Join the Curated Underwear Club

The men’s underwear industry has exploded with innovations and technology. The astonishing amount of different types of underwear and the variations on each of the different men’s underwear styles are too many to count. For example, briefs aren’t just briefs anymore—not at all; briefs come in low-rise, medium-rise, high-rise, multiple cuts that can expose or hide various parts of your body and a dizzying array of different pouches. 

Men’s underwear styles now also feature a never-ending list of underwear “add-ons” including:

  • Waist minimizing waistbands.
  • Butt enhancing cuts.
  • Package boosting pouches.
  • Fast-drying fabrics.
  • Anatomically correct designs.
  • …and many more.

Learning about the types of underwear for men that are available, and the various innovations in men’s underwear styles could be a daunting task. With The Underwear Expert’s men’s underwear styles guide, however, everything is spelled out for you so that you can focus on what really matters: looking good in your underwear.


Undercover Style: The Ultimate Guide to Men’s Underwear

It takes thought and effort to put a quality look together. From outerwear and accessories to the shoes on your feet, you work hard to make sure your style is ever on point. But is that all there is?

Not even close. Because if you’re not as discerning in your choice of underwear as you are in your choice of outerwear, odds are your personal aesthetic isn’t all it could be. In fact, ill-fitting or poorly-chosen underwear aren’t just uncomfortable: they can also ruin your whole look.

Never fear, though, because we’ve got you covered, literally. Read on for everything you need to know to maximize your personal style from the inside out – and the bottom up!

Briefs: A Style Standard

For a lot of us, briefs are sort of the workhorse of our wardrobes: they’re a staple of everyday wear. It’s not hard to understand why, given that a good pair of briefs will hug your body and offer support where you need it..

What makes briefs distinctive is that they don’t sacrifice form over function. Their streamlined design means that you don’t have a lot of excess fabric to worry about, bunching up or showing through pants or shorts. That makes briefs ideal for most every kind of pants, jeans, or shorts, no matter how tight or sheer.

Briefs aren’t without their drawbacks, though. Ill-fitting or worn briefs can sag and chafe, particularly at the thighs. The brief is widely known to flatter your member, but some older styles (particularly the “tight whitey”) aren’t always the sexiest. So, if you’re dressing for a hot date and looking for a style your partner can’t resist, you’re probably going to want to look beyond the basics. 

If you’re in the market for sexier alternatives to the old white cotton standards, designers like CDLP now offer full lines of well-cut briefs in sumptuous fabrics that are particularly soft to the touch and even eco-friendly. So, don’t be afraid to venture outside your comfort zone.

Boxers: A Traditional Classic

Let’s face it: boxers get a bad rap, and sometimes justifiably so. They’ve been mocked as the preferred undergarment of grandpas and men without style everywhere. But, boxers do have a lot to offer if you find the right brand and style. Boxers give full coverage and lots of, well, freedom. That means that what you might lack in frontal support, you’re going to make up for in spaciousness, breathability, and comfort, if your idea of comfort is letting it all hang loose. 

Boxers typically extend around a third to midway down the thigh and are often relatively loose-fitting at the leg. The rise varies depending on your preference, but a mid- or high-rise boxer can be ideal for showing off your assets if you’re into a more subtle display of sexiness. 

Best of all, the style options for boxers are virtually endless. Silk boxers in a solid jewel tone, for instance, can be a great choice for showing off those abs, quads, and glutes to full effect. 

Be aware, though, that if you’re planning on wearing sheer or ultra tight-fitting pants or shorts, boxers may not be your best option, as bunching and show-thru will likely be an issue. A well-fitted boxer is critical.

Boxer Briefs: A Contemporary Twist on an Old Standard

If you’re looking to enjoy the best of both worlds in your intimate apparel, then you pretty much can’t go wrong with trunks or the boxer brief, which as the name suggests, combines the best features of both boxers and briefs. 

Boxer briefs offer the streamlined cut and comfortable support of the standard brief with the long-line coverage of boxers. Boxer briefs are close fitting and typically made at least in part by lycra or a similar figure-hugging and breathable fabric. This means they don’t just conform but also cover, lift, and support both in back and in front. 

Like boxers, the legs of boxer briefs generally extend to at least mid-thigh. Unlike boxers, they cling close to the thigh, which helps to prevent bunching and show-thru in even the most body-conscious pants, jeans, or shorts. Trunks differ in that they have a shorter fit down the leg: usually by a few inches

Boxer briefs and trunks are also extremely versatile. Depending on your choice of styles and fabrics, they can be as suited for an intimate evening with your partner as they are for everyday use. 

The Under Armor, for example, features the popular Boxerjock line, offering coverage, support, comfort, and style for both work and play. Likewise, Blue Buck Underwear is revolutionizing boxer brief design with its breathable, huggable, stay-in-place designs, including organic-cotton based styles for ultimate comfort and frontal support.

Give Us That Thong, Th-Thong, Thong, Thong 

Yeah, you read that right: when it comes to styling for your most intimate moments, a good thong may well be just what you’re looking for. To be sure, thongs can be quite utilitarian. If you don’t want to have to worry about excess fabric, bunching, or show-through, well, a thong is your answer. A jock strap, for example, is about as minimalist as it gets.

Thongs typically consist of a front pouch to secure and support the family jewels, as well as a thin strip of fabric (generally elasticized) encircling the waist and between the butt to hold the front pouch in place.

As you might have guessed, if you’re looking for significant frontal support and little else, a thong could be just what you need. A good jock strap, for instance, provides both support and protection during all sorts of vigorous activities, such as when you’re practicing martial arts or participating in team sports.

But the functionality of thongs is far from their only appeal. In fact, for a lot of men, it’s the sex factor that makes thongs the go-to garment for a hot night with your partner. Thongs can be styled and ornamented in any number of ways, from tassels to chains to beads. The fabric options are virtually limitless here, from leather to silk to satin.

The Takeaway: Don’t Be Overwhelmed by Underwear Styling

Finding your signature underwear style doesn’t have to be overwhelming. Your underwear are fundamental to your entire look, and so it’s imperative to choose garments that fit not only your body, but also your aesthetic and activity level. From boxers and briefs to trunks and jockstraps, there are bound to be plenty of underwear brands, styles, and designs that make you look and feel your best. So, have no fear: try ‘em all, and see what suits you.

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