5 Best Fitting Men’s Underwear in 2019

It doesn't take a genius to see why underwear is the one item of clothing they won't let you try out. Just the idea of wearing undies somebody else has worn is enough to give you a rash.

But if you ignore for a moment the general grossness of the proposition, it’s kind of strange. A correct fit is important for all clothes, but maybe most important of all for underwear. You need to be comfortable down there.

Nothing ruins an otherwise good day like a pair of boxers riding up toward your chin. Or cheap fabric that chafes your inner thighs. Or a waistband that digs in to all the wrong places. Life is too short for ill-fitting underwear.

So with that in mind, check out the best fitting men’s underwear on the market today. This way, you can shop online with confidence and won’t even have to show your face in an underwear store. You’re welcome.

What To Look For When Choosing The Best Fitting Men’s Underwear

We are all different. That’s part of what makes underwear shopping such a dizzying thrill. Men come in all shapes and sizes, especially below the waist. And personal preference is always going to be a factor too. With that said, there are certain things you should look for when trying to choose the best fitting underwear. Things like:


As a general rule, the fewer seams a piece of underwear has, the more comfortable it's going to be. Seams can cause irritation and, in the case of poorly fitting underwear, can dig into your skin. However, if you choose a pair of underwear with flatlock seams, you won't need to worry. These seams are designed to lie flat against your body and be almost impossible to feel.

  • Our patented KeyHole Comfort Technology creates the best and most comfortable underwear experience for men. The 3-dimensional internal pouch provides both unparalleled support and comfort. By cradling the male package, our KeyHole Comfort Technology allows absolute freedom and eliminates the need for any shifting and adjusting.
  • MyPakage garments use a special blend of Modal (95%) and Spandex (5%). This fabric is 50% more moisture absorbent than Cotton while still being incredibly breathable. By using some of the most progressive fabric combinations, your MyPakage underwear will stay wrinkle-free, resistant to pilling, and remaining incredibly soft.
  • Although it often goes unnoticed, the pucker panel is one of the key ingredients in our comfort combination. The panel of fabric allows all critical seams to be removed from your key comfort areas. This ensures you are not sitting on or rubbing against, any seams or stitching.
  • Features a 1-inch logo detailed no-roll waistband with comfortable, high stretch elastic, which comes in a variety of colours. The seamless tag covers waistband stitching to ensure maximum comfort.
  • Hand stitched zones with expanding seams ensures a tailored, ergonomic fit for all body types. While flat locked stitching creates a virtually seamless feel in sensitive areas.


A lot of men's underwear is sized in meaningless classifications such as small, medium, large and so on. Unfortunately, there's no secret council of underwear makers to define what large actually means. Sizes vary from brand to brand, which is why a lot of guys will stick fanatically to a particular brand of underwear once they've found one that works for them. It may require some trial and error. But don't give up. Somewhere out there, the perfect pair of underwear for you is just waiting to be discovered.

  • Patented BallPark Pouch for friction-free support - Designed for contact-free support, this 3D hammock-shaped pouch keeps everything in place
  • Three-D Fit with 9-Panel construction - 3D shaping around glutes, thighs, quads, and hamstrings
  • Non-chafing Flat Out Seams - The softer side of the seam is placed inward, for no-chafe comfort
  • 1 3/8" anti-roll moisture-wicking, twisted-yarn heather jacquard waistband
  • 5" inseam, no fly


We all know those guys who've been getting the same haircut since they were 14 years old. Often, men are more loyal to a particular style that they're used to than women are. It ain't broke, so why fix it? But there's more to your choice of underwear than personal preference. Anyone who's tried going for a run in baggy boxers knows that not every kind of underwear is suitable for every occasion. Consider mixing up different styles of underwear to find the one that best fits your needs. After all, your underwear isn't your wife; it's okay to have more than one.


Jeff Bezos probably wears undies made of solid platinum harvested from the moon. But for the rest of us, price is always going to be an issue. A well-fitting pair of underwear is definitely worth spending money on, but at the same time, you need to stick to a budget that works for you. While cheap underwear can often prove to be a bad investment, there is some good stuff out there at a reasonable price. You just have to find it.

  • Cotton-rich ComfortSoft knit feels good against your skin
  • That's why you'll want to stock up on these Hanes Men's Boxers
  • Fabric-wrapped ComfortSoft waistband stretches for non-binding fit
  • TAGLESS boxers for a comfortable

Top 5 Best Fitting Underwear for Men

1. Saxx Vibe Boxer Modern Fit

Saxx Underwear Mens Vibe Boxer-Brief

Pro: Drawers don’t come any more comfy than this.
Con: Comfort doesn't come cheap. Expect to pay over $30 per pair.

Form fitting: They may be called boxers, but the formfitting elasticated fabric of the Saxx Vibe makes them feel more like a boxer brief. Modern fit apparently is marketing speak for tight – but don't worry.

The rayon spandex blend of the shorts means that they conform to virtually any body. If the mark of a good pair of underwear is that you forget you're wearing it, the Saxx Vibe definitely fit the bill.

The BallPark pouch (yes, that's really what it's called) provides excellent support for the boys while you go about your day. In fact, this underwear could quickly become your go-to brand, suitable for a long day at work or a session at the gym. The no-roll waistband and breathable fabrics mean that you can work up a sweat without worrying about becoming uncomfortable.

About the only bad thing to say about the Saxx Vibe is the price. But once you try a pair of these magnificent beasts, you may find you're unable to settle for anything less.

2. Calvin Klein Modern Cotton Stretch Boxer Briefs

Calvin Klein Modern Cotton Stretch Boxer Briefs

Pro: No need for special care here. These boxers last and last.
Con: Sizing can be hit and miss, with this brand generally running smaller than average.

A familiar brand you can trust: Channel your inner Marty McFly with these boxer briefs from Calvin Klein. CK is one of the oldest names in the underwear game, so you can be sure that these boxer briefs come with a pedigree.

But there’s more going on here than mere brand recognition. Made from 95% cotton and 5% elastane, these shorts provide just the right amount of stretch for a good fit. The fabric is breathable and soft, and the shorts are loose enough to be comfortable while still close-fitting enough to wear under tight pants if that’s what you’re into.

Best of all, if you're the type that is hard on your underwear, these CK boxer briefs seem to last forever. While there are cheaper options out there, you may find that the longevity of this underwear makes them great value.

Since Calvin Klein has been around forever, chances are good you've already tried some of their products. In that case, you may already be aware that CK sizes tend to run a little smaller than average. If you usually wear a medium, you may need to step up to a large for this brand.

3. MyPackage Weekday Boxer Briefs

MyPackage Weekday Boxer Briefs

Pro: Extremely comfortable, with package cradling performance you won’t believe.
Con: These briefs don’t stand up to heavy use.

Protect the jewels: If you're going to call your underwear brand MyPackage, you're inviting attention on one particular aspect of the male underwear-wearing experience. So let's talk about nuts. No man wants to be without them, but let's face it: they're not the most convenient body part sometimes. Supersensitive, inconveniently placed and prone to changes in positioning, male genitals make underwear fitting a challenge.

MyPackage provides unsurpassed support for your boys. The internal pouch keeps everything nicely cradled without feeling claustrophobic. You'll never have to surreptitiously adjust yourself while wearing a pair of these boxers.

And it's not all about balls. This comfortable underwear provides a good fit around thighs, waist, and hips. The modal fabric isn't as long-lasting as some other options, but it does provide excellent comfort and breathability. And the manufacturers have worked hard to design these briefs so that there are no seams in any of your crucial comfort areas. Plus, what seams there are are flatlocked so that they sit comfortably against the skin without rubbing.

As the name implies, these are great boxers for everyday wear. The only downside is that they may not last as long as some other brands. At around $20 a pair, you may feel the shorts are comfortable enough to be worth replacing.

4. Hanes Red Label Comfortwear Knit Boxer

Hanes Red Label Comfortwear Knit Boxer

Pro: Decent quality at a low price.
Con: Lack of durability means you may have to replace these frequently.

Don’t break the bank: High-tech, space-age underwear may make you feel like a visitor from the distant future. But sometimes, all these lab-created fabrics and NASA engineering can seem like overkill. And maybe you have better things to spend your money on than underwear. That plastic banana carrying case or rubber scrotum for your truck isn't going to pay for itself.

If you just want some simple, cheap underwear that is nevertheless high enough quality that you won’t have to be constantly fussing with it, Hanes Red Label could be the answer to your cheapskate prayers. The soft cotton fabric and relaxed fit make them comfortable for all body types.

And while they may not look like something Superman would wear under his costume, they still have enough style that your significant other won’t laugh you out of the bedroom the minute you drop your pants. The flexible waistband makes for a comfortable fit, too. And at around $20 for a pack of five, what’s not to love?

Of course, something has to give. This underwear is great while it lasts, but it doesn't last as long as more expensive brands. In particular, the elastic in the waistband is prone to sagging, leading to a high risk of plumber's crack every time you bend over. Still, at these prices, you can afford to replace your underwear regularly.

5. Under Armor Men’s Original Series 6” Boxerjock

Under Armour The Original 6 inch Boxerjock Boxer Briefs

Pro: Great underwear for an active lifestyle.
Con: After a few hours of exercise, they can start to sag.

Unleash your inner athlete: If you play a lot of sports or workout frequently, you'll know that having well-fitting underwear is a crucial component to performing at your best. Given Under Armor's presence in this market, it's not surprising that they have produced a line of workout underwear.

As you would expect for boxers designed to be worn during exercise, the fabric of this underwear has excellent moisture wicking abilities. The material is lightweight and provides a close fit so that you can keep moving. This underwear weighs next to nothing, so you won't be able to use it as an excuse when you're not keeping up with your teammates.

This is some of the best underwear out there to use while working out. However, if you’re a fan of long sessions, you may find that even these specially designed underwear can start to sag. That doesn’t mean they’re not a great option for the more active among us. But it’s something you need to be aware of before making a purchase decision.

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