The Best Underwear For Well Endowed Men

While a lot of men might wish they were well endowed, there are some downsides to having a big package that you might not realize. One of the most common of which is buying underwear.

You see, most underwear is made for the masses. So they're made for guys with an average size penis. When you're larger than average, you're forced to deal with overstuffing and cramping yourself into underwear and dealing with an obvious dick bulge.

But that doesn't have to be the case.

We've gone out and rounded up the best underwear for well endowed men. These are underwear specifically designed for guys with a big package, so you're secured and can walk around without feeling like your genitals are being strangled by your briefs.

What to Look for When Buying Underwear for Well Endowed Men

To ensure that you get the best underwear for guys with big packages, you’re going to need to consider a handful of factors. Here's the criteria we recommend.


First and foremost, you need to ensure that your underwear is going to provide you plenty of room for your junk. If your underwear is too tight, there is a good chance that you’re going to feel uncomfortable and restricted. Make sure that your underwear provides your genitals with plenty of space.

  • Andrew Christian
  • Apparel


When working out or working on the job, the seams on the underwear will rub you raw and cause chaffing. This is definitely the case for men with large units.

That's why we recommend buying seamless underwear. This will ensure that you do not have to suffer from that painful chaffing.

  • Underwear Style 10305
  • Low rise and full coverage
  • 93% nylon/ 6% spandex/ 1% polyester
  • No-fly design
  • Machine wash and dry

Comfy Fit

You’ll also want to make sure that your underwear will be able to provide you with a comfortable fit. The waistband should be able to sit around your waist at all times. The band should keep the underwear in place so they don't slide up and down when you’re moving about. At the same time, the band shouldn’t be too tight.

  • Fitted boxer brief featuring contoured pouch and two-tone logo waistband

Dry & Cool

Finally, you’re going to want to choose a pair of underwear that keeps you dry and cool all day. That means buying breathable and moisture wicking underwear.

This combination will keep your privates comfortable and cool. It'll also decrease the amount of odor down there from sweat and bacteria.

  • Lightweight, smooth HeatGear fabric & articulated mesh fly panel
  • 4-way stretch construction moves better in every direction
  • Material wicks sweat & dries really fast
  • Anti-odor technology prevents the growth of odor-causing microbes
  • Performance waistband

10 Best Underwear for Well Endowed Men

Now that you know what to look for in a good pair of underwear, let's get into the nitty gritty. Here are our picks for the 10 best underwear for well endowed men:

1. Andrew Christian Men’s Fly Tagless Boxer


Pro: Moves with you
Con: Limited colorways

Contour Fly Pouch: Any man knows there is nothing worse than having to deal with a tight pouch in a pair of underwear. Not only is this restrictive, but it is extremely uncomfortable. Thanks to the contour fly pouch, this is something that you don’t have to worry about when you invest in the Andrew Christian Men’s Fly Tagless Boxers.

The slimming elastic waistband doesn’t hurt the comfort either and it ensures that the underwear stays in place at all times. When you combine all these features with the soft, lightweight stretch cotton, you are truly looking at one of the most comfortable pair of underwear you will ever find.

With all of the extra room in the pouch, you will literally always have the room you need to prevent unwanted chaffing.

2. Jockey’s Men’s Seamfree Boxer Briefs


Pro: Everyday comfort
Con: Might be a little too thin for some guys

Stretch Design Provides Extra Comfort: There is nothing that feels better than a pair of underwear that fits like a glove. Not only do they provide the comfort you need, but also they might even make you feel like a new man.

This is something the Jockey’s Men’s Seamfree Boxer Briefs can provide you with. The super-soft microfiber design doesn’t hurt the comfort either. When you combine this with the extended mid-thigh design, you will truly stay comfortable throughout the entirety of the day while wearing this underwear.

The machine washable design of the underwear makes maintenance easier than ever, as you can just throw the underwear in the washer and go about your daily business.

3. 2(x)ist Men’s Electric No-Show Brief


Pro: Provides support, boost and comfort
Con: Must wash on delicate and be careful with drying

Waistband Fits Two Inches Below The Hips: There is nothing worse than an uncomfortable pair of underwear that rides up or down. Fortunately, that is something the everyday man doesn’t have to worry about when he invests in the 2(x)ist Men’s Electric No-Show Briefs.

The innovative waistband ensures that the underwear always perfectly sits two inches below the hips. In addition to this, the waistband is a no-show design, so you never have to worry about underwear lines.

The 89% nylon and 11% spandex design not only contribute to the comfort, but these materials really make the underwear stretchable and flexible, which can come in handy in a variety of situations.

4. Calvin Klein Men’s Iron Strength Micro Boxer Brief


Pro: Excellent style options
Con: Can lose their shape quickly

Great style and comfort: The Calvin Klein Men’s Iron Strength Micro Boxer Brief is a good choice for men with large units. It is made with 91% nylon and 9% elastane. This ensures that you’re going to have plenty of room for your junk. Plus, this boxer brief is equipped with a contoured pouch. It will hold everything comfortably.

The two-tone logo waistband is also very comfortable. Plus, this underwear is available in tons of different colors. You’ll have no trouble finding one that suits your specific style.

5. Under Armour Men’s Original Series 3” Boxerjock


Pro: Powerful moisture wicking technology
Con: Pricey

No Foul Odors: Under Armour is one of the most trusted brands in men’s clothing. This is why their Boxerjock has become so popular over the past few years.

This product is made with 90% polyester and 10% elastane. This combination ensures that this underwear is going to last a lifetime.

Plus, they feature a 4-way stretch construction. This means that the underwear is going to move with your body. Thanks to the anti-odor technology, you can rest assured knowing that you’re going to remain comfortable and fresh throughout the day. Throw in the moisture wicking material and you’ll never have to worry about foul odors.

6. MyPakage Men’s Weekday Boxer Brief


Pro: Tons of colorways
Con: Irregular sizing

3 Dimensional Pouch: The MyPakage Boxer Brief is designed to support the male unit at all times. After all, it is equipped with a 3-dimensional internal pouch. This pouch is doing to provide the user with exceptional support and comfort. This will provide you with the maximum freedom, while also ensuring that you do not need to shift or adjust your package at any point in time.

This underwear is made with 95% modal and 5% spandex. This makes is very moisture absorbent. You will remain dry and you won’t have to wait long for this underwear to dry.

7. Naked Men’s Active Boxer Brief


Pro: Great for active guys
Con: Can ride up your leg a bit

Move With The Wearer: This underwear is made with 85% nylon and it is made in the United States. It is also machine washable, so you won’t have to jump through hoops to get them clean. They’re designed for athletic individuals who are going to be exercising.

The covered elastic waistband will keep the underwear securely around your waist at all times. This product possesses moisture wicking properties. When you sweat, you won’t have to worry too much about smelling terrible. This underwear will take care of that problem.

8. David Archy Men’s Underwear Separate Pouches


Pro: Great value for the price
Con: Pouch is a little small

Comfort And Style: The David Archy Men’s Underwear With Separate Pouches will prove to be a great investment for many men. Each underwear will come with a breathable panel. This allows air to freely flow through the underwear. This will ensure that your package remains comfortable and cool at all times.

In fact, this underwear is often used by athletes who sweat profusely during their high intensity workouts. The waistband and seams are very durable and totally comfortable. You’re never going to have to deal with pulling or scratching.

9. Emporio Armani Men’s Cotton Boxer Brief


Pro: Silhouette design
Con: Leg rides up

The Real Deal: The Emporio Armani Cotton Boxer Brief is ideal for any man who demands nothing but the best from their underwear. The underwear is a genuine product of Emporio Armani and the logo is embedded into the front of the waistband.

The cotton, spandex design ensures softness, flexibility, comfort, breathability and durability. You can toss the underwear in the washer for a thorough clean, which is always a plus. The size – true to size - range from small to extra-large.

The waistband is designed to offer support and will not ride up the back. However, the legs tend to ride up the leg a bit, which can cause some discomfort.

10. Obviously Original AnatoMAX Boxer Brief


Pro: Great leg length
Con: Doesn't have a flap (fly)

Extra-Long For Additional Support: The Obviously Original AnatoMAX Boxer Brief is ideal for men looking for a little extra support. The legs extend down the leg to just above the knee to eliminate chafing caused by friction.

The pouch is roomy and fits comfortably. While there is no fly or flap, pulling the waistband down is fairly easy and quick. The waistband reaches just above the hips to provide comfort and sex appeal. In addition to this, the logo is embedded to left, front of the waistband.

The Lycra, Lenzing MicroModal materials work together to provide all day comfort, flexibility, breathability and durability. The brief is ideal for teenagers and adults. The size – true to size - ranges from small to extra-large.

While the color options are limited, you can choose from three neutral colors, including black, gray and white. may receive a small percentage of the purchase price for items bought through our links from and other sites.