The Most Comfortable Trunks for Men 2024

Underwear’s most highly sought-after characteristic: Comfort.

This installment in our Most Comfortable Underwear Series is all about the most comfortable trunk underwear for men.

And when we use the term comfortable, you might be wondering what level of comfort we’re actually talking about here.

To make our Most Comfortable List, we’re talking about underwear that fits like a second skin.

Underwear that you’re actually happy to put on and then forget you’re even wearing levels of comfort.

Now, of course, we know that men come in all different shapes and sizes, not to mention have different preferences when it comes to support, fabric type, etc.

For this reason, it’s difficult to promise that each pair of trunks listed here is going to fit and feel perfect to you.

So, while there may be some scrolling and a little trial and error involved, we’re confident that you’ll find a pair of incredibly comfortable trunks on this list that fit just right and become your new favorites.

Go ahead, grab a pair, and step into your most comfortable trunks.

And for even more great options, check out the best trunks available on Amazon.

How We Make Our Picks for Most Comfortable Trunks

Look, we get it.

Determining what makes a great pair of underwear can be a pretty subjective thing.

So, how do we decide which trunks make our list for the most comfortable? 

We tested a wide range of underwear brands and put them through the rigors of daily life and active situations.

And, as a result, we can say for certain that 3 specific qualities make for an objectively more comfortable underwear experience.

Reviewing trunks from leading men's underwear brands.

1. Premium fabric blends that support active bodies.

Your body moves in a wide range of motion throughout the day, and it doesn’t take much for it to overheat or experience distracting irritation.

We prioritized options with naturally soft and breathable fabrics that add a touch of stretch (spandex, elastane, etc.).

We’ve also found that while you may end up paying a little more for premium fabric, it tends to stay in better shape for longer.

2. Comfortable waistbands that stay in place. 

It’s not enough to just have a comfy waistband, and it’s not enough to have a waistband that’s only focused on staying put.

Comfort and function need to work hand in hand here.

We went with trunks that paid extra attention to this crucial detail.

3. Ergonomic features that prioritize the male anatomy.

It’s crazy how many men’s underwear options don’t seem to properly consider the male anatomy in their design.

After all, you’re not a retail display mannequin yet some brands seem to design their underwear that way.

Trunks that pay attention to the human body tend to layer better under clothing, cut down on adjustments and bunching, and help you forget it’s even there.

Testing the Calvin Klein Black Micro Trunks.

Here, you can see us testing one of our top picks, the Calvin Klein Black Micro Trunks, which features all three of these key qualities. 

1. Fabric: Incredibly silky microfiber with added elastane for comfortable stretch.

2. Waistband: Soft and flexible logo waistband with a classic low-rise fit

3. Features: A contour seam pouch that’s both comfy and supportive. 

You can also check out our in-depth product guide of the Calvin Klein Black Micro Trunks over on our YouTube Channel here.

Note: Featured products are independently selected and reviewed by The Underwear Review. If you purchase through our links, we may earn commission.

1. Tommy John Second Skin Trunks

The Tommy John Second Skin Trunks feature a micro modal spandex fabric blend that’s extra soft and has a non-pilling design. These trunks have a stay-put waistband that doesn’t pinch and are also available in a shorter 2-inch square cut trunk.

Shop at Tommy John: Tommy John Second Skin Trunks (4-Inch)

Shop at Tommy John: Tommy John Second Skin Trunks (2-Inch)

Tommy John’s Second Skin Trunks have a gentle contour pouch that doesn’t require adjustment. These trunks feature a signature horizontal fly and come with a best pair guarantee (refund or exchange if unsatisfied).

Our Favorite Feature: Soft and non-pilling micro modal spandex fabric.

2. Tommy John Apollo Trunks

The Tommy John Apollo Trunks are built as a perfect everyday wear option with an incredibly soft feel. These trunks feature a durable construction with stretch and recovery, as well as drirelease technology that wicks moisture and is extra breathable.

Shop at Tommy John: Tommy John Apollo Trunks

Tommy John’s Apollo Trunks feature a stay-put waistband that sits comfortably and never rolls. These trunks have a contour pouch that softly supports and a signature quick draw horizontal fly.

Our Favorite Feature: Extra breathable drirelease in incredibly soft feel.

3. Mack Weldon AIRKNITx HD Trunks

The Mack Weldon AIRKNITx HD Trunks feature extra breathable AIRKNITx fabric in a performance design with targeted cool zones to keep you cool and comfortable. These trunks come in limited-edition HD for enhanced colors and moisture-wicking abilities.

Shop at Mack Weldon: Mack Weldon AIRKNITx HD Trunks

Mack Weldon’s AIRKNITx HD Trunks have moisture-wicking and odor-fighting properties to help you stay dry and feel fresh all day. These trunks have a supportive flyless pouch, stay-put legs, and a comfortable no-roll waistband.

Our Favorite Feature: Extra breathable AIRKNITx fabric.

4. Mack Weldon Silver HD Trunks

The Mack Weldon Silver HD Trunks feature signature limited edition Silver Underwear, which is a silky micro modal fabric with antimicrobial Ionic+ silver. These trunks have an extra soft and smooth feel with lasting freshness.

Shop at Mack Weldon: Mack Weldon Silver HD Trunks

Mack Weldon’s Silver HD Trunks feature a unique double-sided fly for convenience and a no-roll waistband. These trunks use mesh cool zones for extra breathability and comfort.

Our Favorite Feature: Signature antimicrobial Ionic+ silver.

5. Mack Weldon 18-Hour Jersey Trunks

The Mack Weldon 18-Hour Jersey Trunks feature a signature 18-hour jersey fabric that’s incredibly soft and designed for everyday wear. These trunks utilize mesh cool zones for breathability and added stretch for mobility.

Shop at Mack Weldon: Mack Weldon 18-Hour Jersey Trunks

Mack Weldon’s 18-Hour Jersey Trunks have a comfortable and tagless no-roll waistband, as well as a stay-put leg design to reduce bunching and shifting. These trunks are available in multiple colors and patterns.

Our Favorite Feature: Extra soft signature 18-hour jersey fabric.

6. Calvin Klein Black Micro Low Rise Trunks

The Calvin Klein Black Micro Low Rise Trunks feature an incredibly silky microfiber fabric with added soft stretch for the perfect everyday all-day option. These trunks sport a comfortable contoured pouch for added support.

Shop at Calvin Klein: CK Black Micro Low Rise Trunks

Calvin Klein’s Black Micro Low Rise Trunks utilize a classic low-rise trunk silhouette with a flexible fit and great shape retention. These trunks have a soft and flexible logo waistband that stays put and are available in several color options.

Our Favorite Feature: Incredibly silky microfiber fabric with soft stretch.

7. Calvin Klein 1996 Micro Low Rise Trunks

The Calvin Klein 1996 Micro Low Rise Trunks feature a silky soft microfiber blend fabric with a stretchy fit for maximum comfort. These trunks have a sleek silhouette with a seamless back for an extra smooth feel.

Shop at Calvin Klein: CK 1996 Micro Low Rise Trunks 

Calvin Klein’s 1996 Micro Low Rise Trunks have a contoured seam pouch for support and a classic logo waistband that retains its shape. These trunks feature the iconic and stylish CK monogram framed in a box.

Our Favorite Feature: Silky soft and stretchy microfiber fabric.

8. David Archy MicroModal Lightweight Trunks

The David Archy MicroModal Trunks feature extra soft MicroModal natural fibers in a sleek and classic design. These trunks prioritize comfort with a 3D pouch and a highly elastic waistband.

Shop at David Archy: David Archy MicroModal Trunks

15% Off Discount Code: TheUR

David Archy’s MicroModal Trunks utilize an innovative 4-needle and 6-thread sewing technique with smooth inner seams to reduce friction. These trunks have seamless fitting tech for a relaxed feel and stay-fresh antibacterial properties.

Our Favorite Feature: Soft micro modal fabric in sleek and smooth fit.

9. David Archy Bamboo Rayon Trunks

The David Archy Bamboo Rayon Trunks feature an extra soft and smooth bamboo rayon fabric with a 3D contour pouch for comfortable support. These trunks utilize a soft and wide stay-put waistband, as well as flat-locked stitching for a seamless feel.

Shop at David Archy: David Archy Bamboo Rayon Trunks

15% Off Discount Code: TheUR

David Archy’s Bamboo Rayon Trunks have a bamboo rayon and spandex fabric blend that’s lightweight, breathable, and naturally moisture-wicking. These trunks feature a one-piece cut in the back to avoid wedgies and adjustments.

Our Favorite Feature: Extra soft bamboo rayon fabric with 3D contour pouch.

10. Separatec Bamboo Rayon Dual Pouch Trunks

The Separatec Bamboo Rayon Dual Pouch Trunks feature patented dual pouch technology that provides separation for exceptional comfort and support. These trunks utilize silky soft bamboo rayon fabric that’s naturally breathable and moisture-wicking.

Shop at Separatec: Separatec Bamboo Rayon Dual Pouch Trunks 

15% Off Discount Code: TheUR

Separatec’s Bamboo Rayon Dual Pouch Trunks have a non-irritation and stay-put leg design for comfortable all-day wear. These trunks utilize a touch of spandex stretch for a perfect fit and a soft and stylish waistband.

Our Favorite Feature: Patented dual pouch for comfort and support.

11. Skims Stretch Trunks

The Skims Stretch Trunks feature an ultra-soft modal and elastane fabric blend that’s cool to the touch and comfortably stretches to your body. These trunks provide a clean and seamless fit that’s invisible under clothing.

Shop at Skims: Skims Stretch Trunks

Skims’ Stretch Trunks sport an enhanced 2-ply pouch for exceptional support and a velvety-smooth stay-put waistband. These trunks are available in several color options and come in a convenient 3-pack.

Our Favorite Feature: Ultra-soft and cool-to-the-touch fabric in seamless fit.

12. 2(X)IST Sliq Trunks

The 2(X)IST Sliq Trunks feature a sleek low-rise silhouette in a premium fabric that’s supportive, soft, and flexible. These trunks have an ultra-smooth design with a seamless back for a perfect fit under clothing.

Shop at 2(X)IST: 2(X)IST Sliq Trunks

2(X)IST’s Sliq Trunks have a supportive contour pouch, comfortable elastic waistband, and compression stitching on the gusset. These trunks are available in a wide variety of stylish colors and prints.

Our Favorite Feature: Sleek silhouette with soft and smooth fabric.

13. 2(X)IST Dream Low-Rise Trunks

The 2(X)IST Dream Low-Rise Trunks feature premium fabric with added stretch for comfort and mobility, as well as a contour pouch that boosts and supports. Just as the name implies, these trunks fit and feel like a dream.

Shop at 2(X)IST: 2(X)IST Dream Low-Rise Trunks

2(X)IST’s Dream Low-Rise Trunks utilize an incredibly soft pima cotton and modal fabric blend that’s breathable and lightweight. These trunks have a tagless microfiber waistband for extra comfort and are ideal for lounging and recharging.

Our Favorite Feature: Incredibly soft pima cotton and modal fabric blend.

14. Gregg Homme Room-Max Trunks

The Gregg Homme Room-Max Trunks have a unique inner front panel construction that provides a gentle lift for improved freedom and slight volume enhancement. These trunks are crafted with a soft hyper stretch microfiber and stable one-inch waistband.

Shop at HisRoom: Gregg Homme Room-Max Trunks

Gregg Homme’s Room-Max Trunks have a silky smooth nylon spandex blend that offers great stretch and breathability for all-day wear. These trunks are available in several great color options.

Our Favorite Feature: Room-Max front pouch for freedom and enhancement.

15. Tommy Hilfiger Everyday Microfiber Trunks

The Tommy Hilfiger Everyday Microfiber Trunks are a great blend of comfort and function with four-way stretch and brushed fabric for a comfortable feel. These trunks have a sleek elastic waistband that provides an exceptional fit.

Shop at Tommy Hilfiger: Tommy Hilfiger Everyday Microfiber Trunks 

Available on Amazon: Tommy Hilfiger Everyday Microfiber Trunks 

Tommy Hilfiger’s Everyday Microfiber Trunks feature a comfortable polyester and elastane fabric blend with a moisture-wicking finish to keep you dry. As their name suggests, these trunks are a great option for everyday wear.

Our Favorite Feature: Soft brushed fabric in sleek fit.

What to Look for When Purchasing Trunk Underwear

If you’ve spent any time shopping for trunk underwear these days, you’ve likely noticed that there’s no shortage of options available to you.

In fact, there’s a wide variety of fabric choices, garment features, specialty designs, and more.

All the options can be a bit overwhelming. So, if you’re looking for a high-quality pair of trunk underwear, there are a few characteristics you’ll want to keep an eye out for when browsing.

As you’re probably aware, trunks have a shorter leg length than boxer briefs that presents as its signature square-like cut.

Trunks also tend to sit lower on the waist than boxer briefs, otherwise known as a low-rise fit.

Of course, different underwear brands will go about this in different ways.

But the brands that give extra focus to essential characteristics like fabric type, seam detailing, and waistband fit tend to be brands that you’ll come back to time and again.

Look for premium fabrics that prioritize softness, breathability, and moisture-wicking.

These qualities will ensure a comfortable and distraction-free fit that works great for all-day wear.

Also, don’t forget about finding a roomy fit in the front for your anatomy. Look for mention of a contour pouch that provides comfortable support and no-adjustment fits.

And remember that there’s nothing quite as important as the waistband when it comes to making or breaking a pair of underwear.

Look for trunks that emphasize a comfortable and secure waistband that stays put without pinching.

These features tend to make for a great blend of comfort, support, and durability that’s perfect for everyday wear and will last a long time.

If you’re looking to add some great trunks to your rotation, you’ll also want to check out our top picks for the best trunks available on Amazon.

And if you’re all about comfort when it comes to your underwear, be sure to check out the rest of our Most Comfortable Series.