The Most Comfortable Boxer Briefs for Men 2023

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

This installment in our Most Comfortable Underwear Series is all about the most comfortable boxer briefs for men. And when we use the term comfortable, you might be wondering what level of comfort we’re 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 every pair of boxer briefs 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 boxer briefs on this list that fit just right and become your new favorites.

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

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 Boxer Briefs

The Tommy John Second Skin Boxer Briefs feature a micro modal spandex fabric blend that’s extra soft and has a non-pilling design. These boxer briefs have a stay-put waistband that doesn’t pinch and is great for everyday wear.

Shop at Tommy John: Tommy John Second Skin Boxer Briefs

Tommy John’s Second Skin Boxer Briefs have a seamless back with a comfortable contour pouch in the front. These boxer briefs feature a signature horizontal fly and come with a best pair guarantee (refund or exchange if unsatisfied).

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

2. Tommy John Apollo Boxer Briefs

The Tommy John Apollo Boxer Briefs are built as a perfect everyday wear option with an incredibly soft feel. These boxer briefs 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 Boxer Briefs

Tommy John’s Apollo Boxer Briefs feature a stay-put waistband that sits comfortably and never rolls. These boxer briefs have a contour pouch that softly supports, a signature quick draw horizontal fly, and come with a best pair guarantee.

Best Feature: Extra breathable drirelease in incredibly soft feel.

3. David Archy MicroModal Pouch Boxer Briefs

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

Shop at David Archy: David Archy MicroModal Boxer Briefs

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

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

4. David Archy Ultra Soft Boxer Briefs

The David Archy Ultra Soft Boxer Briefs feature a silky soft micro modal fabric with a 3D contour pouch for the perfect blend of room and support. These boxer briefs have durable seam construction, a stay-put waistband, and a no-ride up leg design.

Shop at David Archy: David Archy Ultra Soft Boxer Briefs

David Archy’s Ultra Soft Boxer Briefs utilize an ultra-soft micro modal and spandex fabric blend for a comfortable fit with a touch of stretch. These boxer briefs come with a free refund or exchange if you’re not completely satisfied.

Best Feature: Silky soft micro modal fabric with 3D contour pouch.

5. Mack Weldon AIRKNITx HD Boxer Briefs

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

Shop at Mack Weldon: Mack Weldon AIRKNITx HD Boxer Briefs

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

Best Feature: Extra breathable AIRKNITx fabric.

6. Mack Weldon 18-Hour Jersey Boxer Briefs

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

Shop at Mack Weldon: Mack Weldon 18-Hour Jersey Boxer Briefs

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

Best Feature: Extra soft signature 18-hour jersey fabric.

7. Calvin Klein Ultra Soft Cashmere Boxer Briefs

The Calvin Klein Ultra Soft Cashmere Boxer Briefs feature an incredibly soft and breathable modal cashmere blend. These boxer briefs have a lightweight design that’s infused with stretch for a non-restrictive fit.

Shop at Calvin Klein: CK Ultra Soft Cashmere Boxer Briefs

Calvin Klein’s Ultra Soft Cashmere Boxer Briefs feature comfortable seaming details for a clean and high-quality finish, as well as a supportive pouch and embossed logo waistband.

Best Feature: Incredibly soft modal cashmere fabric blend.

8. Calvin Klein 1996 Micro Boxer Briefs

The Calvin Klein 1996 Micro Boxer Briefs feature a silky soft microfiber blend fabric with a stretchy fit for maximum comfort. These boxer briefs have a sleek silhouette with a seamless back for an extra smooth feel.

Shop at Calvin Klein: CK 1996 Micro Boxer Briefs

Shop at Calvin Klein: CK 1996 Micro Boxer Briefs (3-Pack)

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

Best Feature: Silky soft and stretchy microfiber fabric.

9. 2(X)IST Dream Boxer Briefs

The 2(X)IST Dream Boxer Briefs 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 boxer briefs fit and feel like a dream.

Shop at 2(X)IST: 2(X)IST Dream Boxer Briefs

2(X)IST’s Dream Boxer Briefs utilize an incredibly soft pima cotton and modal fabric blend that is breathable and lightweight. These boxer briefs have a tagless microfiber waistband for extra comfort and are ideal for lounging and recharging.

Best Feature: Incredibly soft pima cotton and modal fabric blend.

10. Separatec Bamboo Rayon Dual Pouch Boxer Briefs

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

Shop at Separatec: Separatec Bamboo Rayon Dual Pouch Boxer Briefs

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

Best Feature: Patented dual pouch for comfort and support.

11. Pair of Thieves SuperFit Boxer Briefs

The Pair of Thieves SuperFit Boxer Briefs feature no-chafe seams and cooling mesh fabric that’s soft and cool-to-the-touch. These boxer briefs are designed with unique micro ventilation throughout, resulting in superior breathability.

Shop at Pair of Thieves: Pair of Thieves SuperFit Boxer Briefs

Available on Amazon: Pair of Thieves SuperFit Boxer Briefs

Pair of Theives’ SuperFit Boxer Briefs utilize a comfortable polyamide and spandex fabric blend that offers comfort and moisture-wicking ability. These boxer briefs have an extra soft waistband that’s tag-free and stays-put.

Best Feature: Cooling mesh fabric with micro vents.

12. Obviously PrimeMan Boxer Briefs

The Obviously PrimeMan Boxer Briefs have a special anatomical design that provides optimal comfort, support, and mobility. These boxer briefs are engineered with movement in mind: anatomical pouch support, breathable fabric, and additional leg length for your thighs.

Available on Amazon: Obviously PrimeMan Boxer Briefs

Obviously’s PrimeMan Boxer Briefs are crafted with soft micro modal and lycra fabric blend that is breathable, anti-bacterial, and has sweat-wicking capability. The waistband stays securely in place and is silky smooth against your skin.

Best Feature: Anatomical design maximizes comfort and support.

13. VEEAMON Ice Silk Boxer Briefs

The VEEAMON Ice Silk Boxer Briefs feature cool-to-the-touch and extra breathable ice silk fabric that has a silky gloss and smooth feel. These boxer briefs have a sleek fit that’s extra comfortable and a mesh ventilation pouch design.

Available on Amazon: VEEAMON Ice Silk Boxer Briefs

VEEAMON’s Ice Silk Boxer Briefs sport a soft and stretchy elastic waistband and no-curl seamless leg hems. These boxer briefs utilize 3D cropping with a seamless side cut and a non-irritating tagless design. Available in multiple colors.

14. Lululemon Always in Motion Boxer Briefs

The Lululemon Always in Motion Boxer Briefs feature an ergonomic design with super soft modal fabric. These boxer briefs have 4-way stretch, sweat-wicking capabilities, and are great for everyday wear and light activity.

Shop at Lululemon: Lululemon Always in Motion Boxer Briefs

Lululemon’s Always in Motion Boxer Briefs feature an ergonomic pouch designed with optimal room and support. These boxer briefs are quick-drying, available in multiple colors, and are also available in breathable mesh fabric.

Best Feature: Ergonomic design with super soft modal fabric.

15. Tommy Hilfiger Everyday Microfiber Boxer Briefs

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

Shop at Tommy Hilfiger: Tommy Hilfiger Everyday Microfiber Boxer Briefs

Available on Amazon: Tommy Hilfiger Everyday Microfiber Boxer Briefs

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

Best Feature: Soft brushed fabric in sleek fit.

16. Ergowear SLK Boxer Briefs

The Ergowear SLK Boxer Briefs feature a sleek and stretchy construction that forms to your body for a comfortable and flattering second-skin fit. These boxer briefs have a subtle yet stylish design and a seamed pouch for support and definition.

Shop at Male Basics: Ergowear SLK Boxer Briefs

Available on Amazon: Ergowear SLK Boxer Briefs

Ergowear’s SLK Boxer Briefs have a fully ergonomic design that offers a non-constrictive fit, functional support, and a longer leg length for full coverage.

Best Feature: Stretchy and comfortable second-skin fit.

What to Look for When Purchasing Boxer Briefs

If you’ve spent any time shopping for boxer briefs 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.

So, if you’re a bit overwhelmed by all the options and not sure where to start, here are a few characteristics that high-quality underwear brands tend to focus on.

A great pair of boxer briefs will pay special attention to design and construction.

Look for boxer briefs that mention flatlock stitching or chafe-free seams for an extra comfortable fit, as well as a waistband that won’t roll or pinch.

Fabric is also key here. Prioritize options with naturally breathable fibers, as well as those that mix in some stretch (such as elastane, spandex, etc.) for a non-constricting full range of movement.

Lots of guys prefer boxer briefs with designs that minimize leg roll and bunching. If you’re one of these guys, go for options with stretchy fabric blends and stay-put leg construction.

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.

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

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