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Men's Underwear

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Men's Underwear

360 Sport Boxer Brief 8360 Sport Boxer Brief 8

360 Sport Boxer Brief 8"

$28.00

Color

Choose Your Size
360 Sport Boxer Brief 8"
$28.00
360 Sport Hammock Pouch™ Boxer Brief 8360 Sport Hammock Pouch™ Boxer Brief 8

360 Sport Hammock Pouch™ Boxer Brief 8"

$30.00

Color

Choose Your Size
360 Sport Hammock Pouch™ Boxer Brief 8"
$30.00
360 Sport Hammock Pouch™ Mid-Length Boxer Brief 6360 Sport Hammock Pouch™ Mid-Length Boxer Brief 6

360 Sport Hammock Pouch™ Mid-Length Boxer Brief 6"

$30.00

Color

Choose Your Size
360 Sport Hammock Pouch™ Mid-Length Boxer Brief 6"
$30.00
360 Sport Hammock Pouch™ Trunk 4360 Sport Hammock Pouch™ Trunk 4

360 Sport Hammock Pouch™ Trunk 4"

$30.00

Color

Choose Your Size
360 Sport Hammock Pouch™ Trunk 4"
$30.00
360 Sport Mid-Length Boxer Brief 6360 Sport Mid-Length Boxer Brief 6

360 Sport Mid-Length Boxer Brief 6"

$28.00

Color

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360 Sport Mid-Length Boxer Brief 6"
$28.00
360 Sport Trunk 4360 Sport Trunk 4

360 Sport Trunk 4"

$28.00

Color

Choose Your Size
360 Sport Trunk 4"
$28.00
Air Boxer Brief 8Air Boxer Brief 8

Air Boxer Brief 8"

$38.00

Color

Choose Your Size
Air Boxer Brief 8"
$38.00
Air BriefAir Brief

Air Brief

$36.00

Color

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Air Brief
$36.00
Air Hammock Pouch™ Boxer Brief 8Air Hammock Pouch™ Boxer Brief 8

Air Hammock Pouch™ Boxer Brief 8"

$40.00

Color

Choose Your Size
Air Hammock Pouch™ Boxer Brief 8"
$40.00
Air Hammock Pouch™ Mid-Length Boxer Brief 6Air Hammock Pouch™ Mid-Length Boxer Brief 6

Air Hammock Pouch™ Mid-Length Boxer Brief 6"

$40.00

Color

Choose Your Size
Air Hammock Pouch™ Mid-Length Boxer Brief 6"
$40.00
Air Hammock Pouch™ Trunk 4Air Hammock Pouch™ Trunk 4

Air Hammock Pouch™ Trunk 4"

$40.00

Color

Choose Your Size
Air Hammock Pouch™ Trunk 4"
$40.00
Air Mid-Length Boxer Brief 6Air Mid-Length Boxer Brief 6

Air Mid-Length Boxer Brief 6"

$38.00

Color

Choose Your Size
Air Mid-Length Boxer Brief 6"
$38.00
Air Trunk 4Air Trunk 4

Air Trunk 4"

$38.00

Color

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Air Trunk 4"
$38.00
Apollo Boxer Brief 8Apollo Boxer Brief 8

Apollo Boxer Brief 8"

$42.00

Color

Choose Your Size
Apollo Boxer Brief 8"
$42.00
Apollo Mid-Length Boxer Brief 6Apollo Mid-Length Boxer Brief 6

Apollo Mid-Length Boxer Brief 6"

$42.00

Color

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Apollo Mid-Length Boxer Brief 6"
$42.00
Apollo Trunk 4Apollo Trunk 4

Apollo Trunk 4"

$42.00

Color

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Apollo Trunk 4"
$42.00
Cool Cotton Boxer Brief 8Cool Cotton Boxer Brief 8
New Colors

Cool Cotton Boxer Brief 8"

$32.00

Color

Choose Your Size
Cool Cotton Boxer Brief 8"
$32.00
Cool Cotton Boxer Brief 8Cool Cotton Boxer Brief 8

Cool Cotton Boxer Brief 8"

$32.00

Color

Choose Your Size
Cool Cotton Boxer Brief 8"
$32.00
Cool Cotton BriefCool Cotton Brief

Cool Cotton Brief

$30.00

Color

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Cool Cotton Brief
$30.00
Cool Cotton Hammock Pouch™ Boxer Brief 8Cool Cotton Hammock Pouch™ Boxer Brief 8

Cool Cotton Hammock Pouch™ Boxer Brief 8"

$34.00

Color

Choose Your Size
Cool Cotton Hammock Pouch™ Boxer Brief 8"
$34.00
Cool Cotton Hammock Pouch™ Mid-Length Boxer Brief 6Cool Cotton Hammock Pouch™ Mid-Length Boxer Brief 6

Cool Cotton Hammock Pouch™ Mid-Length Boxer Brief 6"

$34.00

Color

Choose Your Size
Cool Cotton Hammock Pouch™ Mid-Length Boxer Brief 6"
$34.00
Cool Cotton Hammock Pouch™ Trunk 4Cool Cotton Hammock Pouch™ Trunk 4

Cool Cotton Hammock Pouch™ Trunk 4"

$34.00

Color

Choose Your Size
Cool Cotton Hammock Pouch™ Trunk 4"
$34.00
Cool Cotton Mid-Length Boxer Brief 6Cool Cotton Mid-Length Boxer Brief 6
New Colors

Cool Cotton Mid-Length Boxer Brief 6"

$32.00

Color

Choose Your Size
Cool Cotton Mid-Length Boxer Brief 6"
$32.00
Cool Cotton Mid-Length Boxer Brief 6Cool Cotton Mid-Length Boxer Brief 6
New Colors

Cool Cotton Mid-Length Boxer Brief 6"

$32.00

Color

Choose Your Size
Cool Cotton Mid-Length Boxer Brief 6"
$32.00
Cool Cotton Relaxed Fit Boxer 6Cool Cotton Relaxed Fit Boxer 6

Cool Cotton Relaxed Fit Boxer 6"

$32.00

Color

Choose Your Size
Cool Cotton Relaxed Fit Boxer 6"
$32.00
Cool Cotton Square Cut 2Cool Cotton Square Cut 2

Cool Cotton Square Cut 2"

$32.00

Color

Choose Your Size
Cool Cotton Square Cut 2"
$32.00
Cool Cotton Trunk 4Cool Cotton Trunk 4
New Colors

Cool Cotton Trunk 4"

$32.00

Color

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Cool Cotton Trunk 4"
$32.00
Cool Cotton Trunk 4Cool Cotton Trunk 4
New Colors

Cool Cotton Trunk 4"

$32.00

Color

Choose Your Size
Cool Cotton Trunk 4"
$32.00
Second Skin Boxer Brief 8Second Skin Boxer Brief 8

Second Skin Boxer Brief 8"

$36.00

Color

Choose Your Size
Second Skin Boxer Brief 8"
$36.00
Second Skin Boxer Brief 8Second Skin Boxer Brief 8

Second Skin Boxer Brief 8"

$36.00

Color

Choose Your Size
Second Skin Boxer Brief 8"
$36.00
Second Skin Boxer Brief 8Second Skin Boxer Brief 8

Second Skin Boxer Brief 8"

$36.00

Color

Choose Your Size
Second Skin Boxer Brief 8"
$36.00
Second Skin BriefSecond Skin Brief

Second Skin Brief

$34.00

Color

Choose Your Size
Second Skin Brief
$34.00
Second Skin Hammock Pouch™ Boxer Brief 8Second Skin Hammock Pouch™ Boxer Brief 8

Second Skin Hammock Pouch™ Boxer Brief 8"

$38.00

Color

Choose Your Size
Second Skin Hammock Pouch™ Boxer Brief 8"
$38.00
Second Skin Hammock Pouch™ Mid-Length Boxer Brief 6Second Skin Hammock Pouch™ Mid-Length Boxer Brief 6

Second Skin Hammock Pouch™ Mid-Length Boxer Brief 6"

$38.00

Color

Choose Your Size
Second Skin Hammock Pouch™ Mid-Length Boxer Brief 6"
$38.00
Second Skin Hammock Pouch™ Trunk 4Second Skin Hammock Pouch™ Trunk 4

Second Skin Hammock Pouch™ Trunk 4"

$38.00

Color

Choose Your Size
Second Skin Hammock Pouch™ Trunk 4"
$38.00
Second Skin Luxe Rib Boxer Brief 8Second Skin Luxe Rib Boxer Brief 8
New Colors

Second Skin Luxe Rib Boxer Brief 8"

$38.00

Color

Choose Your Size
Second Skin Luxe Rib Boxer Brief 8"
$38.00
Second Skin Luxe Rib Mid-Length Boxer Brief 6Second Skin Luxe Rib Mid-Length Boxer Brief 6
New Colors

Second Skin Luxe Rib Mid-Length Boxer Brief 6"

$38.00

Color

Choose Your Size
Second Skin Luxe Rib Mid-Length Boxer Brief 6"
$38.00
Second Skin Luxe Rib Trunk 4Second Skin Luxe Rib Trunk 4
New Colors

Second Skin Luxe Rib Trunk 4"

$38.00

Color

Choose Your Size
Second Skin Luxe Rib Trunk 4"
$38.00
Second Skin Mid-Length Boxer Brief 6Second Skin Mid-Length Boxer Brief 6

Second Skin Mid-Length Boxer Brief 6"

$36.00

Color

Choose Your Size
Second Skin Mid-Length Boxer Brief 6"
$36.00
Second Skin Mid-Length Boxer Brief 6Second Skin Mid-Length Boxer Brief 6

Second Skin Mid-Length Boxer Brief 6"

$36.00

Color

Choose Your Size
Second Skin Mid-Length Boxer Brief 6"
$36.00
Second Skin Mid-Length Boxer Brief 6Second Skin Mid-Length Boxer Brief 6

Second Skin Mid-Length Boxer Brief 6"

$36.00

Color

Choose Your Size
Second Skin Mid-Length Boxer Brief 6"
$36.00
Second Skin Mid-Length Boxer Brief 6Second Skin Mid-Length Boxer Brief 6

Second Skin Mid-Length Boxer Brief 6"

$36.00

Color

Choose Your Size
Second Skin Mid-Length Boxer Brief 6"
$36.00
Second Skin Relaxed Fit Boxer 6Second Skin Relaxed Fit Boxer 6
New Colors

Second Skin Relaxed Fit Boxer 6"

$36.00

Color

Choose Your Size
Second Skin Relaxed Fit Boxer 6"
$36.00
Second Skin Square Cut 2Second Skin Square Cut 2

Second Skin Square Cut 2"

$36.00

Color

Choose Your Size
Second Skin Square Cut 2"
$36.00
Second Skin Trunk 4Second Skin Trunk 4

Second Skin Trunk 4"

$36.00

Color

Choose Your Size
Second Skin Trunk 4"
$36.00
Second Skin Trunk 4Second Skin Trunk 4

Second Skin Trunk 4"

$36.00

Color

Choose Your Size
Second Skin Trunk 4"
$36.00
Second Skin Trunk 4Second Skin Trunk 4

Second Skin Trunk 4"

$36.00

Color

Choose Your Size
Second Skin Trunk 4"
$36.00
Second Skin Trunk 4Second Skin Trunk 4

Second Skin Trunk 4"

$36.00

Color

Choose Your Size
Second Skin Trunk 4"
$36.00
SleekHeat™ Long John BottomSleekHeat™ Long John Bottom

SleekHeat™ Long John Bottom

$60.00

Color

Choose Your Size
SleekHeat™ Long John Bottom
$60.00
SleekHeat™ Long John Crew Neck TopSleekHeat™ Long John Crew Neck Top

SleekHeat™ Long John Crew Neck Top

$55.00

Color

Choose Your Size
SleekHeat™ Long John Crew Neck Top
$55.00
TJ Cotton Stretch Boxer Brief 8TJ Cotton Stretch Boxer Brief 8

TJ Cotton Stretch Boxer Brief 8" (2-Pack)

$24.99

Color

Choose Your Size
TJ Cotton Stretch Boxer Brief 8" (2-Pack)
$24.99
TJ Cotton Stretch Hammock Pouch™ Boxer Brief 8TJ Cotton Stretch Hammock Pouch™ Boxer Brief 8

TJ Cotton Stretch Hammock Pouch™ Boxer Brief 8"

$18.00

Color

Choose Your Size
TJ Cotton Stretch Hammock Pouch™ Boxer Brief 8"
$18.00
TJ Cotton Stretch Hammock Pouch™ Boxer Brief 8" (2-Pack)
$36.00 $24.99
TJ Cotton Stretch Hammock Pouch™ Boxer Brief 8" (2-Pack)
$36.00 $24.99
TJ Cotton Stretch Hammock Pouch™ Boxer Brief 8" (2-Pack)
$36.00 $24.99
TJ Cotton Stretch Hammock Pouch™ Mid-Length Boxer Brief 6TJ Cotton Stretch Hammock Pouch™ Mid-Length Boxer Brief 6

TJ Cotton Stretch Hammock Pouch™ Mid-Length Boxer Brief 6"

$18.00

Color

Choose Your Size
TJ Cotton Stretch Hammock Pouch™ Mid-Length Boxer Brief 6"
$18.00
TJ Cotton Stretch Hammock Pouch™ Trunk 4”TJ Cotton Stretch Hammock Pouch™ Trunk 4”

TJ Cotton Stretch Hammock Pouch™ Trunk 4”

$18.00

Color

Choose Your Size
TJ Cotton Stretch Hammock Pouch™ Trunk 4”
$18.00
TJ Cotton Stretch Hammock Pouch™ Trunk 4” (2-Pack)
$36.00 $24.99
TJ Cotton Stretch Hammock Pouch™ Trunk 4” (2-Pack)
$36.00 $24.99
TJ Cotton Stretch Hammock Pouch™ Trunk 4” (2-Pack)
$36.00 $24.99
TJ Cotton Stretch Mid-Length Boxer Brief 6” (2-Pack)TJ Cotton Stretch Mid-Length Boxer Brief 6” (2-Pack)

TJ Cotton Stretch Mid-Length Boxer Brief 6” (2-Pack)

$24.99

Color

Choose Your Size
TJ Cotton Stretch Mid-Length Boxer Brief 6” (2-Pack)
$24.99
TJ Cotton Stretch Trunk 4” (2-Pack)TJ Cotton Stretch Trunk 4” (2-Pack)

TJ Cotton Stretch Trunk 4” (2-Pack)

$24.99

Color

Choose Your Size
TJ Cotton Stretch Trunk 4” (2-Pack)
$24.99

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Men's Underwear

At Tommy John’s, our brand strives each and every day to give our customers the most comfortable pair of underwear they can find. We start with the most breathable, soft fabrics and then move on to the design and patterns. When it comes to our men’s underwear, we offer six different styles so you can find the one that suits you best. Whether you are traveling, working out, or just doing the standard 9-5, this line of men’s briefs, trunks, boxer brief styles and boxers are the ultimate choice for all-day comfort. 

When it comes to your boxers, the last thing you want to worry about is chafing or an uncomfortable waistband without any stretch. With our underwear collection, we ensure a comfortable fit with each and every wear by only using top quality types of fabric. Our lightweight boxer briefs comfortably fit under pants, gym shorts, or even just worn as is. All of our premium men’s underwear comes in a variety of sizes ranging from S to XXL. We even offer some styles in 3XL and 4XL as well.

Comfortable Underwear For Men: Finding The Perfect Style

At Tommy John's, we like to provide variety for personal preference. That's why we've created 6 unique men's briefs styles offered in various color options and patterns so you can look and feel your best on a daily basis. Our traditional Men’s Boxer Brief has an 8” inseam and provides the fullest amount of coverage out of all of our styles. Next, we have our Relaxed Fit Boxers that have a 6.5” inseam and lays looser against the body for a more airy fit. From there, we’ve created 4.5” inseam Trunks. These boxers hit right at mid-thigh, creating a modern yet classy look for everyday wear. If you want to take it one step further, our Square Cut Boxers will be the perfect option for you. With a 3” inseam, these men’s briefs hug the body tight while giving off a contemporary appearance. Last but not least, we’ve got our signature Briefs. Our Men’s Briefs offer minimal coverage while giving the most support.  

Already have a favorite style in mind? Shop all of our underwear for men today to experience the true meaning of comfort for everyday wear.