Skip to search results Skip to filters Skip to sort Skip to selected filters

Men's Size 27 Underwear

44 items found

Sort By

Your Selections

Search Results

Lacoste - Trunks 3-Pack Casual Classic Colorful Waistband. Color Navy Blue/Green/Red/Navy Blue. On sale for $29.75. MSRP $42.50.. 1.0 out of 5 stars

Multi Lacoste Trunks 3-Pack Casual Classic Colorful Waistband

Brand Name: Lacoste
Product Name: Trunks 3-Pack Casual Classic Colorful Waistband
Gender: Men's
Color: Navy Blue/Green/Red/Navy Blue
Price: $29.75MSRP: $42.50
Rating: 1Rated 1 star out of 5(1)

Lacoste - Trunks 3-Pack Casual Lifestyle. Color Navy Blue/White/Silver Chine. On sale for $31.50. MSRP $49.00.. 1.0 out of 5 stars

Multi Lacoste Trunks 3-Pack Casual Lifestyle

Brand Name: Lacoste
Product Name: Trunks 3-Pack Casual Lifestyle
Gender: Men's
Color: Navy Blue/White/Silver Chine
Price: $31.50MSRP: $49.00
Rating: 1Rated 1 star out of 5(1)

SAXX UNDERWEAR - Volt Boxer Brief. Color Canadian Lager. $35.00. 4.4 out of 5 stars

Black SAXX UNDERWEAR Volt Boxer Brief

Black SAXX UNDERWEAR Volt Boxer Brief

+5

Brand Name: SAXX UNDERWEAR
Product Name: Volt Boxer Brief
Gender: Men's
Color: Canadian Lager
Price: $35.00
Rating: 4Rated 4 stars out of 5(8)

PSD - 3-Pack Multi Essentials Cotton. Color Multi. On sale for $39.99. MSRP $45.00..

Multi PSD 3-Pack Multi Essentials Cotton

Multi PSD 3-Pack Multi Essentials Cotton

Brand Name: PSD
Product Name: 3-Pack Multi Essentials Cotton
Gender: Men's
Color: Multi
Price: $39.99MSRP: $45.00
Rating

SAXX UNDERWEAR - Ultra Boxer Brief Fly. Color Beers Of The World/Multi. $34.00. 4.2 out of 5 stars

Multi SAXX UNDERWEAR Ultra Boxer Brief Fly

+23

Brand Name: SAXX UNDERWEAR
Product Name: Ultra Boxer Brief Fly
Gender: Men's
Color: Beers Of The World/Multi
Price: $34.00
Rating: 4Rated 4 stars out of 5(18)

SAXX UNDERWEAR - Droptemp Cooling Cotton Boxer Brief Fly. Color Black. Low Stock. $32.00. 3.7 out of 5 stars

2 left in stock

Black SAXX UNDERWEAR Droptemp Cooling Cotton Boxer Brief Fly

+3

Brand Name: SAXX UNDERWEAR
Product Name: Droptemp Cooling Cotton Boxer Brief Fly
Gender: Men's
Color: Black
Price: $32.00
Rating: 4Rated 4 stars out of 5(3)

SAXX UNDERWEAR - 22nd Century Silk Boxer Brief Fly. Color Dogstooth Camo/Black. Low Stock. $60.00.

3 left in stock

Black SAXX UNDERWEAR 22nd Century Silk Boxer Brief Fly

Brand Name: SAXX UNDERWEAR
Product Name: 22nd Century Silk Boxer Brief Fly
Gender: Men's
Color: Dogstooth Camo/Black
Price: $60.00
Rating

Lacoste - Trunks 3-Pack Casual Lifestyle All Over Print Croc. Color Methylene/Silver Chine/Red. Low Stock. On sale for $29.75. MSRP $47.50.. 5.0 out of 5 stars

6 left in stock

Multi Lacoste Trunks 3-Pack Casual Lifestyle All Over Print Croc

Multi Lacoste Trunks 3-Pack Casual Lifestyle All Over Print Croc

Brand Name: Lacoste
Product Name: Trunks 3-Pack Casual Lifestyle All Over Print Croc
Gender: Men's
Color: Methylene/Silver Chine/Red
Price: $29.75MSRP: $47.50
Rating: 5Rated 5 stars out of 5(1)

Lacoste - Boxer Briefs 3-Pack Casual Classic. Color Black/White/Silver Chine. On sale for $29.75. MSRP $42.50.. 4.3 out of 5 stars

Multi Lacoste Boxer Briefs 3-Pack Casual Classic

Multi Lacoste Boxer Briefs 3-Pack Casual Classic

+3 colors/patterns

Brand Name: Lacoste
Product Name: Boxer Briefs 3-Pack Casual Classic
Gender: Men's
Color: Black/White/Silver Chine
Price: $29.75MSRP: $42.50
Rating: 4Rated 4 stars out of 5(9)

SAXX UNDERWEAR - Non-Stop Stretch Cotton Boxer Brief Fly. Color White. Low Stock. $25.00. 5.0 out of 5 stars

4 left in stock

White SAXX UNDERWEAR Non-Stop Stretch Cotton Boxer Brief Fly

Brand Name: SAXX UNDERWEAR
Product Name: Non-Stop Stretch Cotton Boxer Brief Fly
Gender: Men's
Color: White
Price: $25.00
Rating: 5Rated 5 stars out of 5(1)

SAXX UNDERWEAR - Droptemp Cooling Cotton Brief Fly. Color Tidal Camo/Blue. $30.00.

Multi SAXX UNDERWEAR Droptemp Cooling Cotton Brief Fly

+1

Brand Name: SAXX UNDERWEAR
Product Name: Droptemp Cooling Cotton Brief Fly
Gender: Men's
Color: Tidal Camo/Blue
Price: $30.00
Rating

SAXX UNDERWEAR - Non-Stop Stretch Cotton Trunks Fly 3-Pack. Color Black/Deep Navy/White. Low Stock. On sale for $52.95. MSRP $67.95..

9 left in stock

Multi SAXX UNDERWEAR Non-Stop Stretch Cotton Trunks Fly 3-Pack

Brand Name: SAXX UNDERWEAR
Product Name: Non-Stop Stretch Cotton Trunks Fly 3-Pack
Gender: Men's
Color: Black/Deep Navy/White
Price: $52.95MSRP: $67.95
Rating

SAXX UNDERWEAR - Droptemp Cooling Mesh Boxer Brief Fly 3-Pack. Color Black/Dark Denim/Grey. $99.95. 5.0 out of 5 stars

Multi SAXX UNDERWEAR Droptemp Cooling Mesh Boxer Brief Fly 3-Pack

Brand Name: SAXX UNDERWEAR
Product Name: Droptemp Cooling Mesh Boxer Brief Fly 3-Pack
Gender: Men's
Color: Black/Dark Denim/Grey
Price: $99.95
Rating: 5Rated 5 stars out of 5(1)

Lacoste - Boxer Briefs 3-Pack Casual Lifestyle All Over Print Croc. Color Methylene/Silver Chine/Red. On sale for $29.75. MSRP $42.50.. 4.7 out of 5 stars

Multi Lacoste Boxer Briefs 3-Pack Casual Lifestyle All Over Print Croc

+2 colors/patterns

Brand Name: Lacoste
Product Name: Boxer Briefs 3-Pack Casual Lifestyle All Over Print Croc
Gender: Men's
Color: Methylene/Silver Chine/Red
Price: $29.75MSRP: $42.50
Rating: 5Rated 5 stars out of 5(6)

Lacoste - Trunks 3-Pack Casual Classic. Color Black/White/Silver Chine. On sale for $29.75. MSRP $47.50.. 4.5 out of 5 stars

Multi Lacoste Trunks 3-Pack Casual Classic

+3 colors/patterns

Brand Name: Lacoste
Product Name: Trunks 3-Pack Casual Classic
Gender: Men's
Color: Black/White/Silver Chine
Price: $29.75MSRP: $47.50
Rating: 5Rated 5 stars out of 5(13)

SAXX UNDERWEAR - Ultra Brief Fly. Color Supersize Camo/Black. Low Stock. On sale for $14.40. MSRP $32.00.. 4.8 out of 5 stars

4 left in stock

Black SAXX UNDERWEAR Ultra Brief Fly

Black SAXX UNDERWEAR Ultra Brief Fly

+3

Brand Name: SAXX UNDERWEAR
Product Name: Ultra Brief Fly
Gender: Men's
Color: Supersize Camo/Black
Price: $14.40MSRP: $32.00
Rating: 5Rated 5 stars out of 5(5)

SAXX UNDERWEAR - Non-Stop Stretch Cotton Boxer Brief Fly 3-Pack. Color Black/Deep Navy/White. $52.95.

Multi SAXX UNDERWEAR Non-Stop Stretch Cotton Boxer Brief Fly 3-Pack

+2 colors/patterns

Brand Name: SAXX UNDERWEAR
Product Name: Non-Stop Stretch Cotton Boxer Brief Fly 3-Pack
Gender: Men's
Color: Black/Deep Navy/White
Price: $52.95
Rating

Lacoste - 3-Pack Boxer Brief Causal Fashion Big Croc. Color Navy Blue/White/Silver Chine/Methylene. On sale for $31.50. MSRP $49.50.. 5.0 out of 5 stars

Blue Lacoste 3-Pack Boxer Brief Causal Fashion Big Croc

Blue Lacoste 3-Pack Boxer Brief Causal Fashion Big Croc

Brand Name: Lacoste
Product Name: 3-Pack Boxer Brief Causal Fashion Big Croc
Gender: Men's
Color: Navy Blue/White/Silver Chine/Methylene
Price: $31.50MSRP: $49.50
Rating: 5Rated 5 stars out of 5(1)

SAXX UNDERWEAR - Kinetic HD Boxer Brief. Color Blackout. $38.00. 3.4 out of 5 stars

Black SAXX UNDERWEAR Kinetic HD Boxer Brief

Black SAXX UNDERWEAR Kinetic HD Boxer Brief

Brand Name: SAXX UNDERWEAR
Product Name: Kinetic HD Boxer Brief
Gender: Men's
Color: Blackout
Price: $38.00
Rating: 3Rated 3 stars out of 5(5)

SAXX UNDERWEAR - Vibe Trunk Modern Fit. Color Navy. $34.00. 5.0 out of 5 stars

Navy SAXX UNDERWEAR Vibe Trunk Modern Fit

Brand Name: SAXX UNDERWEAR
Product Name: Vibe Trunk Modern Fit
Gender: Men's
Color: Navy
Price: $34.00
Rating: 5Rated 5 stars out of 5(4)

SAXX UNDERWEAR - Vibe Boxer Brief 2-Pack. Color Black/Grey. $60.95. 4.2 out of 5 stars

Black SAXX UNDERWEAR Vibe Boxer Brief 2-Pack

+4

Brand Name: SAXX UNDERWEAR
Product Name: Vibe Boxer Brief 2-Pack
Gender: Men's
Color: Black/Grey
Price: $60.95
Rating: 4Rated 4 stars out of 5(11)

Tommy John - Second Skin Boxer Brief 8". Color Black. Low Stock. $36.00. 4.2 out of 5 stars

7 left in stock

Black Tommy John Second Skin Boxer Brief 8"

Black Tommy John Second Skin Boxer Brief 8"

+5 colors/patterns

Brand Name: Tommy John
Product Name: Second Skin Boxer Brief 8"
Gender: Men's
Color: Black
Price: $36.00
Rating: 4Rated 4 stars out of 5(495)

Tommy John - Cool Cotton Boxer Brief 8". Color Black. Low Stock. $34.00. 4.4 out of 5 stars

6 left in stock

Black Tommy John Cool Cotton Boxer Brief 8"

+5 colors/patterns

Brand Name: Tommy John
Product Name: Cool Cotton Boxer Brief 8"
Gender: Men's
Color: Black
Price: $34.00
Rating: 4Rated 4 stars out of 5(198)

Under Armour - Tech 9" Boxerjock® 2-Pack. Color Mod Gray Light Heather/Jet Gray Light Heather. On sale for $21.00. MSRP $35.00.. 4.9 out of 5 stars

Gray Under Armour Tech 9" Boxerjock® 2-Pack

Brand Name: Under Armour
Product Name: Tech 9" Boxerjock® 2-Pack
Gender: Men's
Color: Mod Gray Light Heather/Jet Gray Light Heather
Price: $21.00MSRP: $35.00
Rating: 5Rated 5 stars out of 5(13)

Lacoste - 5-Pack Boxer Brief. Color White. On sale for $41.65. MSRP $64.50.. 3.7 out of 5 stars

White Lacoste 5-Pack Boxer Brief

+2 colors/patterns

Brand Name: Lacoste
Product Name: 5-Pack Boxer Brief
Gender: Men's
Color: White
Price: $41.65MSRP: $64.50
Rating: 4Rated 4 stars out of 5(3)

SAXX UNDERWEAR - Hydro Liner. Color Black. $36.00. 5.0 out of 5 stars

Black SAXX UNDERWEAR Hydro Liner

Black SAXX UNDERWEAR Hydro Liner

+3 colors/patterns

Brand Name: SAXX UNDERWEAR
Product Name: Hydro Liner
Gender: Men's
Color: Black
Price: $36.00
Rating: 5Rated 5 stars out of 5(1)

Calvin Klein Underwear - Intense Power Ultra Cooling Low Rise Trunk. Color Blue Shadow. $27.95. 5.0 out of 5 stars

Blue Calvin Klein Underwear Intense Power Ultra Cooling Low Rise Trunk

+2 colors/patterns

Brand Name: Calvin Klein Underwear
Product Name: Intense Power Ultra Cooling Low Rise Trunk
Gender: Men's
Color: Blue Shadow
Price: $27.95
Rating: 5Rated 5 stars out of 5(1)

Calvin Klein Underwear - Intense Power Ultra Cooling Boxer Brief. Color Pompeian Red. $27.95. 4.7 out of 5 stars

Beige Calvin Klein Underwear Intense Power Ultra Cooling Boxer Brief

+3 colors/patterns

Brand Name: Calvin Klein Underwear
Product Name: Intense Power Ultra Cooling Boxer Brief
Gender: Men's
Color: Pompeian Red
Price: $27.95
Rating: 5Rated 5 stars out of 5(3)

Calvin Klein Underwear - Intense Power Pride Micro Underwear Jock Strap. Color White. $29.95.

White Calvin Klein Underwear Intense Power Pride Micro Underwear Jock Strap

Brand Name: Calvin Klein Underwear
Product Name: Intense Power Pride Micro Underwear Jock Strap
Gender: Men's
Color: White
Price: $29.95
Rating

Calvin Klein Underwear - Intense Power Pride Micro Underwear Low Rise Trunk. Color Black. $29.95.

Black Calvin Klein Underwear Intense Power Pride Micro Underwear Low Rise Trunk

Brand Name: Calvin Klein Underwear
Product Name: Intense Power Pride Micro Underwear Low Rise Trunk
Gender: Men's
Color: Black
Price: $29.95
Rating

Calvin Klein Underwear - Pride Cotton Stretch 5-Pack Low Rise Trunk. Color Green Flash/Fuscia Fedora/Dahlia/Blue Atoll/Vibrant Orange. $71.45.

Multi Calvin Klein Underwear Pride Cotton Stretch 5-Pack Low Rise Trunk

Brand Name: Calvin Klein Underwear
Product Name: Pride Cotton Stretch 5-Pack Low Rise Trunk
Gender: Men's
Color: Green Flash/Fuscia Fedora/Dahlia/Blue Atoll/Vibrant Orange
Price: $71.45
Rating

SAXX UNDERWEAR - Daytripper Boxer Brief Fly. Color Camo Flowers/Blue Fog. Low Stock. $27.00. 3.8 out of 5 stars

8 left in stock

Multi SAXX UNDERWEAR Daytripper Boxer Brief Fly

+3

Brand Name: SAXX UNDERWEAR
Product Name: Daytripper Boxer Brief Fly
Gender: Men's
Color: Camo Flowers/Blue Fog
Price: $27.00
Rating: 4Rated 4 stars out of 5(8)

SAXX UNDERWEAR - Volt Breathable Mesh Boxer Brief. Color Timeout/Grey. $35.00. 4.4 out of 5 stars

Gray SAXX UNDERWEAR Volt Breathable Mesh Boxer Brief

+9

Brand Name: SAXX UNDERWEAR
Product Name: Volt Breathable Mesh Boxer Brief
Gender: Men's
Color: Timeout/Grey
Price: $35.00
Rating: 4Rated 4 stars out of 5(9)

SAXX UNDERWEAR - Daytripper Boxer Brief Fly 2-Pack. Color Broadcast Stripe/Black. $48.95. 5.0 out of 5 stars

Black SAXX UNDERWEAR Daytripper Boxer Brief Fly 2-Pack

+2

Brand Name: SAXX UNDERWEAR
Product Name: Daytripper Boxer Brief Fly 2-Pack
Gender: Men's
Color: Broadcast Stripe/Black
Price: $48.95
Rating: 5Rated 5 stars out of 5(2)

SAXX UNDERWEAR - Quest Quick Dry Mesh Boxer Brief Fly. Color Solar Stripe/Twilight. $34.00. 4.9 out of 5 stars

Gray SAXX UNDERWEAR Quest Quick Dry Mesh Boxer Brief Fly

+9

Brand Name: SAXX UNDERWEAR
Product Name: Quest Quick Dry Mesh Boxer Brief Fly
Gender: Men's
Color: Solar Stripe/Twilight
Price: $34.00
Rating: 5Rated 5 stars out of 5(14)

SAXX UNDERWEAR - Droptemp Cooling Mesh Boxer Brief Fly. Color Blue Moon Heather. $38.00. 4.2 out of 5 stars

Blue SAXX UNDERWEAR Droptemp Cooling Mesh Boxer Brief Fly

+7

Brand Name: SAXX UNDERWEAR
Product Name: Droptemp Cooling Mesh Boxer Brief Fly
Gender: Men's
Color: Blue Moon Heather
Price: $38.00
Rating: 4Rated 4 stars out of 5(4)

SAXX UNDERWEAR - Droptemp Cooling Cotton Trunks Fly. Color No Tell Motel/Graphite. $32.00.

Multi SAXX UNDERWEAR Droptemp Cooling Cotton Trunks Fly

+1

Brand Name: SAXX UNDERWEAR
Product Name: Droptemp Cooling Cotton Trunks Fly
Gender: Men's
Color: No Tell Motel/Graphite
Price: $32.00
Rating

Under Armour - 3-Pack Performance Tech Print 6” Boxer Briefs. Color Black. $42.00.

Black Under Armour 3-Pack Performance Tech Print 6” Boxer Briefs

+4

Brand Name: Under Armour
Product Name: 3-Pack Performance Tech Print 6” Boxer Briefs
Gender: Men's
Color: Black
Price: $42.00
Rating

Stance - Mike B Wholester. Color Blue. $35.00. 5.0 out of 5 stars

Blue Stance Mike B Wholester

Brand Name: Stance
Product Name: Mike B Wholester
Gender: Men's
Color: Blue
Price: $35.00
Rating: 5Rated 5 stars out of 5(17)

Calvin Klein Underwear - CK Black Boxer Brief 3-Pack. Color Black/Black/Black. On sale for $66.26. MSRP $78.00..

Black Calvin Klein Underwear CK Black Boxer Brief 3-Pack

+3 colors/patterns

Brand Name: Calvin Klein Underwear
Product Name: CK Black Boxer Brief 3-Pack
Gender: Men's
Color: Black/Black/Black
Price: $66.26MSRP: $78.00
Rating

Calvin Klein Underwear - Calvin Klein Athletic Active Hip Brief. Color Athletic Grey Heather. Low Stock. On sale for $23.96. MSRP $30.00..

3 left in stock

Gray Calvin Klein Underwear Calvin Klein Athletic Active Hip Brief

Brand Name: Calvin Klein Underwear
Product Name: Calvin Klein Athletic Active Hip Brief
Gender: Men's
Color: Athletic Grey Heather
Price: $23.96MSRP: $30.00
Rating

Stance - Seacret Garden Boxer Brief. Color Multi. $30.00.

Multi Stance Seacret Garden Boxer Brief

Multi Stance Seacret Garden Boxer Brief

Brand Name: Stance
Product Name: Seacret Garden Boxer Brief
Gender: Men's
Color: Multi
Price: $30.00
Rating

Calvin Klein Underwear - 1996 Cotton Boxer Brief 3-Pack. Color White/Authentic Grey/Tiger Print/Island Green. On sale for $44.51. MSRP $49.50..

Green Calvin Klein Underwear 1996 Cotton Boxer Brief 3-Pack

Brand Name: Calvin Klein Underwear
Product Name: 1996 Cotton Boxer Brief 3-Pack
Gender: Men's
Color: White/Authentic Grey/Tiger Print/Island Green
Price: $44.51MSRP: $49.50
Rating

Calvin Klein Underwear - CK Black Hip Brief 3-Pack. Color Black/Blue Shadow/Grey Sky. Low Stock. On sale for $42.87. MSRP $78.00..

7 left in stock

Blue Calvin Klein Underwear CK Black Hip Brief 3-Pack

+3 colors/patterns

Brand Name: Calvin Klein Underwear
Product Name: CK Black Hip Brief 3-Pack
Gender: Men's
Color: Black/Blue Shadow/Grey Sky
Price: $42.87MSRP: $78.00
Rating

Get on the List

Subscribe to Zappos emails for exclusive product launches, early notifications for sales, and a few extra-special surprises.