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Gift him love-changing underwear. Shop the Valentine’s Day Gift Guide now.

Three pairs of underwear on a white box. One is black. One is blue. One is grey.

Gifts under $100.

46 Items
Front of Daytripper Boxer Brief Fly 3Pack in Black
Front - Model wearing Daytripper Boxer Brief Fly 3Pk in Black
Back - Model wearing Daytripper Boxer Brief Fly 3Pk in Black
Daytripper (3 Pack)

Comfort Stretch Boxer Brief 5"

$66.00 $22/Pair Up to 20% off in savings

(4.4)

Front of Daytripper Boxer Brief Fly 3-Pack in Sport Blue Heather/Blueberry/Maritime
Front - Model wearing Daytripper Boxer Brief Fly 3Pk in Sport Blue Heather/Blueberry/Maritime
Back - Model wearing Daytripper Boxer Brief Fly 3Pk in Sport Blue Heather/Blueberry/Maritime
Daytripper (3 Pack)

Comfort Stretch Boxer Brief 5"

$66.00 $22/Pair Up to 20% off in savings

(4.4)

Front - Model wearing Gainmaker 2N1 Short 7" in Black
Back - Model wearing Gainmaker 2N1 Short 7" in Black
SAXX Underwear Gainmaker 2N1 Short BallPark Pouch technology graphic
Select Size
Gainmaker 2N1

Athletic Short 7" with liner

$78.00

(4.5)

Front of Ultra Brief Fly 2 Pack in Black/Navy
Front - Model wearing Ultra Super Soft Brief Fly 2Pk in Black/Navy
Back - Model wearing Ultra Super Soft Brief Fly 2Pk in Black/Navy
Ultra Super Soft (2 Pack)

Comfort Blend Brief

$59.00 $30/Pair Up to 20% off in savings

(4.6)

Front of Ultra Super Soft Boxer Brief Fly 3-Pack in Burnt Plum/Turbulence/Black
Front - Model wearing Ultra Super Soft Boxer Brief Fly 3Pk in Burnt Plum/Turbulence/Black
Back - Model wearing Ultra Super Soft Boxer Brief Fly 3Pk in Burnt Plum/Turbulence/Black
Ultra Super Soft (3 Pack)

Comfort Blend Boxer Brief 5"

$92.00 $31/Pair Up to 20% off in savings

(4.5)

Front of DropTemp Cooling Cotton (2 Pack) Boxer Brief in Daybreak Camo/Black
Front - Model wearing Droptemp Cooling Cotton Boxer Brief Fly 2Pk in Daybreak Camo/Black
Back - Model wearing Droptemp Cooling Cotton Boxer Brief Fly 2Pk in Daybreak Camo/Black
Select Size
DropTemp® Cooling Cotton (2 Pack)

Cooling Cotton Boxer Brief 5"

$57.00 $29/Pair Up to 20% off in savings

(4.4)

Front of Ultra Boxer Brief Fly 3Pack in Classic Ultra 18
Front - Model wearing Ultra Super Soft Boxer Brief Fly 3Pk in Classic Ultra 18
Back - Model wearing Ultra Super Soft Boxer Brief Fly 3Pk in Classic Ultra 18
Ultra Super Soft (3 Pack)

Comfort Blend Boxer Brief 5"

$92.00 $31/Pair Up to 20% off in savings

(4.5)

Front of Daytripper Loose Boxer Fly 3-Pack in Black/Navy Heather/Grey Heather
Front - Model wearing Daytripper Boxer Short Fly 3Pk in Black/Navy Heather/Grey Heather
Back - Model wearing Daytripper Boxer Short Fly 3Pk in Black/Navy Heather/Grey Heather
Daytripper (3 Pack)

Comfort Stretch Loose Boxer 5"

$72.00 $24/Pair Up to 20% off in savings

(3.9)

Front of DropTemp Cooling Cotton 2-Pack Trunk in Dark Ink/Black
Front - Model wearing Droptemp Cooling Cotton Trunk Fly 2Pk in Dark Ink/Black
Back - Model wearing Droptemp Cooling Cotton Trunk Fly 2Pk in Dark Ink/Black
Select Size
DropTemp® Cooling Cotton (2 Pack)

Cooling Cotton Trunk 3"

$57.00 $29/Pair Up to 20% off in savings

(4.3)

Front - Model wearing Peakdaze Jogger in Black
Back - Model wearing Peakdaze Jogger in Black
Select Size
PeakDaze

Soft Knit Performance Jogger

$89.00

(4.5)

Front of Ultra Super Soft Boxer Brief Fly 2 Pack in Palm Frond/Maritime
Front - Model wearing Ultra Super Soft Boxer Brief Fly 2 Pack in Palm Frond/Maritime
Back - Model wearing Ultra Super Soft Boxer Brief Fly 2 Pack in Palm Frond/Maritime
Select Size
Ultra Super Soft (2 Pack)

Comfort Blend Boxer Brief 5"

$61.00 $31/Pair Up to 20% off in savings

(4.5)

Front of Daytripper (3 Pack) Boxer Brief in Black/Graphite/Grey Heather
Front - Model wearing Daytripper Boxer Brief Fly in Grey Heather
Back - Model wearing Daytripper Boxer Brief Fly in Grey Heather
Daytripper (3 Pack)

Comfort Stretch Boxer Brief 5"

$66.00 $22/Pair Up to 20% off in savings

(4.4)

Front of Daytripper Boxer Brief Fly 3Pack in Navy Heather
Front - Model wearing Daytripper Boxer Brief Fly 3Pk in Navy
Back - Model wearing Daytripper Boxer Brief Fly 3Pk in Navy
Daytripper (3 Pack)

Comfort Stretch Boxer Brief 5"

$66.00 $22/Pair Up to 20% off in savings

(4.4)

Front of Droptemp Cooling Cotton Boxer Brief Fly 2 Pack in Buzzcut/Black
Front - Model wearing Droptemp Cooling Cotton Boxer Brief Fly 2 Pack in Buzzcut/Black
Back - Model wearing Droptemp Cooling Cotton Boxer Brief Fly 2 Pack in Buzzcut/Black
Select Size
DropTemp® Cooling Cotton (2 Pack)

Cooling Cotton Boxer Brief 5"

$57.00 $29/Pair Up to 20% off in savings

(4.4)

Front of Droptemp Cooling Cotton Boxer Brief Fly 2-Pack in Angler Wrangler/Dark Grey Heather
Front - Model wearing Droptemp Cooling Cotton Boxer Brief Fly 2Pk in Angler Wrangler/Dark Grey Heather
Back - Model wearing Droptemp Cooling Cotton Boxer Brief Fly 2Pk in Angler Wrangler/Dark Grey Heather
Select Size
DropTemp® Cooling Cotton (2 Pack)

Cooling Cotton Boxer Brief 5"

$57.00 $29/Pair Up to 20% off in savings

(4.4)

Front of Vibe Xtra (3 Pack) Boxer Brief in Black/Dark Grey Heather/Navy
Front - Model wearing Vibe Xtra Boxer Brief Fly 3Pk in Black/Dark Grey Heather/Navy
Back - Model wearing Vibe Xtra Boxer Brief Fly 3Pk in Black/Dark Grey Heather/Navy
Select Size
Vibe Xtra (3 Pack)

Soft Comfort Boxer Brief 6"

$92.00 $31/Pair Up to 20% off in savings

(4.9)

Front of DropTemp Cooling Cotton (3 Pack) Boxer Brief in Black
Front - Model wearing Droptemp Cooling Cotton Boxer Brief Fly 3Pk in Black
Back - Model wearing Droptemp Cooling Cotton Boxer Brief Fly 3Pk in Black
Select Size
DropTemp® Cooling Cotton (3 Pack)

Cooling Cotton Boxer Brief 5"

$86.00 $29/Pair Up to 20% off in savings

(4.4)

Front of Ultra Boxer Brief Fly 2 Pack in Black/Grey
Front - Model wearing Ultra Super Soft Boxer Brief Fly 2Pk in Black/Grey
Back - Model wearing Ultra Super Soft Boxer Brief Fly 2Pk in Black/Grey
Ultra Super Soft (2 Pack)

Comfort Blend Boxer Brief 5"

$61.00 $31/Pair Up to 20% off in savings

(4.5)

Back of Non-Stop Stretch Cotton Boxer Brief in White
Front - Model wearing Non-Stop Stretch Cotton Boxer Brief Fly 3Pk in White
Back - Model wearing Non-Stop Stretch Cotton Boxer Brief Fly 3Pk in White
Non-Stop Stretch Cotton (3 Pack)

Stretch Cotton Boxer Brief 5"

$53.00 $18/Pair Up to 20% off in savings

(4.6)

Front of Vibe Xtra Boxer Brief Fly 3 Pack in Wood Camo/Grey Heather/Black
Front - Model wearing Vibe Xtra Boxer Brief Fly 3 Pack in Wood Camo/Grey Heather/Black
Back - Model wearing Vibe Xtra Boxer Brief Fly 3 Pack in Wood Camo/Grey Heather/Black
Select Size
Vibe Xtra (3 Pack)

Soft Comfort Boxer Brief 6"

$92.00 $31/Pair Up to 20% off in savings

(4.9)

Back of Vibe Super Soft Trunk in Black/Grey/Navy
Front - Model wearing Super Soft Vibe Trunk in Navy
Back - Model wearing Vibe Trunk in Navy Heather
Vibe Super Soft (3 Pack)

Comfort Blend Trunk 3"

$91.95 $31/Pair Up to 20% off in savings

(4.5)

Front of Vibe Xtra Boxer Brief Fly 2 Pack in Pineapple Brocade/Black
Front - Model wearing Vibe Xtra Boxer Brief Fly 2 Pack in Pineapple Brocade/Black
Back - Model wearing Vibe Xtra Boxer Brief Fly 2 Pack in Pineapple Brocade/Black
Select Size
Vibe Xtra (2 Pack)

Soft Comfort Boxer Brief 6"

$61.00 $31/Pair Up to 20% off in savings

(4.9)

Front - Model wearing Snooze Short in Supersize Camo- Dark Charcoal
Back - Model wearing Snooze Short in Supersize Camo- Dark Charcoal
Select Size
Snooze

Super Soft Modal Sleep Short 8"

$59.00

(4.7)

Front of Quest Quick-Dry Mesh Baselayer (3 Pack) Long Boxer Brief in Black
Front - Model wearing Quest Quick Dry Mesh Long Boxer Brief Fly in Black
Back - Model wearing Quest Quick Dry Mesh Long Boxer Brief Fly in Black
Quest Quick-Dry Mesh (3 Pack)

Quick-Dry Performance Long Boxer Brief 8"

$98.00 $33/Pair Up to 20% off in savings

(4.6)