Shop Big & Tall Underwear

Men's Big & Tall Underwear 

(168)
Men's Jockey® 5-Pack Lightweight Cotton Blend Brief
Men's Jockey® 5-Pack Lightweight Cotton Blend Brief
$19.38 - $25.84 with
$22.80 - $30.40 $38.00 Reg.
Select Styles on Sale/Clearance
Men's Jockey® 3-Pack Cotton Stretch V-Neck Undershirts
Men's Jockey® 3-Pack Cotton Stretch V-Neck Undershirts
$19.38 - $25.84 with
$22.80 - $30.40 $38.00 Reg.
Select Styles on Sale/Clearance
Men's Jockey® 3-Pack Active Microfiber 5" Boxer Briefs
Men's Jockey® 3-Pack Active Microfiber 5" Boxer Briefs
$19.38 - $25.84 with
$22.80 - $30.40 $38.00 Reg.
Select Styles on Sale/Clearance
Men's Jockey® 3-Pack Cotton Stretch Crewneck Undershirts
Men's Jockey® 3-Pack Cotton Stretch Crewneck Undershirts
$19.38 - $25.84 with
$22.80 - $30.40 $38.00 Reg.
Select Styles on Sale/Clearance
Men's Jockey® Classic 3-pack V-Neck Undershirt
Men's Jockey® Classic 3-pack V-Neck Undershirt
$23.80 with
$28.00 Sale$35.00 Reg.
Men's Jockey® 3-Pack Active Microfiber Briefs
Men's Jockey® 3-Pack Active Microfiber Briefs
$19.38 - $25.84 with
$22.80 - $30.40 $38.00 Reg.
Select Styles on Sale/Clearance
Big & Tall Jockey® 3-Pack Cotton Tall Man Classic A-Shirt Tank Undershirts
Big & Tall Jockey® 3-Pack Cotton Tall Man Classic A-Shirt Tank Undershirts
$17.85 - $23.80 with
$21.00 - $28.00 $35.00 Reg.
Select Styles on Sale/Clearance
Men's Jockey® 3-Pack Infinite Cool Microfiber Stretch 6" Boxer Brief
Men's Jockey® 3-Pack Infinite Cool Microfiber Stretch 6" Boxer Brief
$20.40 - $27.20 with
$24.00 - $32.00 $40.00 Reg.
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Men's Jockey® 2-Pack Hypersoft 360° 6-Inch Boxer Briefs
Men's Jockey® 2-Pack Hypersoft 360° 6-Inch Boxer Briefs
$25.84 with
$30.40 Sale$38.00 Reg.
Big & Tall Jockey® 2-Pack Big Man Chafe Proof Pouch Microfiber 6" Boxer Brief
Big & Tall Jockey® 2-Pack Big Man Chafe Proof Pouch Microfiber 6" Boxer Brief
$18.36 - $20.40 with
$21.60 - $24.00 Clearance
$36.00 - $40.00 Reg.
Big & Tall Jockey® 2-Pack ActiveStretch™ Midway® 7" Long-Leg Boxer Briefs
Big & Tall Jockey® 2-Pack ActiveStretch™ Midway® 7" Long-Leg Boxer Briefs
$19.38 - $25.84 with
$22.80 - $30.40 $38.00 Reg.
Select Styles on Sale/Clearance
Men's Hanes® Ultimate® 3-Pack All Day Dry Boxer Briefs Underwear
Men's Hanes® Ultimate® 3-Pack All Day Dry Boxer Briefs Underwear
$24.48 with
$28.80 Sale$36.00 Reg.
Big & Tall Jockey® 2-Pack Hypersoft 360 Briefs
Big & Tall Jockey® 2-Pack Hypersoft 360 Briefs
$19.38 - $25.84 with
$22.80 - $30.40 $38.00 Reg.
Select Styles on Sale/Clearance
KingSize Men's Big & Tall Cotton Boxer Briefs 3-Pack
KingSize Men's Big & Tall Cotton Boxer Briefs 3-Pack
$37.78 - $43.99 
$41.99 - $43.99
Select Styles on Sale
KingSize Men's Big & Tall 3-Pack Cotton Crewneck Undershirt
KingSize Men's Big & Tall 3-Pack Cotton Crewneck Undershirt
$43.18 - $80.97 
$47.48 - $89.99
Select Styles on Sale
KingSize Men's Big & Tall Heavyweight Thermal Pants
KingSize Men's Big & Tall Heavyweight Thermal Pants
$32.38 - $35.99 $35.99
Select Styles on Sale
KingSize Men's Big & Tall Performance Flex Cycle Briefs
KingSize Men's Big & Tall Performance Flex Cycle Briefs
$28.78 - $31.99 $31.99
Select Styles on Sale
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Men's Big & Tall Underwear

Shopping for basics shouldn’t mean settling. At Kohl’s, we offer underwear designed to fit comfortably and move with you—whether at work, at home, or on the go. Start every day with the support you need, so you can focus on what matters most.

Finding the right big and tall underwear goes beyond the basics—it’s about comfort, confidence, and style every day. This guide helps you explore supportive, stylish options made to fit and feel great.

Three popular types of men’s underwear include boxers for a relaxed fit, briefs for classic support, and boxer briefs that combine the best of both. No matter which you choose, enjoy trusted brands and great value—so you feel confident from the inside out.

Key Features to Look For in Big & Tall Underwear

Once you’ve chosen your style, you need to look at the engineering. Manufacturers are finally waking up to the fact that scaling up a pattern doesn't work; you need features designed specifically for larger bodies.

The Anti-Roll Waistband

There is nothing more frustrating than a waistband that folds over or slides down under your belly. Look for descriptions like comfort flex, fabric-wrapped, or heavy-duty elastic.

The Contoured Pouch

For years, underwear was flat-fronted, which squashed everything down. Modern designs, especially in the big and tall underwear category, feature a contoured pouch. This provides a designated space that supports and separates. This isn't just about aesthetics; it reduces friction and heat buildup, keeping you cooler and more comfortable.

Moisture-Wicking Technology

Bigger guys often run warmer. Sweat management is not just for the gym; it’s a daily necessity. Look for terms that offer moisture-wicking or performance mesh. These technologies pull sweat away from the body to the exterior of the fabric where it can evaporate quickly. This keeps you dry and helps prevent chafing and skin rashes that can occur in damp environments.