10 Best Calvin Klein Men Underwear of 2025

Tested and Reviewed: Top 10 Calvin Klein Men Underwear deals with expert ratings from 8.1 to a perfect 10

March 2026 Edition

Editor's Choice

9.7

Calvin Klein

Calvin Klein Men's Cotton Classics 3-pack Boxer Brief, 3 Black, Medium

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Editor's bottom line:

“This calvin klein men underwear is the best one we tested. In terms of quality, brand and price, we couldn't ask for more.”

Main Highlights

COTTON CLASSIC: Spun in premium cotton yarns for supreme breathability, Calvin Kleins bestselling mens underwear wicks away moisture to keep you cool and dry.
SUPPORT plus COMFORT: Featuring a functional fly and contoured pouch for a supportive fit, Calvin Kleins mens boxer briefs have a soft, flexible logo waistband that stays put without too much compression and retains its shape, wear after wear.
SIGNATURE FIT: Designed with a full rise, a waist that sits the above hip, and a longer leg line that sits low on the thigh.
DESIGNED IN THE USA: Calvin Kleins mens boxers are created by its NYC-based global design team using premium imported materials.
CARE: Machine wash cold, tumble dry low heat. We recommend hang drying your boxer briefs to extend the life of your garment.

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Picked by 397 people today

9.5

Calvin Klein

Calvin Klein Men's Cotton Classics 5-pack Boxer Brief, 5 Black, Medium

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Main Highlights

COTTON CLASSIC: Spun in premium cotton yarns for supreme breathability, Calvin Kleins bestselling mens underwear wicks away moisture to keep you cool and dry.
SUPPORT plus COMFORT: Featuring a functional fly and contoured pouch for a supportive fit, Calvin Kleins mens boxer briefs have a soft, flexible logo waistband that stays put without too much compression and retains its shape, wear after wear.
SIGNATURE FIT: Designed with a full rise, a waist that sits the above hip, and a longer leg line that sits low on the thigh.
DESIGNED IN THE USA: Calvin Kleins mens boxers are created by its NYC-based global design team using premium imported materials.
CARE: Machine wash cold, tumble dry low heat. We recommend hang drying your boxer briefs to extend the life of your garment.

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9.5

Calvin Klein

Calvin Klein Men's Cotton Classics 5-pack Boxer Brief, 2 Blue Shadow Body W/Blue Shadow Waistband, 2 Charcoal Heather Body W/Charcoal Heather Waistband, 1 Black Body W/Black Waistband, Medium

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Main Highlights

COTTON CLASSIC: Spun in premium cotton yarns for supreme breathability, Calvin Kleins bestselling mens underwear wicks away moisture to keep you cool and dry.
SUPPORT + COMFORT: Featuring a functional fly and contoured pouch for a supportive fit, Calvin Kleins mens boxer briefs have a soft, flexible logo waistband that stays put without too much compression and retains its shape, wear after wear.
SIGNATURE FIT: Designed with a full rise, a waist that sits the above hip, and a longer leg line that sits low on the thigh.
DESIGNED IN THE USA: Calvin Kleins mens boxers are created by its NYC-based global design team using premium imported materials.
CARE: Machine wash cold, tumble dry low heat. We recommend hang drying your boxer briefs to extend the life of your garment.

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9.2

Calvin Klein

Calvin Klein Men's Cotton Stretch 5-Pack Boxer Brief, 5 Black, Medium

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Main Highlights

COTTON STRETCH: Spun in pure, premium cotton yarn with a hint of Spandex fibers, Calvin Kleins signature mens underwear wicks away moisture to keep you cool and dry.
SUPPORT plus COMFORT: Featuring a functional fly and contoured pouch for a supportive fit, Calvin Kleins mens boxer briefs have a soft, flexible logo waistband that stays put without too much compression and retains its shape, wear after wear.
SIGNATURE FIT: Designed with a full rise, a waist that sits the above hip, and a longer leg line that sits low on the thigh.
DESIGNED IN THE USA: Calvin Kleins mens boxers are created by its NYC-based global design team using premium imported materials.
CARE: Machine wash cold, tumble dry low heat. We recommend hang drying your boxer briefs to extend the life of your garment

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9.0

Calvin Klein

Calvin Klein Men's Cotton Classics 5-Pack Brief

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Main Highlights

COTTON CLASSIC: Spun in premium cotton yarns for supreme breathability, Calvin Kleins bestselling mens underwear wicks away moisture to keep you cool and dry.
SUPPORT + COMFORT: Featuring a functional fly and contoured pouch for a supportive fit, Calvin Kleins mens briefs have a soft, flexible logo waistband that stays put without too much compression and retains its shape, wear after wear.
SIGNATURE FIT: Designed with full back coverage, a waist that sits the above hip and a functional fly.
DESIGNED IN THE USA: Calvin Klein underwear for men is created by its NYC-based global design team using premium imported materials.
CARE: Machine wash cold, tumble dry low heat. We recommend hang drying your briefs to extend the life of your garment.

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8.8

Calvin Klein

Calvin Klein Men's Cotton Classics 7-pack Boxer Brief, 7 Black, Medium

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Main Highlights

COTTON CLASSIC: Spun in premium cotton yarns for supreme breathability, Calvin Kleins bestselling mens underwear wicks away moisture to keep you cool and dry.
SUPPORT plus COMFORT: Featuring a functional fly and contoured pouch for a supportive fit, Calvin Kleins mens boxer briefs have a soft, flexible logo waistband that stays put without too much compression and retains its shape, wear after wear.
SIGNATURE FIT: Designed with a full rise, a waist that sits the above hip, and a longer leg line that sits low on the thigh.
DESIGNED IN THE USA: Calvin Kleins mens boxers are created by its NYC-based global design team using premium imported materials.
CARE: Machine wash cold, tumble dry low heat. We recommend hang drying your boxer briefs to extend the life of your garment.

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8.6

Calvin Klein

Calvin Klein Men's Cotton Stretch Megapack Boxer Briefs, Black (7 Pack), M

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Main Highlights

COTTON STRETCH: Spun in pure, premium cotton yarn with a hint of Spandex fibers, Calvin Kleins signature mens underwear wicks away moisture to keep you cool and dry.
SUPPORT plus COMFORT: Featuring a functional fly and contoured pouch for a supportive fit, Calvin Kleins mens boxer briefs have a soft, flexible logo waistband that stays put without too much compression and retains its shape, wear after wear.
SIGNATURE FIT: Designed with a full rise, a waist that sits the above hip, and a longer leg line that sits low on the thigh.
DESIGNED IN THE USA: Calvin Kleins mens boxers are created by its NYC-based global design team using premium imported materials.
CARE: Machine wash cold, tumble dry low heat. We recommend hang drying your boxer briefs to extend the life of your garment

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8.3

Calvin Klein

Calvin Klein Men's Cotton Classics 5-pack Boxer Brief, 3 Black Bodies W / Black Wb, 2 Black Bodies W / White Wb, Medium

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Main Highlights

COTTON CLASSIC: Spun in premium cotton yarns for supreme breathability, Calvin Kleins bestselling mens underwear wicks away moisture to keep you cool and dry.
SUPPORT plus COMFORT: Featuring a functional fly and contoured pouch for a supportive fit, Calvin Kleins mens boxer briefs have a soft, flexible logo waistband that stays put without too much compression and retains its shape, wear after wear.
SIGNATURE FIT: Designed with a full rise, a waist that sits the above hip, and a longer leg line that sits low on the thigh.
DESIGNED IN THE USA: Calvin Kleins mens boxers are created by its NYC-based global design team using premium imported materials.
CARE: Machine wash cold, tumble dry low heat. We recommend hang drying your boxer briefs to extend the life of your garment.

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8.1

Calvin Klein

Calvin Klein Men's Cotton Stretch Megapack Boxer Briefs, Blue Multi (7 Pack), M

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Main Highlights

COTTON STRETCH: Spun in pure, premium cotton yarn with a hint of Spandex fibers, Calvin Kleins signature mens underwear wicks away moisture to keep you cool and dry.
SUPPORT plus COMFORT: Featuring a functional fly and contoured pouch for a supportive fit, Calvin Kleins mens boxer briefs have a soft, flexible logo waistband that stays put without too much compression and retains its shape, wear after wear.
SIGNATURE FIT: Designed with a full rise, a waist that sits the above hip, and a longer leg line that sits low on the thigh.
DESIGNED IN THE USA: Calvin Kleins mens boxers are created by its NYC-based global design team using premium imported materials.
CARE: Machine wash cold, tumble dry low heat. We recommend hang drying your boxer briefs to extend the life of your garment

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8.1

Calvin Klein

Calvin Klein Men's Cotton Classics 3-Pack Brief

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Main Highlights

Full back coverage. Full rise waistband sits at the regular level, above hip.
Functional fly.
Soft, flexible logo waistband retains shape wear after wear and stays put, without too much compression.
Comes in a 3-pack.
Model is approximately 6'1" wearing size Medium

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Our Best Overall Choice

Best Choice

9.7

Calvin Klein

Calvin Klein Men's Cotton Classics 3-pack Boxer Brief, 3 Black, Medium

Free Shipping

Editor's bottom line:

“This is the best one we tested. In terms of quality, brand and price, we couldn't ask for more.”

Main Highlights

COTTON CLASSIC: Spun in premium cotton yarns for supreme breathability, Calvin Kleins bestselling mens underwear wicks away moisture to keep you cool and dry.
SUPPORT plus COMFORT: Featuring a functional fly and contoured pouch for a supportive fit, Calvin Kleins mens boxer briefs have a soft, flexible logo waistband that stays put without too much compression and retains its shape, wear after wear.
SIGNATURE FIT: Designed with a full rise, a waist that sits the above hip, and a longer leg line that sits low on the thigh.
DESIGNED IN THE USA: Calvin Kleins mens boxers are created by its NYC-based global design team using premium imported materials.
CARE: Machine wash cold, tumble dry low heat. We recommend hang drying your boxer briefs to extend the life of your garment.

Show Price

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