10 Best Calvin Klein Men's Underwear of 2025

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

April 2026 Edition

Editor's Choice

9.7

Save 32%

Calvin Klein

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

32% Off

Editor's bottom line:

“This calvin klein men's 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

Save 30%

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

30% Off

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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9.5

Save 6%

Calvin Klein

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

6% Off

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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9.2

Save 17%

Calvin Klein

Calvin Klein Men's Cotton Classics 5-Pack Brief

17% Off

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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9.0

Save 35%

Calvin Klein

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

35% Off

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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8.8

Save 35%

Calvin Klein

Calvin Klein Men's Cotton Classics 7-pack Boxer Brief, 3 Black, 2 Grey Heather, 2 White, Medium

35% Off

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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8.6

Save 32%

Calvin Klein

Calvin Klein Men's Underwear Cotton Classics 4 Pack Briefs, White, Large

32% Off

Main Highlights

Soft and breathable cotton underwear
Better elastic for comfortable leg openings
Cotton blend classic Calvin Klein logo waistbands
Classic fit
Best everyday, comfortable cotton packs for men
Country of manufacture, origin and fabric content may vary.
Calvin Klein signature logo waistband
Functional fly
4 per pack

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8.3

Save 37%

Calvin Klein

Calvin Klein Men's Cotton Classics 3-Pack Brief

37% Off

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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Best Value

8.1

Save 40%

Calvin Klein

Calvin Klein Microfiber Stretch Multipack Low Rise Trunks

40% Off

Main Highlights

SILKY SOFT MICROFIBER: The signature mix of fibers offers exceptional stretch, dries fast and wicks away moisture to keep you cool and dry
SUPPORT + COMFORT: Featuring a contoured pouch for a supportive fit, Calvin Kleins mens Trunks 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. Waistband sits at the regular level, above hip. Leg line sits high on thigh
DESIGNED IN THE USA: Calvin Kleins mens trunks 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 trunks to extend the life of your garment.

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8.1

Save 35%

Calvin Klein

Calvin Klein Men's Micro Stretch 7-pack Boxer Brief, 2 Black, 2 Blue Shadow, 2 Medium Grey, 1 Cobalt Water, Medium

35% Off

Main Highlights

SILKY SOFT MICROFIBER: The signature mix of fibers offers exceptional stretch, dries fast and wicks away moisture to keep you cool and dry
SUPPORT + COMFORT: Featuring a 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 waistband that sits the above hip, and a longer leg that sits low on the thigh
DESIGNED IN THE USA: Calvin Kleins mens boxer briefs 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
In a convenient 7 Pack

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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

32% Off

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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