DealNews - Discount Men's Underwear on Sale - Find the Best Sales on Underwear

BOSS Men's Cotton Boxer Briefs 3-Pack (Sz L) for $19 + free shipping w/ Prime

Sat, 23 May 2026 10:05:21 -0400

That's a savings of 54% on this underwear 3-Pack from BOSS, and just around $6.50 per pair. The other sizes are also discounted, but cost slightly more. Buy Now at Amazon

Features

3-pack
Cotton construction
Trunk style
Men's department

Macy's Memorial Day Underwear Sale: Up to 86% off + free shipping w/ $39

Fri, 22 May 2026 10:57:56 -0400

Save on over 500 styles of underwear for this Memorial Day Sale. Star Rewards members receive free shipping on orders over $39 (it's free to join). Non-members can pay $10.95 or get free shipping on orders over $49. Pickup is available on most orders, too. Deal ends May 26 at 3am ET.

Pictured is the Tommy Hilfiger Men's All Day Comfort Knit Boxers 3-Pack for $25 ($15 off).

Shop Now at Macy's

Calvin Klein Men's Underwear Memorial Day Sale for 30% off + 20% off $100+ + free shipping w/ $75

Thu, 21 May 2026 19:02:45 -0400

Take 30% off Calvin Klein men's underwear for their Memorial Day Sale. Plus, an extra 20% off applies to purchases of $100 or more. We've pictured the Calvin Klein Men's Ultra Soft Modal 3-Pack Trunk for $41.65 ($18 off). Shipping adds $9.95, but orders of $75 or more ship for free. Exclusions apply. Sale ends May 26, 2026. Buy Now at Calvin Klein

Macy's Memorial Day Men's Underwear Deals: 20% to 60% off + free shipping w/ $39

Tue, 19 May 2026 07:24:19 -0400

During the Memorial Day Sale, get socks starting from $8, underwear from $8, tanks from $12, and more. We've pictured the Calvin Klein Men's Cotton Classics Briefs Underwear 5-Pack for $34.75 ($70 elsewhere). Star Rewards members receive free shipping on orders over $39 (it's free to join). Non-members can pay $10.95 or get free shipping on orders over $49. Pickup is available on most orders, too. Shop Now at Macy's

Calvin Klein Men's Underwear Deals at Macy's: Up to 50% off + free shipping w/ $39

Wed, 13 May 2026 06:54:05 -0400

Shop over 90 pairs and multipacks. We've pictured these Calvin Klein Men's Cotton Classic Boxer Briefs Underwear 5-Pack for $49.99 ($32 off). Star Rewards members receive free shipping on orders over $39 (it's free to join). Non-members can pay $10.95 or get free shipping on orders over $49. Pickup is available on most orders, too

Shop Now at Macy's

Hanes Men's Boxer Shorts Underwear 2-Pack for $5 + free shipping w/ $35

Thu, 30 Apr 2026 15:57:35 -0400

Walmart offers this Hanes Men 's Boxer Shorts Underwear 2-Pack for $5. That's 50% off, a savings of $5 and the lowest price we could find. Choose free in-store pickup, or get free shipping with an order of $35 of more. Buy Now at Walmart

lululemon Men's We Made Too Much Underwear Specials for Single pairs from $19, multipacks from $64 + free shipping

Fri, 24 Apr 2026 03:52:58 -0400

lululemon Men's Underwear is discounted by up to 32% here, across both single pairs and multipacks. Pictured is the lululemon Men's Always In Motion 7" Boxer Brief 3-Pack for $64 ($24 off). Plus, every order ships for free. Buy Now at lululemon

Amazon Essentials Slim Fit Men's Crew Neck T-Shirt 5-Pack for $11 + free shipping w/ Prime

Thu, 30 Apr 2026 15:33:42 -0400

Amazon offers this Amazon Essentials Slim Fit Men's Crew Neck T-Shirt 5-Pack for $11, a savings of $8 and the best price we could find. Prime members get free shipping. Buy Now at Amazon

Features

Slim fit design
Soft cotton blend
Short-sleeve design
Crew neck with durability
Flexible fit with spandex

Hanes Men's Boxer Briefs 12-Pack for $33 + free shipping

Tue, 28 Apr 2026 15:26:50 -0400

Amazon has the lowest price we could find on this Hanes Men's Boxer Briefs 12-Pack. It's $11 off and the best price we could find. It ships free with Prime. Buy Now at Amazon

Features

Cotton blend that stays soft
Comfort Flex waistband
Moisture-wicking technology
Tag-free design
Sizes available up to 3XL

Hanes Men's Exposed Waistband 5-Pack for $15 + free shipping w/ Prime

Mon, 27 Apr 2026 14:49:07 -0400

Get these Hanes boxers at this price in Exposed Waistband Blue. You'd pay around $10 more elsewhere. Shipping is free for Prime members. Buy Now at Amazon

Calvin Klein Men's Cotton Classics Boxer Brief 3-Pack for From $22.98 + free shipping w/ Prime

Mon, 27 Apr 2026 05:38:19 -0400

That's a half off savings on the lowest starting price. We've pictured them in Medieval Blue, Minnow, Blue Bay, size XL, but other styles/sizes are close in price. Shipping is free for Prime members. Buy Now at Amazon

Lacoste Men's Cotton Stretch Essentials Boxer Briefs 5-Pack for $30 + free shipping

Mon, 13 Apr 2026 05:33:32 -0400

At Amazon, get this Lacoste Men's Cotton Stretch Essentials Boxer Briefs 5-Pack for $29.99. That's $30 less than what Macy's charges. Shipping is free. Buy Now at Amazon

Hanes Men's Underwear Boxer Briefs 12-Pack for $33 + free shipping

Sun, 12 Apr 2026 08:27:15 -0400

Bag this 12-pack at an $11 savings. Each pair costs less than $3. Shipping is free. Buy Now at Amazon

Hanes Men's Cotton Moisture-Wicking Boxer Briefs 6-Pack for $18 + free shipping w/ Prime

Wed, 08 Apr 2026 11:19:34 -0400

That's around $6 less than you'd pay elsewhere for this 6-pack. It's at this price only in Black/Gray or Heather Blue/Red/Black. Prime members get free shipping. Buy Now at Amazon

Hanes Men's Tagless Boxer Briefs 12-Pack for $33 + free shipping w/ Prime

Wed, 08 Apr 2026 10:25:26 -0400

That's $2.75 per pair and around $8 less than you'd pay for this quantity in most local stores. Buy Now at Amazon

Hanes Men’s Exposed Waistband Knit Boxers 5-Pack for $15 + free shipping w/ Prime

Sat, 04 Apr 2026 08:32:09 -0400

This is Amazon's lowest price on the 5-pack of Hanes Men's Exposed Waistband Knit Boxers in years. The best deal we could find for a 5-pack of boxers on Hanes today was $21, so this is a good price. The pack will ship for free from Amazon for Prime members. Buy Now at Amazon

PUMA Men's Performance Boxer Briefs 5-Pack for from $16 + free shipping w/ Prime

Mon, 30 Mar 2026 09:33:18 -0400

At Amazon, get this PUMA Men's Performance Boxer Briefs 5-Pack, with prices starting from $15.82. It's a great price of a 5-pack of PUMA men's underwear in general. Shipping is free for Prime members. Buy Now at Amazon

Fruit of the Loom Men's Coolzone Boxer Briefs 7-Pack for $15 + free shipping w/ Prime

Thu, 26 Mar 2026 11:05:22 -0400

At Amazon, get this Fruit of the Loom Men's Coolzone Boxer Briefs 7-Pack for $15.49. It's the best deal we've seen for this multipack. Shipping is free for Prime members. Buy Now at Amazon

Jockey Men's 7" Long Leg Boxer Brief 4-Pack for $14 + free shipping w/ $35

Thu, 26 Mar 2026 05:46:05 -0400

You'd pay over $20 elsewhere. Choose pickup or spend $35 to avoid the $6.99 shipping charge. Buy Now at Walmart

Everlast Men's Active Performance Boxer Briefs 6-Pack for $12 + free shipping w/ $35

Tue, 24 Mar 2026 05:01:38 -0400

That's over half off and a great price for a 6-pack. Buy Now at Walmart