Free Shipping with $49 purchase + Free Store Pickup. Contiguous US. Exclusions
Macy's Presents: The Edit- A curated mix of fashion and inspiration Check It Out
ADS FROM UNAFFILIATED SITES
  • 94 items in Sales & Discounts Mens Underwear Under 20 Dollars

    • Filter
    • Sort By
    • All Items (94)
    • Free Pick Up
    • Sort by
    • 8 colors
      Alfani Men's 4 Pack. Cotton Boxer Briefs, Created for Macy's
      Limited-Time Special
      $34.00
      Sale $19.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (222)
    • multipack
      Alfani Men's Underwear, Tagless Ribbed Tank Top 5 Pack
      Limited-Time Special
      $34.00
      Sale $19.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (93)
    • multipack
      alfani men's underwear, tagless v neck Undershirt 4 pack
      Limited-Time Special
      $34.00
      Sale $19.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (82)
    • 2 colors
      multipack
      alfani men's underwear, cotton spandex tagless slim fit crew neck Undershirt 2 pack
      Limited-Time Special
      $34.00
      Sale $19.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (62)
    • 2 colors
      multipack
      Alfani Men's Underwear, Tagless Cotton Spandex Slim Fit 2 Pack V Neck Undershirts
      Limited-Time Special
      $34.00
      Sale $19.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (37)
    • 4 colors
      multipack
      2(x)ist Men's Essential 2 Pack Square-Cut Tank
      LAST ACT select colors
      $36.00
      Sale $14.33 - 26.99
      Extra 20% off use: SHOP
      Extra 20% off select merchandise!
      Extra 20% off use: SHOP select colors
      coupon excluded
      Last Act: Extra savings do not apply
      coupon excluded select colors
      (59)
    • 7 colors
      Alfani Men's V-Neck Undershirt, Created for Macy's
      Limited-Time Special
      $14.00
      Sale $7.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (30)
    • 32 Degrees Men's Base-Layer Leggings
      LAST ACT
      $28.00
      Now $8.36
      coupon excluded
      Last Act: Extra savings do not apply
      coupon excluded
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (6)
    • 6 colors
      Alfani Men's Crew-Neck Undershirt
      Limited-Time Special
      $14.00
      Sale $7.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (72)
    • 3 colors
      big & tall
      Alfani Men's Big and Tall Tagless Boxer Brief, 3-Pack
      Everyday Value select colors
      $19.98
      Now $11.98 - 19.98
      Extra 20% off use: SHOP
      Extra 20% off select merchandise!
      Extra 20% off use: SHOP select colors
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (44)
    • 4 colors
      multipack
      adidas Men's Climalite 2 Pack Boxer Brief
      $26.00
      Sale $18.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (16)
    • 4 colors
      32 Degrees Men's Base Layer Crew Neck Shirt
      LAST ACT
      $28.00
      Now $8.36
      coupon excluded
      Last Act: Extra savings do not apply
      coupon excluded
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (84)
    • 4 colors
      multipack
      Jockey Low-Rise Tagless Stretch Briefs, 4 Pack
      Limited-Time Special
      $32.00
      Sale $15.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (15)
    • 4 colors
      Tommy Hilfiger Men's Underwear, Athletic Knit Boxer
      Limited-Time Special
      $24.00
      Sale $13.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (88)
    • big & tall
      Alfani Men's Underwear, Big & Tall 3 Pack Tagless Tank Tops
      $19.98
      Now $11.98
      Extra 20% off use: SHOP
      Extra 20% off select merchandise!
      Extra 20% off use: SHOP
      With offer $9.58
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (11)
    • multipack
      alfani men's underwear, tagless crew neck Undershirt 4 pack
      Limited-Time Special
      $34.00
      Sale $19.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (43)
    • multipack
      Alfani Men's Underwear, Tagless Tank Top 4 Pack
      Limited-Time Special
      $34.00
      Sale $19.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (30)
    • big & tall
      Alfani Men's Underwear, Big & Tall Tagless V Neck 3 Pack Undershirts
      $19.98
      Now $11.98
      Extra 20% off use: SHOP
      Extra 20% off select merchandise!
      Extra 20% off use: SHOP
      With offer $9.58
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (10)
    • 5 colors
      Tommy Hilfiger Men's Printed Cotton Boxers
      Limited-Time Special
      $24.00
      Sale $13.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (30)
    • 3 colors
      Tommy Hilfiger Men's Printed Cotton Boxers
      Limited-Time Special
      $24.00
      Sale $13.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
    • big & tall
      Alfani Men's Underwear, Big & Tall Tagless Tank 4 Pack
      Everyday Value
      $19.98
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (13)
    • 3 colors
      multipack
      adidas Men's Athletic Stretch 2 Pack Boxer Brief
      $24.00
      Sale $17.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (13)
    • 32 Degrees Men's Base Layer Crew Neck Shirt
      LAST ACT
      $28.00
      Now $8.36
      coupon excluded
      Last Act: Extra savings do not apply
      coupon excluded
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (3)
    • multipack
      alfani men's underwear, tagless v neck Undershirt 3 pack
      Limited-Time Special
      $34.00
      Sale $19.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (31)
    • 5 colors
      2(x)ist Men's Sliq Micro Brief
      $26.00
      Sale $18.99
      Extra 20% off use: SHOP
      Extra 20% off select merchandise!
      Extra 20% off use: SHOP
      With offer $15.19
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (11)
    • 3 colors
      32 Degrees Men's Base Layer Turtleneck Shirt
      LAST ACT
      $28.00
      Now $8.36
      coupon excluded
      Last Act: Extra savings do not apply
      coupon excluded
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (25)
    • 2 colors
      Pair of Thieves Men's Core Boxer Briefs
      $20.00
      2 for $20
      Buy 2 pairs and get them both for $20
      2 for $20
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (2)
    • 7 colors
      multipack
      Michael Kors Men's Airsoft Touch Stretch-Woven Boxers, 2-Pack
      LAST ACT select colors
      $39.50
      Now $15.73 - 23.70
      Extra 20% off use: SHOP
      Extra 20% off select merchandise!
      Extra 20% off use: SHOP select colors
      New markdown
      Prices just reduced - Limited Quantities
      New markdown select colors
      (3)
    • 2 colors
      multipack
      adidas Men's Athletic Stretch 2 Pack Trunk
      $24.00
      Sale $17.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (23)
    • multipack
      alfani men's underwear, tagless crew neck Undershirt 3 pack
      Limited-Time Special
      $34.00
      Sale $19.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (17)
    • Pair of Thieves Men's Fractal Printed Boxer Briefs
      $20.00
      2 for $20
      Buy 2 pairs and get them both for $20
      2 for $20
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (2)
    • 3 colors
      2(x)ist Men's Pride No-Show Trunks
      Limited-Time Special
      $30.00
      Sale $17.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (3)
    • 3 colors
      multipack
      Jockey Stretch Tagless Bikini Briefs, 4 Pack
      Limited-Time Special
      $32.00
      Sale $15.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (16)
    • 2 colors
      2(X)IST Shapewear Form Contour Pouch Brief
      $22.00
      Sale $15.99
      Extra 20% off use: SHOP
      Extra 20% off select merchandise!
      Extra 20% off use: SHOP
      With offer $12.79
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (20)
    • big & tall
      Alfani Men's Underwear, Big & Tall 3 Pack Tagless Crew Neck Undershirts
      Everyday Value
      $19.98
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (15)
    • 4 colors
      2(x)ist Men's No-Show Briefs
      Limited-Time Special
      $24.00
      Sale $13.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (2)
    • 4 colors
      Pair of Thieves Men's Blackout Boxer Briefs
      $20.00
      2 for $20
      Buy 2 pairs and get them both for $20
      2 for $20
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
    • 2 colors
      Tommy Hilfiger Men's Printed Cotton Boxers
      Limited-Time Special
      $24.00
      Sale $13.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
    • 2 colors
      Pair of Thieves Men's Crater Printed Boxer Briefs
      $20.00
      2 for $20
      Buy 2 pairs and get them both for $20
      2 for $20
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (2)
    • 3 colors
      2(x)ist Men's Pride No-Show Briefs
      Limited-Time Special
      $26.00
      Sale $14.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (2)