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Men's BOSS Vacation & Resort Clothing, Shoes & Accessories

  • All Shop by Occasion
  • Casual Weekend
  • Concert & Festival Outfits
  • Easter Outfits
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  • Vacation & Resort
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154 items
Rash Print Cotton Short Sleeve Button-Up Shirt
BOSS

Rash Print Cotton Short Sleeve Button-Up Shirt

$49.97Current Price $49.97
(49% off)49% off.
$98.00Comparable value $98.00
(1)
Tessler Tipped Cotton Crewneck T-Shirt
New
BOSS

Tessler Tipped Cotton Crewneck T-Shirt

$49.97Current Price $49.97
(49% off)49% off.
$98.00Comparable value $98.00
Only a few left
Piranha Swim Trunks
BOSS

Piranha Swim Trunks

$39.97Current Price $39.97
(42% off)42% off.
$69.00Comparable value $69.00
Darrel Fisherman Sandal (Men)
BOSS

Darrel Fisherman Sandal (Men)

$59.97Current Price $59.97
(57% off)57% off.
$140.00Comparable value $140.00
(1)
Only a few left
Ellino Linen Camp Shirt
BOSS

Ellino Linen Camp Shirt

$59.97Current Price $59.97
(49% off)49% off.
$118.00Comparable value $118.00
Vibe Swim Trunks
BOSS

Vibe Swim Trunks

$39.97Current Price $39.97
(42% off)42% off.
$69.00Comparable value $69.00
Sienne Tassel Loafer (Men)
BOSS

Sienne Tassel Loafer (Men)

$99.97Current Price $99.97
(49% off)49% off.
$199.00Comparable value $199.00
(2)
Only a few left
Slice Stretch Cotton Shorts
BOSS

Slice Stretch Cotton Shorts

$49.97Current Price $49.97
(49% off)49% off.
$99.00Comparable value $99.00
(1)
Palladio Short Sleeve Button-Up Shirt
New
BOSS

Palladio Short Sleeve Button-Up Shirt

$114.97Current Price $114.97
(49% off)49% off.
$229.00Comparable value $229.00
Thompson Pinstripe Cotton T-Shirt
BOSS

Thompson Pinstripe Cotton T-Shirt

$59.97Current Price $59.97
(49% off)49% off.
$118.00Comparable value $118.00
Piranha Floral Swim Trunks
BOSS

Piranha Floral Swim Trunks

$39.97Current Price $39.97
(42% off)42% off.
$69.00Comparable value $69.00
Taut Floral T-Shirt
New
BOSS

Taut Floral T-Shirt

$74.97Current Price $74.97
(49% off)49% off.
$149.00Comparable value $149.00
Parris Cotton Polo
New
BOSS

Parris Cotton Polo

$64.97Current Price $64.97
(49% off)49% off.
$129.00Comparable value $129.00
Willow Swim Trunks
New
BOSS

Willow Swim Trunks

$39.97Current Price $39.97
(42% off)42% off.
$69.00Comparable value $69.00
Surfley Slide Sandal (Men)
BOSS

Surfley Slide Sandal (Men)

$49.97Current Price $49.97
(47% off)47% off.
$95.00Comparable value $95.00
(2)
Only a few left
Hugo Boss Dolidorio Shorts
BOSS

Hugo Boss Dolidorio Shorts

$89.97Current Price $89.97
(49% off)49% off.
$178.00Comparable value $178.00
(1)
Relaxed Logo T-Shirt
New
BOSS

Relaxed Logo T-Shirt

$39.97Current Price $39.97
(32% off)32% off.
$59.00Comparable value $59.00
Palosh Short Sleeve Polo
New
BOSS

Palosh Short Sleeve Polo

$79.97Current Price $79.97
(32% off)32% off.
$119.00Comparable value $119.00
Velvetfish Stripe Seersucker Camp Shirt
BOSS

Velvetfish Stripe Seersucker Camp Shirt

$49.97Current Price $49.97
(49% off)49% off.
$99.00Comparable value $99.00
Willow Swim Trunks
BOSS

Willow Swim Trunks

$39.97Current Price $39.97
(42% off)42% off.
$69.00Comparable value $69.00
56mm Flat Top Sunglasses
New
BOSS

56mm Flat Top Sunglasses

$69.97Current Price $69.97
(71% off)71% off.
$248.00Comparable value $248.00
(5)
Beach Camp Shirt
BOSS

Beach Camp Shirt

$49.97Current Price $49.97
(49% off)49% off.
$99.00Comparable value $99.00
Piranha Swim Trunks
BOSS

Piranha Swim Trunks

$39.97Current Price $39.97
(42% off)42% off.
$69.00Comparable value $69.00
Dolphin Swim Trunks
BOSS

Dolphin Swim Trunks

$39.97Current Price $39.97
(38% off)38% off.
$65.00Comparable value $65.00
Stitched Logo T-Shirt
BOSS

Stitched Logo T-Shirt

$39.97Current Price $39.97
(41% off)41% off.
$68.00Comparable value $68.00
Commuter Slim Fit Performance Shorts
New
BOSS

Commuter Slim Fit Performance Shorts

$78.97Current Price $78.97
(50% off)50% off.
$159.00Comparable value $159.00
Only a few left
Octopus Swim Shorts
BOSS

Octopus Swim Shorts

$39.97Current Price $39.97
(Up to 42% off)Up to 42% off.
$68.00 – $69.00Comparable value $68.00 to $69.00
Eligino Cotton Camp Shirt
BOSS

Eligino Cotton Camp Shirt

$59.97Current Price $59.97
(49% off)49% off.
$118.00Comparable value $118.00
Dolphin Swim Trunks
BOSS

Dolphin Swim Trunks

$34.97Current Price $34.97
(46% off)46% off.
$65.00Comparable value $65.00
Chaffle Swim Trunks
New
BOSS

Chaffle Swim Trunks

$49.97Current Price $49.97
(36% off)36% off.
$79.00Comparable value $79.00
Tracy Thong Sandal (Men)
BOSS

Tracy Thong Sandal (Men)

$29.97Current Price $29.97
(50% off)50% off.
$60.00Comparable value $60.00
(2)
Noreiles Graphic T-Shirt
BOSS

Noreiles Graphic T-Shirt

$29.97Current Price $29.97
(37% off)37% off.
$48.00Comparable value $48.00
Roan Stretch Cotton Button-Up Shirt
New
BOSS

Roan Stretch Cotton Button-Up Shirt

$69.97Current Price $69.97
(49% off)49% off.
$138.00 – $139.00Comparable value $138.00 to $139.00
Haiti Swim Trunks
New
BOSS

Haiti Swim Trunks

$39.97Current Price $39.97
(32% off)32% off.
$59.00Comparable value $59.00
Piranha Swim Trunks
BOSS

Piranha Swim Trunks

$39.97Current Price $39.97
(42% off)42% off.
$69.00Comparable value $69.00
(1)
Manu Swim Trunks
BOSS

Manu Swim Trunks

$49.97Current Price $49.97
(43% off)43% off.
$88.00Comparable value $88.00
Piranha Floral Swim Trunks
BOSS

Piranha Floral Swim Trunks

$39.97Current Price $39.97
(42% off)42% off.
$69.00Comparable value $69.00
Piranha Swim Trunks
New
BOSS

Piranha Swim Trunks

$39.97Current Price $39.97
(42% off)42% off.
$69.00Comparable value $69.00
Piranha Swim Trunks
BOSS

Piranha Swim Trunks

$39.97Current Price $39.97
(42% off)42% off.
$69.00Comparable value $69.00
Piranha Swim Trunks
BOSS

Piranha Swim Trunks

$39.97Current Price $39.97
(46% off)46% off.
$75.00Comparable value $75.00
Piranha Swim Trunks
BOSS

Piranha Swim Trunks

$39.97Current Price $39.97
(42% off)42% off.
$69.00Comparable value $69.00
Only a few left
Beach Camp Shirt
New
BOSS

Beach Camp Shirt

$49.97Current Price $49.97
(49% off)49% off.
$99.00Comparable value $99.00
Iso Swim Trunks
BOSS

Iso Swim Trunks

$39.97Current Price $39.97
(41% off)41% off.
$68.00Comparable value $68.00
Piranha Recycled Polyester Swim Trunks
BOSS

Piranha Recycled Polyester Swim Trunks

$39.97Current Price $39.97
(Up to 46% off)Up to 46% off.
$68.00 – $75.00Comparable value $68.00 to $75.00
(1)
50mm Square Sunglasses
New
BOSS

50mm Square Sunglasses

$69.97Current Price $69.97
(74% off)74% off.
$276.00Comparable value $276.00
Piranha Swim Shorts
BOSS

Piranha Swim Shorts

$39.97Current Price $39.97
(41% off)41% off.
$68.00Comparable value $68.00
Beach Button-Up Camp Shirt
BOSS

Beach Button-Up Camp Shirt

$49.97Current Price $49.97
(49% off)49% off.
$99.00Comparable value $99.00
Reel Abstract Swim Trunks
BOSS

Reel Abstract Swim Trunks

$39.97Current Price $39.97
(41% off)41% off.
$68.00Comparable value $68.00
Kirk Slide Sandal (Men)
BOSS

Kirk Slide Sandal (Men)

$34.97 – $39.97Current Price $34.97 to $39.97
(Up to 56% off)Up to 56% off.
$80.00Comparable value $80.00
(2)
Mooneye Swim Trunks
New
BOSS

Mooneye Swim Trunks

$29.97Current Price $29.97
(45% off)45% off.
$55.00Comparable value $55.00
54mm Gradient Pilot Sunglasses
New
BOSS

54mm Gradient Pilot Sunglasses

$69.97Current Price $69.97
(69% off)69% off.
$231.00Comparable value $231.00
Springfish Swim Trunks
BOSS

Springfish Swim Trunks

$49.97Current Price $49.97
(49% off)49% off.
$98.00Comparable value $98.00
Cory Short Sleeve Linen Button-Up Shirt
New
BOSS

Cory Short Sleeve Linen Button-Up Shirt

$99.97Current Price $99.97
(52% off)52% off.
$209.00Comparable value $209.00
Abas Swim Trunks
New
BOSS

Abas Swim Trunks

$39.97Current Price $39.97
(38% off)38% off.
$65.00Comparable value $65.00
Luca Swim Trunks
BOSS

Luca Swim Trunks

$99.97Current Price $99.97
(59% off)59% off.
$248.00Comparable value $248.00
Octopus Swim Trunks
BOSS

Octopus Swim Trunks

$39.97Current Price $39.97
(42% off)42% off.
$69.00Comparable value $69.00
Dominica Swim Trunks
New
BOSS

Dominica Swim Trunks

$39.97Current Price $39.97
(38% off)38% off.
$65.00Comparable value $65.00
Only a few left
Atoll Swim Trunks
BOSS

Atoll Swim Trunks

$39.97Current Price $39.97
(49% off)49% off.
$79.00Comparable value $79.00
Parris Cotton Polo
New
BOSS

Parris Cotton Polo

$64.97Current Price $64.97
(49% off)49% off.
$129.00Comparable value $129.00
Iconic Side Stripe Stretch Swim Trunks
BOSS

Iconic Side Stripe Stretch Swim Trunks

$39.97Current Price $39.97
(38% off)38% off.
$65.00Comparable value $65.00
Bari Swim Shorts
BOSS

Bari Swim Shorts

$39.97Current Price $39.97
(41% off)41% off.
$68.00Comparable value $68.00
52mm Square Sunglasses
New
BOSS

52mm Square Sunglasses

$69.97Current Price $69.97
(71% off)71% off.
$248.00Comparable value $248.00
Ebor Short Sleeve Button-Up Shirt
BOSS

Ebor Short Sleeve Button-Up Shirt

$49.97Current Price $49.97
(49% off)49% off.
$98.00Comparable value $98.00
50mm Round Sunglasses
BOSS

50mm Round Sunglasses

$69.97Current Price $69.97
(71% off)71% off.
$248.00Comparable value $248.00
(1)
Beach Camp Shirt
New
BOSS

Beach Camp Shirt

$49.97Current Price $49.97
(49% off)49% off.
$99.00Comparable value $99.00
x NBA Swim Trunks
BOSS

x NBA Swim Trunks

$44.97Current Price $44.97
(48% off)48% off.
$88.00Comparable value $88.00
Tio Swim Trunks
New
BOSS

Tio Swim Trunks

$39.97Current Price $39.97
(40% off)40% off.
$67.00Comparable value $67.00
Zeb Swim Trunks
BOSS

Zeb Swim Trunks

$39.97Current Price $39.97
(37% off)37% off.
$64.00Comparable value $64.00
Only a few left
56mm Polarized Rectangular Sunglasses
BOSS

56mm Polarized Rectangular Sunglasses

$69.97Current Price $69.97
(74% off)74% off.
$278.00Comparable value $278.00
Adria Swim Shorts
BOSS

Adria Swim Shorts

$99.97Current Price $99.97
(59% off)59% off.
$248.00Comparable value $248.00
51mm Square Sunglasses
BOSS

51mm Square Sunglasses

$69.97Current Price $69.97
(74% off)74% off.
$276.00Comparable value $276.00
Pirhana Abstract Floral Swim Trunks
BOSS

Pirhana Abstract Floral Swim Trunks

$39.97Current Price $39.97
(46% off)46% off.
$75.00Comparable value $75.00
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