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Men's Vacation & Resort Swimwear

  • All Men
  • Under $100
  • New Arrivals
  • Shorts
  • Swim
  • Clothing
  • Shoes
  • Accessories
  • Luggage & Travel
  • Travel Essentials
337 items
The Bungalow Water Repellent Swim Trunks

Fair Harbor The Bungalow Water Repellent Swim Trunks

$76 – $88Current Price $76 to $88
The Bayberry Swim Trunks
New

Fair Harbor The Bayberry Swim Trunks

$49.40 – $88Current Price $49.40 to $88
$76 – $88Previous Price $76 to $88
Shorelite Swim Trunks
New

Faherty Shorelite Swim Trunks

$98 – $118Current Price $98 to $118
Calder Buckle 5" Swim Trunk
New

Onia Calder Buckle 5" Swim Trunk

$38 – $285Current Price $38 to $285
$95 – $285Previous Price $95 to $285
The Bungalow Water Repellent Swim Trunks
New

Fair Harbor The Bungalow Water Repellent Swim Trunks

$49.40 – $88Current Price $49.40 to $88
$76 – $88Previous Price $76 to $88
In the Canopy Swim Trunks

Peter Millar In the Canopy Swim Trunks

$65Current Price $65
$100Previous Price $100
Only a few left
Bungalow Swim Trunks

Fair Harbor Bungalow Swim Trunks

$26.97Current Price $26.97
$88Previous Price $88
New Markdown
Only a few left
Breaker Water Repellent Swim Trunks

Fair Harbor Breaker Water Repellent Swim Trunks

$49.99 – $50.70Current Price $49.99 to $50.70
$78Previous Price $78
New Markdown
Breaker Water Repellent Swim Trunks

Fair Harbor Breaker Water Repellent Swim Trunks

$58.50Current Price $58.50
$78Previous Price $78
Bayberry Water Repellent Swim Trunks

Fair Harbor Bayberry Water Repellent Swim Trunks

$88Current Price $88
7-Inch Seersucker Swim Trunks
New

Nordstrom 7-Inch Seersucker Swim Trunks

$49Current Price $49
Shorelite 7-Inch Performance Swim Trunks

Faherty Shorelite 7-Inch Performance Swim Trunks

$98Current Price $98
Only a few left
Somerset Swim Trunks
New

Barbour Somerset Swim Trunks

$85 – $90Current Price $85 to $90
Classic 7-Inch Swim Trunks
New

Chubbies Classic 7-Inch Swim Trunks

$79.50Current Price $79.50
The Bayberry Water Repellent Swim Trunks

Fair Harbor The Bayberry Water Repellent Swim Trunks

$88Current Price $88
Palmoa Fruit & Bird Print Swim Trunks

Peter Millar Palmoa Fruit & Bird Print Swim Trunks

$100Current Price $100
Naples Teeny Martini Print Swim Trunks
New

Tommy Bahama Naples Teeny Martini Print Swim Trunks

$89.50Current Price $89.50
Charles 4" Swim Trunk
New

Onia Charles 4" Swim Trunk

$60 – $240Current Price $60 to $240
$150 – $240Previous Price $150 to $240
The Anchor Swim Trunks

Fair Harbor The Anchor Swim Trunks

$72Current Price $72
Traveler Seersucker Swim Trunks

Polo Ralph Lauren Traveler Seersucker Swim Trunks

$63.99 – $98.50Current Price $63.99 to $98.50
$98.50Previous Price $98.50
Polly Want Swim Trunks

Peter Millar Polly Want Swim Trunks

$75Current Price $75
$100Previous Price $100
Vibe Swim Trunks

BOSS Vibe Swim Trunks

$69Current Price $69
Pirhana Abstract Floral Swim Trunks

BOSS Pirhana Abstract Floral Swim Trunks

$41.40Current Price $41.40
$69Previous Price $69
Tide Lines Swim Trunks

Peter Millar Tide Lines Swim Trunks

$108Current Price $108
Surfsilk Tijuana Board Shorts (Regular & Tall)
New

Quiksilver Surfsilk Tijuana Board Shorts (Regular & Tall)

$24.99 – $59Current Price $24.99 to $59
$59Previous Price $59
Cruise Hybrid Board Shorts

Vuori Cruise Hybrid Board Shorts

$59.20 – $78Current Price $59.20 to $78
$74 – $78Previous Price $74 to $78
All Day Layback Swim Trunks

Billabong All Day Layback Swim Trunks

$39.95Current Price $39.95
Caiman Islands Swim Trunks

Peter Millar Caiman Islands Swim Trunks

$75Current Price $75
$100Previous Price $100
The Anchor Swim Trunks

Fair Harbor The Anchor Swim Trunks

$68 – $88Current Price $68 to $88
Everyday 17" Trippin' Palm Water Repellent Swim Trunks

Quiksilver Everyday 17" Trippin' Palm Water Repellent Swim Trunks

$49Current Price $49
Shark Swim Trunks
New

BOSS Shark Swim Trunks

$79Current Price $79
Tio Swim Trunks
New

BOSS Tio Swim Trunks

$67Current Price $67
Briefly in Paradise 5.5-Inch Swim Trunks
New

Chubbies Briefly in Paradise 5.5-Inch Swim Trunks

$79.50Current Price $79.50
Sunset Palms Swim Trunks

Peter Millar Sunset Palms Swim Trunks

$108Current Price $108
Sintra Geo Print Swim Trunks

Peter Millar Sintra Geo Print Swim Trunks

$44.99Current Price $44.99
$100Previous Price $100
Only a few left
Knox Swim Trunks

Peter Millar Knox Swim Trunks

$108Current Price $108
Only a few left
Vibe Recycled Polyester Swim Trunks

BOSS Vibe Recycled Polyester Swim Trunks

$69Current Price $69
Swim Trunks

MANGO Swim Trunks

$59.99Current Price $59.99
Lineup Layback Swim Trunks

Billabong Lineup Layback Swim Trunks

$69.95Current Price $69.95
Charles 5" Swim Trunk
New

Onia Charles 5" Swim Trunk

$90 – $225Current Price $90 to $225
$130 – $245Previous Price $130 to $245
The Bayberry Floral Swim Trunks

Fair Harbor The Bayberry Floral Swim Trunks

$48Current Price $48
$80Previous Price $80
Only a few left
Gingham Seersucker Swim Trunks
New

Barbour Gingham Seersucker Swim Trunks

$90Current Price $90
Rock-a-Crocks Lined 5.5-Inch Swim Trunks
New

Chubbies Rock-a-Crocks Lined 5.5-Inch Swim Trunks

$79.50Current Price $79.50
DGF Shorelite Performance Swim Trunks

Faherty DGF Shorelite Performance Swim Trunks

$98Current Price $98
Stripe Print Swim Trunks

MANGO Stripe Print Swim Trunks

$69.99Current Price $69.99
Dive Swim Trunks

BOSS Dive Swim Trunks

$69Current Price $69
Water Reactive Leaf Print Swim Trunks
New

Barbour Water Reactive Leaf Print Swim Trunks

$90Current Price $90
Big Blue Swim Trunks

johnnie-O Big Blue Swim Trunks

$89Current Price $89
Floral Stretch Volley Swim Trunks
New

Vintage Summer Floral Stretch Volley Swim Trunks

$49Current Price $49
Men's Stretch Swim Short
New

Cotton On Men's Stretch Swim Short

$39.99Current Price $39.99
Water Reactive Tartan Swim Trunks
New

Barbour Water Reactive Tartan Swim Trunks

$90Current Price $90
One Water Repellent Hybrid Shorts

Fair Harbor One Water Repellent Hybrid Shorts

$72Current Price $72
Floral Stretch Volley Swim Trunks
New

Vintage Summer Floral Stretch Volley Swim Trunks

$49Current Price $49
Clifton Swim Trunks

Peter Millar Clifton Swim Trunks

$108Current Price $108
The Anchor Swim Trunks

Fair Harbor The Anchor Swim Trunks

$72 – $88Current Price $72 to $88
OG Pigment Scallop Board Shorts

O'Neill OG Pigment Scallop Board Shorts

$24.99Current Price $24.99
$59.50Previous Price $59.50
Maverick Shorts
New

Vuori Maverick Shorts

$59.20 – $78Current Price $59.20 to $78
$74 – $78Previous Price $74 to $78
Bungalow Water Repellent Swim Trunks

Fair Harbor Bungalow Water Repellent Swim Trunks

$76Current Price $76
Iconic Side Stripe Swim Trunks
New

BOSS Iconic Side Stripe Swim Trunks

$65Current Price $65
Print Stretch Volley Swim Trunks
New

Vintage Summer Print Stretch Volley Swim Trunks

$49Current Price $49
Volley Swim Trunks
New

Vintage Summer Volley Swim Trunks

$45Current Price $45
Vale Swim Trunks
New

BOSS Vale Swim Trunks

$99Current Price $99
Hermosa Swim Trunks

O'Neill Hermosa Swim Trunks

$60Current Price $60
Naples Surf Seersucker Volley Swim Trunks
New

Tommy Bahama Naples Surf Seersucker Volley Swim Trunks

$89.50Current Price $89.50
Anchor Water Repellent Swim Trunks

Fair Harbor Anchor Water Repellent Swim Trunks

$46.80Current Price $46.80
$72Previous Price $72
Turritella Crown Swim Trunks

Peter Millar Turritella Crown Swim Trunks

$108Current Price $108
Indigo Crazies 5.5-Inch Swim Trunks
New

Chubbies Indigo Crazies 5.5-Inch Swim Trunks

$79.50Current Price $79.50
Demna Swim Trunks
New

Save The Duck Demna Swim Trunks

$99Current Price $99
Staple Logo Embroidered Swim Trunks

Barbour Staple Logo Embroidered Swim Trunks

$80Current Price $80
Mix Pack Volley Floral 17" Swim Trunks
New

Quiksilver Mix Pack Volley Floral 17" Swim Trunks

$62Current Price $62
Seersucker Swim Trunks

MANGO Seersucker Swim Trunks

$69.99Current Price $69.99
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