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Men's 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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4151 items
9-Inch Commuter Shorts
Rhone

9-Inch Commuter Shorts

$56.99Current Price $56.99
(41% off)41% off.
$98.00Comparable value $98.00
New Markdown
(278)
Only a few left
Venice Flat Front Grey Cotton Twill Chino Shorts
New
Hudson Jeans

Venice Flat Front Grey Cotton Twill Chino Shorts

$74.97Current Price $74.97
Roadster Check-In Medium 27-Inch Spinner Suitcase
Porsche Design

Roadster Check-In Medium 27-Inch Spinner Suitcase

$455.00Current Price $455.00
(30% off)30% off.
$650.00Comparable value $650.00
Novelty 53mm Cat Eye Sunglasses
Bottega Veneta

Novelty 53mm Cat Eye Sunglasses

$289.97Current Price $289.97
(46% off)46% off.
$540.00Comparable value $540.00
Roadster Pro Water Repellent Weekend Bag
Porsche Design

Roadster Pro Water Repellent Weekend Bag

$344.97Current Price $344.97
(30% off)30% off.
$495.00Comparable value $495.00
Only a few left
Bazzz Boat Shoe (Men)
New
ALDO

Bazzz Boat Shoe (Men)

$64.97Current Price $64.97
(45% off)45% off.
$120.00Comparable value $120.00
Baja Party Mixer Board Shorts
New
Tommy Bahama

Baja Party Mixer Board Shorts

$49.97Current Price $49.97
(52% off)52% off.
$105.00Comparable value $105.00
(1)
61mm Aviator Sunglasses
Gucci

61mm Aviator Sunglasses

$229.97Current Price $229.97
(54% off)54% off.
$500.00Comparable value $500.00
Willow Swim Trunks
BOSS

Willow Swim Trunks

$39.97Current Price $39.97
(42% off)42% off.
$69.00Comparable value $69.00
Aviator Sunglasses
Vince Camuto

Aviator Sunglasses

$16.23 – $24.97Current Price $16.23 to $24.97
(Up to 75% off select items)Up to 75% off select items.
$65.00Comparable value $65.00
(5)
51mm Rectangular Sunglasses
New
Saint Laurent

51mm Rectangular Sunglasses

$315.97Current Price $315.97
(40% off)40% off.
$535.00Comparable value $535.00
Around the Island Tropical Print Polo
TravisMathew

Around the Island Tropical Print Polo

$59.97Current Price $59.97
(40% off)40% off.
$99.95Comparable value $99.95
(26)
Only a few left
Chest Pocket T-Shirt
DENIM AND FLOWER

Chest Pocket T-Shirt

$14.97Current Price $14.97
60mm Square Sunglasses
Prada

60mm Square Sunglasses

$184.97Current Price $184.97
(47% off)47% off.
$349.00Comparable value $349.00
Only a few left
Layered Band Paper Straw Panama Hat
San Diego Hat

Layered Band Paper Straw Panama Hat

$32.97Current Price $32.97
(31% off)31% off.
$48.00Comparable value $48.00
(1)
Ronan Stripe Oxford Shorts
New
HUGO

Ronan Stripe Oxford Shorts

$58.97Current Price $58.97
(50% off)50% off.
$118.00Comparable value $118.00
Only a few left
Dypsis Leaves Volley Swim Trunks
Hurley

Dypsis Leaves Volley Swim Trunks

$24.97Current Price $24.97
(50% off)50% off.
$50.00Comparable value $50.00
(1)
56mm Rectangular Sunglasses
New
Balenciaga

56mm Rectangular Sunglasses

$239.97Current Price $239.97
(52% off)52% off.
$505.00Comparable value $505.00
57mm Aviator Sunglasses
Ted Baker London

57mm Aviator Sunglasses

$49.97Current Price $49.97
(66% off)66% off.
$149.00Comparable value $149.00
Hendrix Pima Cotton Polo
Bugatchi

Hendrix Pima Cotton Polo

$59.97Current Price $59.97
(59% off)59% off.
$149.00Comparable value $149.00
All Eyes on Me Trucker Hat
Goorin Bros.

All Eyes on Me Trucker Hat

$21.97Current Price $21.97
(56% off)56% off.
$50.00Comparable value $50.00
(1)
Digital Print Cotton Polo Shirt
Bugatchi

Digital Print Cotton Polo Shirt

$59.97Current Price $59.97
(59% off)59% off.
$149.00Comparable value $149.00
(2)
Red White & Booyah Board Shorts
TravisMathew

Red White & Booyah Board Shorts

$49.97Current Price $49.97
(47% off)47% off.
$94.95Comparable value $94.95
(3)
Graffiti Baseball Cap
New
McQueen

Graffiti Baseball Cap

$189.97Current Price $189.97
(57% off)57% off.
$450.00Comparable value $450.00
Wordmark Slide Sandal (Men)
Hurley

Wordmark Slide Sandal (Men)

$14.97Current Price $14.97
(57% off)57% off.
$35.00Comparable value $35.00
(3)
Tracker Cargo Shorts
Hudson Jeans

Tracker Cargo Shorts

$89.97Current Price $89.97
(45% off)45% off.
$165.00Comparable value $165.00
(6)
64mm Aviator Sunglasses
Kenneth Cole

64mm Aviator Sunglasses

$39.97Current Price $39.97
(57% off)57% off.
$95.00Comparable value $95.00
Splat Graphic T-Shirt
Black Owned/Founded
ICECREAM

Splat Graphic T-Shirt

$49.97Current Price $49.97
(28% off)28% off.
$70.00Comparable value $70.00
Dobby Drawstring Shorts
New
Lucky Brand

Dobby Drawstring Shorts

$34.97Current Price $34.97
(49% off)49% off.
$69.50Comparable value $69.50
Kylo Camp Shirt
AllSaints

Kylo Camp Shirt

$88.97Current Price $88.97
(55% off)55% off.
$199.00Comparable value $199.00
Two-Tone Straw Panama Hat
MARCUS ADLER

Two-Tone Straw Panama Hat

$29.97Current Price $29.97
(30% off)30% off.
$42.95Comparable value $42.95
Frye Pinch Crown Fedora
San Diego Hat

Frye Pinch Crown Fedora

$40.97Current Price $40.97
(50% off)50% off.
$82.00Comparable value $82.00
Yarn Dye Stripe Heritage Polo
Original Penguin

Yarn Dye Stripe Heritage Polo

$34.97Current Price $34.97
(56% off)56% off.
$80.00Comparable value $80.00
(4)
Bali Border Floral Jacquard Short Sleeve Silk Button-Up Shirt (Big & Tall)
Tommy Bahama

Bali Border Floral Jacquard Short Sleeve Silk Button-Up Shirt (Big & Tall)

$19.99 – $128.00Current Price $19.99 to $128.00
(Up to 86% off select items)Up to 86% off select items.
$138.00 – $148.00Comparable value $138.00 to $148.00
New Markdown
(406)
Byrds Print Performance Polo
New
TailorByrd

Byrds Print Performance Polo

$29.97Current Price $29.97
(62% off)62% off.
$80.00Comparable value $80.00
53mm Square Sunglasses
New
TOM FORD

53mm Square Sunglasses

$179.97Current Price $179.97
(63% off)63% off.
$495.00Comparable value $495.00
Hilo Waterproof Weekend Bag
Rains

Hilo Waterproof Weekend Bag

$44.97Current Price $44.97
(52% off)52% off.
$95.00Comparable value $95.00
(6)
Marseille Camp Shirt
AllSaints

Marseille Camp Shirt

$124.97Current Price $124.97
(37% off)37% off.
$199.00Comparable value $199.00
53mm Rectangular Sunglasses
Lacoste

53mm Rectangular Sunglasses

$59.97Current Price $59.97
(61% off)61% off.
$155.00Comparable value $155.00
Mercerized Cotton Polo
New
Bugatchi

Mercerized Cotton Polo

$59.97Current Price $59.97
(59% off)59% off.
$149.00Comparable value $149.00
Swimming Pool Graphic T-Shirt
New
Lucky Brand

Swimming Pool Graphic T-Shirt

$19.97Current Price $19.97
(49% off)49% off.
$39.50Comparable value $39.50
Coastline Bisa Check Corduroy Button-Up Shirt
New
Tommy Bahama

Coastline Bisa Check Corduroy Button-Up Shirt

$74.97Current Price $74.97
(49% off)49% off.
$148.00Comparable value $148.00
(4)
Rat Trap Graphic T-Shirt
Volcom

Rat Trap Graphic T-Shirt

$16.97Current Price $16.97
(39% off)39% off.
$28.00Comparable value $28.00
Trinidad 56mm Polarized Aviator Sunglasses
Eco

Trinidad 56mm Polarized Aviator Sunglasses

$64.97Current Price $64.97
(56% off)56% off.
$150.00Comparable value $150.00
(1)
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
Debossed Patch Trucker Hat
San Diego Hat

Debossed Patch Trucker Hat

$19.97Current Price $19.97
(28% off)28% off.
$28.00Comparable value $28.00
Chelsea 28-Inch Softside Spinner Luggage
Kenneth Cole

Chelsea 28-Inch Softside Spinner Luggage

$139.97Current Price $139.97
(64% off)64% off.
$390.00Comparable value $390.00
(1)
Midsize 52mm Square Sunglasses
Roxy

Midsize 52mm Square Sunglasses

$19.97Current Price $19.97
(48% off)48% off.
$39.00Comparable value $39.00
Tropical Volley Swim Trunks
THE ENDLESS SUMMER

Tropical Volley Swim Trunks

$19.97Current Price $19.97
(50% off)50% off.
$40.00Comparable value $40.00
Lakeview 3 Visor
Black Clover

Lakeview 3 Visor

$12.98Current Price $12.98
(62% off)62% off.
$35.00Comparable value $35.00
Mesic Palm Tree Polo
TravisMathew

Mesic Palm Tree Polo

$59.97Current Price $59.97
(40% off)40% off.
$99.95Comparable value $99.95
(46)
Colorblock Stretch Cotton Polo
KARL LAGERFELD PARIS

Colorblock Stretch Cotton Polo

$54.97Current Price $54.97
(38% off)38% off.
$89.00Comparable value $89.00
Only a few left
140mm Mirrored Flat Top Sunglasses
Vince Camuto

140mm Mirrored Flat Top Sunglasses

$24.97Current Price $24.97
(61% off)61% off.
$65.00Comparable value $65.00
(4)
Volley Swim Trunks
Nike

Volley Swim Trunks

$29.97Current Price $29.97
(50% off)50% off.
$60.00Comparable value $60.00
Amalfi Coast Paradiso Sands 6-Inch Board Shorts
Tommy Bahama

Amalfi Coast Paradiso Sands 6-Inch Board Shorts

$44.97Current Price $44.97
(54% off)54% off.
$99.50Comparable value $99.50
(3)
Core Volley Swim Trunks
DKNY

Core Volley Swim Trunks

$24.97Current Price $24.97
(58% off)58% off.
$59.50Comparable value $59.50
(1)
Snappers Elastic Waist 5.5 Inch Stretch Shorts
Vintage 1946

Snappers Elastic Waist 5.5 Inch Stretch Shorts

$34.97Current Price $34.97
(41% off)41% off.
$59.50Comparable value $59.50
(14)
Porter 2.0 Sling Bag
True Religion

Porter 2.0 Sling Bag

$24.97Current Price $24.97
(50% off)50% off.
$50.00Comparable value $50.00
Didicot Geo Print Cotton Seersucker Camp Shirt
Wax London

Didicot Geo Print Cotton Seersucker Camp Shirt

$44.99Current Price $44.99
(72% off)72% off.
$165.00Comparable value $165.00
New Markdown
Watercolor Floral Stretch Volley Swim Shorts
Vintage Summer

Watercolor Floral Stretch Volley Swim Shorts

$13.96Current Price $13.96
(71% off)71% off.
$49.00Comparable value $49.00
New Markdown
(2)
Plaza Active Performance T-Shirt
Obey

Plaza Active Performance T-Shirt

$29.97Current Price $29.97
(57% off)57% off.
$70.00Comparable value $70.00
Sylan Short Sleeve Polo
New
Robert Barakett

Sylan Short Sleeve Polo

$59.97Current Price $59.97
(69% off)69% off.
$195.00Comparable value $195.00
Micro Print Short Sleeve Button-Up Shirt
DENIM AND FLOWER

Micro Print Short Sleeve Button-Up Shirt

$19.97Current Price $19.97
(1)
Blue Check Flannel Shorts
Topman

Blue Check Flannel Shorts

$19.99Current Price $19.99
(66% off)66% off.
$59.99Previous Price $59.99
New Markdown
Welker Double Strap Slide Sandal (Men)
New
Tommy Hilfiger

Welker Double Strap Slide Sandal (Men)

$44.97Current Price $44.97
(43% off)43% off.
$79.00Comparable value $79.00
Max Swim Trunks
New
BOSS

Max Swim Trunks

$39.97Current Price $39.97
(40% off)40% off.
$67.00Comparable value $67.00
Beach Print Slim Fit Camp Shirt
Original Penguin

Beach Print Slim Fit Camp Shirt

$39.97Current Price $39.97
(57% off)57% off.
$95.00Comparable value $95.00
(7)
The Bungalow Water Repellent Swim Trunks
New
Fair Harbor

The Bungalow Water Repellent Swim Trunks

$26.97 – $39.97Current Price $26.97 to $39.97
(Up to 69% off)Up to 69% off.
$76.00 – $88.00Comparable value $76.00 to $88.00
(9)
Icon Stencil Flame Graphic T-Shirt
Obey

Icon Stencil Flame Graphic T-Shirt

$19.97Current Price $19.97
(44% off)44% off.
$36.00Comparable value $36.00
Only a few left
Alberto 55mm Gradient Square Sunglasses
TOM FORD

Alberto 55mm Gradient Square Sunglasses

$179.97Current Price $179.97
(63% off)63% off.
$490.00Comparable value $490.00
Established Works Shorts
Obey

Established Works Shorts

$29.97Current Price $29.97
(40% off)40% off.
$50.00Comparable value $50.00
4-Way Stretch Volley Swim Trunks
Vintage Summer

4-Way Stretch Volley Swim Trunks

$19.97Current Price $19.97
(59% off)59% off.
$49.00Comparable value $49.00
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