Skip to search results Skip to filters Skip to sort Skip to selected filters

Men's Size 8.5 Casual Sperry Products

61 items found

Sort By

Your Selections

Search Results

. Sperry - Authentic Original. Color Sahara. $109.95. 4.5 out of 5 stars

Orange Sperry Authentic Original

Orange Sperry Authentic Original

+9

Brand Name: Sperry
Product Name: Authentic Original
Gender: Men's
Color: Sahara
Price: $109.95
Rating: 4Rated 4 stars out of 5(5494)

Sperry - Bahama II. Color SW White. $69.95. 4.5 out of 5 stars

White Sperry Bahama II

White Sperry Bahama II

+6

Brand Name: Sperry
Product Name: Bahama II
Gender: Men's
Color: SW White
Price: $69.95
Rating: 4Rated 4 stars out of 5(170)

Sperry - Striper II CVO Canvas. Color SW Grey. $69.95. 4.3 out of 5 stars

Gray Sperry Striper II CVO Canvas

Gray Sperry Striper II CVO Canvas

+5

Brand Name: Sperry
Product Name: Striper II CVO Canvas
Gender: Men's
Color: SW Grey
Price: $69.95
Rating: 4Rated 4 stars out of 5(359)

Sperry - Striper II Ltt. Color White. $69.95. 4.5 out of 5 stars

White Sperry Striper II Ltt

White Sperry Striper II Ltt

+4

Brand Name: Sperry
Product Name: Striper II Ltt
Gender: Men's
Color: White
Price: $69.95
Rating: 5Rated 5 stars out of 5(22)

Sperry - Striper II CVO Seasonal. Color Grey Linen. $69.95. 5.0 out of 5 stars

Black Sperry Striper II CVO Seasonal

Black Sperry Striper II CVO Seasonal

+3

Brand Name: Sperry
Product Name: Striper II CVO Seasonal
Gender: Men's
Color: Grey Linen
Price: $69.95
Rating: 5Rated 5 stars out of 5(1)

Sperry - Gold Cup Harpswell Driver. Color Brown Sugar. $174.95. 4.2 out of 5 stars

Brown Sperry Gold Cup Harpswell Driver

Brown Sperry Gold Cup Harpswell Driver

Brand Name: Sperry
Product Name: Gold Cup Harpswell Driver
Gender: Men's
Color: Brown Sugar
Price: $174.95
Rating: 4Rated 4 stars out of 5(122)

Sperry - Billfish 3-Eye Boat Shoe. Color Tan/Beige. $109.95. 4.3 out of 5 stars

Tan Sperry Billfish 3-Eye Boat Shoe

Tan Sperry Billfish 3-Eye Boat Shoe

+3

Brand Name: Sperry
Product Name: Billfish 3-Eye Boat Shoe
Gender: Men's
Color: Tan/Beige
Price: $109.95
Rating: 4Rated 4 stars out of 5(1551)

Sperry - Gold Cup A/O 2-Eye. Color Tan. $174.95. 4.2 out of 5 stars

Tan Sperry Gold Cup A/O 2-Eye

Tan Sperry Gold Cup A/O 2-Eye

Brand Name: Sperry
Product Name: Gold Cup A/O 2-Eye
Gender: Men's
Color: Tan
Price: $174.95
Rating: 4Rated 4 stars out of 5(295)

Sperry - Striper II Slip-On Sneaker. Color SW Navy. $69.95. 3.9 out of 5 stars

Navy Sperry Striper II Slip-On Sneaker

Navy Sperry Striper II Slip-On Sneaker

+3

Brand Name: Sperry
Product Name: Striper II Slip-On Sneaker
Gender: Men's
Color: SW Navy
Price: $69.95
Rating: 4Rated 4 stars out of 5(142)

Sperry - Mako 2-Eye Canoe Moc. Color Amaretto. $109.99. 4.5 out of 5 stars

Brown Sperry Mako 2-Eye Canoe Moc

+2

Brand Name: Sperry
Product Name: Mako 2-Eye Canoe Moc
Gender: Men's
Color: Amaretto
Price: $109.99
Rating: 4Rated 4 stars out of 5(804)

Sperry - Striper II CVO Seacycled. Color Grey Chambray. $69.95. 4.3 out of 5 stars

Gray Sperry Striper II CVO Seacycled

Gray Sperry Striper II CVO Seacycled

+5

Brand Name: Sperry
Product Name: Striper II CVO Seacycled
Gender: Men's
Color: Grey Chambray
Price: $69.95
Rating: 4Rated 4 stars out of 5(75)

Sperry - Davenport Venetian. Color Brown. $109.90. 3.8 out of 5 stars

Brown Sperry Davenport Venetian

Brown Sperry Davenport Venetian

+2

Brand Name: Sperry
Product Name: Davenport Venetian
Gender: Men's
Color: Brown
Price: $109.90
Rating: 4Rated 4 stars out of 5(55)

Sperry - Gold Authentic Original 2-Eye Seasonal. Color Tan Leather. $174.95. 1.0 out of 5 stars

Tan Sperry Gold Authentic Original 2-Eye Seasonal

Tan Sperry Gold Authentic Original 2-Eye Seasonal

+3 colors/patterns

Brand Name: Sperry
Product Name: Gold Authentic Original 2-Eye Seasonal
Gender: Men's
Color: Tan Leather
Price: $174.95
Rating: 1Rated 1 star out of 5(1)

Sperry - Gold Mako. Color Amaretto. $174.90. 4.0 out of 5 stars

Brown Sperry Gold Mako

Brown Sperry Gold Mako

+4

Brand Name: Sperry
Product Name: Gold Mako
Gender: Men's
Color: Amaretto
Price: $174.90
Rating: 4Rated 4 stars out of 5(20)

Sperry - Cold Bay Rubber Chelsea. Color Brown/Gum. On sale for $49.98. MSRP $100.00.. 3.6 out of 5 stars

Brown Sperry Cold Bay Rubber Chelsea

Brown Sperry Cold Bay Rubber Chelsea

+4

Brand Name: Sperry
Product Name: Cold Bay Rubber Chelsea
Gender: Men's
Color: Brown/Gum
Price: $49.98MSRP: $100.00
Rating: 4Rated 4 stars out of 5(81)

Sperry - Authentic Original Double Sole Cross Lace. Color Navy. $119.95. 4.0 out of 5 stars

Navy Sperry Authentic Original Double Sole Cross Lace

Navy Sperry Authentic Original Double Sole Cross Lace

+4

Brand Name: Sperry
Product Name: Authentic Original Double Sole Cross Lace
Gender: Men's
Color: Navy
Price: $119.95
Rating: 4Rated 4 stars out of 5(43)

Sperry - Authentic Original Venetian Double Sole. Color Sand Nubuck. $109.95. 3.3 out of 5 stars

Beige Sperry Authentic Original Venetian Double Sole

Beige Sperry Authentic Original Venetian Double Sole

+3

Brand Name: Sperry
Product Name: Authentic Original Venetian Double Sole
Gender: Men's
Color: Sand Nubuck
Price: $109.95
Rating: 3Rated 3 stars out of 5(3)

Sperry - Billfish 3-Eye. Color Black. $109.90. 3.7 out of 5 stars

Black Sperry Billfish 3-Eye

Black Sperry Billfish 3-Eye

Brand Name: Sperry
Product Name: Billfish 3-Eye
Gender: Men's
Color: Black
Price: $109.90
Rating: 4Rated 4 stars out of 5(15)

Sperry - Striper II Slip On Seasonal. Color Taupe Linen. $69.95.

Taupe Sperry Striper II Slip On Seasonal

Taupe Sperry Striper II Slip On Seasonal

Brand Name: Sperry
Product Name: Striper II Slip On Seasonal
Gender: Men's
Color: Taupe Linen
Price: $69.95
Rating

Sperry - Authentic Original Sirocco. Color Tan Suede. $99.95. 4.0 out of 5 stars

Tan Sperry Authentic Original Sirocco

Tan Sperry Authentic Original Sirocco

Brand Name: Sperry
Product Name: Authentic Original Sirocco
Gender: Men's
Color: Tan Suede
Price: $99.95
Rating: 4Rated 4 stars out of 5(1)

Sperry - Bahama II Seasonal. Color Navy Linen. $79.95. 5.0 out of 5 stars

Navy Sperry Bahama II Seasonal

Navy Sperry Bahama II Seasonal

+3

Brand Name: Sperry
Product Name: Bahama II Seasonal
Gender: Men's
Color: Navy Linen
Price: $79.95
Rating: 5Rated 5 stars out of 5(1)

Sperry - Gold Billfish Plushwave. Color Tan. $174.90. 3.9 out of 5 stars

Tan Sperry Gold Billfish Plushwave

Tan Sperry Gold Billfish Plushwave

+4

Brand Name: Sperry
Product Name: Gold Billfish Plushwave
Gender: Men's
Color: Tan
Price: $174.90
Rating: 4Rated 4 stars out of 5(36)

Sperry - Authentic Original Penny. Color Brown. $109.90. 4.4 out of 5 stars

Brown Sperry Authentic Original Penny

Brown Sperry Authentic Original Penny

+3

Brand Name: Sperry
Product Name: Authentic Original Penny
Gender: Men's
Color: Brown
Price: $109.90
Rating: 4Rated 4 stars out of 5(30)

Sperry - A/O 2-Eye Cross Lace. Color Black. $109.95. 3.4 out of 5 stars

Black Sperry A/O 2-Eye Cross Lace

Black Sperry A/O 2-Eye Cross Lace

+4

Brand Name: Sperry
Product Name: A/O 2-Eye Cross Lace
Gender: Men's
Color: Black
Price: $109.95
Rating: 3Rated 3 stars out of 5(47)

Sperry - Striper II Seacycled. Color White Twill. $69.95. 3.9 out of 5 stars

White Sperry Striper II Seacycled

White Sperry Striper II Seacycled

+3

Brand Name: Sperry
Product Name: Striper II Seacycled
Gender: Men's
Color: White Twill
Price: $69.95
Rating: 4Rated 4 stars out of 5(40)

Sperry - Seacycled Striper II Cvo Twill. Color Tan. $69.95. 4.0 out of 5 stars

Tan Sperry Seacycled Striper II Cvo Twill

Tan Sperry Seacycled Striper II Cvo Twill

+2

Brand Name: Sperry
Product Name: Seacycled Striper II Cvo Twill
Gender: Men's
Color: Tan
Price: $69.95
Rating: 4Rated 4 stars out of 5(4)

Sperry - Authentic Original 2-Eye Double Sole. Color Birch Nubuck. $119.95. 2.3 out of 5 stars

Brown Sperry Authentic Original 2-Eye Double Sole

Brown Sperry Authentic Original 2-Eye Double Sole

Brand Name: Sperry
Product Name: Authentic Original 2-Eye Double Sole
Gender: Men's
Color: Birch Nubuck
Price: $119.95
Rating: 2Rated 2 stars out of 5(3)

Sperry - Striper II Twin Gore Perf Suede. Color Taupe. $79.95. 2.8 out of 5 stars

Taupe Sperry Striper II Twin Gore Perf Suede

Taupe Sperry Striper II Twin Gore Perf Suede

Brand Name: Sperry
Product Name: Striper II Twin Gore Perf Suede
Gender: Men's
Color: Taupe
Price: $79.95
Rating: 3Rated 3 stars out of 5(18)

Sperry - Gold Striper LTT. Color White. $149.95. 4.6 out of 5 stars

White Sperry Gold Striper LTT

White Sperry Gold Striper LTT

Brand Name: Sperry
Product Name: Gold Striper LTT
Gender: Men's
Color: White
Price: $149.95
Rating: 5Rated 5 stars out of 5(12)

Sperry - Gold A/O 2-Eye Tumbled. Color Brown. $174.95. 3.4 out of 5 stars

Brown Sperry Gold A/O 2-Eye Tumbled

Brown Sperry Gold A/O 2-Eye Tumbled

+3

Brand Name: Sperry
Product Name: Gold A/O 2-Eye Tumbled
Gender: Men's
Color: Brown
Price: $174.95
Rating: 3Rated 3 stars out of 5(19)

Sperry - Gold Cup Boat. Color Cymbal. $189.95. 4.4 out of 5 stars

Brown Sperry Gold Cup Boat

Brown Sperry Gold Cup Boat

+2

Brand Name: Sperry
Product Name: Gold Cup Boat
Gender: Men's
Color: Cymbal
Price: $189.95
Rating: 4Rated 4 stars out of 5(470)

Sperry - Hampden Venetian. Color Amaretto. $109.95. 4.6 out of 5 stars

Brown Sperry Hampden Venetian

Brown Sperry Hampden Venetian

Brand Name: Sperry
Product Name: Hampden Venetian
Gender: Men's
Color: Amaretto
Price: $109.95
Rating: 5Rated 5 stars out of 5(140)

Sperry - Racquet Oxford. Color Black. $89.95.

Black Sperry Racquet Oxford

Black Sperry Racquet Oxford

+2

Brand Name: Sperry
Product Name: Racquet Oxford
Gender: Men's
Color: Black
Price: $89.95
Rating

Sperry - Authentic Original 3-Eye Lug. Color Brown. $129.90. 4.1 out of 5 stars

Brown Sperry Authentic Original 3-Eye Lug

Brown Sperry Authentic Original 3-Eye Lug

+3

Brand Name: Sperry
Product Name: Authentic Original 3-Eye Lug
Gender: Men's
Color: Brown
Price: $129.90
Rating: 4Rated 4 stars out of 5(33)

Sperry - Sea Kite Sport Moc. Color Navy 1. $109.95. 4.6 out of 5 stars

Navy Sperry Sea Kite Sport Moc

Navy Sperry Sea Kite Sport Moc

+3

Brand Name: Sperry
Product Name: Sea Kite Sport Moc
Gender: Men's
Color: Navy 1
Price: $109.95
Rating: 5Rated 5 stars out of 5(245)

Sperry - Fairlead. Color Taupe. $69.95. 4.6 out of 5 stars

Taupe Sperry Fairlead

Taupe Sperry Fairlead

+2

Brand Name: Sperry
Product Name: Fairlead
Gender: Men's
Color: Taupe
Price: $69.95
Rating: 5Rated 5 stars out of 5(7)

Sperry - Topsfield Penny Loafer. Color Tan Leather. Low Stock. $129.95. 4.3 out of 5 stars

6 left in stock

Tan Sperry Topsfield Penny Loafer

Tan Sperry Topsfield Penny Loafer

+2

Brand Name: Sperry
Product Name: Topsfield Penny Loafer
Gender: Men's
Color: Tan Leather
Price: $129.95
Rating: 4Rated 4 stars out of 5(27)

Sperry - Cloud Cvo. Color Granite Green. Low Stock. $79.95.

7 left in stock

Green Sperry Cloud Cvo

Green Sperry Cloud Cvo

Brand Name: Sperry
Product Name: Cloud Cvo
Gender: Men's
Color: Granite Green
Price: $79.95
Rating

Sperry - A/O Lug 3-Eye. Color Brown 3. $129.95. 4.2 out of 5 stars

Brown Sperry A/O Lug 3-Eye

Brown Sperry A/O Lug 3-Eye

+3

Brand Name: Sperry
Product Name: A/O Lug 3-Eye
Gender: Men's
Color: Brown 3
Price: $129.95
Rating: 4Rated 4 stars out of 5(13)

Sperry - A/O 2-Eye Seacycled Shearling. Color Java. $124.95. 3.9 out of 5 stars

Brown Sperry A/O 2-Eye Seacycled Shearling

Brown Sperry A/O 2-Eye Seacycled Shearling

+2

Brand Name: Sperry
Product Name: A/O 2-Eye Seacycled Shearling
Gender: Men's
Color: Java
Price: $124.95
Rating: 4Rated 4 stars out of 5(8)

Sperry - Davenport Penny. Color Black 1. $109.95. 3.7 out of 5 stars

Black Sperry Davenport Penny

Black Sperry Davenport Penny

Brand Name: Sperry
Product Name: Davenport Penny
Gender: Men's
Color: Black 1
Price: $109.95
Rating: 4Rated 4 stars out of 5(46)

Sperry - Striper II Lace to Toe Seasonal. Color Taupe Linen. $69.95.

Taupe Sperry Striper II Lace to Toe Seasonal

Taupe Sperry Striper II Lace to Toe Seasonal

+2

Brand Name: Sperry
Product Name: Striper II Lace to Toe Seasonal
Gender: Men's
Color: Taupe Linen
Price: $69.95
Rating

Sperry - A/O Plushwave Lug Chukka. Color Brown 1. $139.95. 4.2 out of 5 stars

Brown Sperry A/O Plushwave Lug Chukka

Brown Sperry A/O Plushwave Lug Chukka

+3

Brand Name: Sperry
Product Name: A/O Plushwave Lug Chukka
Gender: Men's
Color: Brown 1
Price: $139.95
Rating: 4Rated 4 stars out of 5(33)

Sperry - Soletide Seacycled. Color White Multi 1. Low Stock. $79.95. 3.6 out of 5 stars

9 left in stock

Beige Sperry Soletide Seacycled

Beige Sperry Soletide Seacycled

+5

Brand Name: Sperry
Product Name: Soletide Seacycled
Gender: Men's
Color: White Multi 1
Price: $79.95
Rating: 4Rated 4 stars out of 5(36)

Sperry - Headsail. Color Taupe. $99.95. 3.5 out of 5 stars

Taupe Sperry Headsail

Taupe Sperry Headsail

+5

Brand Name: Sperry
Product Name: Headsail
Gender: Men's
Color: Taupe
Price: $99.95
Rating: 3Rated 3 stars out of 5(15)

Sperry - Captain'S Moc Boat Seacycled Baja. Color Navy. Low Stock. $69.90. 4.8 out of 5 stars

4 left in stock

Navy Sperry Captain'S Moc Boat Seacycled Baja

Navy Sperry Captain'S Moc Boat Seacycled Baja

+2

Brand Name: Sperry
Product Name: Captain'S Moc Boat Seacycled Baja
Gender: Men's
Color: Navy
Price: $69.90
Rating: 5Rated 5 stars out of 5(14)

Sperry - Authentic Original 2-Eye Seasonal. Color Tan Debossed. $109.95.

Brown Sperry Authentic Original 2-Eye Seasonal

Brown Sperry Authentic Original 2-Eye Seasonal

+4

Brand Name: Sperry
Product Name: Authentic Original 2-Eye Seasonal
Gender: Men's
Color: Tan Debossed
Price: $109.95
Rating

Sperry - Avenue Duck Boot. Color Tan/Brown. $120.00. 4.1 out of 5 stars

Tan Sperry Avenue Duck Boot

Tan Sperry Avenue Duck Boot

+2

Brand Name: Sperry
Product Name: Avenue Duck Boot
Gender: Men's
Color: Tan/Brown
Price: $120.00
Rating: 4Rated 4 stars out of 5(215)

Sperry - Striper II Hiker. Color Navy. $84.95. 4.3 out of 5 stars

Navy Sperry Striper II Hiker

Navy Sperry Striper II Hiker

+1

Brand Name: Sperry
Product Name: Striper II Hiker
Gender: Men's
Color: Navy
Price: $84.95
Rating: 4Rated 4 stars out of 5(9)

Sperry - Cabo II Penny. Color Sand. $109.90. 3.8 out of 5 stars

Beige Sperry Cabo II Penny

Beige Sperry Cabo II Penny

+3

Brand Name: Sperry
Product Name: Cabo II Penny
Gender: Men's
Color: Sand
Price: $109.90
Rating: 4Rated 4 stars out of 5(20)

Sperry - 7 Seas 3-Eye. Color White 3. $99.95. 3.8 out of 5 stars

White Sperry 7 Seas 3-Eye

White Sperry 7 Seas 3-Eye

+3

Brand Name: Sperry
Product Name: 7 Seas 3-Eye
Gender: Men's
Color: White 3
Price: $99.95
Rating: 4Rated 4 stars out of 5(82)

Sperry - Gold Cup A/O 2-Eye. Color Navy 1. Low Stock. $174.95. 4.3 out of 5 stars

3 left in stock

Navy Sperry Gold Cup A/O 2-Eye

Navy Sperry Gold Cup A/O 2-Eye

+2

Brand Name: Sperry
Product Name: Gold Cup A/O 2-Eye
Gender: Men's
Color: Navy 1
Price: $174.95
Rating: 4Rated 4 stars out of 5(480)

Sperry - Striper Storm Hiker Wp. Color Black. $109.90. 4.6 out of 5 stars

Black Sperry Striper Storm Hiker Wp

Black Sperry Striper Storm Hiker Wp

Brand Name: Sperry
Product Name: Striper Storm Hiker Wp
Gender: Men's
Color: Black
Price: $109.90
Rating: 5Rated 5 stars out of 5(55)

Sperry - Gold Authentic Original 2-Eye Woven. Color Black. Low Stock. $184.90. 4.1 out of 5 stars

7 left in stock

Black Sperry Gold Authentic Original 2-Eye Woven

Black Sperry Gold Authentic Original 2-Eye Woven

+3

Brand Name: Sperry
Product Name: Gold Authentic Original 2-Eye Woven
Gender: Men's
Color: Black
Price: $184.90
Rating: 4Rated 4 stars out of 5(25)

Sperry - Striper II Slip-On Seasonal. Color Navy. $69.95.

Navy Sperry Striper II Slip-On Seasonal

Navy Sperry Striper II Slip-On Seasonal

Brand Name: Sperry
Product Name: Striper II Slip-On Seasonal
Gender: Men's
Color: Navy
Price: $69.95
Rating

Sperry - Striper II Slip-On Pride. Color Blue. Low Stock. $69.90. 5.0 out of 5 stars

6 left in stock

Blue Sperry Striper II Slip-On Pride

Blue Sperry Striper II Slip-On Pride

Brand Name: Sperry
Product Name: Striper II Slip-On Pride
Gender: Men's
Color: Blue
Price: $69.90
Rating: 5Rated 5 stars out of 5(2)

Sperry - Captain's Moc. Color Khaki. Low Stock. $59.90. 4.0 out of 5 stars

1 left in stock

Khaki Sperry Captain's Moc

Khaki Sperry Captain's Moc

Brand Name: Sperry
Product Name: Captain's Moc
Gender: Men's
Color: Khaki
Price: $59.90
Rating: 4Rated 4 stars out of 5(28)

Sperry - Duck Float Zip. Color Olive. $94.90. 3.7 out of 5 stars

Olive Sperry Duck Float Zip

Olive Sperry Duck Float Zip

+3

Brand Name: Sperry
Product Name: Duck Float Zip
Gender: Men's
Color: Olive
Price: $94.90
Rating: 4Rated 4 stars out of 5(10)

Sperry - Moc-Sider Chelsea Premium. Color Tan. On sale for $97.68. MSRP $139.95.. 5.0 out of 5 stars

Tan Sperry Moc-Sider Chelsea Premium

Tan Sperry Moc-Sider Chelsea Premium

+2

Brand Name: Sperry
Product Name: Moc-Sider Chelsea Premium
Gender: Men's
Color: Tan
Price: $97.68MSRP: $139.95
Rating: 5Rated 5 stars out of 5(3)

Sperry - Harbormaster 2.0. Color Navy. On sale for $75.60. MSRP $85.00.. 4.0 out of 5 stars

Navy Sperry Harbormaster 2.0

Navy Sperry Harbormaster 2.0

+2

Brand Name: Sperry
Product Name: Harbormaster 2.0
Gender: Men's
Color: Navy
Price: $75.60MSRP: $85.00
Rating: 4Rated 4 stars out of 5(31)

Sperry - A/O Seacycled Shearling Wool. Color Black Multi. On sale for $50.94. MSRP $99.95.. 5.0 out of 5 stars

Black Sperry A/O Seacycled Shearling Wool

Black Sperry A/O Seacycled Shearling Wool

Brand Name: Sperry
Product Name: A/O Seacycled Shearling Wool
Gender: Men's
Color: Black Multi
Price: $50.94MSRP: $99.95
Rating: 5Rated 5 stars out of 5(2)

Get on the List

Subscribe to Zappos emails for exclusive product launches, early notifications for sales, and a few extra-special surprises.