Sperry Top-Sider Shoes for Men's, Size 8.5 (123)

Select a Sperry Top-Sider Shoe Sperry Top-Sider
  A/O 1-Eye Leather Men's 8.5
A/O 1-Eye Leather Men's 8.5
$90.00
4 Colors Available
Free Shipping to the USA
  A/O 2 Eye Men's 8.5
A/O 2 Eye Men's 8.5
$85.00 $34.99 & up
13 Colors Available
Free Shipping to the USA
  A/O 2-Eye Camo Sole Men's 8.5
A/O 2-Eye Camo Sole Men's 8.5
$90.00 $49.50 & up
3 Colors Available
Free Shipping to the USA
  A/O 2-Eye Corduroy Men's 8.5
A/O 2-Eye Corduroy Men's 8.5
$85.00 $39.99
Burgundy Color
Free Shipping to the USA
  A/O 2-Eye Croc Emboss Men's 8.5
A/O 2-Eye Croc Emboss Men's 8.5
$95.00 $47.50
Dark Brown Color
Free Shipping to the USA
  A/O 2-Eye Espadrille Men's 8.5
A/O 2-Eye Espadrille Men's 8.5
$85.00 $38.25
3 Colors Available
Free Shipping to the USA
  A/O 2-Eye Flag Men's 8.5
A/O 2-Eye Flag Men's 8.5
$95.00
2 Colors Available
Free Shipping to the USA
  A/O 2-Eye Free Time Men's 8.5
A/O 2-Eye Free Time Men's 8.5
$95.00 $51.99
3 Colors Available
Free Shipping to the USA
  A/O 2-Eye Handpainted Men's 8.5
A/O 2-Eye Handpainted Men's 8.5
$110.00
Brown Handpainted Anchor Color
Free Shipping to the USA
  A/O 2-Eye Ice Suede Men's 8.5
A/O 2-Eye Ice Suede Men's 8.5
$95.00 $39.99 & up
2 Colors Available
Free Shipping to the USA
  A/O 2-Eye Neon Men's 8.5
A/O 2-Eye Neon Men's 8.5
$90.00 $49.99
Black/Neon Yellow Color
Free Shipping to the USA
  A/O 2-Eye Soft Canvas Men's 8.5
A/O 2-Eye Soft Canvas Men's 8.5
$80.00 $36.99
Olive Color
Free Shipping to the USA
  A/O 2-Eye Soft Canvas Colored Sole Men's 8.5
A/O 2-Eye Soft Canvas Colored Sole Men's 8.5
$80.00
Black/Blue Color
Free Shipping to the USA
  A/O 2-Eye Stonewashed Men's 8.5
A/O 2-Eye Stonewashed Men's 8.5
$90.00 $41.99 & up
5 Colors Available
Free Shipping to the USA
  A/O 2-Eye Tattoo Men's 8.5
A/O 2-Eye Tattoo Men's 8.5
$90.00 $41.99
Chino Canvas Color
Free Shipping to the USA
  A/O 2-Eye Two-Tone Men's 8.5
A/O 2-Eye Two-Tone Men's 8.5
$90.00
5 Colors Available
Free Shipping to the USA
  A/O 2-Eye Washed Men's 8.5
A/O 2-Eye Washed Men's 8.5
$90.00 $49.99
Coral Color
Free Shipping to the USA
  A/O 2-Eye Winter Men's 8.5
A/O 2-Eye Winter Men's 8.5
$140.00
Tan Winter Color
Free Shipping to the USA
  A/O Burnished Canvas Men's 8.5
A/O Burnished Canvas Men's 8.5
$85.00
3 Colors Available
Free Shipping to the USA
  A/O Chukka Boardwalk Men's 8.5
A/O Chukka Boardwalk Men's 8.5
$110.00
5 Colors Available
Free Shipping to the USA
  A/O Chukka Neon Men's 8.5
A/O Chukka Neon Men's 8.5
$100.00 $44.99 & up
3 Colors Available
Free Shipping to the USA
  A/O Coastal Craftsmen 7-Eye Men's 8.5
A/O Coastal Craftsmen 7-Eye Men's 8.5
$140.00 $76.99
Dark Brown/Tan Color
Free Shipping to the USA
  A/O Gore Men's 8.5
A/O Gore Men's 8.5
$90.00 $41.99 & up
5 Colors Available
Free Shipping to the USA
  A/O Lug 3-Eye Men's 8.5
A/O Lug 3-Eye Men's 8.5
$120.00
Tan Color
Free Shipping to the USA
  A/O Lug Chukka Men's 8.5
A/O Lug Chukka Men's 8.5
$130.00
2 Colors Available
Free Shipping to the USA
  A/O Venetian Suede Men's 8.5
A/O Venetian Suede Men's 8.5
$85.00
2 Colors Available
Free Shipping to the USA
  Authentic Original Men's 8.5
Authentic Original Men's 8.5
$84.95
10 Colors Available
Free Shipping to the USA
  Avenue Duck 3-Eye Men's 8.5
Avenue Duck 3-Eye Men's 8.5
$95.00
2 Colors Available
Free Shipping to the USA
  Avenue Duck Boot Men's 8.5
Avenue Duck Boot Men's 8.5
$110.00
Black Color
Free Shipping to the USA
  Avenue Duck Toggle Men's 8.5
Avenue Duck Toggle Men's 8.5
$95.00
2 Colors Available
Free Shipping to the USA
  Bahama 2 Eye Washable Men's 8.5
Bahama 2 Eye Washable Men's 8.5
$90.00 $41.99 & up
4 Colors Available
Free Shipping to the USA
  Bahama 2-Eye Men's 8.5
Bahama 2-Eye Men's 8.5
$60.00
4 Colors Available
Free Shipping to the USA
  Bahama 2-Eye Heavy Canvas Men's 8.5
Bahama 2-Eye Heavy Canvas Men's 8.5
$65.00
2 Colors Available
Free Shipping to the USA
  Bahama 2-Eye Leather Men's 8.5
Bahama 2-Eye Leather Men's 8.5
$85.00
2 Colors Available
Free Shipping to the USA
  Bahama 2-Eye Leather/Canvas Men's 8.5
Bahama 2-Eye Leather/Canvas Men's 8.5
$65.00 $26.99 & up
2 Colors Available
Free Shipping to the USA
  Bahama 2-Eye Wool Men's 8.5
Bahama 2-Eye Wool Men's 8.5
$75.00
Charcoal/Navy Color
Free Shipping to the USA
  Bahama Chukka Men's 8.5
Bahama Chukka Men's 8.5
$75.00 $34.99
Navy Color
Free Shipping to the USA
  Bahama Chukka Suede Men's 8.5
Bahama Chukka Suede Men's 8.5
$80.00 $44.99
Black Suede 2 Color
Free Shipping to the USA
  Bahama Lace Men's 8.5
Bahama Lace Men's 8.5
$60.00
3 Colors Available
Free Shipping to the USA
  Bahama Lug Chukka Men's 8.5
Bahama Lug Chukka Men's 8.5
$85.00
Brown Color
Free Shipping to the USA
  Bahama Zipper Boot Men's 8.5
Bahama Zipper Boot Men's 8.5
$90.00 $41.99
2 Colors Available
Free Shipping to the USA
  Billfish 3-Eye Boat Shoe Men's 8.5
Billfish 3-Eye Boat Shoe Men's 8.5
$100.00 $64.99 & up
6 Colors Available
Free Shipping to the USA
  Billfish Slip On Men's 8.5
Billfish Slip On Men's 8.5
$100.00
2 Colors Available
Free Shipping to the USA
  Billfish Ultralite 3 Eye Men's 8.5
Billfish Ultralite 3 Eye Men's 8.5
$100.00 $64.99 & up
4 Colors Available
Free Shipping to the USA
  Bristol 3-Eye Men's 8.5
Bristol 3-Eye Men's 8.5
$110.00
3 Colors Available
Free Shipping to the USA
  Bristol Chukka Men's 8.5
Bristol Chukka Men's 8.5
$120.00
2 Colors Available
Free Shipping to the USA
  Bristol Slip On Men's 8.5
Bristol Slip On Men's 8.5
$110.00
Brown Buc Color
Free Shipping to the USA
  Captain's Oxford Men's 8.5
Captain's Oxford Men's 8.5
$90.00 $41.99
Navy Canvas Color
Free Shipping to the USA
  Cloud Chukka Suede Men's 8.5
Cloud Chukka Suede Men's 8.5
$80.00
Grey Color
Free Shipping to the USA
  Cold Bay Boot Men's 8.5
Cold Bay Boot Men's 8.5
$150.00
3 Colors Available
Free Shipping to the USA
  Cruz 2-Eye Men's 8.5
Cruz 2-Eye Men's 8.5
$60.00
2 Colors Available
Free Shipping to the USA
  Cruz 2-Eye Suede Men's 8.5
Cruz 2-Eye Suede Men's 8.5
$70.00
Taupe Suede Color
Free Shipping to the USA
  CVO Canvas Men's 8.5
CVO Canvas Men's 8.5
$60.00 $30.00
Ribbon Red/Blue Atoll/Ivory Color
Free Shipping to the USA
  Dockyard Oxford Chukka Men's 8.5
Dockyard Oxford Chukka Men's 8.5
$125.00
Tan Color
Free Shipping to the USA
  Drifter Chukka Men's 8.5
Drifter Chukka Men's 8.5
$65.00 $41.99
Tan Stripe Color
Free Shipping to the USA
  Espadrille 2-Eye Canvas Men's 8.5
Espadrille 2-Eye Canvas Men's 8.5
$80.00 $36.99 & up
4 Colors Available
Free Shipping to the USA
  Essex Penny Men's 8.5
Essex Penny Men's 8.5
$125.00
Brown Color
Free Shipping to the USA
  Essex Venetian Men's 8.5
Essex Venetian Men's 8.5
$125.00
Black Color
Free Shipping to the USA
  Gold A/O 2-Eye Men's 8.5
Gold A/O 2-Eye Men's 8.5
$150.00
5 Colors Available
Free Shipping to the USA
  Gold A/O 2-Eye Burnished Men's 8.5
Gold A/O 2-Eye Burnished Men's 8.5
$150.00 $96.99
Tan Color
Free Shipping to the USA
  Gold A/O Woven Men's 8.5
Gold A/O Woven Men's 8.5
$200.00
2 Colors Available
Free Shipping to the USA
  Gold ASV Dress Casual Gore Men's 8.5
Gold ASV Dress Casual Gore Men's 8.5
$170.00 $69.99
Dark Brown Suede Color
Free Shipping to the USA
  Gold ASV Dress Casual Venetian Men's 8.5
Gold ASV Dress Casual Venetian Men's 8.5
$170.00 $94.99
Dark Brown Color
Free Shipping to the USA
  Gold Bellingham Cap Toe w/ ASV Men's 8.5
Gold Bellingham Cap Toe w/ ASV Men's 8.5
$180.00 $99.99
Grey Color
Free Shipping to the USA
  Gold Bellingham Wingtip w/ ASV Men's 8.5
Gold Bellingham Wingtip w/ ASV Men's 8.5
$180.00 $81.99 & up
2 Colors Available
Free Shipping to the USA
  Gold Boat w/ASV Men's 8.5
Gold Boat w/ASV Men's 8.5
$170.00
3 Colors Available
Free Shipping to the USA
  Gold Capetown Penny W/ASV Men's 8.5
Gold Capetown Penny W/ASV Men's 8.5
$160.00
Black Color
Free Shipping to the USA
  Gold Cup ASV Boothbay Venetian Loafer Men's 8.5
Gold Cup ASV Boothbay Venetian Loafer Men's 8.5
$170.00
2 Colors Available
Free Shipping to the USA
  Gold Kennebunk w/ASV Men's 8.5
Gold Kennebunk w/ASV Men's 8.5
$175.00
Tan Color
Free Shipping to the USA
  H2O Escape Bungee Men's 8.5
H2O Escape Bungee Men's 8.5
$90.00 $59.99
Orange/Blue Color
Free Shipping to the USA
  Halyard 2-Eye Men's 8.5
Halyard 2-Eye Men's 8.5
$60.00 $49.99
4 Colors Available
Free Shipping to the USA
  Halyard 2-Eye Canvas Men's 8.5
Halyard 2-Eye Canvas Men's 8.5
$60.00 $49.99
Black/Black Cow Silk Color
Free Shipping to the USA
  Halyard 2-Eye Slip-On Men's 8.5
Halyard 2-Eye Slip-On Men's 8.5
$60.00 $39.99 & up
3 Colors Available
Free Shipping to the USA
  Halyard Laceless CVO Men's 8.5
Halyard Laceless CVO Men's 8.5
$60.00 $49.99
3 Colors Available
Free Shipping to the USA
  Halyard Two-Tone Men's 8.5
Halyard Two-Tone Men's 8.5
$60.00 $39.99
Chocolate/Red Color
Free Shipping to the USA
  Harbor Chukka Boot Men's 8.5
Harbor Chukka Boot Men's 8.5
$120.00
Dark Grey Color
Free Shipping to the USA
  Harbor Plain Toe Men's 8.5
Harbor Plain Toe Men's 8.5
$110.00
2 Colors Available
Free Shipping to the USA
  Harbor Slip On Men's 8.5
Harbor Slip On Men's 8.5
$110.00
2 Colors Available
Free Shipping to the USA
  Harbor Wingtip Men's 8.5
Harbor Wingtip Men's 8.5
$110.00
4 Colors Available
Free Shipping to the USA
  Lanyard 2-Eye Men's 8.5
Lanyard 2-Eye Men's 8.5
$90.00 $72.99 & up
6 Colors Available
Free Shipping to the USA
  Largo Slip On Men's 8.5
Largo Slip On Men's 8.5
$69.95
Taupe Suede Color
Free Shipping to the USA
  Leeward 2-Eye Men's 8.5
Leeward 2-Eye Men's 8.5
$85.00 $54.99 & up
6 Colors Available
Free Shipping to the USA
  Leeward 2-Eye Canvas Men's 8.5
Leeward 2-Eye Canvas Men's 8.5
$80.00 $59.99
5 Colors Available
Free Shipping to the USA
  Low Pro Vulc CVO Men's 8.5
Low Pro Vulc CVO Men's 8.5
$65.00 $36.99
Grey Suede Color
Free Shipping to the USA
  Low Pro Vulc Gore Slip On Men's 8.5
Low Pro Vulc Gore Slip On Men's 8.5
$60.00 $26.99 & up
2 Colors Available
Free Shipping to the USA
  Mako 2-Eye Canoe Moc Men's 8.5
Mako 2-Eye Canoe Moc Men's 8.5
$90.00
4 Colors Available
Free Shipping to the USA
  Navigator Driver Venetian Men's 8.5
Navigator Driver Venetian Men's 8.5
$90.00
3 Colors Available
Free Shipping to the USA
  Navigator Venetian Men's 8.5
Navigator Venetian Men's 8.5
$90.00
Amaretto Leather Color
Free Shipping to the USA
  Newport Cup Men's 8.5
Newport Cup Men's 8.5
$85.00 $46.99
4 Colors Available
Free Shipping to the USA
  Pilot Men's 8.5
Pilot Men's 8.5
$90.00 $74.99
Amaretto Color
Free Shipping to the USA
  Razorfish Men's 8.5
Razorfish Men's 8.5
$95.00 $44.99 & up
4 Colors Available
Free Shipping to the USA
  RR Moc Men's 8.5
RR Moc Men's 8.5
$70.00
3 Colors Available
Free Shipping to the USA
  Sea Kite Sport Moc Men's 8.5
Sea Kite Sport Moc Men's 8.5
$100.00
Gray Color
Free Shipping to the USA
  Seaside 2-Eye Woven Men's 8.5
Seaside 2-Eye Woven Men's 8.5
$125.00 $50.00
Black Color
Free Shipping to the USA
  Seaside Moc Penny Men's 8.5
Seaside Moc Penny Men's 8.5
$100.00 $54.99
Navy Color
Free Shipping to the USA
  Seaside Moc Venetian Men's 8.5
Seaside Moc Venetian Men's 8.5
$100.00 $44.99 & up
3 Colors Available
Free Shipping to the USA
  Sedona Men's 8.5
Sedona Men's 8.5
$160.00 $40.00
Navy Suede Color
Free Shipping to the USA
  Shock Light Bungee with ASV Men's 8.5
Shock Light Bungee with ASV Men's 8.5
$90.00 $41.99
Black/Blue Color
Free Shipping to the USA
  Shock Light w/ASV Men's 8.5
Shock Light w/ASV Men's 8.5
$90.00 $59.99 & up
3 Colors Available
Free Shipping to the USA
  Sperry Cup 2-Eye Men's 8.5
Sperry Cup 2-Eye Men's 8.5
$90.00 $49.99 & up
5 Colors Available
Free Shipping to the USA
  Sperry Cup Moc Men's 8.5
Sperry Cup Moc Men's 8.5
$100.00 $44.99 & up
4 Colors Available
Free Shipping to the USA
  Striper CVO Canvas Men's 8.5
Striper CVO Canvas Men's 8.5
$60.00
2 Colors Available
Free Shipping to the USA
  Striper CVO Chambray Men's 8.5
Striper CVO Chambray Men's 8.5
$65.00
2 Colors Available
Free Shipping to the USA
  Striper CVO Chukka Men's 8.5
Striper CVO Chukka Men's 8.5
$70.00
3 Colors Available
Free Shipping to the USA
  Striper CVO Color Pop Men's 8.5
Striper CVO Color Pop Men's 8.5
$60.00
5 Colors Available
Free Shipping to the USA
  Striper CVO Prep Pack Men's 8.5
Striper CVO Prep Pack Men's 8.5
$65.00 $41.99
Seersucker Anchors Color
Free Shipping to the USA
  Striper CVO Salt-Washed Twill Men's 8.5
Striper CVO Salt-Washed Twill Men's 8.5
$60.00
4 Colors Available
Free Shipping to the USA
  Striper CVO Suede Men's 8.5
Striper CVO Suede Men's 8.5
$70.00 $39.99 & up
4 Colors Available
Free Shipping to the USA
  Striper CVO Two-Tone Men's 8.5
Striper CVO Two-Tone Men's 8.5
$65.00 $29.99 & up
2 Colors Available
Free Shipping to the USA
  Striper CVO Wool Men's 8.5
Striper CVO Wool Men's 8.5
$70.00 $39.99 & up
5 Colors Available
Free Shipping to the USA
  The Harbor Chukka Canvas Men's 8.5
The Harbor Chukka Canvas Men's 8.5
$100.00 $54.99
2 Colors Available
Free Shipping to the USA
  The Harbor Plain Toe Men's 8.5
The Harbor Plain Toe Men's 8.5
$90.00 $49.99
2 Colors Available
Free Shipping to the USA
  The Harbor Wingtip Men's 8.5
The Harbor Wingtip Men's 8.5
$90.00 $49.99 & up
3 Colors Available
Free Shipping to the USA
  Tremont Kiltie Tassel Men's 8.5
Tremont Kiltie Tassel Men's 8.5
$90.00 $42.99
2 Colors Available
Free Shipping to the USA
  Voyager Men's 8.5
Voyager Men's 8.5
$120.00
3 Colors Available
Free Shipping to the USA
  Wave Driver Braided Men's 8.5
Wave Driver Braided Men's 8.5
$100.00 & up
3 Colors Available
Free Shipping to the USA
  Wave Driver Convertible Men's 8.5
Wave Driver Convertible Men's 8.5
$90.00 $36.99 & up
10 Colors Available
Free Shipping to the USA
  Wave Driver Convertible Suede Men's 8.5
Wave Driver Convertible Suede Men's 8.5
$90.00 $41.99
Taupe Color
Free Shipping to the USA
  Wave Driver Kiltie Men's 8.5
Wave Driver Kiltie Men's 8.5
$99.95 $54.99
3 Colors Available
Free Shipping to the USA
  Wave Driver Penny Loafer Men's 8.5
Wave Driver Penny Loafer Men's 8.5
$100.00 $39.99
Dark Brown Color
Free Shipping to the USA
  Wave Driver Tattoo Men's 8.5
Wave Driver Tattoo Men's 8.5
$95.00 $44.99
Grey Color
Free Shipping to the USA
  Wool Bahama 2-Eye Men's 8.5
Wool Bahama 2-Eye Men's 8.5
$70.00 $38.50
Burgundy Color
Free Shipping to the USA
  Wool Bahama Chukka Boot Men's 8.5
Wool Bahama Chukka Boot Men's 8.5
$85.00 $46.99
2 Colors Available
Free Shipping to the USA

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