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Men's Waterproof Dress Shoes

  • All Dress Shoes
  • Boots
  • Comfort
  • Derby
  • Dress Sneakers
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  • Monk Strap
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78 items
Porto Derby (Men)

Magnanni Porto Derby (Men)

$299.99Current Price $299.99
$450Previous Price $450
New Markdown
Ramiro Penny Loafer (Men)

Magnanni Ramiro Penny Loafer (Men)

$279.99Current Price $279.99
$425Previous Price $425
New Markdown
Parker Waterproof Plain Toe Derby (Men)

Johnston & Murphy Parker Waterproof Plain Toe Derby (Men)

$139 – $185Current Price $139 to $185
$185Previous Price $185
New Markdown
4.8(18)
'Branning' Waterproof Cap Toe Derby (Men)

Johnston & Murphy 'Branning' Waterproof Cap Toe Derby (Men)

$179Current Price $179
4.3(72)
Copley XC+ Waterproof Penny Loafer (Men)

Johnston & Murphy Copley XC+ Waterproof Penny Loafer (Men)

$195Current Price $195
4.6(5)
Parker Waterproof Wingtip Derby (Men)

Johnston & Murphy Parker Waterproof Wingtip Derby (Men)

$185Current Price $185
5(3)
Durham Waterproof Cap Toe Boot (Men)

Johnston & Murphy Durham Waterproof Cap Toe Boot (Men)

$219Current Price $219
4.9(7)
Taylor Waterproof Plain Toe Derby (Men)

Rockport Taylor Waterproof Plain Toe Derby (Men)

$125Current Price $125
5(3)
A man examining a striped shirt in front of a rack of clothing.A man examining a striped shirt in front of a rack of clothing.

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XC4® Stanton 2.0 Runoff Venetian Loafer (Men)

Johnston & Murphy XC4® Stanton 2.0 Runoff Venetian Loafer (Men)

$179Current Price $179
3.3(3)
Copley XC+ Waterproof Plain Toe Derby (Men)

Johnston & Murphy Copley XC+ Waterproof Plain Toe Derby (Men)

$195Current Price $195
4.5(2)
Stanton Runoff 2.0 XC4 Waterproof Derby (Men)

Johnston & Murphy Stanton Runoff 2.0 XC4 Waterproof Derby (Men)

$179Current Price $179
3(1)
Premium 6-Inch Waterproof Boot (Men)
New

Timberland Premium 6-Inch Waterproof Boot (Men)

$199Current Price $199
4.6(2735)
XC4® Tanner Plain Toe Derby (Men)

Johnston & Murphy XC4® Tanner Plain Toe Derby (Men)

$189Current Price $189
4.5(45)
Copley XC+ Waterproof Plain Toe Derby (Men)

Johnston & Murphy Copley XC+ Waterproof Plain Toe Derby (Men)

$195Current Price $195
5(1)
Stanton 2.0 XC4 Waterproof Derby (Men)

Johnston & Murphy Stanton 2.0 XC4 Waterproof Derby (Men)

$179Current Price $179
16" Cement Rubber Soft Toe Boot

Tecs 16" Cement Rubber Soft Toe Boot

$99Current Price $99
Erroll Waterproof Derby (Men)

Josef Seibel Erroll Waterproof Derby (Men)

$175Current Price $175
5(1)
Roundhill Grand Waterproof Chukka Boot (Men)

Cole Haan Roundhill Grand Waterproof Chukka Boot (Men)

$260Current Price $260
4.3(20)
Classic Seamless Mid Waterproof Boot (Men)

Bogs Classic Seamless Mid Waterproof Boot (Men)

$84Current Price $84
$140Previous Price $140
4.6(22)
Parker Waterproof Chukka Boot (Men)

Johnston & Murphy Parker Waterproof Chukka Boot (Men)

$129.99Current Price $129.99
$189Previous Price $189
4.9(7)
Only a few left
Orford Insulated Waterproof Chelsea Boot (Men)

Hunter Orford Insulated Waterproof Chelsea Boot (Men)

$126.75 – $195Current Price $126.75 to $195
$195Previous Price $195
2.8(6)
Daystorm Horizon Gore-Tex® Weatherproof Boot (Men)

SOREL Daystorm Horizon Gore-Tex® Weatherproof Boot (Men)

$250Current Price $250
5(1)
Wallabee Gore-Tex® Waterproof Shoe (Men)

Clarks® Originals Wallabee Gore-Tex® Waterproof Shoe (Men)

$240Current Price $240
Only a few left
Thermal Waterproof Genuine Shearling Lined Chelsea Boot (Men)

Blundstone Footwear Thermal Waterproof Genuine Shearling Lined Chelsea Boot (Men)

$279.95Current Price $279.95
5(1)
Amp Lt Wedge Waterproof Chelsea Work Boot

Georgia Boot Amp Lt Wedge Waterproof Chelsea Work Boot

$123.75Current Price $123.75
4.1(15)
Messi Waterproof Ice-Gripper Chelsea Boot (Men)

Pajar Messi Waterproof Ice-Gripper Chelsea Boot (Men)

$178.75Current Price $178.75
$275Previous Price $275
New Markdown
Only a few left
Waterproof High Romeo Boot

Georgia Boot Waterproof High Romeo Boot

$105Current Price $105
3(1)
Suffolk Waterproof Insulated Boot (Men)

Hunter Suffolk Waterproof Insulated Boot (Men)

$195Current Price $195
Premium 6-Inch Waterproof Boot (Men)

Timberland Premium 6-Inch Waterproof Boot (Men)

$198Current Price $198
4.6(2735)
Only a few left
Monte Composite Toe Waterproof Work Boot Dark Brown
New

DieHard Monte Composite Toe Waterproof Work Boot Dark Brown

$150Current Price $150
Classic Seamless Tall Waterproof Boot (Men)

Bogs Classic Seamless Tall Waterproof Boot (Men)

$150Current Price $150
4.9(22)
Northfield Waterproof Derby (Men)

Rockport Northfield Waterproof Derby (Men)

$89.99Current Price $89.99
4.3(625)
Only a few left
Side Zip Waterproof Work Wellington

Georgia Boot Side Zip Waterproof Work Wellington

$176Current Price $176
3.9(45)
Chelsea Waterproof Work Boot

Georgia Boot Chelsea Waterproof Work Boot

$120Current Price $120
4.2(39)
Men's Country Dna Arctic Ice Tall Boot + Vibram Agat

MUCK Men's Country Dna Arctic Ice Tall Boot + Vibram Agat

$168.75Current Price $168.75
3.3(28)
Zipper Composite Toe Public Service Boot

Rocky Zipper Composite Toe Public Service Boot

$113.25Current Price $113.25
4.2(182)
Thermal Waterproof Genuine Shearling Lined Chelsea Boot (Men)

Blundstone Footwear Thermal Waterproof Genuine Shearling Lined Chelsea Boot (Men)

$244.95Current Price $244.95
Only a few left
High Romeo Steel Toe Boot

Georgia Boot High Romeo Steel Toe Boot

$108.75Current Price $108.75
4(60)
Waterproof Public Service Boot

Rocky Waterproof Public Service Boot

$104.25Current Price $104.25
4.2(196)
SlipResistant Waterproof  Steel Toe Waterproof Work Boots

Rocky SlipResistant Waterproof Steel Toe Waterproof Work Boots

$112.49Current Price $112.49
4.5(211)
Amp Lt Wedge Waterproof Pull On Work Boot
New

Georgia Boot Amp Lt Wedge Waterproof Pull On Work Boot

$153.75Current Price $153.75
4(17)
Homeland Steel Toe Waterproof Wellington

Georgia Boot Homeland Steel Toe Waterproof Wellington

$101.25Current Price $101.25
3.9(83)
Hamilton Wingtip Waterproof Chukka Boot (Men)

Allen Edmonds Hamilton Wingtip Waterproof Chukka Boot (Men)

$550Current Price $550
4.7(105)
Only a few left
Steel Toe Goretex Waterproof 600G Insulated Work Boot

Rocky Steel Toe Goretex Waterproof 600G Insulated Work Boot

$176.24Current Price $176.24
4.6(69)
Lorde Waterproof Chelsea Boot (Men)

Hunter Lorde Waterproof Chelsea Boot (Men)

$200Current Price $200
3(1)
Homeland Steel Toe Waterproof Work Boot

Georgia Boot Homeland Steel Toe Waterproof Work Boot

$101.25Current Price $101.25
4.1(45)
London Waterproof Boot (Men)

Hunter London Waterproof Boot (Men)

$200Current Price $200
4.3(4)
Wexford Waterproof Chelsea Boot (Men)

Ariat Wexford Waterproof Chelsea Boot (Men)

$209.95Current Price $209.95
4.6(278)
Chelsea Waterproof Work Romeo Boot

Georgia Boot Chelsea Waterproof Work Romeo Boot

$112.50Current Price $112.50
4(42)
Waterproof 600G Outdoor Boot

Rocky Waterproof 600G Outdoor Boot

$127.49Current Price $127.49
4.7(50)
Only a few left
Kicker II Waterproof Chelsea Rain Boot (Men)

Bogs Kicker II Waterproof Chelsea Rain Boot (Men)

$95Current Price $95
4.5(38)
Steel Toe Waterproof Western Work Boot

DURANGO Steel Toe Waterproof Western Work Boot

$173.50Current Price $173.50
4.8(8)
Davy HydroProtect Waterproof Slip-On Men)

Mephisto Davy HydroProtect Waterproof Slip-On Men)

$339Current Price $339
4.5(15)
Only a few left
Sport Utility 1000G Boot

Rocky Sport Utility 1000G Boot

$112.49Current Price $112.49
4.1(109)
Lace Up Boot

DURANGO Lace Up Boot

$185Current Price $185
3.6(11)
Waterproof 800G Insulated Outdoor Boot

Rocky Waterproof 800G Insulated Outdoor Boot

$107.99Current Price $107.99
4(103)
Steel Toe Western Work Boot

DURANGO Steel Toe Western Work Boot

$173.50Current Price $173.50
3.8(13)
Gore-Tex® Waterproof Desert Boot (Men)

Clarks® Originals Gore-Tex® Waterproof Desert Boot (Men)

$240Current Price $240
Only a few left
Steel Toe Wellington

Georgia Boot Steel Toe Wellington

$138.75Current Price $138.75
4.2(79)
Carbotec Lt Waterproof Chelsea Work Boot

Georgia Boot Carbotec Lt Waterproof Chelsea Work Boot

$123.75Current Price $123.75
4.1(7)
Men's Arctic Excursion Ankle Boot

MUCK Men's Arctic Excursion Ankle Boot

$97.50Current Price $97.50
4.4(130)
Zipper Waterproof Public Service Boot

Rocky Zipper Waterproof Public Service Boot

$107.25Current Price $107.25
4.1(445)
Amp Lt Logger Composite Toe Insulated Waterproof Work Boot

Georgia Boot Amp Lt Logger Composite Toe Insulated Waterproof Work Boot

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