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Keep with the classics in the BOSS Hugo Boss Boheme Suede Chukka Boot by HUGO. Suede leather upper. Traditional chukka lace-up construction. Leather sock lining. Stationary, leather-lined... BOSS Hugo Boss Boheme Suede Chukka Boot by HUGO (Dark Blue) Men's Shoes

BOSS Hugo Boss Boheme Suede Chukka...

Zappos.com
Hugo Boss
$245.00 $110.25

55%

Off
Keep with the classics in the BOSS Hugo Boss Boheme Suede Chukka Boot by HUGO. Suede leather upper. Traditional chukka lace-up construction. Leather sock lining. Stationary, leather-lined... BOSS Hugo Boss Boheme Suede Chukka Boot by HUGO (Dark Grey) Men's Shoes

BOSS Hugo Boss Boheme Suede Chukka...

Zappos.com
Hugo Boss
$245.00 $122.50

50%

Off
Keep with the classics in the BOSS Hugo Boss Boheme Suede Chukka Boot by HUGO. Suede leather upper. Traditional chukka lace-up construction. Leather sock lining. Stationary, leather-lined... BOSS Hugo Boss Boheme Suede Chukka Boot by HUGO (Dark Grey) Men's Shoes

BOSS Hugo Boss Boheme Suede Chukka...

Zappos.com
Hugo Boss
$245.00 $122.50

50%

Off
Sizing: True to size. M=standard width. Almond toe. Suede construction. Dual side goring. Back pull-tab. Pull-on. Approx. 6" shaft height, 10.5" opening circumference. Imported Magnanni Bareyo Chelsea Boot Castoro 7.5M at Nordstrom Rack - Mens Shoes - Mens Boots - Footwear

Magnanni Bareyo Chelsea Boot Castoro...

Nordstrom Rack
Magnanni
$395.00 $189.97

52%

Off
Sizing: True to size. M=standard width. Round toe. Leather construction. Lace-up vamp closure. Cushioned footbed. Topstitched details. Stacked sole. Made in Italy To Boot New York Keene Leather Oxford Navy 11.5M at Nordstrom Rack - Mens Formal Footwear - Mens Cap

To Boot New York Keene Leather Oxford...

Nordstrom Rack
To Boot New York
$395.00 $189.97

52%

Off
A derby for all occasions, these smart lace-ups from Hugo Hugo Boss offer comfort and sleek style for the office and beyond. Hugo Hugo Boss Men's Smart Casual Derby Shoes - Light Pastel Grey

Hugo Hugo Boss Men's Smart Casual...

macys.com
Hugo Boss
$248.00 $123.93
Free Shipping

50%

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A derby for all occasions, these smart lace-ups from Hugo Hugo Boss offer comfort and sleek style for the office and beyond. Hugo Hugo Boss Men's Smart Casual Derby Shoes - Light Pastel Grey

Hugo Hugo Boss Men's Smart Casual...

macys.com
Hugo Boss
$248.00 $123.93
Free Shipping

50%

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A derby for all occasions, these smart lace-ups from Hugo Hugo Boss offer comfort and sleek style for the office and beyond. Hugo Hugo Boss Men's Smart Casual Derby Shoes - Light Pastel Grey

Hugo Hugo Boss Men's Smart Casual...

macys.com
Hugo Boss
$248.00 $123.93
Free Shipping

50%

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Finely textured leather elevates a stylish Italian boot crafted with a cushioned arch support footbed for all-day comfort.Sizing: True to size. M=standard width. Round cap toe. Lace-up vamp... To Boot New York Henri Cap Toe Boot Tmoro 8M at Nordstrom Rack - Mens Shoes - Mens Boots - Footwear

To Boot New York Henri Cap Toe Boot...

Nordstrom Rack
To Boot New York
$395.00 $199.97

49%

Off
Brown Boss Leather Cowboy Boot - Men. Wrangle up Western-chic style in these versatile cowboy boots, crafted from enduring leather and set atop a walkable low heel. 1 heel 11 shaft 12.5... Dan Post Men's Western Boots Brown - Brown Boss Leather Cowboy Boot - Men

Dan Post Men's Western Boots Brown -...

zulily
Dan Post
$252.00 $78.29

69%

Off
Brown Boss Leather Cowboy Boot - Men. Wrangle up Western-chic style in these versatile cowboy boots, crafted from enduring leather and set atop a walkable low heel. 1 heel 11 shaft 12.5... Dan Post Men's Western Boots Brown - Brown Boss Leather Cowboy Boot - Men

Dan Post Men's Western Boots Brown -...

zulily
Dan Post
$252.00 $78.29

69%

Off
Brown Boss Leather Cowboy Boot - Men. Wrangle up Western-chic style in these versatile cowboy boots, crafted from enduring leather and set atop a walkable low heel. 1 heel 11 shaft 12.5... Dan Post Men's Western Boots Brown - Brown Boss Leather Cowboy Boot - Men

Dan Post Men's Western Boots Brown -...

zulily
Dan Post
$252.00 $78.29

69%

Off
BOSS by Hugo Boss Boss Zephir Runn Pastel Grey Trainers - Taking inspiration from the golden era of '80s running trainers, this edition of BOSS' popular Zephir model is crafted from a... Boss Zephir Runn Pastel Grey Trainers - Gray - BOSS by Hugo Boss Sneakers

Boss Zephir Runn Pastel Grey Trainers...

Lyst
Hugo Boss
$225.00 $135.00

40%

Off
BOSS by Hugo Boss Boss Titanium Runn Dark Blue Trainers - BOSS' Titanium Runn is designed with distinctive uppers that fuse nubuck leather, reflective elements and technical fabric.... Boss Titanium Runn Dark Blue Trainers - Blue - BOSS by Hugo Boss Sneakers

Boss Titanium Runn Dark Blue Trainers...

Lyst
Hugo Boss
$224.00 $135.00

40%

Off
BOSS by Hugo Boss Boss Titanium Black Knit Runn Trainers - The classic casual trainer gets the BOSS treatment. Featuring a 'sock trainer' design, these trainers are crafted for comfort and... Boss Titanium Black Knit Runn Trainers - Black - BOSS by Hugo Boss Sneakers

Boss Titanium Black Knit Runn...

Lyst
Hugo Boss
$224.00 $112.00

50%

Off
Shoes by Propet. Comes in Tan, Size 8 M. Durable leather uppers are treated with Scotchgard and lined in warm Thinsulate to repel water and keep feet warm. Shock-absorbing insoles are... Men's Propét Blizzard Boots, Tan, Size 8

Men's Propét Blizzard Boots, Tan,...

Blair.com
Propet
$94.99 $49.97

47%

Off
Shoes by Propet. Comes in Tan, Size 8. 5 XW. Durable leather uppers are treated with Scotchgard and lined in warm Thinsulate to repel water and keep feet warm. Shock-absorbing insoles are... Men's Propét Blizzard Boots, Tan, Size 8.5 X Wide Width

Men's Propét Blizzard Boots, Tan,...

Blair.com
Propet
$94.99 $49.97

47%

Off
A derby for all occasions, these smart lace-ups from Hugo Hugo Boss offer comfort and sleek style for the office and beyond. Hugo Hugo Boss Men's Smart Casual Derby Shoes - Dark Blue

Hugo Hugo Boss Men's Smart Casual...

macys.com
Hugo Boss
$248.00 $123.93
Free Shipping

50%

Off
A derby for all occasions, these smart lace-ups from Hugo Hugo Boss offer comfort and sleek style for the office and beyond. Hugo Hugo Boss Men's Smart Casual Derby Shoes - Dark Blue

Hugo Hugo Boss Men's Smart Casual...

macys.com
Hugo Boss
$248.00 $123.93
Free Shipping

50%

Off
A derby for all occasions, these smart lace-ups from Hugo Hugo Boss offer comfort and sleek style for the office and beyond. Hugo Hugo Boss Men's Smart Casual Derby Shoes - Light Pastel Grey

Hugo Hugo Boss Men's Smart Casual...

macys.com
Hugo Boss
$248.00 $123.93
Free Shipping

50%

Off
A derby for all occasions, these smart lace-ups from Hugo Hugo Boss offer comfort and sleek style for the office and beyond. Hugo Hugo Boss Men's Smart Casual Derby Shoes - Dark Blue

Hugo Hugo Boss Men's Smart Casual...

macys.com
Hugo Boss
$248.00 $123.93
Free Shipping

50%

Off
A derby for all occasions, these smart lace-ups from Hugo Hugo Boss offer comfort and sleek style for the office and beyond. Hugo Hugo Boss Men's Smart Casual Derby Shoes - Dark Blue

Hugo Hugo Boss Men's Smart Casual...

macys.com
Hugo Boss
$248.00 $123.93
Free Shipping

50%

Off
A derby for all occasions, these smart lace-ups from Hugo Hugo Boss offer comfort and sleek style for the office and beyond. Hugo Hugo Boss Men's Smart Casual Derby Shoes - Dark Blue

Hugo Hugo Boss Men's Smart Casual...

macys.com
Hugo Boss
$248.00 $123.93
Free Shipping

50%

Off
A derby for all occasions, these smart lace-ups from Hugo Hugo Boss offer comfort and sleek style for the office and beyond. Hugo Hugo Boss Men's Smart Casual Derby Shoes - Dark Blue

Hugo Hugo Boss Men's Smart Casual...

macys.com
Hugo Boss
$248.00 $123.93
Free Shipping

50%

Off
A derby for all occasions, these smart lace-ups from Hugo Hugo Boss offer comfort and sleek style for the office and beyond. Hugo Hugo Boss Men's Smart Casual Derby Shoes - Dark Blue

Hugo Hugo Boss Men's Smart Casual...

macys.com
Hugo Boss
$248.00 $123.93
Free Shipping

50%

Off
A derby for all occasions, these smart lace-ups from Hugo Hugo Boss offer comfort and sleek style for the office and beyond. Hugo Hugo Boss Men's Smart Casual Derby Shoes - Light Pastel Grey

Hugo Hugo Boss Men's Smart Casual...

macys.com
Hugo Boss
$248.00 $123.93
Free Shipping

50%

Off
A derby for all occasions, these smart lace-ups from Hugo Hugo Boss offer comfort and sleek style for the office and beyond. Hugo Hugo Boss Men's Smart Casual Derby Shoes - Dark Blue

Hugo Hugo Boss Men's Smart Casual...

macys.com
Hugo Boss
$248.00 $123.93
Free Shipping

50%

Off
A derby for all occasions, these smart lace-ups from Hugo Hugo Boss offer comfort and sleek style for the office and beyond. Hugo Hugo Boss Men's Smart Casual Derby Shoes - Light Pastel Grey

Hugo Hugo Boss Men's Smart Casual...

macys.com
Hugo Boss
$248.00 $123.93
Free Shipping

50%

Off
A derby for all occasions, these smart lace-ups from Hugo Hugo Boss offer comfort and sleek style for the office and beyond. Hugo Hugo Boss Men's Smart Casual Derby Shoes - Light Pastel Grey

Hugo Hugo Boss Men's Smart Casual...

macys.com
Hugo Boss
$248.00 $123.93
Free Shipping

50%

Off
A derby for all occasions, these smart lace-ups from Hugo Hugo Boss offer comfort and sleek style for the office and beyond. Hugo Hugo Boss Men's Smart Casual Derby Shoes - Dark Blue

Hugo Hugo Boss Men's Smart Casual...

macys.com
Hugo Boss
$248.00 $123.93
Free Shipping

50%

Off
A derby for all occasions, these smart lace-ups from Hugo Hugo Boss offer comfort and sleek style for the office and beyond. Hugo Hugo Boss Men's Smart Casual Derby Shoes - Light Pastel Grey

Hugo Hugo Boss Men's Smart Casual...

macys.com
Hugo Boss
$248.00 $123.93
Free Shipping

50%

Off
A derby for all occasions, these smart lace-ups from Hugo Hugo Boss offer comfort and sleek style for the office and beyond. Hugo Hugo Boss Men's Smart Casual Derby Shoes - Light Pastel Grey

Hugo Hugo Boss Men's Smart Casual...

macys.com
Hugo Boss
$248.00 $123.93
Free Shipping

50%

Off
A derby for all occasions, these smart lace-ups from Hugo Hugo Boss offer comfort and sleek style for the office and beyond. Hugo Hugo Boss Men's Smart Casual Derby Shoes - Light Pastel Grey

Hugo Hugo Boss Men's Smart Casual...

macys.com
Hugo Boss
$248.00 $123.93
Free Shipping

50%

Off
A derby for all occasions, these smart lace-ups from Hugo Hugo Boss offer comfort and sleek style for the office and beyond. Hugo Hugo Boss Men's Smart Casual Derby Shoes - Dark Blue

Hugo Hugo Boss Men's Smart Casual...

macys.com
Hugo Boss
$248.00 $123.93
Free Shipping

50%

Off
A brass bit vamp adds a sultry elegant look to this Italian loafer. M=standard width. Apron toe. Bit vamp. Topstitched details. Slip-on. Lightly padded footbed. Made in Italy To Boot New York Nile Bit Loafer Blu 10M at Nordstrom Rack - Mens Shoes & Footwear - Loafers & Slip-

To Boot New York Nile Bit Loafer Blu...

Nordstrom Rack
To Boot New York
$375.00 $189.97

49%

Off
Sizing: Whole sizes only; for 1/2 sizes, order next size up. Round toe. Lace-up vamp. Suede construction. Broguing and topstitched detail. Welt midsole trim. Grip sole. Approx. 4.75" shaft... Ted Baker London Daiinos Suede Chukka Boot Brown 7 at Nordstrom Rack - Mens Shoes - Mens Boots - Men

Ted Baker London Daiinos Suede Chukka...

Nordstrom Rack
Ted Baker
$280.00 $139.97

50%

Off
Brown Boss Leather Cowboy Boot - Men. Wrangle up Western-chic style in these versatile cowboy boots, crafted from enduring leather and set atop a walkable low heel. 1 heel 11 shaft 12.5... Dan Post Men's Western Boots Brown - Brown Boss Leather Cowboy Boot - Men

Dan Post Men's Western Boots Brown -...

zulily
Dan Post
$252.00 $78.29

69%

Off
Brown Boss Leather Cowboy Boot - Men. Wrangle up Western-chic style in these versatile cowboy boots, crafted from enduring leather and set atop a walkable low heel. 1 heel 11 shaft 12.5... Dan Post Men's Western Boots Brown - Brown Boss Leather Cowboy Boot - Men

Dan Post Men's Western Boots Brown -...

zulily
Dan Post
$252.00 $78.29

69%

Off
Brown Boss Leather Cowboy Boot - Men. Wrangle up Western-chic style in these versatile cowboy boots, crafted from enduring leather and set atop a walkable low heel. 1 heel 11 shaft 12.5... Dan Post Men's Western Boots Brown - Brown Boss Leather Cowboy Boot - Men

Dan Post Men's Western Boots Brown -...

zulily
Dan Post
$252.00 $78.29

69%

Off
Brown Boss Leather Cowboy Boot - Men. Wrangle up Western-chic style in these versatile cowboy boots, crafted from enduring leather and set atop a walkable low heel. 1 heel 11 shaft 12.5... Dan Post Men's Western Boots Brown - Brown Boss Leather Cowboy Boot - Men

Dan Post Men's Western Boots Brown -...

zulily
Dan Post
$252.00 $78.29

69%

Off
Brown Boss Leather Cowboy Boot - Men. Wrangle up Western-chic style in these versatile cowboy boots, crafted from enduring leather and set atop a walkable low heel. 1 heel 11 shaft 12.5... Dan Post Men's Western Boots Brown - Brown Boss Leather Cowboy Boot - Men

Dan Post Men's Western Boots Brown -...

zulily
Dan Post
$252.00 $78.29

69%

Off
Brown Boss Leather Cowboy Boot - Men. Wrangle up Western-chic style in these versatile cowboy boots, crafted from enduring leather and set atop a walkable low heel. 1 heel 11 shaft 12.5... Dan Post Men's Western Boots Brown - Brown Boss Leather Cowboy Boot - Men

Dan Post Men's Western Boots Brown -...

zulily
Dan Post
$252.00 $78.29

69%

Off
Brown Boss Leather Cowboy Boot - Men. Wrangle up Western-chic style in these versatile cowboy boots, crafted from enduring leather and set atop a walkable low heel. 1 heel 11 shaft 12.5... Dan Post Men's Western Boots Brown - Brown Boss Leather Cowboy Boot - Men

Dan Post Men's Western Boots Brown -...

zulily
Dan Post
$252.00 $78.29

69%

Off
Brown Boss Leather Cowboy Boot - Men. Wrangle up Western-chic style in these versatile cowboy boots, crafted from enduring leather and set atop a walkable low heel. 1 heel 11 shaft 12.5... Dan Post Men's Western Boots Brown - Brown Boss Leather Cowboy Boot - Men

Dan Post Men's Western Boots Brown -...

zulily
Dan Post
$252.00 $78.29

69%

Off
Brown Boss Leather Cowboy Boot - Men. Wrangle up Western-chic style in these versatile cowboy boots, crafted from enduring leather and set atop a walkable low heel. 1 heel 11 shaft 12.5... Dan Post Men's Western Boots Brown - Brown Boss Leather Cowboy Boot - Men

Dan Post Men's Western Boots Brown -...

zulily
Dan Post
$252.00 $78.29

69%

Off
Brown Boss Leather Cowboy Boot - Men. Wrangle up Western-chic style in these versatile cowboy boots, crafted from enduring leather and set atop a walkable low heel. 1 heel 11 shaft 12.5... Dan Post Men's Western Boots Brown - Brown Boss Leather Cowboy Boot - Men

Dan Post Men's Western Boots Brown -...

zulily
Dan Post
$252.00 $78.29

69%

Off
Brown Boss Leather Cowboy Boot - Men. Wrangle up Western-chic style in these versatile cowboy boots, crafted from enduring leather and set atop a walkable low heel. 1 heel 11 shaft 12.5... Dan Post Men's Western Boots Brown - Brown Boss Leather Cowboy Boot - Men

Dan Post Men's Western Boots Brown -...

zulily
Dan Post
$252.00 $78.29

69%

Off
Brown Boss Leather Cowboy Boot - Men. Wrangle up Western-chic style in these versatile cowboy boots, crafted from enduring leather and set atop a walkable low heel. 1 heel 11 shaft 12.5... Dan Post Men's Western Boots Brown - Brown Boss Leather Cowboy Boot - Men

Dan Post Men's Western Boots Brown -...

zulily
Dan Post
$252.00 $78.29

69%

Off
Brown Boss Leather Cowboy Boot - Men. Wrangle up Western-chic style in these versatile cowboy boots, crafted from enduring leather and set atop a walkable low heel. 1 heel 11 shaft 12.5... Dan Post Men's Western Boots Brown - Brown Boss Leather Cowboy Boot - Men

Dan Post Men's Western Boots Brown -...

zulily
Dan Post
$252.00 $78.29

69%

Off
Brown Boss Leather Cowboy Boot - Men. Wrangle up Western-chic style in these versatile cowboy boots, crafted from enduring leather and set atop a walkable low heel. 1 heel 11 shaft 12.5... Dan Post Men's Western Boots Brown - Brown Boss Leather Cowboy Boot - Men

Dan Post Men's Western Boots Brown -...

zulily
Dan Post
$252.00 $78.29

69%

Off
Brown Boss Leather Cowboy Boot - Men. Wrangle up Western-chic style in these versatile cowboy boots, crafted from enduring leather and set atop a walkable low heel. 1 heel 11 shaft 12.5... Dan Post Men's Western Boots Brown - Brown Boss Leather Cowboy Boot - Men

Dan Post Men's Western Boots Brown -...

zulily
Dan Post
$252.00 $78.29

69%

Off
Brown Boss Leather Cowboy Boot - Men. Wrangle up Western-chic style in these versatile cowboy boots, crafted from enduring leather and set atop a walkable low heel. 1 heel 11 shaft 12.5... Dan Post Men's Western Boots Brown - Brown Boss Leather Cowboy Boot - Men

Dan Post Men's Western Boots Brown -...

zulily
Dan Post
$252.00 $78.29

69%

Off
Brown Boss Leather Cowboy Boot - Men. Wrangle up Western-chic style in these versatile cowboy boots, crafted from enduring leather and set atop a walkable low heel. 1 heel 11 shaft 12.5... Dan Post Men's Western Boots Brown - Brown Boss Leather Cowboy Boot - Men

Dan Post Men's Western Boots Brown -...

zulily
Dan Post
$252.00 $78.29

69%

Off
Brown Boss Leather Cowboy Boot - Men. Wrangle up Western-chic style in these versatile cowboy boots, crafted from enduring leather and set atop a walkable low heel. 1 heel 11 shaft 12.5... Dan Post Men's Western Boots Brown - Brown Boss Leather Cowboy Boot - Men

Dan Post Men's Western Boots Brown -...

zulily
Dan Post
$252.00 $78.29

69%

Off