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

Men's Size 8.5 Medium Size On Sale Products

39 items found

Sort By

Your Selections

Search Results

Saucony - Shadow 5000. Color Grey/Black. Low Stock. On sale for $103.50. MSRP $115.00. 10% off. 4.0 out of 5 stars

Low Stock

Gray Saucony Shadow 5000

Gray Saucony Shadow 5000

+14

Brand Name: Saucony
Product Name: Shadow 5000
Gender: Unisex
Color: Grey/Black
Price: $103.50MSRP: $115.0010% OFF
Rating: 5Rated 5 stars out of 5(3)

SKECHERS - Go Walk Max Cushioning Hyper Burst Zoltar Hands Free Slip-in. Color Black. On sale for $70.54. MSRP $90.00. 22% off. 3.0 out of 5 stars

Black SKECHERS Go Walk Max Cushioning Hyper Burst Zoltar Hands Free Slip-in

Black SKECHERS Go Walk Max Cushioning Hyper Burst Zoltar Hands Free Slip-in

+3

Brand Name: SKECHERS
Product Name: Go Walk Max Cushioning Hyper Burst Zoltar Hands Free Slip-in
Gender: Men's
Color: Black
Price: $70.54MSRP: $90.0022% OFF
Rating: 3Rated 3 stars out of 5(4)

KEEN - Targhee II. Color Cascade Brown/Golden Yellow. On sale for $129.90. MSRP $154.95. 16% off. 4.2 out of 5 stars

Brown KEEN Targhee II

Brown KEEN Targhee II

Brand Name: KEEN
Product Name: Targhee II
Gender: Men's
Color: Cascade Brown/Golden Yellow
Price: $129.90MSRP: $154.9516% OFF
Rating: 4Rated 4 stars out of 5(921)

Allbirds - Tree Dasher 2. Color Blizzard, Hanami Night (Natural White). On sale for $121.50. MSRP $135.00. 10% off. 4.4 out of 5 stars

White Allbirds Tree Dasher 2

White Allbirds Tree Dasher 2

+10

Brand Name: Allbirds
Product Name: Tree Dasher 2
Gender: Men's
Color: Blizzard, Hanami Night (Natural White)
Price: $121.50MSRP: $135.0010% OFF
Rating: 4Rated 4 stars out of 5(1138)

Dockers - Easedale. Color Dark Brown. On sale for $49.99. MSRP $85.00. 41% off. 1.0 out of 5 stars

Brown Dockers Easedale

Brown Dockers Easedale

+1

Brand Name: Dockers
Product Name: Easedale
Gender: Men's
Color: Dark Brown
Price: $49.99MSRP: $85.0041% OFF
Rating: 1Rated 1 star out of 5(1)

Johnston & Murphy - Calder Chukka. Color Brown Oiled Suede. On sale for $165.00. MSRP $179.00. 8% off. 4.0 out of 5 stars

Brown Johnston & Murphy Calder Chukka

Brown Johnston & Murphy Calder Chukka

+4

Brand Name: Johnston & Murphy
Product Name: Calder Chukka
Gender: Men's
Color: Brown Oiled Suede
Price: $165.00MSRP: $179.008% OFF
Rating: 4Rated 4 stars out of 5(3)

SKECHERS - Hands Free Slip-ins Max Cushioning Glide-step Sneaker. Color Navy. On sale for $85.00. MSRP $100.00. 15% off. 5.0 out of 5 stars

Navy SKECHERS Hands Free Slip-ins Max Cushioning Glide-step Sneaker

Navy SKECHERS Hands Free Slip-ins Max Cushioning Glide-step Sneaker

+2

Brand Name: SKECHERS
Product Name: Hands Free Slip-ins Max Cushioning Glide-step Sneaker
Gender: Men's
Color: Navy
Price: $85.00MSRP: $100.0015% OFF
Rating: 5Rated 5 stars out of 5(1)

Dr. Scholl's - Time Off Mens Lace Up Sneaker. Color White Smooth. On sale for $75.00. MSRP $115.00. 35% off. 4.3 out of 5 stars

White Dr. Scholl's Time Off Mens Lace Up Sneaker

White Dr. Scholl's Time Off Mens Lace Up Sneaker

Brand Name: Dr. Scholl's
Product Name: Time Off Mens Lace Up Sneaker
Gender: Men's
Color: White Smooth
Price: $75.00MSRP: $115.0035% OFF
Rating: 4Rated 4 stars out of 5(9)

SKECHERS - Max Cushioning Endeavour Slip-In. Color Gray/Blue. On sale for $90.00. MSRP $100.00. 10% off.

Blue SKECHERS Max Cushioning Endeavour Slip-In

Blue SKECHERS Max Cushioning Endeavour Slip-In

Brand Name: SKECHERS
Product Name: Max Cushioning Endeavour Slip-In
Gender: Men's
Color: Gray/Blue
Price: $90.00MSRP: $100.0010% OFF
Rating

Dan Post - Albuquerque. Color Mid Brown Oily. On sale for $169.99. MSRP $204.95. 17% off. 4.2 out of 5 stars

Brown Dan Post Albuquerque

Brown Dan Post Albuquerque

+2

Brand Name: Dan Post
Product Name: Albuquerque
Gender: Men's
Color: Mid Brown Oily
Price: $169.99MSRP: $204.9517% OFF
Rating: 4Rated 4 stars out of 5(196)

Marc Joseph New York - River Road. Color Cognac Grainy. On sale for $69.95. MSRP $185.00. 62% off. 5.0 out of 5 stars

Brown Marc Joseph New York River Road

Brown Marc Joseph New York River Road

+3

Brand Name: Marc Joseph New York
Product Name: River Road
Gender: Men's
Color: Cognac Grainy
Price: $69.95MSRP: $185.0062% OFF
Rating: 5Rated 5 stars out of 5(1)

KEEN - Targhee 4 Mid Height Durable Comfortable Waterproof. Color Bison/Black. On sale for $169.99. MSRP $180.00. 6% off. 4.0 out of 5 stars

Brown KEEN Targhee 4 Mid Height Durable Comfortable Waterproof

Brown KEEN Targhee 4 Mid Height Durable Comfortable Waterproof

+5

Brand Name: KEEN
Product Name: Targhee 4 Mid Height Durable Comfortable Waterproof
Gender: Men's
Color: Bison/Black
Price: $169.99MSRP: $180.006% OFF
Rating: 4Rated 4 stars out of 5(465)

Johnston & Murphy - Barrett Zip Boots. Color Charcoal Full Grain. Low Stock. On sale for $93.53. MSRP $199.00. 53% off. 3.0 out of 5 stars

Low Stock

Bronze Johnston & Murphy Barrett Zip Boots

Bronze Johnston & Murphy Barrett Zip Boots

+2

Brand Name: Johnston & Murphy
Product Name: Barrett Zip Boots
Gender: Men's
Color: Charcoal Full Grain
Price: $93.53MSRP: $199.0053% OFF
Rating: 3Rated 3 stars out of 5(1)

Michael Kors - Atlas Trainer. Color Bone. Low Stock. On sale for $148.80. MSRP $248.00. 40% off.

Low Stock

Bone Michael Kors Atlas Trainer

Bone Michael Kors Atlas Trainer

+3

Brand Name: Michael Kors
Product Name: Atlas Trainer
Gender: Men's
Color: Bone
Price: $148.80MSRP: $248.0040% OFF
Rating

etnies - Barge LS. Color Black Raw. On sale for $45.99. MSRP $65.00. 29% off. 3.9 out of 5 stars

Black etnies Barge LS

Black etnies Barge LS

+7

Brand Name: etnies
Product Name: Barge LS
Gender: Men's
Color: Black Raw
Price: $45.99MSRP: $65.0029% OFF
Rating: 4Rated 4 stars out of 5(230)

Timberland PRO - Boondock HD Logger 8" Composite Safety Toe Insulated Waterproof. Color Mocha Brown. On sale for $259.95. MSRP $285.00. 9% off. 3.8 out of 5 stars

Taupe Timberland PRO Boondock HD Logger 8" Composite Safety Toe Insulated Waterproof

Brand Name: Timberland PRO
Product Name: Boondock HD Logger 8" Composite Safety Toe Insulated Waterproof
Gender: Men's
Color: Mocha Brown
Price: $259.95MSRP: $285.009% OFF
Rating: 4Rated 4 stars out of 5(16)

Clarks - DressLite Step. Color Black. On sale for $94.50. MSRP $105.00. 10% off.

Black Clarks DressLite Step

Black Clarks DressLite Step

+2

Brand Name: Clarks
Product Name: DressLite Step
Gender: Men's
Color: Black
Price: $94.50MSRP: $105.0010% OFF
Rating

Dan Post - Milwaukee R Toe. Color Black. On sale for $169.99. MSRP $229.95. 26% off. 4.2 out of 5 stars

Black Dan Post Milwaukee R Toe

Black Dan Post Milwaukee R Toe

Brand Name: Dan Post
Product Name: Milwaukee R Toe
Gender: Men's
Color: Black
Price: $169.99MSRP: $229.9526% OFF
Rating: 4Rated 4 stars out of 5(67)

SKECHERS - Max Cushioning Premier Ascendant Hands Free Slip-Ins. Color Navy. On sale for $102.07. MSRP $116.95. 13% off. 4.5 out of 5 stars

Navy SKECHERS Max Cushioning Premier Ascendant Hands Free Slip-Ins

Navy SKECHERS Max Cushioning Premier Ascendant Hands Free Slip-Ins

+2

Brand Name: SKECHERS
Product Name: Max Cushioning Premier Ascendant Hands Free Slip-Ins
Gender: Men's
Color: Navy
Price: $102.07MSRP: $116.9513% OFF
Rating: 5Rated 5 stars out of 5(306)

Marc Joseph New York - Cooper St. Color Oilve Suede. On sale for $89.95. MSRP $195.00. 54% off. 2.0 out of 5 stars

Olive Marc Joseph New York Cooper St

Olive Marc Joseph New York Cooper St

+6

Brand Name: Marc Joseph New York
Product Name: Cooper St
Gender: Men's
Color: Oilve Suede
Price: $89.95MSRP: $195.0054% OFF
Rating: 2Rated 2 stars out of 5(1)

Wolf & Shepherd - Supercrossover. Color Navy. On sale for $206.50. MSRP $295.00. 30% off.

Navy Wolf & Shepherd Supercrossover

Navy Wolf & Shepherd Supercrossover

+2

Brand Name: Wolf & Shepherd
Product Name: Supercrossover
Gender: Men's
Color: Navy
Price: $206.50MSRP: $295.0030% OFF
Rating

Caterpillar - Striver ST. Color Black. On sale for $79.99. MSRP $95.00. 16% off. 4.2 out of 5 stars

Black Caterpillar Striver ST

Black Caterpillar Striver ST

+2

Brand Name: Caterpillar
Product Name: Striver ST
Gender: Men's
Color: Black
Price: $79.99MSRP: $95.0016% OFF
Rating: 4Rated 4 stars out of 5(4)

KEEN - Zionic Waterproof. Color Steel Grey/Poppy Red. On sale for $143.95. MSRP $159.95. 10% off. 4.0 out of 5 stars

Black KEEN Zionic Waterproof

Black KEEN Zionic Waterproof

+4

Brand Name: KEEN
Product Name: Zionic Waterproof
Gender: Men's
Color: Steel Grey/Poppy Red
Price: $143.95MSRP: $159.9510% OFF
Rating: 4Rated 4 stars out of 5(140)

TravisMathew - The Daily 2.0 Knit. Color Heather Sleet. On sale for $119.95. MSRP $129.95. 8% off. 4.3 out of 5 stars

Gray TravisMathew The Daily 2.0 Knit

Gray TravisMathew The Daily 2.0 Knit

+4

Brand Name: TravisMathew
Product Name: The Daily 2.0 Knit
Gender: Men's
Color: Heather Sleet
Price: $119.95MSRP: $129.958% OFF
Rating: 4Rated 4 stars out of 5(141)

New Balance - Allsite Waterproof Comp Toe EH PR SR. Color Black. On sale for $161.99. MSRP $174.99. 7% off. 3.3 out of 5 stars

Black New Balance Allsite Waterproof Comp Toe EH PR SR

Black New Balance Allsite Waterproof Comp Toe EH PR SR

+2

Brand Name: New Balance
Product Name: Allsite Waterproof Comp Toe EH PR SR
Gender: Men's
Color: Black
Price: $161.99MSRP: $174.997% OFF
Rating: 3Rated 3 stars out of 5(42)

Vibram FiveFingers - V-Run. Color Black/Yellow. Low Stock. On sale for $110.50. MSRP $160.00. 31% off. 4.0 out of 5 stars

Low Stock

Gray Vibram FiveFingers V-Run

Gray Vibram FiveFingers V-Run

+2

Brand Name: Vibram FiveFingers
Product Name: V-Run
Gender: Men's
Color: Black/Yellow
Price: $110.50MSRP: $160.0031% OFF
Rating: 4Rated 4 stars out of 5(32)

KEEN - WK450. Color Black/Star White. On sale for $137.82. MSRP $150.00. 8% off. 4.0 out of 5 stars

Black KEEN WK450

Black KEEN WK450

+3

Brand Name: KEEN
Product Name: WK450
Gender: Men's
Color: Black/Star White
Price: $137.82MSRP: $150.008% OFF
Rating: 4Rated 4 stars out of 5(72)

Laredo - Brentwood. Color Black. On sale for $144.95. MSRP $174.95. 17% off. 4.6 out of 5 stars

Black Laredo Brentwood

Black Laredo Brentwood

Brand Name: Laredo
Product Name: Brentwood
Gender: Men's
Color: Black
Price: $144.95MSRP: $174.9517% OFF
Rating: 5Rated 5 stars out of 5(27)

TravisMathew - The Ringer 2.0. Color White. On sale for $161.95. MSRP $179.95. 10% off. 4.4 out of 5 stars

White TravisMathew The Ringer 2.0

White TravisMathew The Ringer 2.0

+2

Brand Name: TravisMathew
Product Name: The Ringer 2.0
Gender: Men's
Color: White
Price: $161.95MSRP: $179.9510% OFF
Rating: 4Rated 4 stars out of 5(71)

TravisMathew - The Daily Pro Hybrid. Color Heather White. On sale for $134.95. MSRP $149.95. 10% off. 4.3 out of 5 stars

White TravisMathew The Daily Pro Hybrid

White TravisMathew The Daily Pro Hybrid

+9

Brand Name: TravisMathew
Product Name: The Daily Pro Hybrid
Gender: Men's
Color: Heather White
Price: $134.95MSRP: $149.9510% OFF
Rating: 4Rated 4 stars out of 5(209)

Laredo - Breakout. Color Rust Distressed. On sale for $154.95. MSRP $179.95. 14% off. 3.8 out of 5 stars

Orange Laredo Breakout

Orange Laredo Breakout

Brand Name: Laredo
Product Name: Breakout
Gender: Men's
Color: Rust Distressed
Price: $154.95MSRP: $179.9514% OFF
Rating: 4Rated 4 stars out of 5(23)

SKECHERS - Hands Free Slip-Ins Squad Chaos - Solid Tour. Color Navy Multi. On sale for $61.06. MSRP $80.00. 24% off. 4.4 out of 5 stars

Blue SKECHERS Hands Free Slip-Ins Squad Chaos - Solid Tour

Blue SKECHERS Hands Free Slip-Ins Squad Chaos - Solid Tour

Brand Name: SKECHERS
Product Name: Hands Free Slip-Ins Squad Chaos - Solid Tour
Gender: Men's
Color: Navy Multi
Price: $61.06MSRP: $80.0024% OFF
Rating: 4Rated 4 stars out of 5(50)

Bogs - Slate Mid CT. Color Black. On sale for $119.95. MSRP $125.00. 4% off. 4.1 out of 5 stars

Black Bogs Slate Mid CT

Black Bogs Slate Mid CT

Brand Name: Bogs
Product Name: Slate Mid CT
Gender: Men's
Color: Black
Price: $119.95MSRP: $125.004% OFF
Rating: 4Rated 4 stars out of 5(174)

Marc Joseph New York - South Street. Color Cognac Grainy. On sale for $79.95. MSRP $155.00. 48% off. 1.0 out of 5 stars

Brown Marc Joseph New York South Street

Brown Marc Joseph New York South Street

Brand Name: Marc Joseph New York
Product Name: South Street
Gender: Men's
Color: Cognac Grainy
Price: $79.95MSRP: $155.0048% OFF
Rating: 1Rated 1 star out of 5(1)

Under Armour - Charged Revitalize. Color Gray Matter/White/Retro Green. On sale for $57.57. MSRP $70.00. 18% off. 4.0 out of 5 stars

Gray Under Armour Charged Revitalize

Gray Under Armour Charged Revitalize

Brand Name: Under Armour
Product Name: Charged Revitalize
Gender: Men's
Color: Gray Matter/White/Retro Green
Price: $57.57MSRP: $70.0018% OFF
Rating: 4Rated 4 stars out of 5(88)

Michael Kors - Atlas Knit Trainer. Color Light Sand. On sale for $130.26. MSRP $198.00. 34% off.

Beige Michael Kors Atlas Knit Trainer

Beige Michael Kors Atlas Knit Trainer

+4

Brand Name: Michael Kors
Product Name: Atlas Knit Trainer
Gender: Men's
Color: Light Sand
Price: $130.26MSRP: $198.0034% OFF
Rating

Dan Post - Neeley. Color Tan. On sale for $199.95. MSRP $229.95. 13% off.

Tan Dan Post Neeley

Tan Dan Post Neeley

Brand Name: Dan Post
Product Name: Neeley
Gender: Men's
Color: Tan
Price: $199.95MSRP: $229.9513% OFF
Rating

Saucony - Men's Kinvara 14. Color Navy. Low Stock. On sale for $108.00. MSRP $120.00. 10% off. 3.3 out of 5 stars

Low Stock

Navy Saucony Men's Kinvara 14

Navy Saucony Men's Kinvara 14

Brand Name: Saucony
Product Name: Men's Kinvara 14
Gender: Men's
Color: Navy
Price: $108.00MSRP: $120.0010% OFF
Rating: 3Rated 3 stars out of 5(237)

Johnston & Murphy - Brody Chukka. Color Snuff Suede. On sale for $92.40. MSRP $165.00. 44% off.

Brown Johnston & Murphy Brody Chukka

Brown Johnston & Murphy Brody Chukka

+2

Brand Name: Johnston & Murphy
Product Name: Brody Chukka
Gender: Men's
Color: Snuff Suede
Price: $92.40MSRP: $165.0044% OFF
Rating

Join Our List, Get 10% Off

Sign up for Zappos emails—new subscribers get 10% off a future order!* Plus, get early access to sales, coupons, and more. (One code per email address.)