Menu
Your Cart
Free Shipping for orders over $35.

Boots

Being one of the essential pieces of a men’s wardrobe, boots are very important. They need to be cozy, non-slippery, waterproof and comfortable. When shopping for men’s boots, you need to consider many parameters, including your style.

Chukka Boots

These are ankle-high boots, usually with two or three eyelets. Desert boots are one kind of chukka boots. They are a nice fit for comfortable and casual stylish men. They go well with chinos and cuffed jeans. They can go with any casual Sunday brunch or Saturday comfy style. Calvin Klein Men, Clarks Men and INC International Concepts are some brands offered by The Season.

Chelsea Boots

The famous fashion saying ‘less is more’ defines Chelsea boots perfectly. They look plain and simple. They are easy to wear with elastic bands on the sides. They are a must-have because they can go with nearly all outfits ranging from suits to casual chinos. You should check the leather and suede ones. Eastland Men and Tommy Hilfiger Men have stylish and warm options.

 Hiking Boots

These are for hiking and any men who like to be outdoors. They also look good in city with nice outfits. Chinos and flannel shirts are basic combinations of hiking boots. They are also perfect for areas where winter is harsh, but you also want to look fashionable. Rockport Men’s Rugged Bucks can be a good option to check out. 
Alfani Mens Ashton Ankle Boot,Tan,10 Alfani Mens Ashton Ankle Boot,Tan,10
Free Shipping
Brand: Alfani SKU: PSB-1130311177
Bring a balance of casual and dress formal fashion to your wardrobe with the versatile appeal presented by Alfani's Ashton Ankle Boots.Squared-toe pull-up ankle boots Heel pull tab; block heel Durable and flexible outsole; memory foam insole Polyurethane/manmade upper; jersey/polyur..
$55.00
Alfani Men’s Patrick Moc-Toe Utility Boots Alfani Men’s Patrick Moc-Toe Utility Boots
Free Shipping
Brand: Alfani SKU: PSB-191179004
Alfani’s moc-toe utility boots combine comfortable functionality with sleek style and feature an inside zip-up closure for a secure fit to take you through the day.Moccasin toe Lace-up closure with inside zip closure Leather upper; manmade sole Imported..
$64.39
Alfani Men’s Tucker Quilted Lace-Up Chukka Boot Shoes, Green, 10 Alfani Men’s Tucker Quilted Lace-Up Chukka Boot Shoes, Green, 10
Free Shipping
Brand: Alfani SKU: PSB-1748974005
For a classic chukka with a contemporary twist, choose the quilted styling of these Tucker boots from Alfani.Round-toe lace-up chukka boots Quilted upper; stretch laces with toggle closure Memory foam footbed Nylon upper; fabric lining; rubber sole Imported..
$49.90
Alfani Men’s Tucker Quilted Lace-Up Chukka Boot Shoes, Green, 9.5 Alfani Men’s Tucker Quilted Lace-Up Chukka Boot Shoes, Green, 9.5
Free Shipping
Brand: Alfani SKU: PSB-1381429033
For a classic chukka with a contemporary twist, choose the quilted styling of these Tucker boots from Alfani.Round-toe lace-up chukka boots Quilted upper; stretch laces with toggle closure Memory foam footbed Nylon upper; fabric lining; rubber sole Imported..
$49.90
Alfani Men’s Tucker Quilted Lace-Up Chukka Boot Shoes, Tan, 11 Alfani Men’s Tucker Quilted Lace-Up Chukka Boot Shoes, Tan, 11
Free Shipping
Brand: Alfani SKU: PSB-1375322037
For a classic chukka with a contemporary twist, choose the quilted styling of these Tucker boots from Alfani.Round-toe lace-up chukka boots Quilted upper; stretch laces with toggle closure Memory foam footbed Nylon upper; fabric lining; rubber sole Imported..
$39.90
Alfani Men’s Tucker Quilted Lace-Up Chukka Boot Shoes, Tan, 13 Alfani Men’s Tucker Quilted Lace-Up Chukka Boot Shoes, Tan, 13
Free Shipping
Brand: Alfani SKU: PSB-414259748
For a classic chukka with a contemporary twist, choose the quilted styling of these Tucker boots from Alfani.Round-toe lace-up chukka boots Quilted upper; stretch laces with toggle closure Memory foam footbed Nylon upper; fabric lining; rubber sole Imported..
$39.90
Alfani Men’s Tucker Quilted Lace-Up Chukka Boot Shoes, Tan, 7 Alfani Men’s Tucker Quilted Lace-Up Chukka Boot Shoes, Tan, 7
Free Shipping
Brand: Alfani SKU: PSB-312150023
For a classic chukka with a contemporary twist, choose the quilted styling of these Tucker boots from Alfani.Round-toe lace-up chukka boots Quilted upper; stretch laces with toggle closure Memory foam footbed Nylon upper; fabric lining; rubber sole Imported..
$49.90
BareTraps Men’s, Luca Boot Navy 10.5 M BareTraps Men’s, Luca Boot Navy 10.5 M
Free Shipping
Brand: Baretraps SKU: PSC-1843329420
Men's Baretraps, Luca Boot. Feel good and look great with the Baretraps Luca men’s casual boot. The Rebound Technology insole provides extra comfort with a built-in arch support. With an upper made of mesh, this lightweight, flexible style is ready for everyday wear.Lightweight mesh fabric upper Bre..
$45.00
BareTraps Men’s, Luca Boot, Surfer Blue 10 M BareTraps Men’s, Luca Boot, Surfer Blue 10 M
Free Shipping
Brand: Baretraps SKU: PSC-563829556
Men's Baretraps, Luca Boot. Feel good and look great with the Baretraps Luca men’s casual boot. The Rebound Technology insole provides extra comfort with a built-in arch support. With an upper made of mesh, this lightweight, flexible style is ready for everyday wear.Lightweight mesh fabric upper Bre..
$45.00
BareTraps Men’s, Luca Boot, Surfer Blue 8 M BareTraps Men’s, Luca Boot, Surfer Blue 8 M
Free Shipping
Brand: Baretraps SKU: PSC-362990483
Men's Baretraps, Luca Boot. Feel good and look great with the Baretraps Luca men’s casual boot. The Rebound Technology insole provides extra comfort with a built-in arch support. With an upper made of mesh, this lightweight, flexible style is ready for everyday wear.Lightweight mesh fabric upper Bre..
$45.00
BareTraps Men’s, Luca Boot, Surfer Blue 9 M BareTraps Men’s, Luca Boot, Surfer Blue 9 M
Free Shipping
Brand: Baretraps SKU: PSC-676536797
Men's Baretraps, Luca Boot. Feel good and look great with the Baretraps Luca men’s casual boot. The Rebound Technology insole provides extra comfort with a built-in arch support. With an upper made of mesh, this lightweight, flexible style is ready for everyday wear.Lightweight mesh fabric upper Bre..
$45.00
Bass & Co Outdoor Men’s Peak Hiker 2 Mid-Top Hiking Boot  Shoes, Dark Gray, 10 Bass & Co Outdoor Men’s Peak Hiker 2 Mid-Top Hiking Boot  Shoes, Dark Gray, 10
Free Shipping
Brand: Bass Outdoor SKU: PSB-548187896
The Peak Hiker 2 Mid-Top Hiking Boot by G.H. Bass & Co. is a new take on the Peak Hiker; just as comfortable, just as capable, and just as ready to hit the trail. It offers refreshed materials on the upper, BDRY+ waterproofing and BLevel for a natural stride.Round-toe lace-up hiking boot ..
$49.90
Bass & Co. Outdoor Mens Peak Hiker 2 Mid-Top Hiking Boot Shoes, Dark Beige, 10 Bass & Co. Outdoor Mens Peak Hiker 2 Mid-Top Hiking Boot Shoes, Dark Beige, 10
Free Shipping
Brand: Bass Outdoor SKU: PSB-1238756555
The Peak Hiker 2 Mid-Top Hiking Boot by G.H. Bass & Co. is a new take on the Peak Hiker; just as comfortable, just as capable, and just as ready to hit the trail. It offers refreshed materials on the upper, BDRY+ waterproofing and BLevel for a natural stride.Round-toe lace-up hiking boot ..
$49.90
Bass & Co. Outdoor Mens Peak Hiker 2 Mid-Top Hiking Boot Shoes, Dark Beige, 8 Bass & Co. Outdoor Mens Peak Hiker 2 Mid-Top Hiking Boot Shoes, Dark Beige, 8
Free Shipping
Brand: Bass Outdoor SKU: PSB-1408441020
The Peak Hiker 2 Mid-Top Hiking Boot by G.H. Bass & Co. is a new take on the Peak Hiker; just as comfortable, just as capable, and just as ready to hit the trail. It offers refreshed materials on the upper, BDRY+ waterproofing and BLevel for a natural stride.Round-toe lace-up hiking boot ..
$49.90
Bass & Co. Outdoor Mens Peak Hiker 2 Mid-Top Hiking Boot Shoes, Dark Beige, 9 Bass & Co. Outdoor Mens Peak Hiker 2 Mid-Top Hiking Boot Shoes, Dark Beige, 9
Free Shipping
Brand: Bass Outdoor SKU: PSB-1964048577
The Peak Hiker 2 Mid-Top Hiking Boot by G.H. Bass & Co. is a new take on the Peak Hiker; just as comfortable, just as capable, and just as ready to hit the trail. It offers refreshed materials on the upper, BDRY+ waterproofing and BLevel for a natural stride.Round-toe lace-up hiking boot ..
$49.90
Bass & Co. Outdoor Men’s Peak Hiker 2 Mid-Top Hiking Boot  Shoes, Dark Gray, 10.5 Bass & Co. Outdoor Men’s Peak Hiker 2 Mid-Top Hiking Boot  Shoes, Dark Gray, 10.5
Free Shipping
Brand: Bass Outdoor SKU: PSB-1487628598
The Peak Hiker 2 Mid-Top Hiking Boot by G.H. Bass & Co. is a new take on the Peak Hiker; just as comfortable, just as capable, and just as ready to hit the trail. It offers refreshed materials on the upper, BDRY+ waterproofing and BLevel for a natural stride.Round-toe lace-up hiking boot ..
$49.90
Bass & Co. Outdoor Men’s Peak Hiker 2 Mid-Top Hiking Boot  Shoes, Dark Gray, 8.5 Bass & Co. Outdoor Men’s Peak Hiker 2 Mid-Top Hiking Boot  Shoes, Dark Gray, 8.5
Free Shipping
Brand: Bass Outdoor SKU: PSB-1137106764
The Peak Hiker 2 Mid-Top Hiking Boot by G.H. Bass & Co. is a new take on the Peak Hiker; just as comfortable, just as capable, and just as ready to hit the trail. It offers refreshed materials on the upper, BDRY+ waterproofing and BLevel for a natural stride.Round-toe lace-up hiking boot ..
$49.90
Bass & Co. Outdoor Men’s Peak Hiker 2 Mid-Top Hiking Boot  Shoes, Dark Gray, 9 Bass & Co. Outdoor Men’s Peak Hiker 2 Mid-Top Hiking Boot  Shoes, Dark Gray, 9
Free Shipping
Brand: Bass Outdoor SKU: PSB-1674911882
The Peak Hiker 2 Mid-Top Hiking Boot by G.H. Bass & Co. is a new take on the Peak Hiker; just as comfortable, just as capable, and just as ready to hit the trail. It offers refreshed materials on the upper, BDRY+ waterproofing and BLevel for a natural stride.Round-toe lace-up hiking boot ..
$49.90
Bass & Co. Outdoor Men’s Peak Hiker 2 Mid-Top Hiking Boot  Shoes, Dark Gray, 9.5 Bass & Co. Outdoor Men’s Peak Hiker 2 Mid-Top Hiking Boot  Shoes, Dark Gray, 9.5
Free Shipping
Brand: Bass Outdoor SKU: PSB-156663353
The Peak Hiker 2 Mid-Top Hiking Boot by G.H. Bass & Co. is a new take on the Peak Hiker; just as comfortable, just as capable, and just as ready to hit the trail. It offers refreshed materials on the upper, BDRY+ waterproofing and BLevel for a natural stride.Round-toe lace-up hiking boot ..
$49.90
Bass Outdoor Mens G.h. Bass & Co.Peak Hiker 2 Mid-Top Hiking Boot Shoes, Dark Beige, 8.5 Bass Outdoor Mens G.h. Bass & Co.Peak Hiker 2 Mid-Top Hiking Boot Shoes, Dark Beige, 8.5
Free Shipping
Brand: Bass Outdoor SKU: PSB-1126606438
The Peak Hiker 2 Mid-Top Hiking Boot by G.H. Bass & Co. is a new take on the Peak Hiker; just as comfortable, just as capable, and just as ready to hit the trail. It offers refreshed materials on the upper, BDRY+ waterproofing and BLevel for a natural stride.Round-toe lace-up hiking boot Mi..
$59.90
Calvin Klein Men’s Ultan Suede Chukka Boots Calvin Klein Men’s Ultan Suede Chukka Boots
Free Shipping
Brand: Calvin Klein SKU: PSB-455226582
Calvin Klein presents a sophisticated take on a classic style with the rich suede upper of these lace-up Chukka boots.Plain toe Lace-up closure The Chukka Boot featured on The It List Suede upper; rubber/manmade sole Imported..
$74.15
Inc International Concepts Mens Camo Boots, White Camouflage 10.5 Inc International Concepts Mens Camo Boots, White Camouflage 10.5
Free Shipping
Brand: Inc International Concept SKU: PSB-386993913
INC International Concepts® offers a masculine, rugged look with the camo patterning of these handsome boots.Round-toe lace-up boots Metal eyelets; camo pattern; belt strap Durable rubber sole Polyester/polyurethane upper; polyester lining; rubber outsole..
$59.90
Inc International Concepts Mens Camo Boots, White Camouflage 12 Inc International Concepts Mens Camo Boots, White Camouflage 12
Free Shipping
Brand: Inc International Concept SKU: PSB-1130071426
INC International Concepts® offers a masculine, rugged look with the camo patterning of these handsome boots.Round-toe lace-up boots Metal eyelets; camo pattern; belt strap Durable rubber sole Polyester/polyurethane upper; polyester lining; rubber outsole..
$59.90
INC International Concepts Men’s Brix Kiltie Leather Boots INC International Concepts Men’s Brix Kiltie Leather Boots
Free Shipping
Brand: INC International Concepts SKU: PSB-923953782
Increase your cool-guy look with the Brix Kiltie leather boots from I.N.C. International Concepts, styled in leather and finished with a side-zip closure for easy access.Plain toe Lace-up closure with metal eyelets and side zip closure Leather upper; rubber sole Imported..
$47.18
INC International Concepts Men’s Darius Patch Chukka Boot INC International Concepts Men’s Darius Patch Chukka Boot
Free Shipping
Brand: INC International Concepts SKU: PSC-78530952
A classic chukka silhouette gets energized by I.N.C. International Concepts and the addition of an insect patch at the side of the suede upper.Plain toe Lace-up closure with hidden eyelets The Chukka Boot featured on The It List Suede upper; rubber sole Imported..
$54.18
INC International Concepts Men’s Ivan Lace-Up Boots INC International Concepts Men’s Ivan Lace-Up Boots
Free Shipping
Brand: INC International Concepts SKU: PSB-447101395
I.N.C. International Concepts introduces an industrial edge to your casual look with the Ivan leather boots, styled with an ankle-high silhouette and finished with a convenient zip-closure at the side.Plain toe Lace-up closure with metal eyelets and side zip closure Leather upper; rubber..
$64.18
INC International Concepts Men’s Salem Velvet Chukka Boots INC International Concepts Men’s Salem Velvet Chukka Boots
Free Shipping
Brand: INC International Concepts SKU: PSB-1762684875
Crushed velvet at the upper creates the rich look and feel of the Salem Chukkas from I.N.C. International Concepts, designed to add a dramatic streak to your dress-casual style.Plain toe Lace-up closure The Chukka Boot featured on The It List Velvet upper; rubber sole Imported..
$39.90
International Concepts Mens Camo Boots, Camouflage 10 International Concepts Mens Camo Boots, Camouflage 10
Free Shipping
Brand: Inc International Concept SKU: PSB-483399506
INC International Concepts® offers a masculine, rugged look with the camo patterning of these handsome boots.Round-toe lace-up boots Metal eyelets; camo pattern; belt strap Durable rubber sole Polyester/polyurethane upper; polyester lining; rubber outsole..
$59.90
Kenneth Cole Men’s Roll Boots Kenneth Cole Men’s Roll Boots
Free Shipping
Brand: Kenneth Cole SKU: PSB-1087518349
Quality and comfort, the Roll boot from Unlisted by Kenneth Cole offers both--along with solid durability and timeless style.Cap toe Lace-up closure with metal eyelets Manmade upper; rubber sole Imported..
$65.00
Kenneth Cole New York Rhode Suede Chukka Boot, Walnut, 10.5 Kenneth Cole New York Rhode Suede Chukka Boot, Walnut, 10.5
Free Shipping
Brand: Kenneth Cole New York SKU: PSC-1222305359
IT'S ALL IN THE DETAILS Experience comfort with our Rhode chukka boot in a smooth suede finish boosted with a cushioned insole and a lug sole for traction. This ankle-length style has a traditional chukka lace-up closure and a back pull tab for easy on-and-off. Men's chukka bootLace-up closure..
$55.00
Kenneth Cole New York Rhode Suede Chukka Boot, Walnut, 8 Kenneth Cole New York Rhode Suede Chukka Boot, Walnut, 8
Free Shipping
Brand: Kenneth Cole New York SKU: PSC-1726364785
IT'S ALL IN THE DETAILS Experience comfort with our Rhode chukka boot in a smooth suede finish boosted with a cushioned insole and a lug sole for traction. This ankle-length style has a traditional chukka lace-up closure and a back pull tab for easy on-and-off. Men's chukka bootLace-up closure..
$55.00
Kenneth Cole New York, Rhode Chukka Boot, Black, 11 Kenneth Cole New York, Rhode Chukka Boot, Black, 11
Free Shipping
Brand: Kenneth Cole SKU: PSC-200346511
Experience comfort with our Rhode chukka boot in a smooth suede finish boosted with a cushioned insole and a lug sole for traction. This ankle-length style has a traditional chukka lace-up closure and a back pull tab for easy on-and-off.Men's chukka boot Lace-up closure with back pull tab f..
$55.00
Kenneth Cole New York, Rhode Chukka Boot, Black, 8.5 Kenneth Cole New York, Rhode Chukka Boot, Black, 8.5
Free Shipping
Brand: Kenneth Cole SKU: PSC-1947880307
Experience comfort with our Rhode chukka boot in a smooth suede finish boosted with a cushioned insole and a lug sole for traction. This ankle-length style has a traditional chukka lace-up closure and a back pull tab for easy on-and-off.Men's chukka boot Lace-up closure with back pull tab f..
$55.00
Kenneth Cole New York, Rhode Chukka Boot,Black, 9 Kenneth Cole New York, Rhode Chukka Boot,Black, 9
Free Shipping
Brand: Kenneth Cole SKU: PSC-1607336025
Experience comfort with our Rhode chukka boot in a smooth suede finish boosted with a cushioned insole and a lug sole for traction. This ankle-length style has a traditional chukka lace-up closure and a back pull tab for easy on-and-off.Men's chukka boot Lace-up closure with back pull tab f..
$55.00
Kenneth Cole New York, Rhode Chukka Boot,Black,10 Kenneth Cole New York, Rhode Chukka Boot,Black,10
Free Shipping
Brand: Kenneth Cole SKU: PSC-203298983
Experience comfort with our Rhode chukka boot in a smooth suede finish boosted with a cushioned insole and a lug sole for traction. This ankle-length style has a traditional chukka lace-up closure and a back pull tab for easy on-and-off.Men's chukka boot Lace-up closure with back pull tab f..
$55.00
Kenneth Cole Reaction Men’s Desert Sun Perforated Chukka Boots (Blush, 10) Kenneth Cole Reaction Men’s Desert Sun Perforated Chukka Boots (Blush, 10)
Free Shipping
Brand: Kenneth Cole SKU: PSC-1174541825
Kenneth Cole Reaction pairs supple suede in a daring hue with perforation detailing to reinvent a classic chukka profile.Plain toe Lace-up closure with hidden eyelets Includes second pair of laces Suede upper; rubber sole Imported..
$62.72
Kenneth Cole Unlisted, Men’s Bainx Hiker Boots, Charcoal, 13M Kenneth Cole Unlisted, Men’s Bainx Hiker Boots, Charcoal, 13M
Free Shipping
Brand: Unlisted SKU: PSB-528862278
A practical short hiker boot with lots of character and comfortable details, ready for any weather.Shoe width-medium Lace up hiker boot Cushioned tongue and collar Speed loop hooks for quicker, more secure lacing Lug detailing through rubber outsole for added traction and grip T..
$59.90
Kenneth Cole, New York, Rhode Chukka Boot,Black, 10.5 Kenneth Cole, New York, Rhode Chukka Boot,Black, 10.5
Free Shipping
Brand: Kenneth Cole SKU: PSC-325572772
Experience comfort with our Rhode chukka boot in a smooth suede finish boosted with a cushioned insole and a lug sole for traction. This ankle-length style has a traditional chukka lace-up closure and a back pull tab for easy on-and-off.Men's chukka boot Lace-up closure with back pull tab f..
$55.00
Kenneth Cole, New York, Rhode Chukka Boot,Black,12 Kenneth Cole, New York, Rhode Chukka Boot,Black,12
Free Shipping
Brand: Kenneth Cole SKU: PSC-437527676
Experience comfort with our Rhode chukka boot in a smooth suede finish boosted with a cushioned insole and a lug sole for traction. This ankle-length style has a traditional chukka lace-up closure and a back pull tab for easy on-and-off.Men's chukka boot Lace-up closure with back pull tab f..
$55.00
Polo Ralph Lauren Men’s Army Boots, 9 D Polo Ralph Lauren Men’s Army Boots, 9 D
Free Shipping
Brand: Polo Ralph Lauren SKU: PSB-472197024
Lace-up boot with leather upper Cotton teill lining for comfortable wear Heel pull tabs with Polo logo embroidery Leather laces Rubber outsole for durability and traction The Polo Ralph Lauren Army Boot is imported. Designed for adventure and stylish enough for any occasion, the Men's Polo Ralph Lau..
$129.90
Polo Ralph Lauren Men’s Army Boots, 9.5 D (M) Polo Ralph Lauren Men’s Army Boots, 9.5 D (M)
Free Shipping
Brand: Polo Ralph Lauren SKU: PSC-1471457968
 Lace-up boot with leather upper Cotton teill lining for comfortable wear Heel pull tabs with Polo logo embroidery Leather laces Rubber outsole for durability and traction The Polo Ralph Lauren Army Boot is imported. Designed for adventure and stylish enough for any occasion, the Men's Polo Ralph La..
$129.90
Polo Ralph Lauren Men’s Claus Boot (Rob Royal, 8) Polo Ralph Lauren Men’s Claus Boot (Rob Royal, 8)
Free Shipping
Brand: Polo Ralph Lauren SKU: PSB-530517982
If you love the vintage look, then you'll love the stylish Polo Ralph Lauren Claus Lace-Up boots designed for utmost comfort. Leather and rubber upper. Leather and textile lining. Leather and textile insole.Lace-up closure with metal eyelets. Brand shield embossed on the shaft. Round toe..
$129.90
Tommy Hilfiger Men’s Gainer Suede Chelsea Boots (Tan) Tommy Hilfiger Men’s Gainer Suede Chelsea Boots (Tan)
Free Shipping
Brand: Tommy Hilfiger SKU: PSB-939476240
Contrasting gore at the smooth suede upper creates the distinctly modern style of these comfortable pull-on Chelsea boots from Tommy Hilfiger.Plain toe Slip-on style Suede upper; manmade sole Imported..
$79.90
Showing 1 to 48 of 52 (2 Pages)