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Shop Groupon Solo Men's Side-Zip Carlos Boots (Sizes 9 & 11)
ALMOST GONE
Solo Men's Side-Zip Carlos Boots (Sizes 9 & 11)
(106)
$64.99
Shop Groupon London Fog Men's Canvas Chukka Boots
London Fog Men's Canvas Chukka Boots
750+ bought
$59.99 $29.97
(315)
Sale Ends 5/21
Shop Groupon Rocawear Amboy Men's Boots
Rocawear Amboy Men's Boots
580+ bought
$49.99 $22.97
(91)
Sale Ends 5/21
Shop Groupon Rocawear Men's Canton Boots
Rocawear Men's Canton Boots
120+ bought
$59.99 $21.97
(3)
Sale Ends 5/21
Shop Groupon Harrison Chelsea Boots w/ Functional Brass Zipper(8.5, 11, 12, 13)
Harrison Chelsea Boots w/ Functional Brass Zipper(8.5, 11, 12, 13)
70+ bought
(138)
$36.99
Shop Groupon Reserved Men's Leather Safford Mid-Top Boot (Sizes  9.5 & 13)
Reserved Men's Leather Safford Mid-Top Boot (Sizes 9.5 & 13)
10+ bought
(4)
$199 $49.97
Shop Groupon Joseph Abboud Men's Daniel Chelsea Style Boots
Joseph Abboud Men's Daniel Chelsea Style Boots
160+ bought
$150 $27.97
(12)
Sale Ends 5/21
Shop Groupon Jach's Men's Cooper Casual Chelsea Boots
Jach's Men's Cooper Casual Chelsea Boots
560+ bought
$75 $16.97
(69)
Sale Ends 5/21
Shop Groupon Kenneth Cole Unlisted Men's Leather Boots
Kenneth Cole Unlisted Men's Leather Boots
1,000+ bought
$95 $19.97
(213)
Sale Ends 5/21
Shop Groupon Harrison Men's Boots. Multiple Styles Available. (Size 8)
Harrison Men's Boots. Multiple Styles Available. (Size 8)
10+ bought
(40)
$20.99
Shop Groupon Jach's Men's Oscar Leather and Flannel Cap Toe Boot (8, 9, 9.5)
Jach's Men's Oscar Leather and Flannel Cap Toe Boot (8, 9, 9.5)
440+ bought
$160 $29.97
(61)
Sale Ends 5/21
Shop Groupon Henry Ferrera Men's Pull-On Zipper Ankle Boots
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Henry Ferrera Men's Pull-On Zipper Ankle Boots
480+ bought
(94)
$26.99
Shop Groupon UNIONBAY Men's Casual Leather Ankle Boots (Size 13)
UNIONBAY Men's Casual Leather Ankle Boots (Size 13)
670+ bought
(47)
$129.99 $24.99
Shop Groupon Harrison Men's Casual Desert Boots in Medium Width
Harrison Men's Casual Desert Boots in Medium Width
260+ bought
(203)
$89 $29.99
Shop Groupon Vincent Cavallo Men's Lace-up Combat Boots (Sizes 11 & 12)
Vincent Cavallo Men's Lace-up Combat Boots (Sizes 11 & 12)
9 bought
(41)
$100 $29.97
Shop Groupon Jach's Men's Leather Welted Sneaker Boots
Jach's Men's Leather Welted Sneaker Boots
180+ bought
$160 $24.97
(36)
Sale Ends 5/21
Shop Groupon Hawke & Co Men's Kalahari Chukka Boot
Hawke & Co Men's Kalahari Chukka Boot
450+ bought
$110 $19.97
(59)
Sale Ends 5/21
Shop Groupon Rocawear Men's Lincoln Boots
Rocawear Men's Lincoln Boots
50+ bought
$49.99 $21.97
(10)
Sale Ends 5/21
Shop Groupon Miko Lotti Men's Chukka and Chelsea Boots (Sizes 7.5, 9.5, 11, 13)
Miko Lotti Men's Chukka and Chelsea Boots (Sizes 7.5, 9.5, 11, 13)
10+ bought
(29)
$29.97
Shop Groupon Jachs Men's Dylan Leather and Canvas Boots
Jachs Men's Dylan Leather and Canvas Boots
40+ bought
$160 $24.97
(8)
Sale Ends 5/21
Shop Groupon Vincent Cavallo Men's Cap-Toe Combat Boots with Side Zipper (Size 10)
Vincent Cavallo Men's Cap-Toe Combat Boots with Side Zipper (Size 10)
7 bought
(7)
$29.99
Shop Groupon Vincent Cavallo Men's Monk Strap Dress Boots (Sizes 9 & 12)
Vincent Cavallo Men's Monk Strap Dress Boots (Sizes 9 & 12)
120+ bought
(85)
$120 $35.99
Shop Groupon Harrison Men's Moc-Toe or Round-Toe Boots (Sizes 10 & 11)
Harrison Men's Moc-Toe or Round-Toe Boots (Sizes 10 & 11)
80+ bought
(205)
$24.99
Shop Groupon Harrison Men's Casual Combat Boots (Sizes 9, 12, 13)
Harrison Men's Casual Combat Boots (Sizes 9, 12, 13)
30+ bought
(21)
$89 $24.97
Shop Groupon Harrison Men's Casual Boots
Harrison Men's Casual Boots
(86)
$24.99
Shop Groupon Reserved Footwear Men's Hawser Chukka Dress Boots (Size 11)
Reserved Footwear Men's Hawser Chukka Dress Boots (Size 11)
6 bought
(4)
$99.99 $34.99
Shop Groupon Marco Vitale Men's Fashion Two-Tone Boots
Marco Vitale Men's Fashion Two-Tone Boots
(21)
$109.99 $34.99

Top Product Reviews

Joseph Abboud Lucca Men's Chukka Boots

Mitchell
Verified Purchaser
May 15, 2019
I have tried other shoes off here and hated them. They were cheaply made so I got what I paid for, not these. They actually look good. Feel good and while not a shoe that I would rave about but for the price a very good shoes.

Rocawear Amboy Men's Boots

Josh
Verified Purchaser
May 17, 2019
These boots seem very well made, nice look as well! I suggest going 1/2 size down from what your regular shoe size is. I bought the navy and am saving them until winter, but couldn't pass up the price

Harrison Chelsea Boots w/ Functional Brass Zipper(8.5, 11, 12, 13)

Angela
Verified Purchaser
February 6, 2019
The books arrive on time and my son likes them. They fit true to size but a little stiff initially as new boots can be.

Kenneth Cole Unlisted Men's Leather Boots

Alex
Verified Purchaser
May 17, 2019
Nice design and comfortable. The finishing is not up to standards, that’s why it deserves a 4 star considering the cost.

Harrison Men's Casual Desert Boots in Medium Width

Robert
Verified Purchaser
February 22, 2019
The boots look great. They are narrow around the toes. Since there is minimal heel support, it takes getting used to when walking. I've worn them twice and they seem comfortable and true to size. Time will tell as to how they wear. Good price.

Shop Men’s Boots Every Day on Groupon

A good pair of men's boots is equally functional and fashionable. If you're looking for a pair of casual shoes with a bit more insulation than a traditional pair of sneakers, grab a pair of chukkas. Facing a rainstorm? Keep your feet dry in a pair of rubber boots. When winter is coming, it's crucial to get a pair of well-insulated winter boots before the first snow of the year—especially ones that go with your cold-weather outfits. When you search Groupon's inventory, you'll find there are men's boots to suit every occasion.

Jazz Up Your Wardrobe

The right pair of men's boots can make the difference between a good outfit and a great one. For casual outfits, try wearing a pair of chukkas or desert boots from Groupon's exclusive Oak & Rush line with your favorite pair of jeans to create a sophisticated and laid-back look. Timberland boots are equally stylish, but are typically more durable and weather-resistant, making them a better option for wet or snowy weather. Stumped on which color to choose? Brown boots are versatile enough to be worn with either jeans or khakis.

Keep Your Feet Warm and Safe

Many types of men's boots are designed specifically to keep you comfortable under the toughest conditions. For example, durable, insulated work boots are designed to provide comfort and support for folks who spend the day on their feet, such as construction workers or painters. Steel-toe shoes provide an extra bit of protection from falling objects or other hazards. If it starts to rain, opt for a pair of rubber boots—and when that rain freezes, keep your feet warm with a pair of men's snow boots (and be sure to care for them properly so they last as long as possible). If you're headed to a formal event during the winter, opt for a pair of men's dress boots to stay stay comfortable without sacrificing style points.