Skip to content

SALE
NEW ARRIVALS
MENS
- Footwear
- - Boots
  - Winter Boots
  - Work Boots
  - Casual Shoes
  - Dress Shoes
  - Sandals
  - Slippers
  - Sneakers
- Apparel
- - Outerwear
  - Pants
  - Tops
  - Workwear
  - Accessories
- Workwear
- - Work Boots
  - Outerwear
  - Pants
  - Tops
- Featured Brands
- - Brooks
  - Carhartt
  - Helly Hansen
  - Hoka
  - Timberland
  - The North Face
WOMENS
- Footwear
- - Boots
  - Work Boots
  - Winter Boots
  - Casual Shoes
  - Dress Shoes
  - Slippers
  - Sneakers
  - Sandals
- Apparel
- - Outerwear
  - Pants
  - Tops
  - Workwear
  - Accessories
- Workwear
- - Work Boots
  - Outerwear
  - Pants
  - Tops
- Featured Brands
- - Brooks
  - Helly Hansen
  - Hoka
  - Taos
  - The North Face
  - Trotters
WORKWEAR
- Mens Workwear
- - Work Boots
  - Outerwear
  - Pants
  - Tops
- Womens Workwear
- - Work Boots
  - Outerwear
  - Pants
  - Tops
KIDS
- Footwear
- - Boots
  - Winter Boots
  - Shoes
  - Sneakers
  - Slippers
- Apparel
- - Outerwear
  - Tops
  - Pants
  - Accessories
- Book A Fitting Appointment
- Featured Brands
BRANDS
IN-STORE SPECIALS
Log In/Create Account

Search

FREE US SHIPPING on all orders over $125

Keep in touch & Get exclusive updates - Subscribe Here

SALE
NEW ARRIVALS
MENS
WOMENS
WORKWEAR
KIDS
BRANDS
IN-STORE SPECIALS

Home › Mens Work Boots

Mens Work Boots

Mens Work Boots

91 products

Sort by

Featured
Most relevant
Best selling
Alphabetically, A-Z
Alphabetically, Z-A
Price, low to high
Price, high to low
Date, old to new
Date, new to old

Gender

Mens (91)

Product type

BOOTS (91)

Size

5 (5)
5.5 (7)
6 (20)
6.5 (22)
7 (73)
07 (1)
7.5 (73)
8 (87)
8.5 (85)
9 (86)
9.5 (86)
10 (89)
10.5 (85)
11 (88)
11.5 (80)
12 (88)
12.5 (1)
13 (81)
14 (40)
15 (13)
16 (3)
105 (1)

Color

Beige(2)
Black(19)
Brown(65)
Gray(2)
Tan(10)

Brand

ARIAT BOOTS (20)
BRUNT (13)
CARHARTT BOOTS (8)
CAROLINA SHOE CO. (5)
CATAPILLAR BOOTS (8)
CHIPPEWA SHOE CO. (4)
MERRELL (1)
REDWING SHOE CO. (13)
TIMBERLAND (5)
TIMBERLAND PRO (14)

Price

From $

To $

The Sullivan Waterproof (Soft Toe) Work Boot

The Sullivan Waterproof (Soft Toe) Work Boot

BRUNT The Sullivan Waterproof (Soft Toe) Work Boot

Regular Price: $149.99

Sale Price: $149.99
Regular Price: ~~$149.99~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

The Marin BRUNT Toe Waterproof (Comp Toe) Work Boot

The Marin BRUNT Toe Waterproof (Comp Toe) Work Boot

BRUNT The Marin BRUNT Toe Waterproof (Comp Toe) Work Boot

Regular Price: $184.99

Sale Price: $184.99
Regular Price: ~~$184.99~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

The Marin Waterproof (Comp Toe) Work Boot

The Marin Waterproof (Comp Toe) Work Boot

BRUNT The Marin Waterproof (Comp Toe) Work Boot

Regular Price: $164.99

Sale Price: $164.99
Regular Price: ~~$164.99~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

The Marin 6” Waterproof (Soft Toe) Work Boot - Brown

The Marin 6” Waterproof (Soft Toe) Work Boot - Brown

BRUNT The Marin 6” Waterproof (Soft Toe) Work Boot - Brown

Regular Price: $154.99

Sale Price: $154.99
Regular Price: ~~$154.99~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Save 13%

Wingshooter 7" Waterproof Wedge Boot

Wingshooter 7" Waterproof Wedge Boot

REDWING SHOE CO. Wingshooter 7" Waterproof Wedge Boot

Regular Price: $199.99

Sale Price: $199.99
Regular Price: ~~$229.99~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Boondock Ultralight 8" Composite Toe Waterproof Insulated Work Boot

Boondock Ultralight 8" Composite Toe Waterproof Insulated Work Boot

TIMBERLAND PRO Boondock Ultralight 8" Composite Toe Waterproof Insulated Work Boot

Regular Price: $199.95

Sale Price: $199.95
Regular Price: ~~$199.95~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Mt. Maddsen Mid Waterproof Hiking Boot - Dark Brown

Mt. Maddsen Mid Waterproof Hiking Boot - Dark Brown

TIMBERLAND Mt. Maddsen Mid Waterproof Hiking Boot - Dark Brown

Regular Price: $129.95

Sale Price: $129.95
Regular Price: ~~$129.95~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Save 0%

Redwood Falls Waterproof Boot

Redwood Falls Waterproof Boot

TIMBERLAND Redwood Falls Waterproof Boot

Regular Price: $144.99

Sale Price: $144.99
Regular Price: ~~$145.00~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Timberland Classic 6" Waterproof Boot

Timberland Classic 6" Waterproof Boot

TIMBERLAND Timberland Classic 6" Waterproof Boot

Regular Price: $179.95

Sale Price: $179.95
Regular Price: ~~$179.95~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Save 11%

Power Shift Slip-Resistant Work Sneaker

Power Shift Slip-Resistant Work Sneaker

TIMBERLAND PRO Power Shift Slip-Resistant Work Sneaker

Regular Price: $79.99

Sale Price: $79.99
Regular Price: ~~$90.00~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Save 6%

Direct Attach 6" Soft Toe Waterproof Work Boot

Direct Attach 6" Soft Toe Waterproof Work Boot

TIMBERLAND PRO Direct Attach 6" Soft Toe Waterproof Work Boot

Regular Price: $154.95

Sale Price: $154.95
Regular Price: ~~$165.00~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Wedge 6" Moc-Toe Work Boot

Wedge 6" Moc-Toe Work Boot

TIMBERLAND PRO Wedge 6" Moc-Toe Work Boot

Regular Price: $125.00

Sale Price: $125.00
Regular Price: ~~$124.99~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Redwood Falls Waterproof Moc-Toe Boot

Redwood Falls Waterproof Moc-Toe Boot

TIMBERLAND Redwood Falls Waterproof Moc-Toe Boot

Regular Price: $160.00

Sale Price: $160.00
Regular Price: ~~$160.00~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Save 6%

Direct Attach 8" Steel Toe Waterproof Work Boot

Direct Attach 8" Steel Toe Waterproof Work Boot

TIMBERLAND PRO Direct Attach 8" Steel Toe Waterproof Work Boot

Regular Price: $164.99

Sale Price: $164.99
Regular Price: ~~$175.00~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Save 6%

Direct Attach 6" Waterproof Insulated Steel-Toe Work Boot

Direct Attach 6" Waterproof Insulated Steel-Toe Work Boot

TIMBERLAND PRO Direct Attach 6" Waterproof Insulated Steel-Toe Work Boot

Regular Price: $159.95

Sale Price: $159.95
Regular Price: ~~$169.95~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Save 7%

TiTAN™ Casual Alloy Toe Oxford Work Shoe

TiTAN™ Casual Alloy Toe Oxford Work Shoe

TIMBERLAND PRO TiTAN™ Casual Alloy Toe Oxford Work Shoe

Regular Price: $139.99

Sale Price: $139.99
Regular Price: ~~$150.00~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Save 9%

Direct Attach 6" Soft Toe Waterproof Work Boot - Brown

Direct Attach 6" Soft Toe Waterproof Work Boot - Brown

TIMBERLAND PRO Direct Attach 6" Soft Toe Waterproof Work Boot - Brown

Regular Price: $160.00

Sale Price: $160.00
Regular Price: ~~$175.00~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Save 11%

Direct Attach 6" Waterproof Insulated Steel-Toe Work Boot

Direct Attach 6" Waterproof Insulated Steel-Toe Work Boot

TIMBERLAND PRO Direct Attach 6" Waterproof Insulated Steel-Toe Work Boot

Regular Price: $164.99

Sale Price: $164.99
Regular Price: ~~$185.00~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Save 9%

Direct Attach 6" Soft Toe Waterproof Work Boot - Black

Direct Attach 6" Soft Toe Waterproof Work Boot - Black

TIMBERLAND PRO Direct Attach 6" Soft Toe Waterproof Work Boot - Black

Regular Price: $160.00

Sale Price: $160.00
Regular Price: ~~$175.00~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Timberland Classic 6" Waterproof Boot

Timberland Classic 6" Waterproof Boot

TIMBERLAND Timberland Classic 6" Waterproof Boot

Regular Price: $179.95

Sale Price: $179.95
Regular Price: ~~$179.95~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Save 9%

Boondock 6" Composite Toe Waterproof Work Boot

Boondock 6" Composite Toe Waterproof Work Boot

TIMBERLAND PRO Boondock 6" Composite Toe Waterproof Work Boot

Regular Price: $204.99

Sale Price: $204.99
Regular Price: ~~$225.00~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Save 7%

TiTAN™ Casual Soft Toe Oxford Work Shoe

TiTAN™ Casual Soft Toe Oxford Work Shoe

TIMBERLAND PRO TiTAN™ Casual Soft Toe Oxford Work Shoe

Regular Price: $134.99

Sale Price: $134.99
Regular Price: ~~$145.00~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Save 6%

Direct Attach 8" Waterproof Work Boot

Direct Attach 8" Waterproof Work Boot

TIMBERLAND PRO Direct Attach 8" Waterproof Work Boot

Regular Price: $164.99

Sale Price: $164.99
Regular Price: ~~$175.00~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

SOLD OUT

Waterproof 8-Inch Moc Toe Wedge Boot

Waterproof 8-Inch Moc Toe Wedge Boot

CARHARTT BOOTS Waterproof 8-Inch Moc Toe Wedge Boot

Regular Price: $189.99

Sale Price: $189.99
Regular Price: ~~$189.99~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Chelsea Wedge Boot

Chelsea Wedge Boot

CARHARTT BOOTS Chelsea Wedge Boot

Regular Price: $149.99

Sale Price: $149.99
Regular Price: ~~$149.99~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

6" Steel Toe Wedge Boot

CARHARTT BOOTS 6" Steel Toe Wedge Boot

Regular Price: $174.99

Sale Price: $174.99
Regular Price: ~~$174.99~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Waterproof 6" Moc Toe Wedge Boot

Waterproof 6" Moc Toe Wedge Boot

CARHARTT BOOTS Waterproof 6" Moc Toe Wedge Boot

Regular Price: $169.99

Sale Price: $169.99
Regular Price: ~~$169.99~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Waterproof 6" Moc Toe Wedge Boot

Waterproof 6" Moc Toe Wedge Boot

CARHARTT BOOTS Waterproof 6" Moc Toe Wedge Boot

Regular Price: $169.99

Sale Price: $169.99
Regular Price: ~~$169.99~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Rugged Flex Waterproof Insulated 8" Soft Toe Work Boot

Rugged Flex Waterproof Insulated 8" Soft Toe Work Boot

CARHARTT BOOTS Rugged Flex Waterproof Insulated 8" Soft Toe Work Boot

Regular Price: $179.99

Sale Price: $179.99
Regular Price: ~~$179.99~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Rugged Flex Waterproof 6" Soft Toe Work Boot

Rugged Flex Waterproof 6" Soft Toe Work Boot

CARHARTT BOOTS Rugged Flex Waterproof 6" Soft Toe Work Boot

Regular Price: $164.99

Sale Price: $164.99
Regular Price: ~~$164.99~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

Cart Error Some items became unavailable. Update the quantity and try again.

Showing items 61-90 of 91.

1 2 3 4

More Information

About
Get in Touch
Size Guide
Search

Policies

Returns & Refunds
Shipping
Terms of Service
Privacy

Contact

Shoppennyworths.com
Pennyworths Inc
136 Boston Street
Lynn, MA 01904

Call us: (781) 595-6710
Email: info@shoppennyworths.com

Keep in touch & Get exclusive updates

Join our mailing list

Enter Email Address

Copyright © 2026 Pennyworth's

Search

Cart

0 Item(s)

or

Join our mailing list

For updates on products and new releases

Enter Email Address

*By completing this form you're signing up to receive our emails and can unsubscribe at any time.