Mens Boots at at Pennyworth's – Page 2

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 Boots

Mens Boots

Mens Boots

51 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

14
Clear all

Gender

Mens (51)

Product type

BOOTS (51)

Size

4 (1)
5 (7)
5.5 (7)
6 (23)
6.5 (22)
7 (96)
07 (1)
7.5 (90)
8 (110)
8.5 (103)
9 (109)
9.5 (104)
10 (112)
10.5 (102)
11 (113)
11.5 (98)
12 (112)
12.5 (2)
13 (105)
14 (51)
15 (17)
16 (3)
105 (1)

Color

Beige(1)
Black(11)
Brown(33)
Gray(2)
Green(1)
Tan(7)
Yellow(1)

Brand

ARIAT BOOTS (5)
BOGS (1)
BRUNT (8)
CARHARTT BOOTS (5)
CAROLINA SHOE CO. (0)
CATAPILLAR BOOTS (0)
CHIPPEWA SHOE CO. (4)
KAMIK (1)
MERRELL (6)
OBOZ (0)
REDWING SHOE CO. (6)
TIMBERLAND (5)
TIMBERLAND PRO (10)

Price

From $

To $

Men's Moab 3

Men's Moab 3

MERRELL Men's Moab 3

Regular Price: $140.00

Sale Price: $140.00
Regular Price: ~~$140.00~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

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

Men's Moab 3 Mid

Men's Moab 3 Mid

MERRELL Men's Moab 3 Mid

Regular Price: $140.00

Sale Price: $140.00
Regular Price: ~~$140.00~~

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.

Essential Insulated Tall

Essential Insulated Tall

BOGS Essential Insulated Tall

Regular Price: $110.00

Sale Price: $110.00
Regular Price: ~~$110.00~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

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

Forester Khaki Winter Boot

Forester Khaki Winter Boot

KAMIK Forester Khaki Winter Boot

Regular Price: $74.99

Sale Price: $74.99
Regular Price: ~~$74.99~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

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

Save 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 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.

Mt. Maddsen Mid Waterproof Mid Hiking Boot - Black

Mt. Maddsen Mid Waterproof Mid Hiking Boot - Black

TIMBERLAND Mt. Maddsen Mid Waterproof Mid Hiking Boot - Black

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 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.

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.

Save 6%

Ground Force Waterproof 6" Composite Toe Work Boot

Ground Force Waterproof 6" Composite Toe Work Boot

CARHARTT BOOTS Ground Force Waterproof 6" Composite Toe Work Boot

Regular Price: $169.99

Sale Price: $169.99
Regular Price: ~~$180.00~~

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 31-51 of 51.

1 2

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.