Mens Boots at at Pennyworth's – Page 3

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

90 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

7.5
Clear all

Gender

Mens (90)

Product type

BOOTS (90)

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(2)
Black(19)
Brown(63)
Gray(6)
Green(1)
Tan(7)
Yellow(1)

Brand

ARIAT BOOTS (17)
BOGS (0)
BRUNT (12)
CARHARTT BOOTS (1)
CAROLINA SHOE CO. (3)
CATAPILLAR BOOTS (7)
CHIPPEWA SHOE CO. (0)
KAMIK (0)
MERRELL (11)
OBOZ (2)
REDWING SHOE CO. (13)
TIMBERLAND (10)
TIMBERLAND PRO (14)

Price

From $

To $

Save 10%

Boondock Ultralight 6" Composite Toe Waterproof Work Boot

Boondock Ultralight 6" Composite Toe Waterproof Work Boot

TIMBERLAND PRO Boondock Ultralight 6" Composite Toe Waterproof Work Boot

Regular Price: $179.95

Sale Price: $179.95
Regular Price: ~~$199.99~~

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.

Redwood Falls Chelsea Boot

Redwood Falls Chelsea Boot

TIMBERLAND Redwood Falls Chelsea Boot

Regular Price: $129.99

Sale Price: $129.99
Regular Price: ~~$129.99~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

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

Save 15%

Mt. Maddsen Mid Waterproof Hiking Boot - Wheat

Mt. Maddsen Mid Waterproof Hiking Boot - Wheat

TIMBERLAND Mt. Maddsen Mid Waterproof Hiking Boot - Wheat

Regular Price: $109.95

Sale Price: $109.95
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 17%

Men's MOAB 2 Mid Ventilator in Walnut

Men's MOAB 2 Mid Ventilator in Walnut

MERRELL Men's MOAB 2 Mid Ventilator in Walnut

Regular Price: $99.99

Sale Price: $99.99
Regular Price: ~~$120.00~~

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 Waterproof

Men's Moab 3 Waterproof

MERRELL Men's Moab 3 Waterproof

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.

Men's Moab 3 Mid Waterproof

Men's Moab 3 Mid Waterproof

MERRELL Men's Moab 3 Mid Waterproof

Regular Price: $170.00

Sale Price: $170.00
Regular Price: ~~$170.00~~

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

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.

Men's Sawtooth X Low B-DRY Shoes (23501)

Men's Sawtooth X Low B-DRY Shoes (23501)

OBOZ Men's Sawtooth X Low B-DRY Shoes (23501)

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 20%

Men's Bridger Low B-DRY Shoes

Men's Bridger Low B-DRY Shoes

OBOZ Men's Bridger Low B-DRY Shoes

Regular Price: $128.00

Sale Price: $128.00
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.

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.

Euro Sprint Jet Black

Euro Sprint Jet Black

TIMBERLAND Euro Sprint Jet Black

Regular Price: $130.00

Sale Price: $130.00
Regular Price: ~~$130.00~~

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.

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.

Showing items 61-90 of 90.

1 2 3

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.