Mens Boots at at Pennyworth's

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
- Newburyport
- Lynn
Log In/Create Account

Search

FREE US SHIPPING on all orders over $125

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

Home › Mens Boots

Mens Boots

Mens Boots

60 products

Sort by

Featured
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
Clear all

Gender

Mens (57)
Womens (0)

Product type

BOOTS (60)

Size

Color

Beige(2)
Black(16)
Blue(0)
Brown(31)
Gray(6)
Green(4)
Tan(6)

Brand

BIRKENSTOCK (0)
BOGS (7)
CARHARTT BOOTS (1)
COLUMBIA SPORTSWEAR (2)
FLORSHEIM (0)
KAMIK (6)
MERRELL (6)
OBOZ (5)
OLUKAI (0)
SOREL (5)
THE NORTH FACE (2)
TIMBERLAND (9)
TIMBERLAND PRO (16)
UGG (1)

Price

From $

To $

Save 17%

Men's Bugaboot III Boot - 2024 model

Men's Bugaboot III Boot - 2024 model

COLUMBIA SPORTSWEAR Men's Bugaboot III Boot - 2024 model

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.

6 IN Boondock Ultralight CT WP (TB0A63FY)

6 IN Boondock Ultralight CT WP (TB0A63FY)

TIMBERLAND PRO 6 IN Boondock Ultralight CT WP (TB0A63FY)

Regular Price: $199.99

Sale Price: $199.99
Regular Price: ~~$0.00~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

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

8 Boondock Ultralight CT WP INS 400G (TB0A646F)

8 Boondock Ultralight CT WP INS 400G (TB0A646F)

TIMBERLAND PRO 8 Boondock Ultralight CT WP INS 400G (TB0A646F)

Regular Price: $209.99

Sale Price: $209.99
Regular Price: ~~$0.00~~

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 Buxton Lace-Up Boot (1760181)

Men's Buxton Lace-Up Boot (1760181)

SOREL Men's Buxton Lace-Up Boot (1760181)

Regular Price: $150.00

Sale Price: $150.00
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 25%

Men's Buxton Pull-On Boot (1760171)

Men's Buxton Pull-On Boot (1760171)

SOREL Men's Buxton Pull-On Boot (1760171)

Regular Price: $111.99

Sale Price: $111.99
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.

Sauvie Basin II (73109)

Sauvie Basin II (73109)

BOGS Sauvie Basin II (73109)

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.

Men's Mt. Maddsen Waterproof Hiking Boot (TB12730R)

Men's Mt. Maddsen Waterproof Hiking Boot (TB12730R)

TIMBERLAND Men's Mt. Maddsen Waterproof Hiking Boot (TB12730R)

Regular Price: $120.00

Sale Price: $120.00
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 Redwood Falls Chelsea Boot (TB0A288FF13)

Men's Redwood Falls Chelsea Boot (TB0A288FF13)

TIMBERLAND Men's Redwood Falls Chelsea Boot (TB0A288FF13)

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 17%

Men's Mt. Maddsen Mid (A64TV231)

Men's Mt. Maddsen Mid (A64TV231)

TIMBERLAND Men's Mt. Maddsen Mid (A64TV231)

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.

Save 0%

Men's Redwood Falls WP Boot (TB1A44MYF13)

Men's Redwood Falls WP Boot (TB1A44MYF13)

TIMBERLAND Men's Redwood Falls WP Boot (TB1A44MYF13)

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.

Men's 6in Classic Boot (19039)

Men's 6in Classic Boot (19039)

TIMBERLAND Men's 6in Classic Boot (19039)

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.

Men's Caribou Waterproof Boot (1002871)

Men's Caribou Waterproof Boot (1002871)

SOREL Men's Caribou Waterproof Boot (1002871)

Regular Price: $225.00

Sale Price: $225.00
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 34%

Men's Buxton Lite Lace Waterproof Boot (2047401)

Men's Buxton Lite Lace Waterproof Boot (2047401)

SOREL Men's Buxton Lite Lace Waterproof Boot (2047401)

Regular Price: $94.99

Sale Price: $94.99
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 20%

Men's 1964 Pac Nylon Waterproof Boot (1855191)

Men's 1964 Pac Nylon Waterproof Boot (1855191)

SOREL Men's 1964 Pac Nylon Waterproof Boot (1855191)

Regular Price: $144.00

Sale Price: $144.00
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.

Men's Firecamp Boot (2099741)

Men's Firecamp Boot (2099741)

COLUMBIA SPORTSWEAR Men's Firecamp Boot (2099741)

Regular Price: $100.00

Sale Price: $100.00
Regular Price: ~~$100.00~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

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

Save 17%

Men's MOAB 2 Mid Ventilator in Walnut (J06045)

Men's MOAB 2 Mid Ventilator in Walnut (J06045)

MERRELL Men's MOAB 2 Mid Ventilator in Walnut (J06045)

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: ~~$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 Waterproof

Men's Moab 3 Mid Waterproof

MERRELL Men's Moab 3 Mid Waterproof

Regular Price: $170.00

Sale Price: $170.00
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.

Men's Moab 3 Mid GORE-TEX

Men's Moab 3 Mid GORE-TEX

MERRELL Men's Moab 3 Mid GORE-TEX

Regular Price: $190.00

Sale Price: $190.00
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.

Mens Moab 3

Mens Moab 3

MERRELL Mens Moab 3

Regular Price: $140.00

Sale Price: $140.00
Regular Price: ~~$139.99~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

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

Mens Moab 3 Mid

Mens Moab 3 Mid

MERRELL Mens Moab 3 Mid

Regular Price: $150.00

Sale Price: $150.00
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.

Men's Gritstone 6" Soft Toe Work Boot (TB0A1WG2)

Men's Gritstone 6" Soft Toe Work Boot (TB0A1WG2)

TIMBERLAND PRO Men's Gritstone 6" Soft Toe Work Boot (TB0A1WG2)

Regular Price: $109.99

Sale Price: $109.99
Regular Price: ~~$109.99~~

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 Direct Attach 6" Soft Toe Waterproof Work Boot (TB065030)

Men's Direct Attach 6" Soft Toe Waterproof Work Boot (TB065030)

TIMBERLAND PRO Men's Direct Attach 6" Soft Toe Waterproof Work Boot (TB065030)

Regular Price: $159.99

Sale Price: $159.99
Regular Price: ~~$159.99~~

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 Wedge 6" Moc-Toe Work Boot (TB153009)

Men's Wedge 6" Moc-Toe Work Boot (TB153009)

TIMBERLAND PRO Men's Wedge 6" Moc-Toe Work Boot (TB153009)

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 Classic Ultra Mini (1137391)

Men's Classic Ultra Mini (1137391)

UGG Men's Classic Ultra Mini (1137391)

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.

SALE

Digger Slip On (72667)

Digger Slip On (72667)

BOGS Digger Slip On (72667)

Regular Price: $60.00

Sale Price: $60.00
Regular Price: ~~$75.00~~

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 Bergen Leather Waterproof Boots (NF0A8A9M)

Men's Bergen Leather Waterproof Boots (NF0A8A9M)

THE NORTH FACE Men's Bergen Leather Waterproof Boots (NF0A8A9M)

Regular Price: $159.00

Sale Price: $159.00
Regular Price: ~~$159.00~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

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

Alborg Tan Snow Boot

Alborg Tan Snow Boot

KAMIK Alborg Tan Snow Boot

Regular Price: $119.99

Sale Price: $119.99
Regular Price: ~~$0.00~~

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 Chilkat V Lace WP (NF0A5LW3)

Men's Chilkat V Lace WP (NF0A5LW3)

THE NORTH FACE Men's Chilkat V Lace WP (NF0A5LW3)

Regular Price: $135.00

Sale Price: $135.00
Regular Price: ~~$135.00~~

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%

Essential Insulated Tall (73031)

Essential Insulated Tall (73031)

BOGS Essential Insulated Tall (73031)

Regular Price: $80.00

Sale Price: $80.00
Regular Price: ~~$100.00~~

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 1-30 of 60.

1 2

More Information

About
Get in Touch
Size Guide
Fitting Appointments
Search

Policies

Returns & Refunds
Shipping
Terms of Service
Privacy

Contact

Shoppennyworths.com
Pennyworths Inc
45 Storey Avenue
Newburyport, MA 01950

Call us: (978) 462-2711
Email: info@shoppennyworths.com

Copyright © 2025 Pennyworth's

Search

Cart

0 Item(s)

or

One or more of the items in your cart is a recurring or deferred purchase. By continuing, I agree to the cancellation policy and authorize you to charge my payment method at the prices, frequency and dates listed on this page until my order is fulfilled or I cancel, if permitted.

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.