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 Footwear

Mens Footwear

Boots

Work Boots

Winter Boots

Casual Shoes

Dress Shoes

Sandals

Slippers

Sneakers

Mens Footwear

149 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 (148)
Womens (11)

Product type

ATHLETIC (21)
BOOTS (112)
CASUAL (8)
INNERSOLES (2)
SANDALS (3)
SLIPPERS (3)

Size

Color

Beige(7)
Black(49)
Blue(3)
Brown(82)
Cream(2)
Gray(14)
Green(2)
Silver(1)
Tan(11)
White(1)

Brand

ARIAT BOOTS (17)
BIRKENSTOCK (8)
BOGS (4)
BROOKS (3)
BRUNT (12)
CARHARTT BOOTS (8)
CAROLINA SHOE CO. (5)
CATAPILLAR BOOTS (8)
CHIPPEWA SHOE CO. (5)
HOKA (5)
KAMIK (3)
MERRELL (13)
NEW BALANCE (7)
OBOZ (2)
REDWING SHOE CO. (13)
SAS (2)
SKECHERS (5)
TIMBERLAND (11)
TIMBERLAND PRO (14)
UGG (4)

Price

From $

To $

Super DNA 8" Waterproof Insulated Work Boot

Super DNA 8" Waterproof Insulated Work Boot

CHIPPEWA SHOE CO. Super DNA 8" Waterproof Insulated Work Boot

Regular Price: $284.95

Sale Price: $284.95
Regular Price: ~~$284.95~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

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

Super DNA 9" Waterproof Steel Toe Insulated Logger Work Boot - Black

Super DNA 9" Waterproof Steel Toe Insulated Logger Work Boot - Black

CHIPPEWA SHOE CO. Super DNA 9" Waterproof Steel Toe Insulated Logger Work Boot - Black

Regular Price: $319.95

Sale Price: $319.95
Regular Price: ~~$319.95~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

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

Super DNA 9" Waterproof Steel Toe Insulated Logger Work Boot - Brown

Super DNA 9" Waterproof Steel Toe Insulated Logger Work Boot - Brown

CHIPPEWA SHOE CO. Super DNA 9" Waterproof Steel Toe Insulated Logger Work Boot - Brown

Regular Price: $319.95

Sale Price: $319.95
Regular Price: ~~$319.95~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

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

Super DNA 8" Waterproof Steel Toe Insulated

Super DNA 8" Waterproof Steel Toe Insulated

CHIPPEWA SHOE CO. Super DNA 8" Waterproof Steel Toe Insulated

Regular Price: $294.95

Sale Price: $294.95
Regular Price: ~~$294.95~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

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

Save 31%

Excavator Superlite Waterproof Carbon Comp Toe Boot

Excavator Superlite Waterproof Carbon Comp Toe Boot

CATAPILLAR BOOTS Excavator Superlite Waterproof Carbon Comp Toe Boot

Regular Price: $119.99

Sale Price: $119.99
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.

Save 32%

Excavator Superlite Waterproof Work Boot

Excavator Superlite Waterproof Work Boot

CATAPILLAR BOOTS Excavator Superlite Waterproof Work Boot

Regular Price: $114.99

Sale Price: $114.99
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.

Elm 8" Steel Toe Waterproof Logger

Elm 8" Steel Toe Waterproof Logger

CAROLINA SHOE CO. Elm 8" Steel Toe Waterproof Logger

Regular Price: $199.99

Sale Price: $199.99
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.

Elm 8" Waterproof Logger

Elm 8" Waterproof Logger

CAROLINA SHOE CO. Elm 8" Waterproof Logger

Regular Price: $194.99

Sale Price: $194.99
Regular Price: ~~$194.99~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

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

Journeyman 8" Soft Toe Insulated Waterproof Work Boot

Journeyman 8" Soft Toe Insulated Waterproof Work Boot

CAROLINA SHOE CO. Journeyman 8" Soft Toe Insulated Waterproof 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.

Engineer 6" Soft Toe Waterproof Work Boot

Engineer 6" Soft Toe Waterproof Work Boot

CAROLINA SHOE CO. Engineer 6" Soft Toe Waterproof Work Boot

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.

Outpace Composite Toe Work Shoe

Outpace Composite Toe Work Shoe

ARIAT BOOTS Outpace Composite Toe Work Shoe

Regular Price: $124.95

Sale Price: $124.95
Regular Price: ~~$124.95~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

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

Treadfast 6" Waterproof Work Boot

Treadfast 6" Waterproof Work Boot

ARIAT BOOTS Treadfast 6" Waterproof Work Boot

Regular Price: $124.95

Sale Price: $124.95
Regular Price: ~~$124.95~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

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

Treadfast 6" Waterproof Steel Toe Work Boot

Treadfast 6" Waterproof Steel Toe Work Boot

ARIAT BOOTS Treadfast 6" Waterproof Steel Toe Work Boot

Regular Price: $134.95

Sale Price: $134.95
Regular Price: ~~$134.95~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

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

Turbo 6" Waterproof Work Boot

Turbo 6" Waterproof Work Boot

ARIAT BOOTS Turbo 6" Waterproof Work Boot

Regular Price: $164.95

Sale Price: $164.95
Regular Price: ~~$164.95~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

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

Endeavor 6" Waterproof Work Boot

Endeavor 6" Waterproof Work Boot

ARIAT BOOTS Endeavor 6" Waterproof Work Boot

Regular Price: $189.95

Sale Price: $189.95
Regular Price: ~~$189.95~~

Unit Price: per

Added to Cart View Cart or Continue Shopping.

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

Turbo 6" Waterproof Carbon Toe Work Boot

Turbo 6" Waterproof Carbon Toe Work Boot

ARIAT BOOTS Turbo 6" Waterproof Carbon Toe Work Boot

Regular Price: $174.95

Sale Price: $174.95
Regular Price: ~~$174.95~~

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 Clifton 10 (1162030)

Men's Clifton 10 (1162030)

HOKA Men's Clifton 10 (1162030)

Regular Price: $155.00

Sale Price: $155.00
Regular Price: ~~$155.00~~

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 - Black

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

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

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.

The Marin 8" Waterproof (Soft Toe) Work Boot

The Marin 8" Waterproof (Soft Toe) Work Boot

BRUNT The Marin 8" Waterproof (Soft 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 Ohman 6” (Soft Toe) Work Boot

The Ohman 6” (Soft Toe) Work Boot

BRUNT The Ohman 6” (Soft Toe) Work Boot

Regular Price: $144.99

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

Unit Price: per

Added to Cart View Cart or Continue Shopping.

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

The 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.

Men's Minimel (1177035)

Men's Minimel (1177035)

UGG Men's Minimel (1177035)

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 Tasman II Nubuck (1175070)

Men's Tasman II Nubuck (1175070)

UGG Men's Tasman II Nubuck (1175070)

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 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.

Boston Suede Soft Footbed Clog - Regular Width

Boston Suede Soft Footbed Clog - Regular Width

BIRKENSTOCK Boston Suede Soft Footbed Clog - Regular Width

Regular Price: $169.95

Sale Price: $169.95
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.

Men's Ascot (1101110)

Men's Ascot (1101110)

UGG Men's Ascot (1101110)

Regular Price: $115.00

Sale Price: $115.00
Regular Price: ~~$115.00~~

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.

Showing items 61-90 of 149.

1 2 3 4 5

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.