StoreDeal.ai store
Shop
  • Deals
  • Deal checker
  • Black Friday
  • Buying guides
  • Brands
  • Stores
Travel
  • Flight deals
  • Hotel deals
Company
  • Research
  • Press
  • deal.ai apps
Black Friday 2026
  • Walmart
  • Best Buy
  • Target
  • TVs
  • Laptops
  • Headphones
  • Apple
  • Gaming
  • Vacuums
  • Kitchen
  • Toys
  • Smartwatches
  • Tablets
  • Furniture
  • Mattresses
© Deal.ai Inc.
TermsPrivacy
Deal.ai › Dockers
Dockers
Dockers Men's Derrick Rugged Chukka Boot

Dockers Men's Derrick Rugged Chukka Boot

Best price now

$47.50at Macy'sChecked 4 h ago

21% under what the other stores charge

Compared across 10 stores. Prices are checked against each store and labelled with when.

Visit Macy's

Ask our agent about this product

It checks today's price at every store, compares the alternatives and answers in about a minute.

Enter to send, Shift+Enter for a new line

Price facts

  • Last seen at $47.50 at Macy's on Nov 10.
  • Checked at 10 stores.

Our take on the Dockers Men's Derrick Rugged Chukka Boot

The Dockers Derrick is a men's chukka boot built for casual wear with a rugged look. It pairs a synthetic upper with a cushioned EVA footbed and a thick rubber outsole for traction. The moc-toe shape and breathable, moisture-wicking lining keep it comfortable for all-day wear. It sits at the affordable end of the chukka market, so it trades leather uppers and stitched construction for lighter weight and a lower entry point than leather boots from Clarks or Timberland.

Best forCasual everyday wearMen who want a rugged look without leather upkeepLong days on your feetBudget-minded shoppers
Pros
  • Cushioned EVA footbed with massaging texture
  • Thick rubber outsole with traction
  • Breathable, moisture-wicking lining
  • Lightweight synthetic upper needs little care
  • Moc-toe chukka styling suits jeans and chinos
Cons
  • Synthetic upper will not age or patina like leather
  • Less durable than stitched leather chukkas
  • Massaging footbed texture is not for everyone
  • Limited support for heavy work use despite the rugged label

Dockers Men's Derrick Rugged Chukka Boot prices at every store

  • Macy'sNew

    In stock

    $47.50Checked 4 h ago
    Visit Macy's
  • Shoe StationNew

    In stock

    $49.98Checked 4 h ago
    Visit Shoe Station
  • Zappos.comNew

    In stock

    $57.00Checked 4 h ago
    Visit Zappos.com
  • ShopSimonNew

    In stock

    $59.99Checked 4 h ago
    Visit ShopSimon
  • Shoe CarnivalNew

    In stock

    $75.99Checked 4 h ago
    Visit Shoe Carnival
  • TargetNew

    Availability unknown

    $59.85Checked 4 h ago
    Visit Target
  • Nordstrom RackNew

    Availability unknown

    $59.97Checked 4 h ago
    Visit Nordstrom Rack
  • Famous FootwearNew

    Availability unknown

    $69.99Checked 4 h ago
    Visit Famous Footwear
  • DSWNew

    Availability unknown

    $69.99Checked 4 h ago
    Visit DSW
  • Kohl'sNew

    Availability unknown

    $80.75Checked 4 h ago
    Visit Kohl's

Dockers Men's Derrick Rugged Chukka Boot price history

Lowest price we've seen: $47.50 on Nov 11 at Macy's. Tracked across 10 stores since Nov 11.

What reviewers say

Owner feedback is limited, but the boot is generally described as comfortable out of the box and easy to wear casually. Complaints center on the synthetic upper feeling less sturdy than leather.

What people mention
  • ComfortPraisedOwners say the cushioned footbed is comfortable for standing and walking through the day.
  • BuildCriticisedSome note the synthetic upper feels less substantial than leather chukkas.
  • TractionPraisedThe thick rubber outsole is described as grippy on pavement and light trails.
  • Break-inPraisedReviewers report little to no break-in period.

About the Dockers Men's Derrick Rugged Chukka Boot

The Dockers Derrick is a men's chukka boot with a rugged design and a moc toe. It has a synthetic upper and a lace-up closure, and it is made for casual wear.

The boot has a thick rubber outsole with traction. The EVA footbed is cushioned and massaging, and it gives underfoot support through the day. A sock lining is breathable and wicks moisture.

Style
Chukka boot, rugged design
Upper
Synthetic
Closure
Lace-up
Toe
Moc toe
Outsole
Thick rubber outsole with traction
Footbed
EVA, cushioned, massaging
Lining
Sock lining, breathable, moisture-wicking
Occasion
Casual
Department
Men's

Specifications

Gender
Men's
Material
Synthetic (upper), EVA (footbed), Rubber (outsole)
Boot Style
Chukka Boot
Type
Boots
Closure Style
Lace-up
Occasion
Casual
Sole Material
Rubber, EVA
Sole Style

Questions and answers

Is the Dockers Derrick a real leather boot?
No. The upper is synthetic, so it will not develop a leather patina. It is lighter and easier to wipe clean than leather.
Can I wear these for work?
They suit light casual work and standing jobs. The cushioned footbed helps, but there is no steel toe or heavy-duty support.
How does it fit?
Most buyers find it true to size with a roomy moc-toe. If you wear thick socks or have wide feet, consider going up half a size.
Are they waterproof?
No. The synthetic upper and breathable lining resist light splashes but are not waterproof.
How do they compare with leather chukkas like Clarks Desert Boot?
The Derrick is lighter and needs less care, but leather boots last longer and mold to the foot. Choose the Derrick for casual comfort, leather for longevity.
What is the sole made of?
A thick rubber outsole over an EVA midsole, with a cushioned EVA footbed inside.
Where is the Dockers Men's Derrick Rugged Chukka Boot cheapest?
At Macy's, for $47.50, 21% under what the other stores charge, as of our latest check.
Where can I buy the Dockers Men's Derrick Rugged Chukka Boot?
10 stores we checked sell it, including Macy's, Shoe Station, Zappos.com, Target, Nordstrom Rack.

Stores we've priced the Dockers Men's Derrick Rugged Chukka Boot at

  • Famous Footwear deals and prices
  • Kohl's deals and prices
  • Macy's deals and prices
  • Nordstrom Rack deals and prices
  • Shoe Station deals and prices
  • ShopSimon deals and prices
  • Target deals and prices
  • Zappos.com deals and prices

More from Dockers

  • D
    Dockers Royce Rugged Casual Boot
    Dockers Royce Rugged Casual Boot
  • D
    Dockers Benton Men's Oxford
    Dockers Benton Men's Oxford
  • D
    Dockers Men's Fairborne Oxford
    Dockers Men's Fairborne Oxford
  • D
    Dockers Men's Cooper
    Dockers Men's Cooper
  • D
    Dockers Mens Carlton Chukka Boot
    Dockers Mens Carlton Chukka Boot
  • D
    Dockers Frederick Casual Sneaker
    Dockers Frederick Casual Sneaker
  • D
    Dockers Benton Oxford
    Dockers Benton Oxford
  • D
    Dockers Fairborne Men's Oxford
    Dockers Fairborne Men's Oxford
All Dockers deals and products →

More men's boots

  • X
    Xtratuf Legacy Leather Chelsea Boot
    Xtratuf Legacy Leather Chelsea Boot
  • L
    Lugz Men's Bedrock Hi
    Lugz Men's Bedrock Hi
  • C
    Chris Boot
    Chris Boot
  • D
    Dr. Martens 1460 Women's Boots
    Dr. Martens 1460 Women's Boots
  • T
    Timberland Men's 8" Premium Waterproof
    Timberland Men's 8" Premium Waterproof
  • S
    Sorel Men's Ankeny II Mid
    Sorel Men's Ankeny II Mid
  • D
    Dr. Martens Men's 1460 SR
    Dr. Martens Men's 1460 SR
  • F
    Forsake Halden Mid Men's Shoes
    Forsake Halden Mid Men's Shoes
Thick sole
Traction Features
Traction
Department
Men's
Outsole Material
Rubber
Outsole Style
Thick outsole
Outsole Support
Traction
Insole Support Type
Underfoot support
Insole Features
Daylong underfoot support, Cushioned
Footbed Features
Massaging
Lining Material
Sock lining
Lining Type
Moisture-wicking, Breathable
Toe Style
Moc-toe
Breathable
Yes
Moisture Wicking
Yes
Design Style
Rugged