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 › Timberland › Hiking Shoes
Timberland
Timberland Men's Mt. Maddsen Slip On

Timberland Men's Mt. Maddsen Slip On

Best price now

$99.99at DSWObserved at 6:13 AM

Compared across 8 stores. Prices are checked against each store and labelled with when. Store links may earn us a commission. Price via Klarna.

Visit DSW

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

  • Lowest price today: $99.99 at DSW (checked Nov 9, 2026).
  • Checked at 8 stores.

Our take on the Timberland Men's Mt. Maddsen Slip On

The Timberland Mt. Maddsen Slip-On is a men's low hiking shoe with a leather and fabric upper, a waterproof membrane, and an EVA midsole under a rubber lug outsole. The slip-on design with elastic goring skips laces, which makes it quicker to put on than the laced Mt. Maddsen hikers in the same line. It suits casual walkers, campers and travel use more than technical trail work, since the EVA midsole is soft and the upper gives little ankle support. Owners like the easy on-off and the weatherproofing; the common complaints are a stiff break-in and a fit that runs narrow for wide feet.

Best forCasual day hikes and flat trailsCampers and travelers who want quick on-offWet-weather errands and dog walksShoppers who dislike laces
Pros
  • Waterproof leather and fabric upper keeps feet dry in rain and puddles
  • Slip-on construction with elastic goring goes on fast
  • Rubber lug outsole grips dirt and gravel well
  • EVA midsole and insole cushion underfoot
  • Recycled fabric lining
Cons
  • No laces means no fine-tuning of fit or heel lockdown
  • Stiff leather needs a break-in period
  • Little ankle support for rough or steep terrain
  • Runs narrow; wide-footed buyers often size up

Timberland Men's Mt. Maddsen Slip On prices at every store

  • DSWNew

    In stock

    $99.99+ $7.95 shippingObserved at 6:13 AM
    Visit DSW
  • Famous FootwearNew

    In stock

    $99.99+ $9.95 shippingObserved at 6:13 AM
    Visit Famous Footwear
  • ShoebaccaNew

    In stock

    $109.95Free shippingObserved at 6:13 AM
    Visit Shoebacca
  • Academy SportsNew

    In stock

    $109.99Free shippingObserved at 6:13 AM
    Visit Academy Sports
  • Champs SportsNew

    In stock

    $110.00Free shippingObserved at 6:13 AM
    Visit Champs Sports
  • Foot LockerNew

    In stock

    $110.00Free shippingObserved at 6:13 AM
    Visit Foot Locker
  • NordstromNew

    In stock

    $110.00Free shippingObserved at 6:13 AM
    Visit Nordstrom
  • Dick's Sporting GoodsNew

    In stock

    $109.99+ $9.99 shippingObserved at 6:13 AM
    Visit Dick's Sporting Goods

Store links may earn us a commission. Some prices via Klarna.

Timberland Men's Mt. Maddsen Slip On price history

Lowest price we've seen: $99.99 on Nov 9 at Famous Footwear. Tracked across 8 stores since Nov 9.

What reviewers say

Owners of the Mt. Maddsen Slip-On generally like the convenience and the waterproofing, and many wear them as everyday shoes as much as for light hiking. The recurring complaints are a stiff first few wears and a narrow fit, and some find the slip-on hold looser than a laced shoe on uneven ground.

What people mention
  • FitCriticisedSeveral owners say the shoe runs narrow and recommend sizing up, especially for wide feet.
  • Break-inCriticisedThe leather upper feels stiff for the first several wears before it softens.
  • WaterproofingPraisedBuyers report dry feet through rain, wet grass and shallow puddles.
  • ConveniencePraisedThe slip-on design with elastic goring is the main reason people buy and keep them.
  • Heel holdMixedWithout laces, some wearers notice the heel moving on uneven ground.
  • ComfortPraisedThe EVA midsole and insole are described as comfortable for long walks and standing.

Specifications

Gore-Tex
NoSource
Manufacturer Color
-Source
Color
BrownSource
Outsole
RubberSource
Gender

Questions and answers

Is the Mt. Maddsen Slip-On actually waterproof?
Yes. It has a waterproof membrane plus a leather and fabric upper, so it handles rain, wet grass and puddles. It is not a Gore-Tex model, and standing in deep water can still soak through.
How does it compare with the laced Mt. Maddsen?
Same cushioned EVA midsole and rubber outsole family, but the slip-on trades laces for elastic goring. You gain speed and lose the ability to tighten the fit, so the laced version is better for steep or rough trails.
Should I size up?
If you have wide feet or wear thick socks, going up a half size is common. The shoe runs narrow, and there are no laces to loosen the fit.
Can I hike in these or are they just casual shoes?
They work for easy day hikes, flat trails and camp wear. The soft EVA midsole and low slip-on upper give little ankle support, so skip them for steep, rocky or long backcountry routes.
What is the upper made of?
Leather and fabric, with a recycled fabric lining and an EVA insole. The rubber outsole has lugs for traction on dirt and gravel.
Do they need a break-in period?
Yes. The leather starts stiff, and most owners report a few days to a couple of weeks of wear before the upper softens and molds to the foot.
Where is the Timberland Men's Mt. Maddsen Slip On cheapest?
At DSW, for $99.99, as of our latest check.
Where can I buy the Timberland Men's Mt. Maddsen Slip On?
8 stores we checked sell it, including Famous Footwear, DSW, Shoebacca, Academy Sports, Dick's Sporting Goods.

Stores we've priced the Timberland Men's Mt. Maddsen Slip On at

  • dickssportinggoods.com deals and prices
  • Famous Footwear deals and prices
  • Foot Locker deals and prices
  • nordstrom.com deals and prices

More from Timberland

  • T
    Timberland Men's Redwood Edge Mid Lace Up Boot
    Timberland Men's Redwood Edge Mid Lace Up Boot
  • T
    Timberland Men's Motion Scramble Mid Waterproof Hiking Boots
    Timberland Men's Motion Scramble Mid Waterproof Hiking Boots
  • T
    Timberland Men's 8" Premium Waterproof
    Timberland Men's 8" Premium Waterproof
  • T
    Timberland Toddler 6 Premium
    Timberland Toddler 6 Premium
  • T
    Timberland Women's Ellendale Mid Chelsea Boot
    Timberland Women's Ellendale Mid Chelsea Boot
  • T
    Timberland PRO Women's Reaxion Composite Toe Boot
    Timberland PRO Women's Reaxion Composite Toe Boot
  • T
    Timberland Men's Euro Trekker Mid
    Timberland Men's Euro Trekker Mid
  • T
    Timberland Women's Courmayeur Valley Shearling
    Timberland Women's Courmayeur Valley Shearling
All Timberland deals and products →

More men's boots

  • N
    NRS Boundary Boots
    NRS Boundary Boots
  • 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
  • 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
  • W
    Wolverine Men's 1000 Mile Legacy Plain Toe Boot
    Wolverine Men's 1000 Mile Legacy Plain Toe Boot
MaleSource
Insole
EVASource
Fastening
Slip-OnSource
Age Group
AdultSource
Lining
Recycled FabricSource
Upper Material
Leather, FabricSource
Midsole
EVASource