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Deal.ai › Cole Haan › Chukka Boots
Cole Haan
Men's Roundhill Grand Waterproof Chukka Boots
Cole Haan

Men's Roundhill Grand Waterproof Chukka Boots

Best price now

$259.95at ZapposChecked 49 min ago

Compared across 2 stores. Prices are checked against each store and labelled with when. Store links may earn us a commission. Price via Klarna.

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Price facts

  • Lowest price today: $259.95 at Zappos (checked Nov 10, 2026).
  • Checked at 2 stores.

Our take on the Men's Roundhill Grand Waterproof Chukka Boots

The Cole Haan Roundhill Grand is a waterproof leather chukka boot with a rubber outsole and textile lining, built for wet-weather wear that still looks smart. Its Grand.OS-style cushioned footbed and lightweight construction make it more comfortable for all-day walking than traditional leather chukkas, which tend to be stiffer and heavier. Reviewers generally like the clean silhouette and the waterproofing, though some find the leather stiff at first and the fit runs narrow. It suits commuters, travelers and anyone who wants a dress-casual boot that handles rain.

Best forWet-weather commutingBusiness casual and smart-casual outfitsTravel and all-day walkingFall and winter wear
Pros
  • Waterproof leather upper keeps feet dry in rain
  • Cushioned footbed is comfortable for long days
  • Lightweight for a leather boot
  • Clean chukka shape works with jeans or trousers
  • Rubber outsole grips wet pavement
Cons
  • Leather can feel stiff out of the box
  • Fit runs narrow for some wearers
  • Textile lining limits breathability in warm weather
  • Not built for deep snow or heavy trail use

Men's Roundhill Grand Waterproof Chukka Boots prices at every store

  • ZapposNew

    In stock

    $259.95Free shippingChecked 49 min ago
    Visit Zappos
  • Cole HaanNew

    In stock

    $260.00Free shippingChecked 49 min ago
    Visit Cole Haan

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

Men's Roundhill Grand Waterproof Chukka Boots price history

Lowest price we've seen: $259.95 on Nov 10 at Zappos. Tracked across 2 stores since Nov 10.

What reviewers say

Owners generally praise the Roundhill Grand as a comfortable, genuinely waterproof chukka that looks dressier than a rain boot. Complaints center on a narrow fit and stiff leather that needs breaking in.

What people mention
  • WaterproofingPraisedOwners say feet stay dry through rain and wet sidewalks.
  • ComfortPraisedThe cushioned footbed and light weight suit long days on foot.
  • FitCriticisedSeveral buyers find the boot narrow and suggest sizing up or trying before buying.
  • Break-inMixedThe leather softens over time but feels stiff for the first few wears.
  • BreathabilityCriticisedThe textile lining traps heat, so the boot runs warm in mild weather.

Specifications

Size (US)
10.5Source
Fastening
LacedSource
Color
BrownSource
Outsole
RubberSource
Age Group

Questions and answers

Are the Roundhill Grand boots fully waterproof?
Yes. The leather upper is treated for waterproofing and the construction is sealed, so rain and shallow puddles are fine. They are not designed for standing in deep water or heavy snow.
How does the fit compare to other Cole Haan shoes?
The boot runs narrow, closer to a dress shoe than a sneaker. If you are between sizes or have wide feet, size up or look for a wide option.
Do they need breaking in?
Expect a short break-in period. The leather starts stiff around the ankle and flex point, then softens after several wears.
Can I wear them with a suit?
They work with smart-casual and business-casual outfits. The chukka shape is too casual for a formal suit.
What is the outsole made of?
A rubber outsole with a low-profile tread. It grips wet pavement well but is not a lugged hiking sole.
Are they good for winter?
For wet cold weather, yes. For ice, slush or deep snow, a boot with a heavier lug sole and insulation is the better choice.
Where is the Men's Roundhill Grand Waterproof Chukka Boots cheapest?
At Zappos, for $259.95, as of our latest check.
Where can I buy the Men's Roundhill Grand Waterproof Chukka Boots?
2 stores we checked sell it, including Zappos, Cole Haan.

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Buying guides that pick the Men's Roundhill Grand Waterproof Chukka Boots

  • Best men's waterproof boots for everyday wear

Stores we've priced the Men's Roundhill Grand Waterproof Chukka Boots at

  • Zappos.com deals and prices

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Adult
Source
Lining
TextileSource
Gender
MaleSource
Upper Material
LeatherSource