Bennett waterproof hiking boots worn outdoors in snow, front view
Bennett waterproof hiking boots worn on model, studio front view
Close-up of Bennett hiking boot lace-up detail and mesh panel
Bennett waterproof hiking boots worn on model, side view in motion
Bennett waterproof hiking boots in alternate colorway, front view
Bennett waterproof hiking boots in green colorway, side view
Bennett waterproof hiking boots worn outdoors in snow, front view
Bennett waterproof hiking boots worn on model, studio front view
Close-up of Bennett hiking boot lace-up detail and mesh panel
Bennett waterproof hiking boots worn on model, side view in motion
Bennett waterproof hiking boots in alternate colorway, front view
Bennett waterproof hiking boots in green colorway, side view
4.7 from 2800+ reviews

Bennett | Men's Waterproof Mid-Top Hiking Boots

$79.95
/
Color
Size
Low Stock due to our fall sale
  • Free shipping on every order
  • Not right? Return within 30 days
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Fall Sale — Mix & Match

The more you add, the more you save

2 items 10%
3 items 15%
4 items 20%
5+ items 25%

Mix any styles, colors and sizes. Applied automatically at checkout.

Meet Bennett, the boot built for mornings when the trail is frosted over and the sidewalk is slick. Bennett slips on with a snug lace-up fit and settles into a daily rhythm of dog walks, commutes, and weekend hikes without missing a beat. Its structured silhouette gives your ankle steady support while the flexible build lets your stride move naturally. Whether it's a quick errand in the cold or a longer trek through snow, Bennett stays dependable step after step.

Why You Will Love It

  • Waterproof upper keeps feet dry through snow, slush, and wet pavement
  • Plush inner lining locks in warmth even in freezing temperatures
  • Deep-lugged rubber outsole delivers reliable traction on ice and snow
  • Surprisingly lightweight and flexible build for all-day wear

Tech Specs and Care

  • Design: Mid-top lace-up hiking boot with a durable synthetic upper, reinforced toe cap, and reflective detailing for a bold outdoor look
  • Fit: True to size with a regular fit; refer to the Size Chart for exact measurements
  • Season: Built for fall and winter conditions, ideal for snow, rain, and cold-weather adventures
  • Care: Wipe clean with a damp cloth and air dry; avoid machine washing

Not the perfect fit? No worries! You can return your order within 30 days of delivery. To ensure a smooth process, please reach out to us at info@winston-newyork.com for instructions.

We offer Free Shipping on all orders within the United States.

Our team is ready to assist you during our customer service hours:

  • Monday to Friday | Opening hours: 8:00 AM – 6:00 PM Eastern Time (ET)
  • Weekends | Opening hours: 08:00 AM - 05:00 PM Eastern Time (ET)

Read more on our contact us page.

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Stock Up for the Cold Months

FALL SALE

Warm jackets, solid knitwear and easy everyday pieces built to last the season. A comfortable fit, made for how you actually live.

  • Buy 2 items — save 10%
  • Buy 3 items — save 15%
  • Buy 4 items — save 20%
  • Buy 5+ items — save 25%

Mix and match any styles, colors and sizes. Your savings are applied automatically at checkout.

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Tried, tested, approved

Straight talk from real customers about fit, comfort and quality.

4.7 Based on 2800+ reviews
5 stars78%
4 stars15%
3 stars4%
2 stars2%
1 star1%
Frank D., Rochester, New York
★★★★★

"Shovelled the walk and stayed warm"

“I am 60 and I am the one who clears the walk, so my boots have to work. These came this morning and I had them on ten minutes later, straight out into six inches of snow. Feet stayed dry, stayed warm, and the tread gripped on the icy step where I usually slip. They slip on and off without bending down, which my back appreciates. The fleece lining is a nice touch you feel immediately. I cleared the whole drive and did not once think about my feet. That is the whole point.”

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Marcus T., Savannah, Georgia
★★★★★

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“I am 61 and I have worn dress shirts for forty years, so I know when one is cut properly. This is. The navy is deep and true, the collar holds its shape without a stiff stay, and the fabric breathes even at an outdoor party in September. I wore it untucked with grey trousers and it looked intentional rather than sloppy. No gaping at the buttons, no riding up when I raise my arms. Washed it twice, still sharp, no fading. My wife said I looked like the version of myself from twenty years ago. I will take that.”

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Elena V., Tucson, Arizona
★★★★★

"Lovely cardigan, sizing ran a touch large for me"

“I am 57 and I bought this cardigan for the colour more than anything, that soft dusty pink. The knit is genuinely lovely, light enough for a warm afternoon but still warm enough for a cool morning, and it works over a white tee with jeans exactly as I hoped. My only note is sizing. I ordered my usual medium and it hung a bit loose through the body, so I would go down a size next time. Not a fault in the cardigan itself, just worth knowing. I wore it to the nursery and got two compliments before I reached the car.”

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Gerald P., Minneapolis, Minnesota
★★★★★

"My feet have never been happier"

“I am 63 and I put off buying winter boots every year because they are always heavy and ugly. These are neither. The lining is soft and warm, the sole has real grip, and they pull on fast, which matters when the dog needs out and it is ten degrees. I put them on to try them and ended up with my feet on the ottoman reading the paper, coffee beside me, in no hurry to take them off. That is a first. True to size. The blue is a nice change from black.”

Gerald P., Minneapolis, Minnesota✓ Verified buyer
Walter S., Ely, Minnesotad
★★★★★

"My winter uniform, honestly"

“I am 69 and I have a leather chair, a fireplace and a short window of daylight. This sweater suits all three. The red is warm and rich without being loud, the wool is soft rather than scratchy, and the turtleneck actually stays up instead of collapsing. I wore it with grey flannels and slippers and read half a book without adjusting it once. It is warm enough that I turned the thermostat down, which my wife noticed. She has now ordered one for herself. Good sign, that.”

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"Perfect for a day in the orchard"

“I am 58 and I wanted something I could throw over a t-shirt for apple picking without looking like I had tried. This grey cord shirt is exactly that. Soft, warm enough for a cool October morning, and it did not wrinkle when I was reaching into trees all afternoon. The pockets are useful and the fit is relaxed without being shapeless. I wore it with jeans and a tote of apples and felt completely at ease. Washed well, still soft. My son has already asked to borrow it, which tells me everything.”

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Raymond H., Bozeman, Montana
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"Warm, tough, and it looks good too"

“I am 66 and I live where the mornings start below freezing and end mild. This shirt jacket handles both. The wool blend is warm without weight, the flannel lining inside is genuinely soft, and the corduroy cuffs hold their edge. I wore it out to the fence line with coffee in hand and never felt the wind. It is a proper layer, not a costume. Beanies, boots, and this thing, and I am set until real winter. The fit is generous in the shoulders, which I need. Worth it.”

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4.7/5 from 2800+ reviews

4.7/5 from 2800+ reviews

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