Boot season isn't just about staying warm, it's about having the right pair for whatever the day throws at you. This collection covers rugged waterproof hikers, work-ready pull-ons, and clean Chelsea boots that go from the trail to the office without missing a step.
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Utility Men's San Jose 6" Waterproof Cascade Brown/Black
Regular price $189.95Regular priceUnit price perSale price $189.95 -
Men's York M2M-8156C1 Olmo
Regular price $239.95Regular priceUnit price perSale price $239.95 -
2250 Antique Brown
Regular price $284.95Regular priceUnit price perSale price $284.95 -
587 Rustic Black
Regular price $219.95Regular priceUnit price perSale price $219.95 -
585 Rustic Brown
Regular price $219.95Regular priceUnit price perSale price $219.95 -
500 Stout Brown
Regular price $209.95Regular priceUnit price perSale price $209.95 -
2130 Auburn
Regular price $224.95Regular priceUnit price perSale price $224.95 -
1609 Antique Brown
Regular price $229.95Regular priceUnit price perSale price $229.95 -
Men's Targhee II Mid Wide Waterproof Shitake/Brindle
Regular price $169.95Regular priceUnit price perSale price $169.95Sold out -
Men's Durand II Mid WP Cascade Brown/Gargoyle
Regular price $219.95Regular priceUnit price perSale price $219.95 -
Men's Moab 3 Mid Waterproof Olive/Gum
Regular price $149.95Regular priceUnit price perSale price $149.95 -
Men's Neumel Chelsea Boot Chestnut
Regular price $129.95Regular priceUnit price perSale price $129.95
Built for the Trail
Waterproof hiking boots from brands like Merrell and Keen are built with GTX-lined uppers and aggressive outsoles for uneven terrain, deep mud, and wet trails. A secure lace-up fit and reinforced toe keep your foot stable over rocks and roots.
Chelsea and Pull-On Styles for Everyday Wear
Not every boot needs laces. Chelsea boots and pull-on styles from Blundstone and Amberjack offer a clean, low-maintenance look that works with jeans on the weekend and slacks in the office, no bending down required.
Quality Construction That Lasts
A well-built boot outlasts a cheap one by years, not months. Leather uppers and reinforced stitching hold up to daily wear far better than glued synthetic construction, which is why the boots here lean toward brands known for durability over trend.
Waterproofing That Actually Works
Sealed seams and GTX linings keep water out through slush, rain, and standing puddles, not just light drizzle. If waterproofing across other shoe types matters too, our full waterproof collection covers more than just boots.
Dressing Boots Up or Down
A Chelsea boot pairs as easily with a suit as it does with jeans, while a hiking boot stays firmly in casual territory. If you need something dressier for the office specifically, our oxfords offer a similar polished look without the boot shaft.
Price Ranges by Style
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Style |
Price Range |
What to Expect |
|
Waterproof hiking boots |
$110–$240 |
Rugged traction, sealed against wet trails |
|
Chelsea and pull-on boots |
$140–$285 |
Clean look, quick on and off |
|
Work-style boots |
$150–$195 |
Durable builds for long days on your feet |
Fit Tips Before You Order
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Break-in time is longer with full-grain leather, shorter with treated or synthetic uppers
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Sizing up half a size helps if you plan to wear thicker socks through winter
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Free 2-3 day priority shipping applies across the full men's footwear collection
Explore More: All Men's Footwear · Waterproof · Oxfords · Sneakers


