Preserved in like-new condition. Item may have been used as a display product and has no noticeable marks or wear to hardware.
Pristine
Preserved in almost-new condition. Item has few or no noticeable marks or wear to hardware.
Very Good
Item may have some hardly noticeable marks or wear to hardware.
Good
Item may have some noticeable marks or wear to hardware.
Fair
Item may have multiple, noticeable marks or wear to hardware.
Authenticity Ensured
Merchandise is shipped and sold by the brand or store directly or from trusted independent sellers. In all cases, we stand by the authenticity of every product sold on our site and app.
Free Shipping Details
Free Shipping will apply only to standard shipping on eligible purchases and is not available for shipments to AK or HI. Additional charges will apply for expedited delivery or oversized items. Return shipping charges will be applied where applicable. Free shipping is an exclusive benefit (the “Benefit”) and cannot be shared, transferred, or sold. Return-shipping charges will be applied where applicable. Not valid on prior orders. No cash value.
Void where prohibited by law. ShopSimon reserves the right to (i) revoke or prohibit your use of the Benefit for any reason, at any time, in our sole discretion, without notice, including when we suspect fraud or misuse; and/or (ii) terminate or modify the Benefit at any time without notice to you. The Benefit and the ShopSimon loyalty program are subject to the complete Terms of Service. For California residents, the value of the Benefit is reasonably related to the value of the personal information you provide; for more information, please see the Notice of Financial Incentives in the Privacy Policy.
FREE SHIPPING & EASY RETURNS
Usually ships within 1-2 business days
Details
Stay ready for the weather with the Men's Larchmont Waterproof Chukka Boot. Crafted with a waterproof premium Timberland® leather upper, these boots feature seam-sealed construction for protection. The ReBOTL™ fabric lining contains 50% recycled PET plastic, while the OrthoLite® footbed and Gripstick™ rubber outsole help with all-day comfort and traction. With a TPR welt and patented L7 lug design for grip, these boots are for outdoor adventures.
https://shop.simon.com/products/mens-larchmont-waterproof-chukka-boot7746485256252Men's Larchmont Waterproof Chukka Boot150.00//shop.simon.com/cdn/shop/files/7f445882b83541129d6ffff681a20ec8.webp?v=1723618105//shop.simon.com/cdn/shop/files/7f445882b83541129d6ffff681a20ec8_large.webp?v=1723618105USDInStockmen/shoes/boots-chukkasAll General Apparel BrandsBoot CollectionBoot ShopBoots & Booties ClearoutCurated Group 4Everything Under $100February Shoes EventGift Guide by PricingGift Guide for HimMenMen's Boots & ChukkasMen's ShoesMen's Shoes & AccessoriesNew Arrivals Under $150New Arrivals Under $500ProductsShoesTimberlandTimberland Extra 30% Off FootwearTimberland Extra 40Top Trending Shoe SaleUnder $200Stay ready for the weather with the Men's Larchmont Waterproof Chukka Boot. Crafted with a waterproof premium Timberland® leather upper, these boots feature seam-sealed construction for protection. The ReBOTL™ fabric lining contains 50% recycled PET plastic, while the OrthoLite® footbed and Gripstick™ rubber outsole help with all-day comfort and traction. With a TPR welt and patented L7 lug design for grip, these boots are for outdoor adventures.2582brand-type_0brand_Timberlandcollection_Timberland_BFExtra40_1128collection_Timberland_Extra30_1205footwear-toe-style_Closed Toehandling-time_3-5dOUTLETproduct-condition_NewvariantID_b174e2cf-3593-42b2-989c-4a7665be5a652024-08-10//shop.simon.com/cdn/shop/files/750a30a708db4bae94820ed45a1176ea.webp?v=1723618105//shop.simon.com/cdn/shop/files/c3d7c4f913664bcfb41d9dc3c85024b3.webp?v=1723618105//shop.simon.com/cdn/shop/files/ca90e09c869244ca8e44295b7116f2b5.jpg?v=172361810542085818040380US 10.5 / dark brown full-grain / Regular150.00150.00//shop.simon.com/cdn/shop/files/7f445882b83541129d6ffff681a20ec8.webp?v=1723618105https://shop.simon.com/products/mens-larchmont-waterproof-chukka-boot?variant=42085818040380InStockUS 10.5dark brown full-grainRegular42085818073148US 7.5 / dark brown full-grain / Regular150.00150.00//shop.simon.com/cdn/shop/files/7f445882b83541129d6ffff681a20ec8.webp?v=1723618105https://shop.simon.com/products/mens-larchmont-waterproof-chukka-boot?variant=42085818073148OutOfStockUS 7.5dark brown full-grainRegular42085818105916US 8.5 / dark brown full-grain / Regular150.00150.00//shop.simon.com/cdn/shop/files/7f445882b83541129d6ffff681a20ec8.webp?v=1723618105https://shop.simon.com/products/mens-larchmont-waterproof-chukka-boot?variant=42085818105916OutOfStockUS 8.5dark brown full-grainRegular42085818138684US 10 / dark brown full-grain / Regular150.00150.00//shop.simon.com/cdn/shop/files/7f445882b83541129d6ffff681a20ec8.webp?v=1723618105https://shop.simon.com/products/mens-larchmont-waterproof-chukka-boot?variant=42085818138684InStockUS 10dark brown full-grainRegular42085818171452US 13 / dark brown full-grain / Regular150.00150.00//shop.simon.com/cdn/shop/files/7f445882b83541129d6ffff681a20ec8.webp?v=1723618105https://shop.simon.com/products/mens-larchmont-waterproof-chukka-boot?variant=42085818171452InStockUS 13dark brown full-grainRegular42085818204220US 7 / dark brown full-grain / Regular150.00150.00//shop.simon.com/cdn/shop/files/7f445882b83541129d6ffff681a20ec8.webp?v=1723618105https://shop.simon.com/products/mens-larchmont-waterproof-chukka-boot?variant=42085818204220OutOfStockUS 7dark brown full-grainRegular42085818236988US 11 / dark brown full-grain / Regular150.00150.00//shop.simon.com/cdn/shop/files/7f445882b83541129d6ffff681a20ec8.webp?v=1723618105https://shop.simon.com/products/mens-larchmont-waterproof-chukka-boot?variant=42085818236988InStockUS 11dark brown full-grainRegular42085818269756US 9.5 / dark brown full-grain / Regular150.00150.00//shop.simon.com/cdn/shop/files/7f445882b83541129d6ffff681a20ec8.webp?v=1723618105https://shop.simon.com/products/mens-larchmont-waterproof-chukka-boot?variant=42085818269756OutOfStockUS 9.5dark brown full-grainRegular42085818302524US 11.5 / dark brown full-grain / Regular150.00150.00//shop.simon.com/cdn/shop/files/7f445882b83541129d6ffff681a20ec8.webp?v=1723618105https://shop.simon.com/products/mens-larchmont-waterproof-chukka-boot?variant=42085818302524OutOfStockUS 11.5dark brown full-grainRegular42085818335292US 12 / dark brown full-grain / Regular150.00150.00//shop.simon.com/cdn/shop/files/7f445882b83541129d6ffff681a20ec8.webp?v=1723618105https://shop.simon.com/products/mens-larchmont-waterproof-chukka-boot?variant=42085818335292InStockUS 12dark brown full-grainRegular42085818368060US 9 / dark brown full-grain / Regular150.00150.00//shop.simon.com/cdn/shop/files/7f445882b83541129d6ffff681a20ec8.webp?v=1723618105https://shop.simon.com/products/mens-larchmont-waterproof-chukka-boot?variant=42085818368060OutOfStockUS 9dark brown full-grainRegular42085818400828US 8 / dark brown full-grain / Regular150.00150.00//shop.simon.com/cdn/shop/files/7f445882b83541129d6ffff681a20ec8.webp?v=1723618105https://shop.simon.com/products/mens-larchmont-waterproof-chukka-boot?variant=42085818400828OutOfStockUS 8dark brown full-grainRegular42588641984572US 10.5 / dark brown / Regular150.00150.00//shop.simon.com/cdn/shopifycloud/shopify/assets/no-image-2048-5e88c1b20e087fb7bbe9a3771824e743c244f437e4f8ba93bbf7b11b53f7824c.gifhttps://shop.simon.com/products/mens-larchmont-waterproof-chukka-boot?variant=42588641984572OutOfStockUS 10.5dark brownRegular42588642017340US 8.5 / dark brown / Regular150.00150.00//shop.simon.com/cdn/shopifycloud/shopify/assets/no-image-2048-5e88c1b20e087fb7bbe9a3771824e743c244f437e4f8ba93bbf7b11b53f7824c.gifhttps://shop.simon.com/products/mens-larchmont-waterproof-chukka-boot?variant=42588642017340OutOfStockUS 8.5dark brownRegular42588642050108US 10 / dark brown / Regular150.00150.00//shop.simon.com/cdn/shopifycloud/shopify/assets/no-image-2048-5e88c1b20e087fb7bbe9a3771824e743c244f437e4f8ba93bbf7b11b53f7824c.gifhttps://shop.simon.com/products/mens-larchmont-waterproof-chukka-boot?variant=42588642050108OutOfStockUS 10dark brownRegular42588642082876US 13 / dark brown / Regular150.00150.00//shop.simon.com/cdn/shopifycloud/shopify/assets/no-image-2048-5e88c1b20e087fb7bbe9a3771824e743c244f437e4f8ba93bbf7b11b53f7824c.gifhttps://shop.simon.com/products/mens-larchmont-waterproof-chukka-boot?variant=42588642082876OutOfStockUS 13dark brownRegular42588642115644US 11 / dark brown / Regular150.00150.00//shop.simon.com/cdn/shopifycloud/shopify/assets/no-image-2048-5e88c1b20e087fb7bbe9a3771824e743c244f437e4f8ba93bbf7b11b53f7824c.gifhttps://shop.simon.com/products/mens-larchmont-waterproof-chukka-boot?variant=42588642115644OutOfStockUS 11dark brownRegular42588642148412US 9.5 / dark brown / Regular150.00150.00//shop.simon.com/cdn/shopifycloud/shopify/assets/no-image-2048-5e88c1b20e087fb7bbe9a3771824e743c244f437e4f8ba93bbf7b11b53f7824c.gifhttps://shop.simon.com/products/mens-larchmont-waterproof-chukka-boot?variant=42588642148412OutOfStockUS 9.5dark brownRegular42588642181180US 12 / dark brown / Regular150.00150.00//shop.simon.com/cdn/shopifycloud/shopify/assets/no-image-2048-5e88c1b20e087fb7bbe9a3771824e743c244f437e4f8ba93bbf7b11b53f7824c.gifhttps://shop.simon.com/products/mens-larchmont-waterproof-chukka-boot?variant=42588642181180OutOfStockUS 12dark brownRegular
Product Info
Shopping Assistant
Things I can help you find
Not your average loading screen. We’re crafting a masterpiece of shopping delight.
Hold tight, we're untangling virtual shopping bags and decoding the latest trends.
Preparing to dazzle your wardrobe... It's not procrastination; it's fashion anticipation!
Calculating the perfect shopping spree... This may take a fashionably short moment.
In the meantime, imagine a runway walk while we fetch the latest styles for you.
Calculating the couture quotient… Your next style obsession is loading.
Just a sprinkle of tech magic before your runway-worthy styles are revealed.
Beta
Introducing our innovative beta feature: AI search assistant!
The Shopping Assistant is an AI-powered tool designed to help you find products, provide information about items and suggest recommendations based on your specific questions. This new feature delivers prompt answers to your queries in a chat interface and helps you dig deeper and explore more with suggested follow-on searches.
This software is currently in a beta phase. We will continue to improve and expand this experience based on your feedback. We appreciate your collaboration in refining this product before its official release. As we continue to develop this feature, you can expect regular updates that enhance performance and introduce new functionalities.
Join us in shaping the future of shopping!
Reset
Reset your search to start a whole new conversation?
Cancel
Search with Photo
See how it works: select a photo below to shop similar items.
Upload a photo to shop similar items.
SELECT PHOTO
TAKE PHOTO
SELECT PHOTO
There was an error uploading your photo. Please try again.