$69.99
Regular price
$100.00
WHAT DOES THE SLASH-THROUGH PRICE MEAN?
The slash-through price near the selling price on our site is provided to us by the retailer selling the
item and represents the price at which the retailer previously sold the item or, in some instances, is
based
on the price at which an item or comparable item may, in general and as reasonably determined by the
retailer, be sold at retail stores, including specialty or department stores and other non-discount
sellers.
You may wish to use the slash-through price as a guide in your evaluation of prices on our site. Because
the
retailer’s merchandise is sold over the Internet on a national basis, the slash-through price may not
always
represent the prevailing price in any particular location or at any particular time.
Sale price
30% off
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.
Ship Unlimited Items for Only $4.95
Usually ships within 1-2 business days
Details
The Men’s Westmore Chukka Boot combines classic craftsmanship with modern comfort. The upper is made with premium Timberland® leather and 100% cotton laces; it features an OrthoLite® footbed, EVA midsole, and SensorFlex™ Comfort System for flexibility, support, and lightweight cushioning. Timberland supports responsible manufacturing of leather via the Leather Working Group.
https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot8709412192316Men's Westmore Moc-Toe Chukka Boot69.99//shop.simon.com/cdn/shop/files/52a446677a334b22b24bb558c3e1b4f1.jpg?v=1762192179//shop.simon.com/cdn/shop/files/52a446677a334b22b24bb558c3e1b4f1_large.jpg?v=1762192179USDOutOfStockmen/shoes/boots-chukkasAll General Apparel BrandsDoorbustersGift Guide for HimGifts for YouMen's Essential ShoesMen's Shoes & AccessoriesShoe Gift GuideShoesTimberland Buy 1 Get 1Top BrandsThe Men’s Westmore Chukka Boot combines classic craftsmanship with modern comfort. The upper is made with premium Timberland® leather and 100% cotton laces; it features an OrthoLite® footbed, EVA midsole, and SensorFlex™ Comfort System for flexibility, support, and lightweight cushioning. Timberland supports responsible manufacturing of leather via the Leather Working Group.100.002582brand-type_0brand_Timberlandcollection_Timberland_BOGO70_1125collection_Timberland_BOGOShoes_1121collection_TimberlandBOGOFootwear_1209footwear-toe-style_Closed Toehandling-time_3-5dproduct-condition_Newpromo_Buy 1 Get 1 50% Off with Code: TIMBER50_11/21/2025_11/25/2025_TIMBER50promo_Buy 1 Get 1 50% Off with Code: TIMBER50_12/09/2025_12/18/2025_TIMBER50promo_Buy 1 Get 1 70% Off with Code: TIMBER70_11/25/2025_12/04/2025_TIMBER70Slack_2026-06-06T00:26:15.075ZvariantID_9a9e6598-a123-40a5-82c7-894b536c2fad2025-11-03//shop.simon.com/cdn/shop/files/abf5b901d5d0416d9125eaaf7553580e.jpg?v=1762192179//shop.simon.com/cdn/shop/files/8d46fbc8ee304b53ae5d42b8767d821d.jpg?v=1762192180//shop.simon.com/cdn/shop/files/b07ea22dec174335ae5d3c2151628172.jpg?v=1762192179//shop.simon.com/cdn/shop/files/cbe9be6e14434aee9ad224a020b365b3.jpg?v=176219217943638154035260US 13 / canteen / Regular69.99100.00//shop.simon.com/cdn/shop/files/52a446677a334b22b24bb558c3e1b4f1.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154035260OutOfStockUS 13canteenRegular43638154068028US 7 / tortoiseshell / Regular89.99100.00//shop.simon.com/cdn/shop/files/cbe9be6e14434aee9ad224a020b365b3.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154068028OutOfStockUS 7tortoiseshellRegular43638154100796US 6.5 / tortoiseshell / Wide89.99100.00//shop.simon.com/cdn/shop/files/cbe9be6e14434aee9ad224a020b365b3.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154100796OutOfStockUS 6.5tortoiseshellWide43638154133564US 11 / canteen / Regular69.99100.00//shop.simon.com/cdn/shop/files/52a446677a334b22b24bb558c3e1b4f1.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154133564OutOfStockUS 11canteenRegular43638154166332US 8 / canteen / Regular89.99100.00//shop.simon.com/cdn/shop/files/52a446677a334b22b24bb558c3e1b4f1.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154166332OutOfStockUS 8canteenRegular43638154199100US 8 / tortoiseshell / Wide89.99100.00//shop.simon.com/cdn/shop/files/cbe9be6e14434aee9ad224a020b365b3.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154199100OutOfStockUS 8tortoiseshellWide43638154231868US 8.5 / canteen / Wide89.99100.00//shop.simon.com/cdn/shop/files/52a446677a334b22b24bb558c3e1b4f1.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154231868OutOfStockUS 8.5canteenWide43638154264636US 6 / canteen / Regular89.99100.00//shop.simon.com/cdn/shop/files/52a446677a334b22b24bb558c3e1b4f1.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154264636OutOfStockUS 6canteenRegular43638154297404US 9.5 / canteen / Regular89.99100.00//shop.simon.com/cdn/shop/files/52a446677a334b22b24bb558c3e1b4f1.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154297404OutOfStockUS 9.5canteenRegular43638154330172US 7.5 / canteen / Regular89.99100.00//shop.simon.com/cdn/shop/files/52a446677a334b22b24bb558c3e1b4f1.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154330172OutOfStockUS 7.5canteenRegular43638154362940US 8.5 / canteen / Regular89.99100.00//shop.simon.com/cdn/shop/files/52a446677a334b22b24bb558c3e1b4f1.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154362940OutOfStockUS 8.5canteenRegular43638154395708US 7 / tortoiseshell / Wide89.99100.00//shop.simon.com/cdn/shop/files/cbe9be6e14434aee9ad224a020b365b3.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154395708OutOfStockUS 7tortoiseshellWide43638154428476US 7.5 / tortoiseshell / Wide89.99100.00//shop.simon.com/cdn/shop/files/cbe9be6e14434aee9ad224a020b365b3.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154428476OutOfStockUS 7.5tortoiseshellWide43638154461244US 6 / canteen / Wide89.99100.00//shop.simon.com/cdn/shop/files/52a446677a334b22b24bb558c3e1b4f1.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154461244OutOfStockUS 6canteenWide43638154494012US 8 / canteen / Wide89.99100.00//shop.simon.com/cdn/shop/files/52a446677a334b22b24bb558c3e1b4f1.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154494012OutOfStockUS 8canteenWide43638154526780US 7 / canteen / Regular89.99100.00//shop.simon.com/cdn/shop/files/52a446677a334b22b24bb558c3e1b4f1.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154526780OutOfStockUS 7canteenRegular43638154559548US 6.5 / canteen / Regular89.99100.00//shop.simon.com/cdn/shop/files/52a446677a334b22b24bb558c3e1b4f1.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154559548OutOfStockUS 6.5canteenRegular43638154592316US 6.5 / canteen / Wide89.99100.00//shop.simon.com/cdn/shop/files/52a446677a334b22b24bb558c3e1b4f1.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154592316OutOfStockUS 6.5canteenWide43638154625084US 8.5 / tortoiseshell / Regular69.99100.00//shop.simon.com/cdn/shop/files/cbe9be6e14434aee9ad224a020b365b3.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154625084OutOfStockUS 8.5tortoiseshellRegular43638154657852US 7.5 / canteen / Wide89.99100.00//shop.simon.com/cdn/shop/files/52a446677a334b22b24bb558c3e1b4f1.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154657852OutOfStockUS 7.5canteenWide43638154690620US 7 / canteen / Wide89.99100.00//shop.simon.com/cdn/shop/files/52a446677a334b22b24bb558c3e1b4f1.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154690620OutOfStockUS 7canteenWide43638154723388US 7.5 / tortoiseshell / Regular89.99100.00//shop.simon.com/cdn/shop/files/cbe9be6e14434aee9ad224a020b365b3.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154723388OutOfStockUS 7.5tortoiseshellRegular43638154756156US 9 / canteen / Regular69.99100.00//shop.simon.com/cdn/shop/files/52a446677a334b22b24bb558c3e1b4f1.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154756156OutOfStockUS 9canteenRegular43638154788924US 9 / canteen / Wide69.99100.00//shop.simon.com/cdn/shop/files/52a446677a334b22b24bb558c3e1b4f1.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154788924OutOfStockUS 9canteenWide43638154821692US 10.5 / canteen / Regular69.99100.00//shop.simon.com/cdn/shop/files/52a446677a334b22b24bb558c3e1b4f1.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154821692OutOfStockUS 10.5canteenRegular43638154854460US 10 / canteen / Regular69.99100.00//shop.simon.com/cdn/shop/files/52a446677a334b22b24bb558c3e1b4f1.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154854460OutOfStockUS 10canteenRegular43638154887228US 11.5 / canteen / Regular69.99100.00//shop.simon.com/cdn/shop/files/52a446677a334b22b24bb558c3e1b4f1.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154887228OutOfStockUS 11.5canteenRegular43638154919996US 6.5 / tortoiseshell / Regular69.99100.00//shop.simon.com/cdn/shop/files/cbe9be6e14434aee9ad224a020b365b3.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154919996OutOfStockUS 6.5tortoiseshellRegular43638154952764US 8 / tortoiseshell / Regular89.99100.00//shop.simon.com/cdn/shop/files/cbe9be6e14434aee9ad224a020b365b3.jpg?v=1762192179https://shop.simon.com/products/mens-westmore-moc-toe-chukka-boot?variant=43638154952764OutOfStockUS 8tortoiseshellRegular
Product Info
What can we help you find today?
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.