$93.15
Regular price
$121.10
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
23% 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
Men’s Wingtip Brogue Ankle Boots a polished blend of classic craftsmanship and modern materials. These chukka-style boots feature iconic wingtip and brogue detailing for traditional character, paired with a refined ankle height that works seamlessly with suits, business casual attire, or smart weekend looks. The interior is lined with genuine leather for breathable comfort that conforms to your foot over time, while the durable polyurethane (PU) outer offers an attractive, low-maintenance finish that stands up to daily wear. A secure lace-up closure ensures an adjustable fit and dependable support, and the thoughtfully engineered sole delivers traction and stability for confident strides all day long.
https://shop.simon.com/products/wingtip-brogue-ankle-boots-leather-lined-chukka-dress-shoes-28688196223036Wingtip Brogue Ankle Boots Leather Lined Chukka Dress Shoes93.15//shop.simon.com/cdn/shop/files/d11c8c5c9e90483eb8ffda2bc3647f5b.webp?v=1759774025//shop.simon.com/cdn/shop/files/d11c8c5c9e90483eb8ffda2bc3647f5b_large.webp?v=1759774025USDInStockmen/shoes/boots-chukkasAll ProductsFinal FewMenMen's Boots & ChukkasMen's ShoesMen's Shoes & AccessoriesNew Arrivals Under $150New Arrivals Under $500ShoesTru Clothing SaleTruClothingTruClothing Extra 15Under $100
Men’s Wingtip Brogue Ankle Boots a polished blend of classic craftsmanship and modern materials. These chukka-style boots feature iconic wingtip and brogue detailing for traditional character, paired with a refined ankle height that works seamlessly with suits, business casual attire, or smart weekend looks. The interior is lined with genuine leather for breathable comfort that conforms to your foot over time, while the durable polyurethane (PU) outer offers an attractive, low-maintenance finish that stands up to daily wear. A secure lace-up closure ensures an adjustable fit and dependable support, and the thoughtfully engineered sole delivers traction and stability for confident strides all day long.
121.102932brand-type_0brand_TruClothingcollection_Tru_Extra10_0320collection_Tru_Extra15_0213footwear-toe-style_Closed Toehandling-time_1-2dproduct-condition_Newproduct-material_Leather (Faux)Slack_2026-03-23T07:07:45.973ZvariantID_e9d58c37-4d10-464e-b23a-61da93aa66022025-10-07//shop.simon.com/cdn/shop/files/7cd2a585568a49cb88ed8fede1c74305.webp?v=1759774025//shop.simon.com/cdn/shop/files/19782ad4900e47f0a1288906ab0d20fb.webp?v=1759774025//shop.simon.com/cdn/shop/files/7b2792a7fd3c41318a52a19180ad93c9.webp?v=1759774025//shop.simon.com/cdn/shop/files/3332f10307b541698e9a6a79ab876c27.webp?v=1759774025//shop.simon.com/cdn/shop/files/cb76a38c5c124aee82924ddec4a77e2e.webp?v=175977402543561333751868US 13 / navy / Regular93.15121.10//shop.simon.com/cdn/shop/files/d11c8c5c9e90483eb8ffda2bc3647f5b.webp?v=1759774025https://shop.simon.com/products/wingtip-brogue-ankle-boots-leather-lined-chukka-dress-shoes-2?variant=43561333751868InStockUS 13navyRegular43561333784636US 9 / navy / Regular93.15121.10//shop.simon.com/cdn/shop/files/d11c8c5c9e90483eb8ffda2bc3647f5b.webp?v=1759774025https://shop.simon.com/products/wingtip-brogue-ankle-boots-leather-lined-chukka-dress-shoes-2?variant=43561333784636InStockUS 9navyRegular43561333817404US 7 / navy / Regular93.15121.10//shop.simon.com/cdn/shop/files/d11c8c5c9e90483eb8ffda2bc3647f5b.webp?v=1759774025https://shop.simon.com/products/wingtip-brogue-ankle-boots-leather-lined-chukka-dress-shoes-2?variant=43561333817404InStockUS 7navyRegular43561333850172US 12 / navy / Regular93.15121.10//shop.simon.com/cdn/shop/files/d11c8c5c9e90483eb8ffda2bc3647f5b.webp?v=1759774025https://shop.simon.com/products/wingtip-brogue-ankle-boots-leather-lined-chukka-dress-shoes-2?variant=43561333850172InStockUS 12navyRegular43561333882940US 11 / navy / Regular93.15121.10//shop.simon.com/cdn/shop/files/d11c8c5c9e90483eb8ffda2bc3647f5b.webp?v=1759774025https://shop.simon.com/products/wingtip-brogue-ankle-boots-leather-lined-chukka-dress-shoes-2?variant=43561333882940InStockUS 11navyRegular43561333915708US 8 / navy / Regular93.15121.10//shop.simon.com/cdn/shop/files/d11c8c5c9e90483eb8ffda2bc3647f5b.webp?v=1759774025https://shop.simon.com/products/wingtip-brogue-ankle-boots-leather-lined-chukka-dress-shoes-2?variant=43561333915708InStockUS 8navyRegular43561333948476US 10 / navy / Regular93.15121.10//shop.simon.com/cdn/shop/files/d11c8c5c9e90483eb8ffda2bc3647f5b.webp?v=1759774025https://shop.simon.com/products/wingtip-brogue-ankle-boots-leather-lined-chukka-dress-shoes-2?variant=43561333948476InStockUS 10navyRegular
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.