Sign in or join Simon+^®

Search with AI

Search with photo

Search with color

Recent Searches Clear

Cancel

Search with AI

Search with photo

Search with color

Recent Searches Clear

Windsorsmith Brown Leather Chelsea Ankle Boots - Sergio

Find Similar

Windsorsmith Brown Leather Chelsea Ankle Boots - Sergio

Find Similar

Windsorsmith Brown Leather Chelsea Ankle Boots - Sergio

Find Similar

Windsorsmith Brown Leather Chelsea Ankle Boots - Sergio

Find Similar

Windsorsmith Brown Leather Chelsea Ankle Boots - Sergio

Find Similar

Windsorsmith Brown Leather Chelsea Ankle Boots - Sergio

Find Similar

Windsorsmith Brown Leather Chelsea Ankle Boots - Sergio

Windsorsmith Brown Leather Chelsea Ankle Boots - Sergio

Windsorsmith Brown Leather Chelsea Ankle Boots - Sergio

Windsorsmith Brown Leather Chelsea Ankle Boots - Sergio

Windsorsmith Brown Leather Chelsea Ankle Boots - Sergio

Windsorsmith Brown Leather Chelsea Ankle Boots - Sergio

Windsorsmith

Windsorsmith

Ships and sold by

Infinity Leather

brown leather chelsea ankle boots - sergio

$127.99 17% off

Get 128 Simon+^® Points with this purchase.

Learn More

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

Size (Adult - Men)

EU 40

EU 42

EU 41

Color — brown

brown

[{"id":42644460830780,"title":"EU 44 \/ brown","option1":"EU 44","option2":"brown","option3":null,"sku":"d13b1f97-c2fa-4816-89cf-c0967f4d47d4","requires_shipping":true,"taxable":true,"featured_image":{"id":40649630351420,"product_id":7957347893308,"position":1,"created_at":"2025-03-15T19:14:53-04:00","updated_at":"2025-03-15T19:14:56-04:00","alt":null,"width":1732,"height":1509,"src":"\/\/shop.simon.com\/cdn\/shop\/files\/0789a418a48c4c2ba73530634dbeccfc.jpg?v=1742080496","variant_ids":[42644460830780,42644460863548,42644460896316,42644460929084,42644460961852,42644460994620,42644461027388]},"available":false,"name":"Windsorsmith Brown Leather Chelsea Ankle Boots - Sergio - EU 44 \/ brown","public_title":"EU 44 \/ brown","options":["EU 44","brown"],"price":15499,"weight":544,"compare_at_price":15499,"inventory_management":"shopify","barcode":"9320841203387","featured_media":{"alt":null,"id":32158851465276,"position":1,"preview_image":{"aspect_ratio":1.148,"height":1509,"width":1732,"src":"\/\/shop.simon.com\/cdn\/shop\/files\/0789a418a48c4c2ba73530634dbeccfc.jpg?v=1742080496"}},"requires_selling_plan":false,"selling_plan_allocations":[],"quantity_rule":{"min":1,"max":null,"increment":1}},{"id":42644460863548,"title":"EU 46 \/ brown","option1":"EU 46","option2":"brown","option3":null,"sku":"79e8732d-89f6-4d6c-a06d-dd0b1bc45a1b","requires_shipping":true,"taxable":true,"featured_image":{"id":40649630351420,"product_id":7957347893308,"position":1,"created_at":"2025-03-15T19:14:53-04:00","updated_at":"2025-03-15T19:14:56-04:00","alt":null,"width":1732,"height":1509,"src":"\/\/shop.simon.com\/cdn\/shop\/files\/0789a418a48c4c2ba73530634dbeccfc.jpg?v=1742080496","variant_ids":[42644460830780,42644460863548,42644460896316,42644460929084,42644460961852,42644460994620,42644461027388]},"available":false,"name":"Windsorsmith Brown Leather Chelsea Ankle Boots - Sergio - EU 46 \/ brown","public_title":"EU 46 \/ brown","options":["EU 46","brown"],"price":15499,"weight":544,"compare_at_price":15499,"inventory_management":"shopify","barcode":"9320841203400","featured_media":{"alt":null,"id":32158851465276,"position":1,"preview_image":{"aspect_ratio":1.148,"height":1509,"width":1732,"src":"\/\/shop.simon.com\/cdn\/shop\/files\/0789a418a48c4c2ba73530634dbeccfc.jpg?v=1742080496"}},"requires_selling_plan":false,"selling_plan_allocations":[],"quantity_rule":{"min":1,"max":null,"increment":1}},{"id":42644460896316,"title":"EU 40 \/ brown","option1":"EU 40","option2":"brown","option3":null,"sku":"6c33f102-487d-41f4-9e26-2870fa640b2e","requires_shipping":true,"taxable":true,"featured_image":{"id":40649630351420,"product_id":7957347893308,"position":1,"created_at":"2025-03-15T19:14:53-04:00","updated_at":"2025-03-15T19:14:56-04:00","alt":null,"width":1732,"height":1509,"src":"\/\/shop.simon.com\/cdn\/shop\/files\/0789a418a48c4c2ba73530634dbeccfc.jpg?v=1742080496","variant_ids":[42644460830780,42644460863548,42644460896316,42644460929084,42644460961852,42644460994620,42644461027388]},"available":true,"name":"Windsorsmith Brown Leather Chelsea Ankle Boots - Sergio - EU 40 \/ brown","public_title":"EU 40 \/ brown","options":["EU 40","brown"],"price":12799,"weight":544,"compare_at_price":15499,"inventory_management":"shopify","barcode":"9320841203349","featured_media":{"alt":null,"id":32158851465276,"position":1,"preview_image":{"aspect_ratio":1.148,"height":1509,"width":1732,"src":"\/\/shop.simon.com\/cdn\/shop\/files\/0789a418a48c4c2ba73530634dbeccfc.jpg?v=1742080496"}},"requires_selling_plan":false,"selling_plan_allocations":[],"quantity_rule":{"min":1,"max":null,"increment":1}},{"id":42644460929084,"title":"EU 42 \/ brown","option1":"EU 42","option2":"brown","option3":null,"sku":"3575046f-1e9b-4cc7-b7fe-7d112b8b814d","requires_shipping":true,"taxable":true,"featured_image":{"id":40649630351420,"product_id":7957347893308,"position":1,"created_at":"2025-03-15T19:14:53-04:00","updated_at":"2025-03-15T19:14:56-04:00","alt":null,"width":1732,"height":1509,"src":"\/\/shop.simon.com\/cdn\/shop\/files\/0789a418a48c4c2ba73530634dbeccfc.jpg?v=1742080496","variant_ids":[42644460830780,42644460863548,42644460896316,42644460929084,42644460961852,42644460994620,42644461027388]},"available":true,"name":"Windsorsmith Brown Leather Chelsea Ankle Boots - Sergio - EU 42 \/ brown","public_title":"EU 42 \/ brown","options":["EU 42","brown"],"price":12799,"weight":544,"compare_at_price":15499,"inventory_management":"shopify","barcode":"9320841203363","featured_media":{"alt":null,"id":32158851465276,"position":1,"preview_image":{"aspect_ratio":1.148,"height":1509,"width":1732,"src":"\/\/shop.simon.com\/cdn\/shop\/files\/0789a418a48c4c2ba73530634dbeccfc.jpg?v=1742080496"}},"requires_selling_plan":false,"selling_plan_allocations":[],"quantity_rule":{"min":1,"max":null,"increment":1}},{"id":42644460961852,"title":"EU 45 \/ brown","option1":"EU 45","option2":"brown","option3":null,"sku":"d73dbf46-9103-49ed-8f4b-cd0cba93680a","requires_shipping":true,"taxable":true,"featured_image":{"id":40649630351420,"product_id":7957347893308,"position":1,"created_at":"2025-03-15T19:14:53-04:00","updated_at":"2025-03-15T19:14:56-04:00","alt":null,"width":1732,"height":1509,"src":"\/\/shop.simon.com\/cdn\/shop\/files\/0789a418a48c4c2ba73530634dbeccfc.jpg?v=1742080496","variant_ids":[42644460830780,42644460863548,42644460896316,42644460929084,42644460961852,42644460994620,42644461027388]},"available":false,"name":"Windsorsmith Brown Leather Chelsea Ankle Boots - Sergio - EU 45 \/ brown","public_title":"EU 45 \/ brown","options":["EU 45","brown"],"price":15499,"weight":544,"compare_at_price":15499,"inventory_management":"shopify","barcode":"9320841203394","featured_media":{"alt":null,"id":32158851465276,"position":1,"preview_image":{"aspect_ratio":1.148,"height":1509,"width":1732,"src":"\/\/shop.simon.com\/cdn\/shop\/files\/0789a418a48c4c2ba73530634dbeccfc.jpg?v=1742080496"}},"requires_selling_plan":false,"selling_plan_allocations":[],"quantity_rule":{"min":1,"max":null,"increment":1}},{"id":42644460994620,"title":"EU 43 \/ brown","option1":"EU 43","option2":"brown","option3":null,"sku":"2fa3048a-f7a4-4aa9-b23e-d135c815a18c","requires_shipping":true,"taxable":true,"featured_image":{"id":40649630351420,"product_id":7957347893308,"position":1,"created_at":"2025-03-15T19:14:53-04:00","updated_at":"2025-03-15T19:14:56-04:00","alt":null,"width":1732,"height":1509,"src":"\/\/shop.simon.com\/cdn\/shop\/files\/0789a418a48c4c2ba73530634dbeccfc.jpg?v=1742080496","variant_ids":[42644460830780,42644460863548,42644460896316,42644460929084,42644460961852,42644460994620,42644461027388]},"available":false,"name":"Windsorsmith Brown Leather Chelsea Ankle Boots - Sergio - EU 43 \/ brown","public_title":"EU 43 \/ brown","options":["EU 43","brown"],"price":15499,"weight":544,"compare_at_price":15499,"inventory_management":"shopify","barcode":"9320841203370","featured_media":{"alt":null,"id":32158851465276,"position":1,"preview_image":{"aspect_ratio":1.148,"height":1509,"width":1732,"src":"\/\/shop.simon.com\/cdn\/shop\/files\/0789a418a48c4c2ba73530634dbeccfc.jpg?v=1742080496"}},"requires_selling_plan":false,"selling_plan_allocations":[],"quantity_rule":{"min":1,"max":null,"increment":1}},{"id":42644461027388,"title":"EU 41 \/ brown","option1":"EU 41","option2":"brown","option3":null,"sku":"5eae43c0-40d1-4ef1-997a-4cde7052ba4f","requires_shipping":true,"taxable":true,"featured_image":{"id":40649630351420,"product_id":7957347893308,"position":1,"created_at":"2025-03-15T19:14:53-04:00","updated_at":"2025-03-15T19:14:56-04:00","alt":null,"width":1732,"height":1509,"src":"\/\/shop.simon.com\/cdn\/shop\/files\/0789a418a48c4c2ba73530634dbeccfc.jpg?v=1742080496","variant_ids":[42644460830780,42644460863548,42644460896316,42644460929084,42644460961852,42644460994620,42644461027388]},"available":true,"name":"Windsorsmith Brown Leather Chelsea Ankle Boots - Sergio - EU 41 \/ brown","public_title":"EU 41 \/ brown","options":["EU 41","brown"],"price":12799,"weight":544,"compare_at_price":15499,"inventory_management":"shopify","barcode":"9320841203356","featured_media":{"alt":null,"id":32158851465276,"position":1,"preview_image":{"aspect_ratio":1.148,"height":1509,"width":1732,"src":"\/\/shop.simon.com\/cdn\/shop\/files\/0789a418a48c4c2ba73530634dbeccfc.jpg?v=1742080496"}},"requires_selling_plan":false,"selling_plan_allocations":[],"quantity_rule":{"min":1,"max":null,"increment":1}}]

Details

The Windsorsmith Sergio boots are the epitome of casual sophistication, crafted from distressed waxy/oil cow leather. Featuring an elastic side gusset and a convenient pull tab at the back, these Chelsea boots offer easy on-and-off access. The rugged finish, round toe, and lightweight sole ensure comfort without sacrificing style. Premium Distressed Leather - Crafted from durable, waxy/oil cow leather for a rugged charm, Comfortable Non-Leather Lining - Provides a soft touch against the foot for all-day wear, Reliable Non-Slip Sole - T.P.R sole designed for superior traction and stability, Easy Access Design - Features double-sided elastic gussets for effortless slipping on and off, Stylish Round Toe - Classic shape for a sophisticated look, Practical Heel Height - 25 mm heel for added elevation without compromising comfort. Convenient Pull Tab - Located at the back for quick and easy entry. Signature Branding - Adorned with the Windsorsmith bullhead metal logo on the back tab, showcasing brand quality. Versatile Chelsea Style - A timeless design that pairs well with various outfits for any occasion.

Read More

Sponsored

Sponsored

Write A Review

https://shop.simon.com/products/windsorsmith-brown-leather-chelsea-ankle-boots-sergio 7957347893308 Windsorsmith Brown Leather Chelsea Ankle Boots - Sergio 154.99 //shop.simon.com/cdn/shop/files/0789a418a48c4c2ba73530634dbeccfc.jpg?v=1742080496 //shop.simon.com/cdn/shop/files/0789a418a48c4c2ba73530634dbeccfc_large.jpg?v=1742080496 USD InStock men/shoes/boots-chukkas All Products Fall Preview-First Look Final Few In Season Infinity Leather Men Men's Boots & Chukkas Men's Shoes Men's Shoes & Accessories New Arrivals Under $150 New Arrivals Under $500 Shoes The Logo Collection Under $200 The Windsorsmith Sergio boots are the epitome of casual sophistication, crafted from distressed waxy/oil cow leather. Featuring an elastic side gusset and a convenient pull tab at the back, these Chelsea boots offer easy on-and-off access. The rugged finish, round toe, and lightweight sole ensure comfort without sacrificing style. Premium Distressed Leather - Crafted from durable, waxy/oil cow leather for a rugged charm, Comfortable Non-Leather Lining - Provides a soft touch against the foot for all-day wear, Reliable Non-Slip Sole - T.P.R sole designed for superior traction and stability, Easy Access Design - Features double-sided elastic gussets for effortless slipping on and off, Stylish Round Toe - Classic shape for a sophisticated look, Practical Heel Height - 25 mm heel for added elevation without compromising comfort. Convenient Pull Tab - Located at the back for quick and easy entry. Signature Branding - Adorned with the Windsorsmith bullhead metal logo on the back tab, showcasing brand quality. Versatile Chelsea Style - A timeless design that pairs well with various outfits for any occasion. 2935 brand-type_0 brand_Windsorsmith handling-time_1-2d OUTLET product-condition_New Slack_2026-01-08T19:36:03.348Z variantID_97cb9afb-9680-4c9d-94b3-245fed1fe5bc 2025-03-20 //shop.simon.com/cdn/shop/files/62bf5cffc5364915aba443f2a8248472.jpg?v=1742080496 //shop.simon.com/cdn/shop/files/97bbb5b8a48f47b792ec0061e14c97a0.jpg?v=1742080496 //shop.simon.com/cdn/shop/files/00f9560062b54e42989379eb5634803f.jpg?v=1742080496 //shop.simon.com/cdn/shop/files/e4fd8b04824e4c90a0ed4882e34fc1c1.jpg?v=1742080496 //shop.simon.com/cdn/shop/files/c4075a5fd702433f82143f82662c3bad.jpg?v=1742080496 42644460830780 EU 44 / brown 154.99 154.99 //shop.simon.com/cdn/shop/files/0789a418a48c4c2ba73530634dbeccfc.jpg?v=1742080496 https://shop.simon.com/products/windsorsmith-brown-leather-chelsea-ankle-boots-sergio?variant=42644460830780 OutOfStock EU 44 brown 42644460863548 EU 46 / brown 154.99 154.99 //shop.simon.com/cdn/shop/files/0789a418a48c4c2ba73530634dbeccfc.jpg?v=1742080496 https://shop.simon.com/products/windsorsmith-brown-leather-chelsea-ankle-boots-sergio?variant=42644460863548 OutOfStock EU 46 brown 42644460896316 EU 40 / brown 127.99 154.99 //shop.simon.com/cdn/shop/files/0789a418a48c4c2ba73530634dbeccfc.jpg?v=1742080496 https://shop.simon.com/products/windsorsmith-brown-leather-chelsea-ankle-boots-sergio?variant=42644460896316 InStock EU 40 brown 42644460929084 EU 42 / brown 127.99 154.99 //shop.simon.com/cdn/shop/files/0789a418a48c4c2ba73530634dbeccfc.jpg?v=1742080496 https://shop.simon.com/products/windsorsmith-brown-leather-chelsea-ankle-boots-sergio?variant=42644460929084 InStock EU 42 brown 42644460961852 EU 45 / brown 154.99 154.99 //shop.simon.com/cdn/shop/files/0789a418a48c4c2ba73530634dbeccfc.jpg?v=1742080496 https://shop.simon.com/products/windsorsmith-brown-leather-chelsea-ankle-boots-sergio?variant=42644460961852 OutOfStock EU 45 brown 42644460994620 EU 43 / brown 154.99 154.99 //shop.simon.com/cdn/shop/files/0789a418a48c4c2ba73530634dbeccfc.jpg?v=1742080496 https://shop.simon.com/products/windsorsmith-brown-leather-chelsea-ankle-boots-sergio?variant=42644460994620 OutOfStock EU 43 brown 42644461027388 EU 41 / brown 127.99 154.99 //shop.simon.com/cdn/shop/files/0789a418a48c4c2ba73530634dbeccfc.jpg?v=1742080496 https://shop.simon.com/products/windsorsmith-brown-leather-chelsea-ankle-boots-sergio?variant=42644461027388 InStock EU 41 brown

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.