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Description:
Rugged and built for everyday wear, this Chelsea boot brings together timeless style and dependable comfort. The elastic side panels and pull tab make it easy to slip on and go, while the durable sole adds traction and longevity. Whether you're dressing up or keeping it casual, it's a refined finish to your look. -
Description:
Built with an EasyCare upper designed for minimal maintenance, these boots keep their polished look without demanding your time or attention. The plain toe gives them a clean, modern feel, striking that perfect balance between laid‑back and put‑together. Inside, your feet get the treat of breathable stretch textile linings, soft and flexible enough for all‑day comfort. And thanks to KORE technology, each step gets a little boost, biomechanically designed to make walking feel smoother, steadier, and surprisingly effortless. The upper is crafted from durable manmade leather, giving you long‑lasting wear without weighing you down. Underfoot, a sturdy manmade sole keeps you grounded while offering dependable support for everyday adventures. -
Description:
Take the rugged road in stride with these Eastland boots crafted from full-grain leather. Equal parts sturdy and stylish, they're your all-season sidekicks, offering comfort and classic charm. Crafted for durability with a plain toe design, they walk the fine line between polished and laid-back. Whether you're tackling city streets or weekend getaways, these boots stay ready to roll. Lace up, step out, and let them carry you wherever adventure calls. They're a versatile win for your casual wardrobe upgrade. -
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43J8_43_EASTLAND_OAK_SW?$swatch$ -
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43J8_01_EASTLAND_BLACK_SW?$swatch$
Description:
Step into effortless style with these boots from Eastland. Designed for the modern man who values both versatility and comfort, they feature a timeless plain toe look that pairs as easily with your office wardrobe as it does with your weekend denim. The elastic side panels and pull tab make slipping them on a breeze. Built with durable leather and a sturdy sole, they're ready to wander wherever you're headed. Whether it's coffee runs or a night on the town, these boots keep you grounded in style. -
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Description:
Built for everyday versatility, this chukka boot features a full-grain leather upper that adds a rich, polished finish to casual and business-casual looks alike. The durable, super lightweight rubber and EVA combo outsole delivers comfort without the bulk, making it ideal for long days on your feet. Pair it with slim-fit jeans and a Henley for a relaxed weekend vibe, or style it with tailored trousers and a sport coat for a modern office-ready ensemble. -
Description:
With a smooth leather upper that's easy to care for, this pull-on boot delivers everyday polish with minimal effort. The Active Memory Foam comfort insole cushions each step, while the flexible TPR outsole moves with you for all-day wearability. Slip it on with slim jeans and a utility jacket for a casual, go-anywhere look, or pair it with khakis and a sweater for a laid-back office outfit. -
Description:
Crafted for everyday wear, the Whitby chukka delivers a modern take on a timeless favorite. Its smooth synthetic leather upper pairs effortlessly with both jeans and chinos, while the lightweight EVA outsole adds a sporty edge. With a cushioned insole and breathable lining, it's built for comfort without compromising style. -
Description:
The Braxton chukka boot is crafted from rich leather with subtle stitched details. Designed for flexibility and durability, they have a cushioned footbed and sturdy outsole that provide support whether you're heading to the office or exploring the city. The ankle-high profile delivers a tailored look that pairs effortlessly with denim, chinos, or even casual suiting, making it a go-to choice for transitional dressing and year-round wear. -
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43KA_42_JOHNSTON_MURPHY_WALNUT_SW?$swatch$ -
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43KA_38_JOHNSTON_MURPHY_BROWN_SW?$swatch$ -
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43KA_43_JOHNSTON_MURPHY_MAHOGANY_SW?$swatch$
Description:
The Calder boot brings together versatile design and everyday functionality. Crafted from rich leather, they feature elastic side panels and a pull tab for easy on-and-off wear. A natural fit for both dressier occasions and casual outings, this pair features a cushioned footbed and soft lining for lasting comfort. The durable outsole offers reliable traction. Pair them with denim, chinos, or tailored trousers for effortless style you can rely on. -
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Online ExclusiveThe sale price is $179.00Please choose a color.
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43KD_01_JOHNSTON_MURPHY_BLACK_SW?$swatch$ -
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43KD_38_JOHNSTON_MURPHY_BROWN_SW?$swatch$
Description:
Bridging rugged charm and refined style, the Johnston & Murphy Calder Chukka Boots are a versatile staple for a modern wardrobe. Crafted from premium leather, these ankle-high boots have subtle stitching and a classic lace-up design. The cushioned footbed and soft lining provide all-day comfort, while the durable outsole offers reliable traction on a variety of surfaces. -
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Going FastOnline ExclusiveThe sale price is $135.00Please choose a color.
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43JF_41_FLORSHEIM_COGNAC_SW?$swatch$ -
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43JF_01_FLORSHEIM_BLACK_SW?$swatch$
Description:
Polished yet practical, these Florsheim chukka boots deliver everyday versatility with a refined edge. Crafted from rich leather and set on a durable rubber sole, it pairs classic chukka styling with modern comfort features. A cushioned footbed and soft Suedetec lining provide support from morning commutes to evening plans, while the clean plain toe keeps your look sharp. Whether you're dressing up denim or adding a relaxed touch to tailored trousers, this boot moves effortlessly through the week. -
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Description:
Modern and versatile, the Stacy Adams Townsend boot is crafted from rich tumbled leather with gore panels for easy on-and-off wear. It pairs effortlessly with both casual and dress looks, while the RedZone cushioned footbed provides anatomical arch support and a molded heel cup for enhanced comfort. A lightweight sole adds flexibility and durability, making this Chelsea boot a reliable choice for everyday style with a refined edge. -
Online ExclusiveThe sale price is $140.00Please choose a color.
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43JK_38_FLORSHEIM_BROWN_CH_SW?$swatch$ -
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43JK_01_FLORSHEIM_BLACK_SW?$swatch$
Description:
An instant classic, these Florsheim chukka Boots blend smooth leather with modern stitching and a cool stacked heel. Its versatile design pairs effortlessly with chinos or jeans, making it your go-to for countless occasions. Inside, you'll find soft, comfortable Suedetec linings and a fully cushioned footbed with Ortholite high-rebound foam for exceptional all-day comfort, all supported by a durable rubber sole. -
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Description:
A smooth leather upper and stacked heel give this chukka boot a versatile, stylish look, while breathable textile linings add all-day ease. The removable footbed features OrthoLite high-rebound foam and a molded EVA heel cup for superior cushioning and support. A durable rubber outsole completes the design, offering reliable traction with every step. -
Description:
Made with a smooth leather upper and a modern stacked heel, this Florsheim boot slips on easily thanks to flexible side gore panels. Inside, a breathable textile lining and cushioned, removable footbed with OrthoLite high-rebound foam, and a molded EVA heel cup deliver lasting support. A durable rubber outsole rounds out the design, offering reliable traction for workdays and weekends alike. -
Description:
A blend of durability and sophisticated style, these Florsheim boots feature a smooth leather upper with elegant lines of stitching and a plain toe design. While it offers a secure lace-up closure, a convenient side zipper ensures an easy-on, easy-off fit. Its versatile style is complemented by a modern lug outsole, providing durability, traction, and comfort. Inside, breathable textile linings and a fully cushioned, removable footbed with OrthoLite high rebound foam and a molded EVA heel cup offer exceptional long-term wearability and support. -
Online ExclusiveThe sale price is $150.00Please choose a color.
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43J4_40_BORN_SHOES_CHOCOLATE_SW?$swatch$ -
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43J4_01_BORN_SHOES_BLACK_SW?$swatch$
Description:
Crafted from full-grain leather, this pull-on boot showcases timeless style and rich character that only improves with wear. A breathable leather and microfiber lining, paired with a foam-cushioned, leather-covered footbed, delivers exceptional comfort. Finished with a high-traction, lightweight rubber outsole and stacked wood-finish heel, it's built for stability and style, while the Opanka handcrafted construction ensures lasting durability and flexibility. -
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Going FastOnline ExclusiveThe sale price is $145.00Please choose a color.
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43JB_38_FLORSHEIM_BROWN_CH_SW?$swatch$ -
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43JB_45_FLORSHEIM_MOCHA_SW?$swatch$ -
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43JB_16_FLORSHEIM_SADDLE_TAN_SW?$swatch$ -
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43JB_01_FLORSHEIM_BLACK_SW?$swatch$
Description:
Classic design meets modern edge in these Florsheim Chukka boots. With a clean three-eyelet profile and stacked heel, they bring effortless style to everything from office hours to off-duty adventures. Crafted from rich leather, these boots pair perfectly with jeans and a sport coat for a look that's both polished and relaxed. Inside, soft Suedetec linings and a cushioned, removable EVA footbed wrapped in leather provide lasting comfort and flexibility, while the durable rubber outsole ensures reliable traction wherever the day takes you. -
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43JC_16_FLORSHEIM_SADDLE_TAN_SW?$swatch$ -
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43JC_38_FLORSHEIM_BROWN_CH_SW?$swatch$ -
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43JC_45_FLORSHEIM_MOCHA_SW?$swatch$ -
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43JC_01_FLORSHEIM_BLACK_SW?$swatch$
Description:
Effortlessly stylish and endlessly versatile, these Florsheim boots are designed to keep up with wherever life takes you. Crafted in rich leather, their clean lines and modern silhouette make them a natural match for everything from tailored trousers to worn-in denim. Inside, soft Suedetec linings and a fully cushioned, removable EVA footbed wrapped in leather deliver comfort that lasts all day. Finished with a durable rubber outsole for added traction and flexibility, it's the kind of boot you'll want to keep on rotation. -
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Description:
These Chelsea boots blend classic style with modern innovation for unmatched all-day comfort. The refined silhouette transitions effortlessly from office to evening. Inside, Cole Haan's FlexCraft™ technology delivers hidden foam cushioning and enhanced flexibility, making each step feel smooth and supported. The lightweight Grand.OS energy foam sole adds responsive comfort and shock absorption, while the durable construction ensures lasting wear. Perfect for professionals on the move, these boots elevate your look without compromising on comfort. -
Online ExclusiveThe sale price is $110.00Please choose a color.
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438P_01_CLARKS_BLACK_SW?$swatch$ -
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438P_20_CLARKS_SAND_SW?$swatch$
Description:
Rooted in heritage but made for today, this evolution of the iconic Clarks Desert boot brings modern comfort to a timeless silhouette. With premium leather, a streamlined profile, and a lightweight EVA outsole, they have the same classic style with enhanced cushioning and flexibility. It's a smart, everyday staple that pairs effortlessly with jeans, chinos, and more. -
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Online ExclusiveThe sale price is $169.00Please choose a color.
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40GR_70_JOHNSTON_MURPHY_BLUE_SW?$swatch$ -
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40GR_12_JOHNSTON_MURPHY_IVORY_SW?$swatch$
Description:
Crafted from soft nubuck leather, these perforated plain toe Oxfords bring a modern, breathable twist to a classic lace‑up silhouette. The smooth leather lining enhances comfort, while a removable, contoured footbed with memory foam provides personalized cushioning that supports you throughout the day. An ultra‑light TRUFOAM midsole delivers responsive comfort without added weight, complemented by a padded collar and tongue for an easy, secure fit. Finished with durable rubber pods on the outsole for reliable traction, this style blends everyday versatility with elevated, lightweight comfort. -
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Online ExclusiveThe sale price is $65.95More Colors for Florsheim Vibe Jr. Boys Plain Toe Chukka Boots. Link will open product details page.Please choose a color.
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43L1_38_FLORSHEIM_BROWN_CH_SW?$swatch$ -
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43L1_01_FLORSHEIM_BLACK_SW?$swatch$
Description:
Stylish enough for special occasions and tough enough for everyday play, this kids' plain toe chukka boot delivers grown-up looks with all the comfort a young wearer needs. The durable manmade upper stands up to school days and weekend adventures, while soft Suedetec lining keep things cozy inside. A cushioned memory foam footbed ensures all-day support, and the lightweight outsole with Flexsole Technology offers flexibility and traction right out of the box. -
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Online ExclusiveThe sale price is $120.00Please choose a color.
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43DK_40_NUNN_BUSH_BROWN_CZ_HORSE_SW?$swatch$ -
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43DK_18_NUNN_BUSH_TAN_CZ_HORSE_SW?$swatch$ -
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43DK_01_NUNN_BUSH_BLACK_TUMBLE_SW?$swatch$
Description:
Rich leather, subtle perfing, and a stacked-look sole give these Nunn Bush chukkas a refined yet relaxed feel that transitions effortlessly from office hours to after hours. Crafted from genuine crazy horse or tumbled leather with soft Suedetec linings, they deliver a smooth, comfortable fit. Underfoot, the molded Dual Comfort footbed made with recycled content blends cushioning and arch support for all-day ease. Finished with a lightweight EVA and durable rubber sole, these chukkas are built for style, comfort, and everyday wearability. -
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All offers can be modified or canceled anytime and are subject to product availability. Selection varies by store and online. Offers are valid on new orders only. Offers cannot generally be combined with other offers. Discounts are not redeemable for cash or credit. Customers returning purchased items will forfeit any discounts applied to those items at the time of purchase; the Jos. A. Bank return policy will apply to the remainder of the purchase. Bank Account Rewards® points are earned only on amounts expended by you in connection with the purchase and are deducted for any returns.
All online orders over $50 (before taxes) placed and shipped within the U.S. are eligible for free standard shipping.
Deal of the Day: Select styles and colors. Additional charge for Big & Tall sizes. Excludes Custom. Ends 11:59 p.m. CT.
