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  • Gift Badge For Johnston & Murphy Calder Chelsea Boots
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    Online Exclusive
    The sale price is   $179.00
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    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.
  • Gift Badge For Johnston & Murphy Calder Chukka Boots
    New
    The sale price is   $179.00
    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.
  • Gift Badge For Johnston & Murphy Braxton Chukka Boots
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    Online Exclusive
    The sale price is   $159.00
    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.
  • Gift Badge For Florsheim Plain Toe Chukka Boots
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    The sale price is   $135.00
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    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.
  • Gift Badge For Stacy Adams Townsend Plain Toe Chelsea Boots
    New
    The regular price is   $150.00 The sale price is   $105.00 sale

    30% Off Select Shoes! 2 Days Only! (Price reflects discount)

    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.
  • Gift Badge For Jos. A. Bank Dress Chelsea Boots
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    Online Exclusive
    The regular price is   $145.00 The sale price is   $101.50 sale

    30% Off Select Shoes! 2 Days Only! (Price reflects discount)

    Description:
    Timeless and versatile, these classic leather Chelsea boots add polish to your wardrobe. Featuring clean lines, elastic side gores, and a streamlined silhouette, they slip on easily and pair effortlessly with both tailored looks and casual denim. Crafted from smooth leather, they offer durability, comfort, and refined style in equal measure.
  • Gift Badge For Jos. A. Bank Chelsea Boots
    New
    The regular price is   $145.00 The sale price is   $101.50 sale

    30% Off Select Shoes! 2 Days Only! (Price reflects discount)

    Description:
    For a refined yet versatile footwear option, consider the Joseph Abboud Beaumont Suede Chelsea Boots from Jos. A. Bank. Crafted from soft suede, these boots feature elastic side gores for easy slip-on and removal, ensuring both style and convenience. The tapered toe design and welt profile provide a modern silhouette that pairs effortlessly with both chinos and casual denim.
  • Gift Badge For Stacy Adams Brumley Moc Toe Lace Up Boots
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    The regular price is   $160.00 The sale price is   $112.00 sale

    30% Off Select Shoes! 2 Days Only! (Price reflects discount)

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    Description:
    Rugged meets refined in the Brumley boot, a versatile style from the brand's FlexZone collection. Featuring a rich, hand-burnished upper with a modern mix of materials, colors, and textures, this boot is designed for both visual impact and all-day comfort. The FlexZone cushioned footbed includes a molded heel cup and sustainable microfiber cover, offering anatomical arch support that adapts to your stride. Soft microfiber linings enhance comfort, while the lace-up design and moc toe silhouette add a classic touch to a contemporary silhouette.
  • Gift Badge For Florsheim Forge Plain Toe Chukka Boots
    New
    Online Exclusive
    The sale price is   $130.00
    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.
  • Gift Badge For Florsheim Lodge Chukka Boots
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    Online Exclusive
    The sale price is   $140.00
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    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.
  • Gift Badge For Jos. A. Bank Pebbled Leather Chukka Boots
    New
    The regular price is   $140.00 The sale price is   $98.00 sale

    30% Off Select Shoes! 2 Days Only! (Price reflects discount)

    Description:
    For a versatile and stylish addition to your footwear collection, consider the leather chukka boots from Jos. A. Bank. Crafted with a rich leather upper, they offer a timeless appeal suitable for various occasions. The classic silhouette is enhanced with a durable lug sole, providing added traction and making them ideal for navigating unpredictable weather or exploring off-the-beaten-path. Whether paired with chinos for a polished look or jeans for a more casual ensemble, these boots are designed to elevate your style effortlessly.
  • Gift Badge For Jos. A. Bank Chukka Boots
    New
    The regular price is   $140.00 The sale price is   $98.00 sale

    30% Off Select Shoes! 2 Days Only! (Price reflects discount)

    Description:
    Refined yet rugged, this Jos. A. Bank chukka boot strikes the perfect balance between polish and versatility. Crafted from smooth leather with classic eyelet styling, it's designed for comfort and easy pairing from tailored trousers to your favorite jeans. A timeless staple built for seasons of wear.
  • Gift Badge For Stacy Adams Henry Cap Toe Lace Boots
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    The regular price is   $165.00 The sale price is   $115.50 sale

    30% Off Select Shoes! 2 Days Only! (Price reflects discount)

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    Description:
    A modern take on a classic silhouette, the Henry boot is perfect for elevating your professional or casual style. Crafted with a polished upper and a distinctive cap-toe design, this boot offers a refined look that's both timeless and on-trend. The secure lace-up closure and durable stacked heel provide both a comfortable fit and lasting quality. Whether you pair it with a tailored suit or with dark denim, it's a versatile staple for your wardrobe.
  • Gift Badge For Florsheim Forge Plain Toe Chelsea Boots
    New
    Online Exclusive
    The sale price is   $130.00
    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.
  • Gift Badge For Florsheim Forge Plain Toe Lace Up Boots
    New
    Online Exclusive
    The sale price is   $135.00
    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.
  • Gift Badge For Born Reed Pull On Boots
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    Online Exclusive
    The sale price is   $150.00
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    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.
  • Gift Badge For Born Ryker Boots
    New
    The sale price is   $150.00
    Description:
    Step into rugged style with Born. Made from hand-finished leather, this cap toe boot combines classic looks with modern comfort. A cushioned footbed and breathable lining keep you comfortable all day, while the durable rubber outsole and stacked heel offer reliable traction and a polished finish. With Born's signature Opanka construction, the Ryker delivers flexibility, support, and timeless appeal perfect for everyday wear or dressing up your look.
  • Gift Badge For Florsheim Anthem Plain Toe Chukka Boots
    New
    Online Exclusive
    The sale price is   $145.00
    Please choose a color.
    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.
  • Gift Badge For Florsheim Anthem Plain Toe Chelsea Boots
    New
    Online Exclusive
    The sale price is   $145.00
    Please choose a color.
    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.
  • Gift Badge For Cole Haan Chamberlin Grand Cap Toe Boots
    New
    Online Exclusive
    The regular price is   $150.00 The sale price is   $105.00 sale

    30% Off Select Shoes! 2 Days Only! (Price reflects discount)

    Description:
    Refined yet rugged, these cap toe boots are built for versatility and comfort. They showcase meticulous upper detailing and premium materials, delivering a polished silhouette with a touch of edge. Designed with a smart outsole featuring multi-directional flex grooves, the boot mimics the foot's natural motion for smoother transitions and reduced fatigue. A quality internal lining enhances comfort, while the structured cap toe and durable construction make it ideal for both dressier occasions and everyday wear.
  • Gift Badge For Cole Haan Chamberlain Grand Chelsea Boots
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    The regular price is   $150.00 The sale price is   $105.00 sale

    30% Off Select Shoes! 2 Days Only! (Price reflects discount)

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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.
  • Gift Badge For Nunn Bush Ozark II Plain Toe Chukkas
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    The regular price is   $120.00 The sale price is   $84.00 sale

    30% Off Select Shoes! 2 Days Only! (Price reflects discount)

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    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.
  • Gift Badge For Nunn Bush Otis II Plain Toe Chelsea Boots
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    Online Exclusive
    The regular price is   $120.00 The sale price is   $84.00 sale

    30% Off Select Shoes! 2 Days Only! (Price reflects discount)

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    Description:
    Classic Chelsea styling meets modern comfort in this plain toe boot designed for all-day wear. Crafted from genuine leather with soft Suedetec linings, it offers a smooth fit and feel from the moment you slip it on. A Dual Comfort footbed featuring layered EVA foam and built-in arch support made with recycled content delivers sustainable cushioning. Finished with a durable yet lightweight sole that blends EVA and rubber, this boot brings together timeless design and advanced comfort in one versatile package.
  • Gift Badge For Nunn Bush Odell II Wingtip Boots
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    Online Exclusive
    The regular price is   $120.00 The sale price is   $84.00 sale

    30% Off Select Shoes! 2 Days Only! (Price reflects discount)

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    Description:
    Step into effortless style with these Nunn Bush wingtip boots, where classic masculine appeal meets modern lightweight comfort. Crafted from genuine leather paired with a durable manmade upper, this boot blends rugged charm with contemporary versatility. Inside, soft Suedetec linings provide a smooth, comfortable feel, while Dual Comfort technology combines two EVA foam compounds and built-in arch support for all-day cushioning with an eco-friendly touch. The outsole balances lightweight EVA with durable rubber.