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Cushioned Insoles Leather Casual Shoes

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  • Gift Badge For Eastland Oxfords
    Online Exclusive
    The regular price is   $110.00 The sale price is   $82.50 sale

    25% Off Select Shoes! Holiday Kick-Off Sale! (Price reflects discount)

    Description:
    A timeless classic, this Eastland Oxford delivers heritage style with everyday comfort. The handsewn moccasin construction gives it a crafted, authentic feel, while the full-grain leather upper is both durable and low-maintenance. Inside, Eastland's exclusive Active Memory Foam insole molds to your foot for personalized support, and the flexible natural rubber outsole absorbs shock and adds reliable traction.
  • Gift Badge For Eastland Boat Shoes
    Online Exclusive
    The regular price is   $110.00 The sale price is   $82.50 sale

    25% Off Select Shoes! Holiday Kick-Off Sale! (Price reflects discount)

    Description:
    Easygoing style meets everyday comfort in this versatile casual shoe, a fresh take on the classic boat shoe. Crafted with a full-grain leather upper and breathable nylon mesh panels, it s built for laid-back weekends and beyond. The padded tongue and supersoft, moisture-wicking insole deliver step-in comfort from day one, while a durable TPR rubber outsole offers reliable traction and support.
  • Gift Badge For Florsheim Fleet Knit Elastic Lace Sneakers
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    The sale price is   $120.00
    Please choose a color.
    Description:
    This sneaker offers a modern blend of comfort and style with its breathable knit upper and the convenience of a SupaStep hands-free design. Simply step in and go, thanks to the clever construction. Convenient elastic laces provide a secure and flexible fit, while the versatile design makes these perfect for casual outings or a more relaxed office vibe. A cushioned insole keeps you light on your feet throughout the day.
  • Gift Badge For Florsheim Motor Knit Moc Toe Penny Loafers
    Online Exclusive
    The sale price is   $110.00
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    Description:
    Laid-back style meets modern comfort in this lightweight knit penny loafer. Designed with a breathable upper and classic moc toe detailing, it's a fresh take on a timeless silhouette. The cushioned footbed and flexible sole deliver all-day comfort, making it an easy choice for everything from weekend outings to casual Fridays.
  • Gift Badge For Ben Sherman Richmond Sneakers
    The regular price is   $90.00 The sale price is   $67.50 sale

    25% Off Select Shoes! Holiday Kick-Off Sale! (Price reflects discount)

    Description:
    Retro vibes with a new attitude. The Richmond from Ben Sherman is dressed to impress in the most laid-back way with a leather upper rich with a mix of texture and strategically placed, signature stripes. Detailed with a perforated toe, padded collar, cushioned insole, and thick rubber outsole, these chic lace-ups wear well with chinos, jeans, and athletic-leisure wear.
  • Gift Badge For Stacy Adams Brinkley Moc Toe Shoes
    Online Exclusive
    The sale price is   $140.00
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    Description:
    Elevate your footwear game with these Stacy Adams slip ons. Featuring a moccasin-inspired toe and a polished bit detail across the upper, this slip-on effortlessly blends classic style with modern sophistication. The FlexZone removable footbed with molded heel offers customized comfort and support, ensuring all-day wearability. Ideal for both business and casual occasions, this versatile shoe is the perfect balance of style and practicality.
  • Gift Badge For Jos. A. Bank Plain Toe Oxfords
    The regular price is   $100.00 The sale price is   $75.00 sale

    25% Off Select Shoes! Holiday Kick-Off Sale! (Price reflects discount)

    Description:
    Elevate your footwear game with the timeless sophistication of these Oxfords. Featuring a smooth leather upper that transitions effortlessly from smart-casual to dressier occasions, its minimalist design pairs well with tailored suits, dress slacks, or even denim. A comfortable fit and durable construction ensure out-of-the-box wearability.
  • Gift Badge For Clarks Mapstone Sneakers
    Online Exclusive
    The sale price is   $130.00
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    Description:
    The perfect fusion of casual style and everyday comfort. Designed for versatility, this sneaker features a low-profile silhouette for a modern, laid-back look. The cushioned insole and lightweight EVA midsole provide superior comfort and support, making it ideal for all-day wear. A durable rubber outsole ensures excellent traction, whether you're exploring the city or running errands.
  • Gift Badge For Johnston & Murphy Upton Plain Toe Oxfords
    Online Exclusive
    The sale price is   $159.00
    Description:
    Timeless and versatile, these plain toe Oxfords are a true wardrobe staple. With their clean lines and smooth leather construction, they easily transition from office to evening. A classic lace-up design keeps the look polished, while thoughtful details like cushioned comfort and durable outsoles ensure they're as practical as they are stylish. Whether paired with a suit or dressed down with chinos, they deliver effortless sophistication every step of the way.
  • Gift Badge For Rockport ProWalker Eureka Plus Slip-On Shoes
    Online Exclusive
    The regular price is   $120.00 The sale price is   $90.00 sale

    25% Off Select Shoes! Holiday Kick-Off Sale! (Price reflects discount)

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    Description:
    Engineered with topnotch walking shoe technology, the Rockport ProWalker Eureka Plus is practical, fashionable, and incredibly comfortable. The richly pebbled leather upper features a fine moc toe, distinctive topstitching, and dual elastic gores for easy on and off. These trusty slip-ons have removable footbeds made with memory foam, as well the EVA midsole and heel cup that cushions every step. Featuring truTECH® for lightweight shock absorption, breathable mesh lining, and moisture wicking properties, these loafers are secured with a slip-resistant rubber sole.
  • Gift Badge For Born Langley Penny Loafers
    Online Exclusive
    The regular price is   $140.00 The sale price is   $105.00 sale

    25% Off Select Shoes! Holiday Kick-Off Sale! (Price reflects discount)

    Description:
    <p>These Born shoes offer a fresh, modern take on the classic loafer, combining style with lightweight comfort. Signature Opanka hand-crafted construction and&nbsp;hand-finished&nbsp;soft Italian leather upper&nbsp;result in trusted and luxurious quality.&nbsp; The microfiber suede covered footbed has extra foam for added comfort. The lightweight rubber outsoles provide strong&nbsp;traction.&nbsp; With a sleek penny strap detail and streamlined design, these loafers&nbsp;effortlessly transition from business casual to weekend wear, offering a versatile, easygoing option for any occasion.</p>
  • Gift Badge For Born Todd Plain Toe Oxfords
    Online Exclusive
    The regular price is   $120.00 The sale price is   $90.00 sale

    25% Off Select Shoes! Holiday Kick-Off Sale! (Price reflects discount)

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    Description:
    Distinctive stitching over soft, hand-finished leather defines the smooth attitude of these Todd shoes. Created by Born, these laid-back Oxfords are crafted with two-way Opanka patented construction for an unbelievably flexible fit. The removable, soft fabric suede covered footed has added foam for extra comfort, and the EVA outsole is both lightweight and high-traction.
  • Gift Badge For Cole Haan Grand Remix Plain Toe Oxfords
    The regular price is   $130.00 The sale price is   $97.50 sale

    25% Off Select Shoes! Holiday Kick-Off Sale! (Price reflects discount)

    Description:
    The is a modern take on a timeless classic, merging elegant style with contemporary comfort. Crafted with a smooth leather upper, this Oxford has a polished look ideal for both professional and dress-casual occasions. Its lightweight construction and Grand cushioning technology ensure all-day comfort, while the rubber outsole provides durability and traction. Versatile and refined, this shoe is perfect for anyone seeking a sophisticated yet comfortable option for daily wear.
  • Gift Badge For Born Marcel Moc Toe Driving Loafers
    Online Exclusive
    The sale price is   $110.00
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    Description:
    Quite possibly the most cozy loafers you'll ever wear outdoors, the Marcel exudes cool comfort and style. Created by Born, these debonaire drivers have a buttery soft, hand-finished leather upper, removable, plush foam footbed, and a lightweight, flexible rubber sole. Sewn with two-way Opanka handcrafted construction, these chic moc toes feature Born's signature Quad Gore Flex with two stretch points in the front and back. You can even forget your socks thanks to their soft and breathable moisture-wicking lining.
  • Gift Badge For Rockport Garrett Plain Toe Oxfords
    Online Exclusive
    The regular price is   $125.00 The sale price is   $93.75 sale

    25% Off Select Shoes! Holiday Kick-Off Sale! (Price reflects discount)

    Description:
    Upgrade your everyday footwear with Rockport. These oxfords combine classic style with modern comfort, making them a versatile choice. The smooth leather upper has a sophisticated look that transitions seamlessly from workday to weekend. A memory foam footbed and lightweight construction provide all-day comfort, while a flexible EVA outsole ensures a smooth, comfortable stride. Rock them with confidence, knowing you'll look sharp and feel great wherever you go.
  • Gift Badge For Johnston & Murphy XC4 Prentiss 2.0 Sneakers
    Online Exclusive
    The sale price is   $179.00
    Please choose a color.
    Description:
    This versatile shoe combines style and comfort with modern functionality. Designed with water-resistant leather, it offers durability while maintaining a polished look, suitable for both business and casual settings. The shoe features a memory-foam footbed and moisture-wicking lining, ensuring lasting comfort throughout the day. Additionally, its lightweight, flexible construction and rubber sole provide excellent traction and ease of movement, making it a solid choice for those who need a reliable, all-day wearing shoe with understated sophistication.
  • Gift Badge For Cole Haan Zerogrand Remastered Wingtip Oxfords
    The sale price is   $220.00
    Description:
    Create a look that's classic, creative, and sustainable. Cole Haan's ZERGRAND Remastered Wingtip Oxfords are crafted with a recycled leather upper adorned with ornate brogue detailing. These sneaker-like, lightweight lace-ups have been updated to reduce heel friction and add room at the toe. They feature a patented FlowerFoam&trade; EVA sole made from a minimum of 25% natural dandelion rubber. Cole Haan creates time-honored footwear and accessories rooted in craft, innovation and design. Reimagining tradition since 1928.
  • Gift Badge For Stacy Adams Synchro Plain Toe Shoes
    Online Exclusive
    The sale price is   $115.00
    Please choose a color.
    Description:
    This versatile shoe from Stacy Adams seamlessly blends classic dress shoe elegance with modern sneaker comfort. The result? A sophisticated yet relaxed look that transitions effortlessly from the office to a night out, or even a weekend getaway. Crafted with a rich leather upper and featuring a convenient elastic lace system, the Synchro offers both style and practicality.
  • Gift Badge For Eastland Leap Trainer Boat Shoes
    Online Exclusive
    The regular price is   $135.00 The sale price is   $101.25 sale

    25% Off Select Shoes! Holiday Kick-Off Sale! (Price reflects discount)

    Please choose a color.
    Description:
    Navigate any adventure in style and comfort with these boat shoes from Eastland. Designed for the modern explorer, they feature a timeless silhouette crafted from premium, full-grain leather for both durability and sophistication. Conquer any deck with the sewn-on rubber sole for superior traction on wet or dry surfaces, while the supportive footbed and moisture-wicking lining keep your feet cool and dry all day long.
  • Gift Badge For Eastland Baldwin Penny Loafers
    Online Exclusive
    The regular price is   $125.00 The sale price is   $93.75 sale

    25% Off Select Shoes! Holiday Kick-Off Sale! (Price reflects discount)

    Please choose a color.
    Description:
    The classic penny loafer gets a refresh with sleek lines and innovative materials. This updated design retains the timeless elegance of the original while offering a touch of contemporary flair, perfect for the modern wardrobe.
  • Gift Badge For Eastland Yarmouth Boat Shoes
    Online Exclusive
    The regular price is   $110.00 The sale price is   $82.50 sale

    25% Off Select Shoes! Holiday Kick-Off Sale! (Price reflects discount)

    Description:
    Embrace timeless moc comfort and effortless style with these Eastland boat shoes. This one-eyelet slip-on combines classic aesthetics with modern functionality. Handsewn moccasin construction provides a flexible and supportive fit, while the easy-to-care-for, soft and smooth leather upper offers both durability and luxurious comfort. Active memory foam comfort insoles mold to your foot for all-day support, and the shock-absorbing, flexible natural rubber outsole ensures reliable traction on any surface.
  • Gift Badge For Florsheim Dash Wing Tip Oxfords
    Online Exclusive
    The sale price is   $115.00
    Description:
    Make a statement without compromising comfort with these Oxfords from Florsheim. The classic wingtip design adds a touch of sophistication, while the athletic-inspired wedge sole offers unexpected flair. The soft suede linings and fully cushioned footbed ensure all-day comfort, making it perfect for those who value both style and practicality.
  • Gift Badge For Cole Haan Grand Crosscourt II Sneakers
    Online Exclusive
    The regular price is   $120.00 The sale price is   $90.00 sale

    25% Off Select Shoes! Holiday Kick-Off Sale! (Price reflects discount)

    Description:
    A casual classic that's always on-trend, these sneakers feature Cole Haan engineering inside and out. With a Grandfoam insole, you get all-day comfort and cushioned, lightweight steps.
  • Gift Badge For Cole Haan Grandpro Rally Laser Cut Sneakers
    Online Exclusive
    The sale price is   $160.00
    Description:
    A sneaker so light, your feet will thank you. The GrandPro Rally Laser Cut Sneaker combines a stylishly perforated leather upper with an Ortholite&reg; footbed for a soft, cushioned landing. Ventilating details and temp-regulating materials allow you to stay dry all day, everyday. The lightweight EVA outsole and minimally reinforced upper reduce weight without sacrificing comfort, while an anatomical last ensures an ideal fit.