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Cushioned Insoles Leather Casual Shoes

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  • Gift Badge For Jos. A. Bank Hybrid Wingtip Shoes
    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:
    Bridging the gap between dress shoe and sneaker, these versatile shoes feature a classic wingtip upper crafted from smooth leather for a touch of sophistication. But look underneath, and you'll find a crisp white sole, a modern twist that injects a touch of sporty flair. This unexpected detail makes them perfect for dressed-down office looks or weekend adventures.
  • Gift Badge For Jos. A. Bank Hybrid Derby Shoes
    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:
    Bridging the gap between dress shoe and sneaker, these versatile shoes feature a classic derby upper crafted from smooth leather for a touch of sophistication. But look underneath, and you'll find a crisp white sole, a modern twist that adds a touch of sporty flair. This unexpected detail makes them perfect for dressed-down office looks or weekend adventures.
  • Gift Badge For Florsheim Remi Plain Toe Oxfords
    The regular price is   $135.00 The sale price is   $101.25 sale

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

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    Description:
    Clean lines over a smooth leather upper lend classic style to these plain-toe Oxfords from Florsheim. With a padded footbed, soft and comfortable Suedetec lining, and rubber sole, these versatile lace-ups can be worn with anything from slacks to chinos to jeans.
  • Gift Badge For Florsheim Capitol Canvas Plain Toe Lace Up 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:
    Lighten up for warm weather without missing a step in this casually cool Oxford from Florsheim. Leather details add rich contrast to the smooth canvas upper. Soft, comfortable Suedetec lining. Durable rubber sole. Imported.
  • Gift Badge For Florsheim Finance Cap Toe Oxfords
    The regular price is   $140.00 The sale price is   $105.00 sale

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

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    Description:
    Smooth and stylish, these classic cap-toe oxfords will complete your dress-wear look. Breathable, durable, and soft leather quarter linings and sock liner. Fully cushioned insole with removable footbed with ortholite high rebound foam. Flexible rubber sole. Full grain leather upper. Spot clean. Imported.
  • Gift Badge For Belvedere Fernando Woven Slip On Sneakers
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    The regular price is   $219.00 The sale price is   $164.25 sale

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

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    Description:
    Where ease meets craftsmanship, this Belvedere sneaker is a study in understated luxury. Handwoven Nappa leather panels form the upper, offering breathable texture and a striking visual finish. Smooth leather trim and dual elastic side gores ensure a flexible, slip-on fit, while the cushioned leather-lined interior and lightweight rubber sole provide all-day comfort and modern polish. Handmade in Brazil and designed in California, this versatile sneaker transitions effortlessly from weekday to weekend.
  • Gift Badge For Florsheim Vibe Jr. Boys Plain Toe Chukka Boots
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    The sale price is   $65.95
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    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.
  • Gift Badge For Florsheim Croquet Jr Boys Moc Toe Penny Loafers
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    The sale price is   $65.95
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    Description:
    These penny loafers bring grown-up style to little feet with smooth vegan leather uppers, a lightweight unlined design, and cushy memory foam footbeds that keep him comfortable all day long. Whether dressing up for a special occasion or a school function, this loafer delivers timeless style with kid-tough durability thanks to its sturdy rubber sole.
  • Gift Badge For Florsheim Rucci Jr. Boys Cap Toe Oxfords
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    The sale price is   $59.95
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    Description:
    Ready for special occasions, this cap toe Oxford brings grown-up style to little feet with its smooth faux leather upper and modern profile. Inside, soft Suedetec lining and a cushioned memory foam footbed keep him comfortable all day long, while the durable rubber sole is built to keep up with every step, from school ceremonies to family celebrations.
  • Gift Badge For Johnston & Murphy Anders Perforated U Throat Sneakers
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    The sale price is   $159.00
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    Description:
    Sporty yet sophisticated, these Johnston & Murphy sneakers offer a fresh take on casual footwear. Perforated leather uppers add texture and breathability while maintaining a modern look. The cushioned interior and flexible sole provide all-day comfort, making them ideal for travel, weekend outings, or everyday wear. They pair effortlessly with everything from jeans to chinos.
  • Gift Badge For Florsheim Monopoli Elastic Lace-To-Toe Sneakers
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    The sale price is   $120.00
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    Description:
    Designed for ease without sacrificing style, these Florsheim sneakers with elastic no-tie laces make getting out the door faster and more comfortable than ever. The richly burnished leather upper adds a polished touch, while the athletic sole keeps your look grounded and versatile. Inside, soft Suedetec linings and a fully cushioned, removable Comfortech footbed with molded SupaCush EVA provide all-day support and flexibility. Finished with a durable rubber outsole, these sneakers are built for wherever your day takes you no laces required.
  • Gift Badge For Born Allegheny II Sneakers
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    The sale price is   $130.00
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    Description:
    These shoes bring back a modern classic with rugged style and a relaxed, broken-in look. Crafted in hand-finished full-grain leather, they're built for comfort with a breathable microsuede lining and a removable, foam-cushioned footbed. The lightweight rubber outsole offers flexibility and traction, while Born's signature 2-Way Opanka construction ensures lasting durability. Finished with a subtle 1-inch heel, it's a versatile everyday staple with handcrafted character.
  • Gift Badge For Ben Sherman Boxwell Sneakers
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    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:
    The Boxwell sneaker by Ben Sherman delivers a retro-inspired silhouette with modern updates. The synthetic leather upper is accented by a contrast suede heel patch and subtle logo details, while a cushioned footbed and soft lining offer everyday comfort. Finished with a vulcanized rubber sole, it's a versatile sneaker that pairs effortlessly with casual looks.
  • Gift Badge For Ben Sherman Centre Sneakers
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    The regular price is   $65.00 The sale price is   $48.75 sale

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

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    Description:
    Designed for comfort and versatility, these sneakers feature a cushioned memory foam insole and a synthetic nubuck upper. The lace-up closure ensures a secure fit, while the rubber outsole provides reliable traction for everyday wear. Available in neutral tones, they pair effortlessly with casual or smart-casual outfits.
  • Gift Badge For Ben Sherman Hampton Sneakers
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    The regular price is   $65.00 The sale price is   $48.75 sale

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

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    Description:
    With a crisp silhouette and retro-inspired design, these low-top sneakers bring a modern edge to classic court style. The synthetic leather upper is accented by Ben Sherman's signature mod stripe, while added padding on the tongue and collar enhances comfort. A cushioned insole and breathable lining make them ideal for all-day wear, and the rubber outsole ensures durability with every step.
  • Gift Badge For Florsheim Monopoli Lace-To-Toe Sneakers
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    The sale price is   $120.00
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    Description:
    Elevate your everyday look with these Florsheim sneakers a perfect blend of sport and sophistication. The richly burnished leather upper adds a refined touch, while the athletic-inspired sole keeps things casual and comfortable. Inside, soft Suedetec linings and a fully cushioned, removable Comfortech footbed with molded SupaCush EVA deliver support that lasts from your morning commute to after-hours plans. Finished with a durable rubber outsole, it's the kind of sneaker that moves seamlessly between dressed-up and laid-back.
  • Gift Badge For Cole Haan GrandPro Half Court SkyWeave Sneakers
    Online Exclusive
    The sale price is   $180.00
    Description:
    A modern take on the classic court sneaker, this pair is crafted with a breathable SkyWeave™ upper and ultra-lightweight construction. They're engineered for comfort with responsive cushioning, a molded footbed for arch support, and a flexible rubber outsole for traction. Relaxed enough for casual wear, supportive enough for all-day movement.
  • Gift Badge For Nunn Bush Kore EZ Icon Plain Toe Oxfords
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    The regular price is   $110.00 The sale price is   $82.50 sale

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

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    Description:
    Versatile and built for comfort, these Nunn Bush Oxfords are a wardrobe staple with a modern edge. Crafted from smooth leather, they feature breathable, fully padded linings for all-around comfort and moisture control. The Dual Comfort footbed combines two EVA foam layers with arch support for cushioned support throughout the day. A dual-density KORE midsole and slip-resistant rubber sole offer shock absorption and traction, while Flex Technology and an EZ rigid heel make for easy movement and effortless on-and-off wear.
  • Gift Badge For Nunn Bush Griff Plain Toe Oxfords
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    The regular price is   $110.00 The sale price is   $82.50 sale

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

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    Description:
    With a polished leather upper and an athletic-inspired sole, these Nunn Bush Oxfords effortlessly blends dressy style with everyday comfort. A hidden elastic gore patch ensures easy on-and-off and a flexible, personalized fit, while fully padded mesh linings keep your feet cool and supported. The Dual Comfort footbed crafted with two EVA foam layers and arch support offers cushioning that lasts all day, and the lightweight sole with a rubber heel pod absorbs impact with every step.
  • Gift Badge For Cole Haan Grand Crosscourt Daily Laser Sneakers
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    The regular price is   $130.00 The sale price is   $97.50 sale

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

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    Description:
    A stylish fusion of athletic comfort and refined design, these Cole Haan sneakers offer exceptional versatility for everyday wear. The upper features laser-cut details, which provide a modern aesthetic and enhanced breathability. Engineered with GRANDFOAM cushioning, they ensure responsive, all-day comfort and support, making them a polished choice for elevated casual looks.
  • Gift Badge For Clarks Eldredge Step Slip-On Shoes
    The sale price is   $130.00
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    Description:
    The Eldredge Step blends polished looks with Clarks signature comfort technology. Effortlessly versatile, this slip-on shoe combines classic style with everyday comfort. Made from smooth leather with subtle stitching details, it features elastic side gores for easy on-and-off wear. A cushioned EVA footbed and slip-resistant rubber sole provide support and stability, making it an ideal choice for work, travel, or casual outings.
  • Gift Badge For Cole Haan Grand Crosscourt Daily Lace-to-Toe Sneakers
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    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:
    Versatile and modern, these lace-to-toe sneakers have a sharp, minimalist look that works just as well with jeans as it does with chinos. Made from fine leather with subtle perforated accents, they feature a lightweight EVA outsole with rubber pods for added grip. A cushioned GrandFoam footbed ensures lasting comfort throughout the day.
  • Gift Badge For Clarks Wallabee EVO Shoes
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    The sale price is   $100.00
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    Description:
    Expanding on a classic, this updated version arrives in premium leather or suede for versatile, everyday style. The natural crepe-effect rubber outsole adds a retro-cool vibe while delivering durability and traction. With a supersoft footbed and signature suede logo fobs, each step feels easy and unmistakably authentic.
  • Gift Badge For Belvedere Studio Marcio Double Buckle Monk Strap Shoes
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    The regular price is   $179.00 The sale price is   $134.25 sale

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

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    Description:
    Sophisticated and distinctive, these shoes from Belvedere make a bold statement with a trim silhouette and rich leather construction. The double monk strap design adds a modern twist to classic craftsmanship, offering both elegance and edge. Finished with fine detailing and a cushioned insole for comfort, these shoes are a standout choice for dressing up your tailored looks or elevating everyday style.