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Cushioned Insoles Leather Shoes

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  • Gift Badge For Vintage Foundry Dwight Dress Penny Loafers
    Online Exclusive
    The sale price is   $110.00
    Please choose a color.
    Description:
    Refined and timeless, these penny loafers from Vintage Foundry are a nod to classic sophistication. Crafted from smooth leather with a signature penny keeper strap, it's the kind of shoe that transitions seamlessly from boardroom to dinner out. Cushioned for comfort and built to last, these shoes are a smart staple for your footwear collection.
  • Gift Badge For Eastland Sea Dog Boat Shoes
    Online Exclusive
    The sale price is   $110.00
    Please choose a color.
    Description:
    Anchor your style with these Eastland boat shoes. Built for life on and off the water, they feature soft, full-grain leather uppers, classic handsewn moccasin construction, and a 360-degree rawhide lacing system with rustproof eyelets for a secure fit. Inside, a leather-lined, molded EVA insole cushions and supports your foot's natural shape for lasting comfort. A shock-absorbing, flexible natural rubber outsole offers dependable durability and traction.
  • Gift Badge For Rockport Garrett Plain Toe Shoes
    Online Exclusive
    The sale price is   $135.00
    Description:
    Clean lines and all-day comfort come together in this versatile plain toe Oxford. Made from smooth leather with a lightweight EVA outsole, it offers a polished look that transitions easily from work to weekend. Heel cushioning and a removable memory foam footbed deliver comfort with every step.
  • Gift Badge For Born Captain Sneakers
    Online Exclusive
    The sale price is   $130.00
    Description:
    These sneakers combine casual style with exceptional comfort. Handcrafted with full-grain leather and a breathable leather lining, they offer a relaxed yet refined look that's perfect for everyday wear. A cushioned footbed and lightweight, flexible outsole ensure all-day support, making it an ideal choice for weekend outings or laid-back office days.
  • Gift Badge For Rockport ProWalker Eureka Plus Slip-On Shoes
    Online Exclusive
    The sale price is   $120.00
    Please choose a color.
    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 Florsheim Finance Plain Toe Oxfords
    Online Exclusive
    The sale price is   $149.50
    Please choose a color.
    Description:
    These Florsheim Oxfords offer a sophisticated, streamlined look ideal for both professional and dressier settings. Crafted from high-quality leather, they feature a simple yet refined plain toe design that pairs well with a variety of looks. The cushioned footbed provides comfort throughout the day, while the durable outsole ensures reliable traction.
  • Gift Badge For Born Langley Penny Loafers
    Online Exclusive
    The sale price is   $140.00
    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 Florsheim Remi Cap Toe Oxfords
    Online Exclusive
    The sale price is   $135.00
    Please choose a color.
    Description:
    These plain toe Oxfords from Florsheim have a clean, elegant design that perfectly complements your dress or dress-casual style. Crafted with genuine leather uppers, they also feature a fully cushioned footbed for all-day comfort.
  • Gift Badge For Born Todd Plain Toe Oxfords
    Online Exclusive
    The sale price is   $120.00
    Please choose a color.
    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 sale price is   $130.00
    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 Rockport Garrett Plain Toe Oxfords
    Online Exclusive
    The sale price is   $125.00
    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 Eastland Leap Trainer Boat Shoes
    Online Exclusive
    The sale price is   $135.00
    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 sale price is   $125.00
    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 sale price is   $110.00
    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 Remi Plain Toe Oxfords
    The sale price is   $135.00
    Please choose a color.
    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 Newtown Plain Toe Lace-Up Oxfords
    Online Exclusive
    The sale price is   $135.00
    Please choose a color.
    Description:
    We love the versatility of these Oxfords from Florsheim. They pair just as perfectly with jeans and chinos as they do with dress slacks. The soft, comfortable Suedetec linings are smooth to the touch, while the fully cushioned, Comfortech footbed with molded EVA offers long-term wearability. Flexible TPU midsole for enhanced comfort. Durable and lightweight TPU outsole with Flexsole technology for out-of-the-box comfort.
  • Gift Badge For Florsheim Capitol Canvas Plain Toe Lace Up Oxfords
    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 Remi Moc Toe Slip-On
    Online Exclusive
    The sale price is   $135.00
    Please choose a color.
    Description:
    These moc toe slip-on shoes from Florsheim have a clean, elegant design that perfectly complements any dress or casual style. Crafted with genuine leather uppers, they also feature fully cushioned footbeds for all-day comfort.
  • Gift Badge For Florsheim Finance Cap Toe Oxfords
    The sale price is   $140.00
    Please choose a color.
    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 Silvano Formal Sneakers
    New
    The sale price is   $169.00
    Description:
    Step into elevated style with Belvedere. Crafted from rich black velvet and accented with genuine patent leather, their hip style blends luxury with modern edge. Hidden elastic laces create a smooth look and are easy wearing, while a padded collar and tongue ensure all-day comfort. Finished with a breathable lining and durable rubber sole, it's the perfect choice for dressing up without sacrificing ease.
  • Gift Badge For Belvedere Eros Formal Sneakers
    New
    Online Exclusive
    The sale price is   $169.00
    Description:
    Elevate your formal footwear game with Belvedere. This low-top sneaker features a luxurious velvet upper paired with smooth leather accents at the toe, heel, and eyestay. Hidden elastic laces offer a clean, slip-on fit, while the fully padded tongue and collar ensure comfort with every step. A breathable lining and foam-cushioned insole enhance wearability, and the durable rubber sole provides reliable grip and flexibility. The Eros is ideal for pairing with tailored suiting or upscale casual looks.
  • Gift Badge For Johnston & Murphy XC Flex Harrison Penny Loafers
    New
    Online Exclusive
    The sale price is   $169.00
    Please choose a color.
    Description:
    Polished and performance-driven, these penny loafers reimagine a timeless silhouette with modern comfort technology. Its classic penny strap and moc toe design offer understated good looks, while Johnston & Murphy's XC Flex construction ensures flexibility and support with every step. A removable memory-foam footbed provides personalized cushioning, and the ultralight TRUFOAM midsole delivers high-rebound comfort ideal for long days on your feet. Finished with a flexible, grooved sole and rubber pod inserts for enhanced traction, this loafer is perfect for travel, commuting, or everyday wear.
  • Gift Badge For Johnston & Murphy XC Flex Harrison Bit Loafers
    New
    Online Exclusive
    The sale price is   $169.00
    Please choose a color.
    Description:
    Refined and ready for anything, the Harrison loafer combines timeless style with advanced comfort features. The soft suede upper is accented by a metal bit, adding a touch of polish to the classic moc toe silhouette. Built with Johnston & Murphy's XC Flex technology, this loafer features a high-rebound TRUFOAM midsole and a flexible, grooved sole with rubber pod inserts for lightweight cushioning and excellent traction. Inside, a removable memory-foam footbed offers personalized support, while the antimicrobial-treated leather and mesh lining ensures lasting freshness. Whether you're dressing for the office or heading out for the weekend, this loafer delivers all-day comfort.
  • Gift Badge For Johnston & Murphy Braxton Plain Toe Oxfords
    New
    Online Exclusive
    The sale price is   $149.00
    Please choose a color.
    Description:
    The Braxton's smooth leather upper and minimalist design make it a versatile choice for both professional and polished casual looks. The plain toe keeps the profile simple, while subtle stitching adds just the right amount of detail. Inside, a cushioned footbed provides all-day comfort, and the durable outsole ensures reliable traction and wear. Whether paired with tailored trousers or dark denim, this shoe is one to keep on your footwear rotation.