skip to main content

Cushioned Insoles Leather Shoes

Refine your results

Filter
Clear All Filters
Total: 171 Products
Load More button at the bottom of this region will load more content above the button.
  • Gift Badge For Johnston & Murphy Dawson Perfed U-Throat Sneakers
    Online Exclusive
    The sale price is   $165.00
    Please choose a color.
    Description:
    Step into lightweight versatility with the Dawson sneaker, crafted for breathable comfort and modern refinement. Designed with a contoured, removable POWERFOAM footbed, these sneakers deliver cushioned support that keeps you comfortable from morning to night. The leather and mesh lining enhance airflow while providing a smooth, premium feel against the foot. A full‑grain leather upper pairs with a high‑rebound TRUFOAM midsole that adds bouncy, responsive comfort to every step. Finished with a padded tongue and collar for a secure, plush fit and a grooved rubber traction sole that offers flexibility and grip, these sneakers are built for everyday ease with elevated style.
  • Gift Badge For Johnston & Murphy Cort Moc Venetian Loafers
    Online Exclusive
    The sale price is   $155.00
    Please choose a color.
    Description:
    Easygoing sophistication comes naturally in this ultra‑flexible Venetian loafer, crafted with genuine handsewn moccasin construction that moves comfortably with every step. The combination of soft sheepskin and microfiber linings adds a touch of unexpected luxury inside. Underfoot, the highly cushioned, molded, and removable TruFoam footbed delivers lightweight rebound and all‑day support, making this an effortless choice for polished style that feels as good as it looks.
  • Gift Badge For Johnston & Murphy Tyson Perfed Plain Toe Oxfords
    Online Exclusive
    The sale price is   $169.00
    Please choose a color.
    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.
  • Gift Badge For Carrucci Moc Bit Patent Leather Loafers
    Online Exclusive
    The sale price is   $175.00
    Please choose a color.
    Description:
    Step into standout sophistication with these loafers from Carrucci, a refined, formal essential designed to elevate your most dressed?up looks. Crafted with a leather upper and full leather lining, this shoe offers a smooth, premium feel that pairs perfectly with its high?shine finish. The hand?finished patent leather, complete with a subtly burnished toe, adds depth and dimension to the polished silhouette. At the center, the loafer features exclusive horse bit hardware for a touch of timeless elegance. Ideal for tuxedos and other formal wear, it's built with comfort in mind too: a full?length cushioned, leather?lined footbed delivers support during long evenings or special occasions. The rubber sole is designed with an exclusive tread pattern that provides enhanced grip and slip resistance.
  • Gift Badge For Florsheim Jasper Jr. Boys Moc Toe Venetian Loafers
    Online Exclusive
    The sale price is   $65.95
    Please choose a color.
    Description:
    Keep him looking sharp and feeling comfortable in these Florsheim loafers. This classic slip-on features a clean, unadorned vamp and a stitched toe for timeless style that works for school, family events, or special occasions. Built for all-day wear, it includes a fully cushioned memory foam footbed for superior comfort and a durable rubber sole for long-lasting performance. Inside, breathable, moisture-wicking Suedetec linings help keep feet cool and dry, while the smooth faux leather upper adds a polished finish parents will love.
  • Gift Badge For Florsheim Vibe Jr. Boys Plain Toe Chukka Boots
    Online Exclusive
    The sale price is   $65.95
    Please choose a color.
    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
    Online Exclusive
    The sale price is   $65.95
    Please choose a color.
    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
    Online Exclusive
    The sale price is   $59.95
    Please choose a color.
    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 Florsheim Supacush Jr. Boys Plain Toe Oxfords
    Online Exclusive
    The sale price is   $65.95
    Please choose a color.
    Description:
    Create a casual yet polished look for the young gentleman in your life with the Supacush Jr. from Florsheim's Boys collection. Made with richly textured, milled leather and a smooth, plain toe, these Oxfords have a fully cushioned footbed and breathable Suedetec linings that wick away moisture with every step. The dual-density EVA midsole offers extra cushioning and rebound responsiveness while the rubber outsole is non-marking and slip-resistant.
  • Gift Badge For Florsheim Great Lakes Jr. Boys Wingtip Oxfords
    Online Exclusive
    Description:
    Striking the perfect balance between dress and casual, the Great Lakes Jr. from Florsheim's Boys collection will make a versatile, comfortable, and stylish addition to your young gentleman's wardrobe. Crafted from milled leather in classic wingtip fashion, these Oxfords feature a fully cushioned footbed and breathable Suedetec linings that wick away moisture with every step. The dual-density EVA midsole offers extra cushioning and rebound responsiveness while the rubber outsole is non-marking and slip-resistant.
  • Gift Badge For Belvedere Fernando Woven Slip On Sneakers
    Online Exclusive
    The regular price is   $219.00 The sale price is   $153.30 sale

    30% Off Select Shoes! (Price reflects discount)

    Please choose a color.
    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 Belvedere Silvano Formal Sneakers
    The regular price is   $169.00 The sale price is   $118.30 sale

    30% Off Select Shoes! (Price reflects discount)

    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
    Online Exclusive
    The regular price is   $169.00 The sale price is   $118.30 sale

    30% Off Select Shoes! (Price reflects discount)

    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 Nunn Bush Odell II Wingtip Boots
    Online Exclusive
    The regular price is   $120.00 The sale price is   $84.00 sale

    30% Off Select Shoes! (Price reflects discount)

    Please choose a color.
    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.
  • Gift Badge For Nunn Bush Griff Moc Toe Oxfords
    The regular price is   $110.00 The sale price is   $77.00 sale

    30% Off Select Shoes! (Price reflects discount)

    Please choose a color.
    Description:
    Versatile for both casual days and dressier occasions, these Nunn Bush Oxfords blend polished style with long-lasting comfort. A genuine leather upper pairs with breathable, fully padded mesh linings for moisture control and soft support. The EVA footbed, enhanced with eco-conscious Dual Comfort technology, cushions every step while offering arch support. An elastic gore patch adds slip-on ease and a flexible fit, and the lightweight sole with a shock-absorbing rubber heel pod keeps you moving comfortably from morning to night.
  • Gift Badge For Nunn Bush Griff Plain Toe Oxfords
    Online Exclusive
    The regular price is   $110.00 The sale price is   $77.00 sale

    30% Off Select Shoes! (Price reflects discount)

    Please choose a color.
    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 Belvedere Maurizio Hybrid Penny Loafers
    Online Exclusive
    The regular price is   $179.00 The sale price is   $125.30 sale

    30% Off Select Shoes! (Price reflects discount)

    Please choose a color.
    Description:
    This hybrid penny loafer blends timeless design with modern comfort. Crafted from supple Nappa leather, it features a classic silhouette complemented by a two-tone rubber gel sole for enhanced durability and traction. The foam-cushioned insole and soft lining ensure all-day comfort, making it suitable for both formal occasions and everyday wear.
  • Gift Badge For Belvedere Olivier Sneakers
    Online Exclusive
    The regular price is   $199.00 The sale price is   $139.30 sale

    30% Off Select Shoes! (Price reflects discount)

    Description:
    Crafted from rich suede with leather accents, this low-top sneaker delivers a clean, elevated look with a sporty edge. A contrast stripe and minimalist sole add modern flair, while the cushioned interior keeps every step comfortable. Versatile enough for jeans, joggers, or casual pants, it brings everyday luxury to your rotation. Distinctive color options make it easy to stand out.
  • Gift Badge For Florsheim Finance Plain Toe Oxfords
    The regular price is   $149.50 The sale price is   $104.65 sale

    30% Off Select Shoes! (Price reflects discount)

    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 Florsheim Remi Cap Toe Oxfords
    The regular price is   $135.00 The sale price is   $94.50 sale

    30% Off Select Shoes! (Price reflects discount)

    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 Jos. A. Bank Hybrid Wingtip Shoes
    The regular price is   $120.00 The sale price is   $84.00 sale

    30% Off Select Shoes! (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   $84.00 sale

    30% Off Select Shoes! (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   $94.50 sale

    30% Off Select Shoes! (Price reflects discount)

    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 regular price is   $144.50 The sale price is   $101.15 sale

    30% Off Select Shoes! (Price reflects discount)

    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.