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Black Cushioned Insoles Shoes

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  • Gift Badge For Cole Haan Morse Grand Wingtip Oxfords
    The sale price is   $140.00
    Description:
    Combining classic brogue flair with modern comfort, this wingtip Oxford features premium leather uppers detailed with timeless perforations. Built on Cole Haan s Grand.OS platform with an EVA midsole, it delivers lightweight cushioning and natural flexibility. The rubber outsole adds durable traction, while textile linings and padded footbeds ensure all day wearability. Perfect for bridging the gap between formal and casual, these shoes seamlessly elevate both dress pants and jeans.
  • Gift Badge For Rockport Ellworth Slip-On Shoes
    Online Exclusive
    The sale price is   $130.00
    Please choose a color.
    Description:
    Combining hands-free convenience with everyday polish, this slip-on features Rockport's Step Activated technology, which allows you to step in and out with ease. A molded heel keeps your foot securely in place. The leather and textile upper balances durability with a relaxed look, and the removable cushioned insole accommodates custom orthotics. Finished with a rubber outsole for reliable traction, it's a smart, low-effort option for daily wear.
  • Gift Badge For Eastland Beacon No-Toggle Lace Sneakers
    The sale price is   $90.00
    Please choose a color.
    Description:
    The Beacon is the ultimate summer sneaker, offering unmatched comfort and lightweight convenience. It features an extra thick cushioned insole, a no-tie toggle lace system, and breathable mesh uppers. Rubber tread soles provide traction and will hold up against the elements to give you all day comfort.
  • 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 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 Rockport ProWalker Eureka Plus Slip-On Shoes
    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 Born Todd Plain Toe Oxfords
    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 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 Rockport LiteCourt Sneakers
    New
    Online Exclusive
    The sale price is   $130.00
    Please choose a color.
    Description:
    Keep it casually cool with the ultra-comfy LiteCourt Sneakers. Made by Rockport, these laid-back lace-ups are fashioned from genuine, durable leather. They're both stylish and orthopedic friendly with their padded collar and tongue, cushioned insole, EVA midsole, and truTECH® technology for lightweight shock absorption. Complete with a thick and grippy rubber outsole, these kicks are sure to become an instant wardrobe favorite.
  • Gift Badge For Johnston & Murphy Higgins Bit Loafers
    New
    Online Exclusive
    The sale price is   $185.00
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    Description:
    Step into elevated ease with the Higgins Bit Loafers from Johnston & Murphy, where refined design meets lightweight, flexible comfort. Crafted with an unlined suede upper, these loafers offer a soft, relaxed feel from the very first wear, while the leather-covered TRUFOAM footbed delivers ultra-light, rebound cushioning for all-day comfort. A bit detail adds a sophisticated touch, complemented by a durable leather outsole with a rubber toplift for enhanced traction and longevity. Finished with ultra-flexible construction that bends naturally with every step, this classic bit loafer is designed for effortless, everyday refinement.
  • Gift Badge For Florsheim Remi Moc Toe Penny Loafer
    New
    The sale price is   $139.50
    Please choose a color.
    Description:
    Get ready to love your new go-to shoes; the Florsheim Remi Moc Toe Loafer instantly elevates both your business and casual attire. Crafted with a genuine leather upper, this slip-on features a refined moc toe and a classic penny loafer saddle, delivering a distinguished, contemporary look. Florsheim built the Remi for all-day performance, incorporating a fully cushioned footbed and soft Suedetec linings to ensure lasting comfort. With its flexible rubber outsole, this loafer moves easily from the boardroom to a weekend outing, proving the perfect blend of polished style and modern wearability.
  • Gift Badge For Jos. A. Bank Moc Toe Loafers
    New
    The sale price is   $119.50
    Description:
    Embrace comfy luxury with these definitive dress loafers. From Jos. A. Bank, these sophisticated slip-ons are comprised of smooth, premium leather with a fine moc toe and dual elastic gores for easy on-and-off. Detailed with cushioning on the insole and traction on the rubber outsole, they are well-suited for both business and leisure.
  • Gift Badge For Born Nigel Loafers
    Online Exclusive
    The sale price is   $125.00
    Please choose a color.
    Description:
    Everything you need in an everyday shoe, this style combines effortless wear with premium comfort. Crafted from soft, hand-finished full-grain leather, it features a breathable microsuede lining and a removable footbed with added foam for superior cushioning. The high-traction, lightweight rubber outsole ensures flexibility and durability, while 2-way Opanka handcrafted construction delivers exceptional quality and comfort. Perfect for slipping on and off with ease, these loafers are designed for all-day wear.
  • Gift Badge For Carrucci Bit Dress Loafers
    The sale price is   $175.00
    Please choose a color.
    Description:
    Designed for elegance without compromise, this shoe combines timeless style with advanced comfort technology. Experience craftsmanship and comfort in every step. Handsewn XC Flex construction delivers superior flexibility and durability, ensuring your shoes move naturally with you. The soft glove leather offers a luxurious feel and a polished finish, while the leather-covered latex footbed with built-in arch support provides cushioning and stability for all-day wear.
  • Gift Badge For Nunn Bush Centro Flex Formal Plain Toe Oxfords
    Online Exclusive
    Description:
    With its smooth plain toe, stacked heel, and refined profile, the Centro Flex Plain Toe Oxford offers formidable fashion for your formal occasions. Whether you're heading to a wedding or dressing up for an event, this patent leather shoe offers high-sheen style with thoughtful comfort built in. The easy-care upper requires minimal maintenance, while breathable stretch linings keep your feet cool. A Comfort Gel footbed with molded EVA, memory foam, and a signature heel pod provides luxe cushioning and support all day and all night long. Finished with a lightweight TPR sole and Flex Technology, it moves effortlessly with you from start to finish.
  • Gift Badge For Nunn Bush Centro Flex Formal Slip-On Shoes
    Online Exclusive
    The sale price is   $85.00
    Description:
    Step into timeless elegance with the Nunn Bush Centro. Made for formal occasions, this shoe features a plain toe design and a smooth, easy-care upper for a refined look. Comfort meets sophistication with a fully cushioned memory foam footbed, comfort gel heel pod, and Flex Technology for superior flexibility and shock absorption. The lightweight outsole ensures all-day comfort, making it the perfect choice for weddings and black-tie events.
  • Gift Badge For Rockport Style Leader 2 Plain Toe Oxfords
    Online Exclusive
    The sale price is   $130.00
    Description:
    Designed for the modern professional, this plain toe Oxford blends timeless style with advanced comfort features. The TRUTECH® sport technology provides shock-absorbing heel cushioning to help reduce foot fatigue, while the moisture-wicking lining keeps you feeling fresh throughout the day. A cushioned insole adds extra support, making it a smart choice for long hours at the office or dress wear events. Pair it with a tailored suit for a polished look or dress it down with chinos and a blazer for business casual ease.
  • Gift Badge For Rockport Keefe Cap Toe Oxfords
    The sale price is   $120.00
    Please choose a color.
    Description:
    <p>Dress shoes that don&#39;t act like dress shoes. The Keefe Oxford brings the best of both worlds; sharp style and serious comfort. With an almond-shaped toe and cushioned insole, they look polished but feel like a dream. Thanks to Stretch Adapt, they flex and move with your feet for a custom fit that keeps up with your day. And with truTECH &reg; shock absorption, every step feels lighter.</p>
  • Gift Badge For Rockport Cory Penny Loafers
    Online Exclusive
    The sale price is   $140.00
    Please choose a color.
    Description:
    A masterful blend of tradition and innovation, these Rockport loafers are crafted for the gentleman who values both style and substance. The embossed leather upper and woven detailing lend a distinguished touch, while the classic penny keeper anchors the design in timeless elegance. With a cushioned insole and Rockport's signature truTECH® technology for lightweight shock absorption, these slip-ons offer day-to-night comfort without compromising sophistication. Whether paired with tailored trousers or dressed-down denim, they're a wardrobe essential that speaks volumes quietly.
  • Gift Badge For Rockport Cory Slip-On Dress Penny Loafer
    Online Exclusive
    The sale price is   $140.00
    Description:
    The Rockport Cory Slip-On Dress Penny Loafer delivers exceptional comfort without compromising a classic, handsome appearance, making it an essential piece of footwear for your business and formal wear. Constructed with a smooth, premium leather upper, this penny loafer offers a timeless profile and a versatile finish. Engineered for those on their feet, the shoe incorporates Rockport's truTECH® technology—a lightweight, shock-absorbing foam into the EVA footbed and heel area, ensuring superior underfoot cushioning and all-day support. Easy to put on and durable with a sturdy rubber outsole, the Cory Loafer is the perfect functional addition to your favorite polished outfits.
  • Gift Badge For Rockport Keelan Plain Toe Oxfords
    The sale price is   $130.00
    Please choose a color.
    Description:
    Experience the perfect blend of polished style and all-day comfort with these Rockport dress Oxfords. These distinguished lace-ups feature the innovative Stretch Adapt system, precision-engineered to flex with your foot's natural movement for a truly personalized fit. With the truTECH® system for lightweight shock absorption and a cushioned insole for 360 degrees of support, these Oxfords ensure you maintain a confident, comfortable stride no matter how long your day lasts.
  • Gift Badge For Rockport Style Leader 2 Bike Toe Loafers
    The sale price is   $130.00
    Please choose a color.
    Description:
    The Rockport Style Leader 2 Bike Toe Slip-On is the essential dress shoe for the working professional. It features a polished full-grain leather upper with a modern bike-toe detail, ensuring a sharp look with no fuss. Dual elastic side panels make for quick and easy wear. The shoe is built for endurance: an EVA outsole provides lightweight shock absorption, and truTECH® technology cushions the heel, drastically reducing foot fatigue. Additionally, DEWIX linings manage moisture and fight odor. This durable, easy-to-care-for shoe handles long days on your feet while maintaining a sophisticated appearance.
  • Gift Badge For Johnston & Murphy XC Flex Landry Bit Moc Toe Loafers
    The sale price is   $159.00
    Please choose a color.
    Description:
    Designed for effortless style and all-day comfort, this loafer blends classic sophistication with modern performance. The moc toe design is elevated by a metal bit detail, giving it a polished, versatile look that transitions seamlessly from office to evening. Built with Johnston & Murphy's XC Flex technology, it features a high-rebound TRUFOAM midsole and a flexible, grooved sole with rubber pod inserts for lightweight cushioning and superior traction. Inside, a removable memory-foam footbed offers personalized support, while the leather and mesh lining treated with antimicrobial protection ensures lasting freshness.

WHY OUR MEN’S SHOES ARE WORTH AN EXTRA LOOK:

We began as a purveyor of fine suits and sport jackets, but we pride ourselves on our ability to deliver great looks from head to toe. That means you’ll find a wide selection of well-crafted men’s dress shoes and casual shoes in our stores. Our dress shoes for men are made from rich materials like leather and suede and offered in classic looks ranging from dressy wingtips to stylish Oxfords or Derby shoes. There are sleek dress boots to consider as well. The looks and styles of shoes are many; with pointed, square and cap toes, shiny and matte looks, and details without end. For our more casual shoes, you’ll see loafers, boat shoes and less formal boots or chukkas. Every pair of shoes is a personal choice, and size is everything when you want a shoe that feels as great as it looks. You’ll want to allow your sales associate to measure your foot carefully for the proper size. Then try on several variations, preferably with the pants you intend to wear and a dress sock in the appropriate style. That’s the beauty of shopping for shoes as part of your overall decision-making. It’s all right there. And with a little help, it all works together.