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  • Gift Badge For Jos. A. Bank Cap Toe Oxfords
    The regular price is   $119.50 The sale price is   $83.65 sale

    30% Off Jos. A. Bank & Joseph Abboud Shoes! (Price reflects discount)

    Please choose a color.
    Description:
    These Oxfords seamlessly blend timeless design with modern innovation. The classic cap-toe silhouette and rich leather upper ensure a sophisticated and professional look, while a comfort sole provides superior cushioning and flexibility. This versatile shoe goes beyond the boardroom, transitioning from formal wear with suits to business casual with chinos and a blazer, all while offering a relaxed yet polished look. Invest in style and comfort with a dependable and stylish staple in your wardrobe.
  • Gift Badge For Joseph Abboud Soiree Formal Oxfords
    The regular price is   $125.00 The sale price is   $87.50 sale

    30% Off Jos. A. Bank & Joseph Abboud Shoes! (Price reflects discount)

    Description:
    Polished and refined, Joseph Abboud s Soiree formal Oxford adds sophistication to dress occasions. The classic lace-up silhouette pairs effortlessly with suiting, while a cushioned footbed offers lasting comfort throughout the evening.
  • Gift Badge For Johnston & Murphy Richland Monk Strap Shoes
    The sale price is   $165.00
    Please choose a color.
    Description:
    Classic sophistication meets modern craftsmanship in these Johnston & Murphy shoes. Featuring a single-strap design and smooth leather upper, they offer a refined alternative to traditional dress shoes. Cushioned insoles and a flexible sole provide all-day comfort, making them ideal for everything from office wear to dressier occasions.
  • Gift Badge For Johnston & Murphy Braxton Plain Toe Oxfords
    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.
  • Gift Badge For Florsheim Anthem Wingtip Oxfords
    Online Exclusive
    The sale price is   $135.00
    Please choose a color.
    Description:
    Rich leather and intricate brogue detailing meet modern design in these Florsheim Oxfords. A stacked sole adds a contemporary edge, while soft Suedetec linings and a cushioned, removable EVA footbed wrapped in leather deliver comfort that lasts from morning meetings to evening plans. With a durable rubber outsole providing reliable traction, this versatile style is built to move with you wherever the season takes you.
  • Gift Badge For Carrucci Monk Strap Plain Toe Dress Shoes
    Online Exclusive
    The sale price is   $175.00
    Please choose a color.
    Description:
    Step up your style with this dress shoe from Carrucci, a refined classic designed with versatility and comfort in mind. Crafted from soft milled leather, this monk strap pair showcases a smooth, plain toe silhouette enhanced by a hand‑finished, burnished toe. Inside, you'll find a full‑length, cushioned, leather‑lined footbed that adds comfort and support with every step. The leather upper and lining elevate the feel, while the rubber sole with an exclusive tread pattern delivers dependable grip and slip resistance. Thoughtfully constructed and easy to style, this shoe offers a polished look you can rely on from workdays to weekend outings.
  • Gift Badge For Johnston & Murphy Tyson Cap Toe Dress Shoes
    New
    Online Exclusive
    The sale price is   $169.00
    Please choose a color.
    Description:
    A clean cap toe design meets modern comfort tech in this refined dress shoe crafted from full‑grain leather with a smooth leather lining for a truly elevated feel. Beneath the classic exterior, a removable contoured footbed with memory foam provides plush, personalized cushioning, while the ultra‑light TruFoam midsole adds soft, responsive support that keeps you comfortable from the first meeting to the last. Finished with durable rubber pods for steady traction, it's a smart blend of timeless style and everyday ease, making it perfect for days when looking polished and feeling great need to go hand in hand.
  • Gift Badge For Stacy Adams Lockwood Wingtip Ornament Slip On Shoes
    New
    Online Exclusive
    The sale price is   $140.00
    Please choose a color.
    Description:
    Meet the slip‑on that proves classic style can still have a little swagger. The Stacy Adams Lockwood brings together timeless wingtip detailing with a modern silhouette. It's the perfect shoe for moments when you want to look sharp without putting in too much effort. Crafted with a rich mix of burnished smooth leather and textured leather, the upper has depth, dimension, and that just‑right touch of polish. Inside, textile linings keep things breathable and comfortable, so your feet stay cool. And for all‑day support, the Lockwood features the RedZone removable footbed with a molded heel cup: a cushioned, supportive base that keeps every step feeling steady and comfortable.
  • Gift Badge For Nunn Bush Stark Plain Toe Oxfords
    Online Exclusive
    The sale price is   $100.00
    Please choose a color.
    Description:
    Stepping into a pair of shoes has never felt this easy. Crafted from naturally soft genuine leather, this style delivers that rich, classic look while staying wonderfully comfortable from day one. Smooth SuedeTec linings greet your feet with a soft, glove‑like feel, making every wear effortlessly comfortable. The Comfort Gel footbed, where molded EVA support meets a memory‑foam insole, creates a cushiony, step‑softening feel you'll notice immediately. Clean lines keep the silhouette timeless, while the modern sole adds lightweight flexibility perfect for both work and weekend outings. Stylish, comfortable, and never fussy, this Oxford is designed to look sharp while keeping life simple.
  • Gift Badge For Carrucci Hybrid Lace‑Up Cap Toe Oxfords
    Online Exclusive
    The sale price is   $175.00
    Please choose a color.
    Description:
    Experience a smarter kind of sophistication with the Carrucci Hybrid Oxford. Designed for those who want classic style with modern comfort, this pair blends elevated craftsmanship with a lightweight, flexible hybrid sole that's perfect for daily wear. Made from a single piece of leather, the upper and leather lining create a seamless profile that showcases Carrucci's attention to detail. The hand‑stained, two‑tone patina brings rich depth and dimension, giving each shoe a unique, artisanal finish. Inside, a full‑length cushioned, leather‑lined footbed delivers lasting comfort and support. The EVA and rubber outsole keeps things light and responsive, while the mini‑lug tread adds dependable traction without compromising the refined silhouette.
  • Gift Badge For Johnston & Murphy Higgins Penny Loafers
    Online Exclusive
    The sale price is   $185.00
    Please choose a color.
    Description:
    Smooth, effortless style starts with a loafer that knows how to balance classic craftsmanship with laid‑back comfort. This pair is crafted from soft, full‑grain leather and features an unlined upper that flexes naturally with every step, backed by a leather‑covered footbed that feels instantly broken‑in. A molded TruFoam footbed delivers that surprisingly lightweight, springy rebound you'll notice the moment you slip them on. Finished with a leather outsole and a rubber toplift for durability and easy traction, these loafers bring together refinement, ease, and all‑day comfort in one quietly confident package.
  • Gift Badge For Johnston & Murphy Higgins Bit Loafers
    Online Exclusive
    The sale price is   $185.00
    Please choose a color.
    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
    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
    The regular price is   $119.50 The sale price is   $83.65 sale

    30% Off Jos. A. Bank & Joseph Abboud Shoes! (Price reflects discount)

    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 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 Johnston & Murphy Braxton Chukka Boots
    Online Exclusive
    The sale price is   $159.00
    Description:
    The Braxton chukka boot is crafted from rich leather with subtle stitched details. Designed for flexibility and durability, they have a cushioned footbed and sturdy outsole that provide support whether you're heading to the office or exploring the city. The ankle-high profile delivers a tailored look that pairs effortlessly with denim, chinos, or even casual suiting, making it a go-to choice for transitional dressing and year-round wear.
  • 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.
  • Gift Badge For Johnston & Murphy Upton One-Piece Perfed Plain Toe
    Online Exclusive
    The sale price is   $175.00
    Please choose a color.
    Description:
    Ready to kick your style into high gear? Meet the Upton Oxfords, the shoes that are all about looking good and feeling even better. They're crafted from one solid piece of premium leather and feature subtle perforated details that not only look cool but also give your feet some breathing room. Whether you're acing a big presentation or celebrating a win with friends, the versatile plain-toe design means they're the perfect partner for any outfit. Plus, with a soft leather lining and a super durable sole, you can confidently stride through your day, knowing your feet are as comfortable as they are stylish.
  • Gift Badge For Johnston & Murphy Calder Chelsea Boots
    Online Exclusive
    The sale price is   $179.00
    Please choose a color.
    Description:
    The Calder boot brings together versatile design and everyday functionality. Crafted from rich leather, they feature elastic side panels and a pull tab for easy on-and-off wear. A natural fit for both dressier occasions and casual outings, this pair features a cushioned footbed and soft lining for lasting comfort. The durable outsole offers reliable traction. Pair them with denim, chinos, or tailored trousers for effortless style you can rely on.
  • Gift Badge For Johnston & Murphy Calder Chukka Boots
    The sale price is   $179.00
    Please choose a color.
    Description:
    Bridging rugged charm and refined style, the Johnston & Murphy Calder Chukka Boots are a versatile staple for a modern wardrobe. Crafted from premium leather, these ankle-high boots have subtle stitching and a classic lace-up design. The cushioned footbed and soft lining provide all-day comfort, while the durable outsole offers reliable traction on a variety of surfaces.
  • Gift Badge For Johnston & Murphy Flynch Plain Toe Oxfords
    Online Exclusive
    The sale price is   $328.00
    Please choose a color.
    Description:
    Understated and versatile, the Flynch offers a modern profile that's perfect for everyday wear. Crafted with a smooth leather upper and minimal detailing, it delivers a polished look that transitions easily from office to evening. A cushioned footbed and durable outsole ensure comfort and support with every step, making it a reliable go-to for refined, low-profile style.
  • Gift Badge For Florsheim Plain Toe Chukka Boots
    Online Exclusive
    The sale price is   $135.00
    Please choose a color.
    Description:
    Polished yet practical, these Florsheim chukka boots deliver everyday versatility with a refined edge. Crafted from rich leather and set on a durable rubber sole, it pairs classic chukka styling with modern comfort features. A cushioned footbed and soft Suedetec lining provide support from morning commutes to evening plans, while the clean plain toe keeps your look sharp. Whether you're dressing up denim or adding a relaxed touch to tailored trousers, this boot moves effortlessly through the week.
  • Gift Badge For Stacy Adams Brumley Moc Toe Lace Up Boots
    Online Exclusive
    The sale price is   $160.00
    Please choose a color.
    Description:
    Rugged meets refined in the Brumley boot, a versatile style from the brand's FlexZone collection. Featuring a rich, hand-burnished upper with a modern mix of materials, colors, and textures, this boot is designed for both visual impact and all-day comfort. The FlexZone cushioned footbed includes a molded heel cup and sustainable microfiber cover, offering anatomical arch support that adapts to your stride. Soft microfiber linings enhance comfort, while the lace-up design and moc toe silhouette add a classic touch to a contemporary silhouette.

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.