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Men's Orthopedic & Diabetic Dress Shoes

Stylish and comfortable men's orthopedic shoes available in a variety of sizes and colors to match your preference. We know fashion and orthopedic shoes are often not found together, but we offer a large number of brands that offer a diverse selection of men's dress footwear.

We offer orthopedic and diabetic dress shoes that provide comfort and support to keep you on your feet - for longer. Browse our selection of men's dress shoes from popular, podiatrist-respected brands like Drew Shoe, P.W. Minor, Vionic, and more!

DressThere are 82 products.

per page
  • $ 159.95

    Exude confidence and a strong fashion sense with the Harrison. The Harrison features a classic wing tip dress shoe design along with an adjustable monk strap and metal buckle closure. The durable leather uppers and rubber outsole creates a lasting dress shoe that will be your go-to for your dress attire. The removable, supportive insoles help with lower...

    $ 159.95
    In Stock
  • $ 164.95

    One of Drew Shoe's best sellers is the Drifter. The Drifter features a soft padded tongue and collar as well as a stretchable vamp for extra toe room. The lightweight construction allows for a easy to wear feel and there are two removable insoles for those needing extra room inside the shoe for swelling, hammertoes, AFO accommodation and more. The Drifter...

    $ 164.95
    In Stock
  • $ 94.95

    Classic design with contemporary stitch-work make this lace-up leather upper a great professional comfort shoe. A micro-fiber lining and padded tongue not only give this shoe a high-end look, but give you the support you need for long days at work or long walks around town. The open cell foam design allow air to circulate, keeping your feet naturally cool...

    $ 94.95
    In Stock
  • $ 94.95

    Protect your feet and walk as long as you want to in this ultra-supportive leather upper. The micro-fiber lining, padded collar and tongue create a comfort package that will cradle all parts of your feet. The open cell foam design allow air to circulate, keeping your feet naturally cool and dry. In black and brown, works well with work or casual styles....

    $ 94.95
    In Stock
  • $ 175.95

    The ultra-lightweight construction and large, single strap closure of the Drew Watson makes this style and ideal shoe for anyone wanting minimal effort for getting on and off the shoes and mobility. The vamp is made with a stretchable material to provide some give in the toe box area. Inside the shoe is a moisture wicking lining to help keep your feet dry...

    $ 175.95
    In Stock
  • $ 71.99

    Sophisticated comfort is the essence of the Luca. Made of leather uppers and a durable rubber outsole, you can be sure this will be the staple to your daily casual attire. A sleek design with stylish stitching around the vamp and garnished with a dapper lacing. The removable insoles offer support to relieve pain at the arches and heel. The contoured...

    $ 71.99
    In Stock
  • $ 119.95

    Get the therapeutic benefit of soft leather upper and leather linings paired with supportive insoles and a wide toe box area. The Copenhagen is a classic gentlemen's dress shoe with a long strap overlay - great for an adjustable fit. The durability and comfort of this men's dress shoe surpasses most in its category. The insoles are removable to...

    $ 119.95
    In Stock
  • $ 119.95

    A stretch men's dress casual shoe that offers exceptional comfort and functional features for a variety of foot conditions. The leather and stretch lyrca combo uppers bring durability and provide a way to reduce rubbing with the stretch material on the vamp. The single strap closure make for an easy closure and the supportive removable insoles allow for...

    $ 119.95
    In Stock
  • $ 167.99

    Dress up or down in this versatile men’s chukka boot. A classic design loaded with features for ultimate foot comfort. The Bronx features premium leather uppers and lightweight polyurethane outsole with a gentlemen’s heel notch. Inside the boot is a high arch support insole that can be removed for your own prescribed orthotics. Stay fresh with the Drilex®...

    $ 167.99
    In Stock
  • $ 94.95

    The Vinn is a great everyday casual dress shoe. With it's soft leather uppers and knit mesh padded collar and tongue, you can't go wrong. A classic design infused with comfort features to make this style worthy of all day wear. Stay fresh with the breathable open cell polyurethane insoles that keep your feet healthy and cool. Be on your feet longer with...

    $ 94.95
    In Stock
  • $ 89.95

    A classic chukka boot with detailed stitching and quality construction. The suede uppers give the boot a gentle look  with plenty of durability. Feel the difference with each step as the cushioned EVA layer midsole provides some shock absorption as the rubber outsole brings your foot back up. Unlike traditional boots, the high density removable...

    $ 89.95
    In Stock
  • $ 139.95

    A rugged look that comes with desired comfort and support. The 7" shaft boot is a durable leather welt construction boot made to last. It's easy lace closure and pull tab make for an adjustable fit and easy pull on feature. The flat bottomed sole is made with a EVA and rubber compound for a lighter boot and overall comfort and durability. Keep cool...

    $ 139.95
    In Stock
  • $ 145.95

    Extra supra-depth to accommodate very severe edema/swollen feet. Features heel counter cushioned with expandable elastic foam/fabric, designed for sensitive ankle/instep severe edema, comes in 10E, 14E, the widths available for all other style as modification orders.

    $ 145.95
    In Stock
  • $ 139.95

    A men's extra depth casual shoe made with durable leather uppers and seamless linings for reduced friction to prevent abrasions. The extra depth is perfect for those need more room for AFOs, orthotics or internal modifications. Also, the sole can be easily modified with the symmetrical cut-line. The 9608 can accommodate a variety of foot conditions - and...

    $ 139.95
    In Stock
  • $ 68.19

    A casual style with a sophisticated look, the Propét Otis has it all. Easy to slip on, you'll love the stretch gore on the sides for a custom fit. The footbed is removable allowing for insertion of your own orthotics. Comes in a variety of widths making them great for those with hard to fit feet.

    $ 68.19
    In Stock
  • $ 177.99

    Doubler offers proven benefits for feet in need of special care. Double the added depth provides 20 percent more in-shoe capacity than traditional footwear. Ideal for extra-thick orthotics, or extreme foot conditions. Moldable deerskin linings without toe seams protect the sensitive or hyposensitive foot.    

    $ 177.99
    In Stock
  • $ 71.99

    A sleek, sophisticated slip-on dress shoe that will have you looking and feeling great. The slim goring panels give the feel of quality comfort and adjustability. Plus, the accented burnished toe and quality premium leather uppers give the look of luxury. The removable leather insoles can be kept in to reduce common lower body aches including heel...

    $ 71.99
    In Stock
  • $ 149.95

    The Vionic with Orthaheel Technology Bruno Oxford is a practical and professional wardrobe staple. Contrast stitching and optional contrast laces update this Oxford silhouette, while a rubber outsole lends versatility. Genuine leather-skinned removable insole. Grey and Dark Brown colorways are water resistant.  

    $ 149.95
    In Stock
  • $ 129.95

    Men's Apis 502 Dress Shoes are double depth and made of genuine leather on the uppers and the lining. Accommodates moderate bunions, hammer toes, pronated/flat foot, & high instep/swelling.  Works well with Partial foot and AFO's. The closure is made of velcro.

    $ 129.95
    In Stock
  • $ 149.95

    Get ready to live life and have fun in the Graham. You’ll love wearing the shoes with slacks, corduroy pants, and other types of urban wear. The premium leather version works great for suits and office attire while the soft suede version works great for casual events. Notice the tongue of the grey suede version. It features a warm walnut color adding a...

    $ 149.95
    In Stock
  • $ 139.95

    A Velcro strap closure on a quality and stylish dress shoe. The dual straps allow for a wider opening to insert your foot and a perfect fitting when fastened. The padded collar and extended medial counter provide added comfort and stability. The uppers are made with soft genuine Napa leather that is seamlessly stitched to a lightweight EVA outsole.

    $ 139.95
    In Stock
  • $ 94.95

    Hand stitched construction for flexibility, supple grain leather uppers with lined quarters, padded collar and tongue. External and internal heel counter for extra firmness, Poliyou air insoles for moisture and odor absorption, enhancing foot comfort. Polyurethane sole for shock absorption and durability.    

    $ 94.95
    In Stock
  • $ 144.95

    The Double Strap Ambulator Conform provides unsurpassed comfort and protection with unique features such as Hidden-Depth Rocker soles, removable comfort orthotics and Plastazote foam linings molds to the foot to provide customized fit. Multiple removable insoles provide a 1/2" of removable depth for maximum protection and fitting flexibility.  

    $ 144.95
    In Stock
  • $ 104.95

    Hand-stitched construction for flexibility, grain leather uppers with lined quarters, adjustable fasteners. ( Padded collar, external and internal heel counters for extra firmness.      

    $ 104.95
    In Stock
  • $ 62.39

    A quality men's dress shoe that will last you and keep your feet refreshed - even during all-day wear. The open-cell PU foam allows your feet to breath to allow for moisture control. And if you have your own orthotic, the removable footbed in the Grisham can be removed to insert your own.  The full-grain leather upper and sponge rubber outsole make this a...

    $ 62.39
    In Stock
  • $ 144.95

    The Ambulator Single Strap features a genuine full grain leather upper, a single strap closure for fitting flexibility, soft leather linings for maximum comfort and breathability, a lightweight, slip resistant polyurethane sole for maximum comfort and protection and 1/2" removable depth.  

    $ 144.95
    In Stock
  • $ 144.95

    Designed to limit stress at the areas of the foot most susceptible to pain, Ambulator Biomechanical footwear provide unsurpassed comfort and protection with unique features.  

    $ 144.95
    In Stock
  • $ 135.95

    These shoes offer very attractive looks combined with soft genuine leather, a foam padded upper with extra foam padding in the tongue and collar. This shoe also features a breathable, protective lining, an anatomical last with extra width across the midfoot and toe-box, two removable spacers in 2mm and 3mm thick, cushioning sole made of lightweight EVA...

    $ 135.95
    In Stock
  • $ 149.95

    Get ready to take on those meetings in style with the new Shane premium leather dress shoe. You’ll love wearing the shoes with slacks, suits, and other types of formal wear. The detailed stitching adds to the classic look of the shoe while the leather insole helps provide breathability. Additionally, Vionic shoes come with their podiatrist-designed...

    $ 149.95
    In Stock
  • $ 144.95

    The Ariya Collection is crafted form the finest full grain leathers and technologically advanced fabrics available. The outsole features high quality polyurethane to provide light weight resiliency and shock absorption.  

    $ 144.95
    In Stock
  • $ 129.95

    A classic design with therapeutic features for bunions, hammertoes, diabetes, and more. The quality of the soft genuine leather uppers and lightweight EVA outsole will have you preferring this shoe over others. Easily secure this shoe to fit any foot size or condition with a hook-and-loop strap.

    $ 129.95
    In Stock
  • $ 129.95

    Added depth for a variety of foot conditions, including moderate bunions and AFOs. From swelling feet to custom orthotics, this shoe will comfortably fit to your foot with the added depth and removable inserts.

    $ 129.95
    In Stock
  • $ 159.95

    From the desert to the city streets, this boot will be your best friend for adventure. The Chase chukka boot is waterproofed and sealed at the seams to outlast natural wear and tear.  

    $ 159.95
    In Stock
  • $ 89.95

    A light-as-air take on a classic, the Gus oxford from Hush Puppies weighs in at four times less than its contemporaries. With its Strobel construction for athletic ease and flexibility, and the ZeroG system for shock absorption and utter weightlessness, it's possible you'll forget that you're wearing them.    

    $ 89.95
    In Stock
  • $ 94.95

    So light, they're almost weightless. Hook and loop closure gets you in and out easily. In smooth leather. Take a classic, mix in an offbeat detail, and stir. The creation you'll have? The Gil slip-on from Hush Puppies. A hook-and-loop closure on this moccasin-style shoe adds a touch of ease and contemporary interest.

    $ 94.95
    In Stock
  • $ 68.19

    The Galway slip-on is made with tumbled, full-grain leather upper with leather lining. Its stitch to sole construction and added room in the toe box make this a unique shoe that offers therapeutic benefits. Wears nicely with dress pants or blue jeans. The padded collar and tongue provide an additional area to make wearing these shoes a delight.

    $ 68.19
    In Stock
  • $ 62.39

    Receive the ultimate adjustability and fit from this men's slip-on dress shoe. The Grant features two stretchable side gores that allow you to easily slide in your feet while providing some give in the midstep for the perfect fit. The classic dress shoe design make the Grant a hit. But it doesn't stop at looks. The full-grain leather uppers make for...

    $ 62.39
    In Stock
  • $ 137.99

    A classic wingtip oxford style available in medium to extra-wide widths. Made with the finest suede leathers and includes a quality, breathable lining and steel shank. This provides added support and stability for your feet throughout the day. The Delaware displays a traditional style with an innovative support structure. HCPCS Code A5500

    $ 137.99
    In Stock
  • $ 139.95

    Take your formal wear up a notch in the Snyder. The Snyder loafer boasts a classic and powerful look. You’ll love wearing the shoes with all types of formal wear. Try wearing these loafers with skinny jeans or jeans with a rolled cuff to express your laid back and fashionable side.  Additionally, Vionic shoes come with their podiatrist-designed Orthaheel...

    $ 139.95
    In Stock
  • $ 95.95

    A traditional moc front walking shoe, featuring an EVA crepe sole for lightweight comfort. Hush Puppies' exclusive Comfort Curve flexes where your feet flex. Breathable linings and contoured removable footbeds make these walking casuals that take you anywhere.

    $ 95.95
    In Stock
  • $ 148.95

    Flow Feet is proud to offer Dr. Lin's Bodin Casual Men's Shoe from Oasis. These slip resistant shoes include a pair of pre-molded inserts and a pair of removable spacers. Both the pre-molded inserts and spacers can be removed to accommodate a custom orthotic. The anti-microbial treatment used to enhance the anti-microbial properties found in the Trek-Dry®...

    $ 148.95
    In Stock
  • $ 119.95

    A classically designed chukka dress boot - made for style. It's supple full grain leather uppers and shock absorbent soles make nice features to this boot. Available in widths up to men's XXW(5E) and sizes 15. Look great in the Propét Grady!

    $ 119.95
    In Stock
  • $ 129.95

    A solid dress shoe that is durable and therapeutic for a variety of foot conditions. The added depth provides room for custom orthotics and the extended lateral counter offers support and stability. This lightweight shoe is designed to be stylish and can be worn for long periods with removable cushion inserts. There are three inserts that can be taken out...

    $ 129.95
    In Stock
  • $ 149.95

    The Vionic Preston is a casual men's leather slip-on loafer with elastic goring and stitching accents. A slip-on loafer making it the perfect casual for work or weekend. An athletic-inspired rubber outsole lends versatility and durability.    

    $ 149.95
    In Stock
  • $ 94.95

    So light, they're almost weightless! Hush Puppies' Zero G system reduces weight by removing bulky innersoles and using a special outsole that's four times lighter than normal shoes. Comes in smooth leather.  

    $ 94.95
    In Stock
  • $ 115.95

    A simple, yet durable and comfortable casual dress shoe - for a variety of foot conditions and uses. The three removable cushion inserts make for flexible fitting for AFOs and internal modifications. Uppers are made soft genuine leather and outsole is injected with EVA to make this an extremely lightweight shoe.

    $ 115.95
    In Stock
  • $ 144.95

    Designed to limit stress at the areas of the foot most susceptible to pain. These shoes are often recommended for diabetes, arthritis or for anyone seeking a shoe that provides maximum comfort.  

    $ 144.95
    In Stock
  • $ 62.39

    A sophisticated dress shoe with the convenience of a hook and loop strap. The Graham is a solid choice for any formal occasion to keep you comfortable with the firm heel counter and sponge rubber outsole. And no need to worry about the shoes lasting over time, the full-grain leather upper and open-cell PU foam help make the shoe last through high-level...

    $ 62.39
    In Stock
  • $ 119.95

    A classic men's lace-up dress shoe available in medium, wide, and extra-wide widths to accommodate a variety of foot conditions and/or orthotics. Feel the difference with Surefit's comfort design and quality construction. A perfect choice for all formal occasions.

    $ 119.95
    In Stock
  • $ 139.95

    Extra wide ankle opening to accommodate for foot braces and custom AFOs. The extra-long Velcro straps allow for wider opening and a perfect fit. With genuine leather uppers stitched to a quality outsole - you will feel the difference with this surgical opening shoe.

    $ 139.95
    In Stock
  • $ 146.99

    For casual orthopedic shoe with a unique style and fit, the Mansfield from Drew Shoe is the right choice! This casual shoe has all the added foot health features and accommodations including two removable insoles. Keep both insoles in to provide you with added depth, remove one for a double depth shoe. Stay in style and comfort with the Mansfield...

    $ 146.99
    In Stock
  • $ 189.95

    Look and feel your best in the Drew Essex. This style features smooth leather uppers and a convenient Gentlemen’s heel notch to prevent your heel from getting caught on or snagging your pants. The footbed is made with maximum arch build-up; however, is removable if needed to allow for custom orthotic insertion. This style also features a sturdy tempered...

    $ 189.95
    In Stock
  • $ 115.95

    An orthopedic shoe designed to accommodate moderate hammer toes, bunions, and deformities. Also, the added depth helps for fitting with swollen feet, substantial foot thickness, AFOs, foot braces, and internal modifications. Premiere Insert Layers are included for comfort and fitting - Top layer 6mm thick Diabetic insert with 3mm thick EVA Foam filler....

    $ 115.95
    In Stock
  • $ 155.95

    The Accommodator 502-E has a heel counter cushioned with expandable elastic foam/fabric and is designed for sensitive feet and ankles. Accommodates very severe edema and swollen feet.

    $ 155.95
    In Stock
  • $ 114.95

    A dress boot that features waterproof, supple leather uppers. The soft leather allows flexibility. The faux fur lining is soft and the single adjustable strap allows for more room in the entry area to easily get your foot inside the boot. 

    $ 114.95
    In Stock
  • $ 138.95

    All leather classic design with traditional lace closure. Features a lightweight outsole and fine leather uppers to offer your feet comfort that will last. Available in Black or Chestnut.

    $ 138.95
    In Stock
  • $ 138.95

    A men's wing tip dress shoe from Dr. Comfort. Made with quality leather uppers, a lightweight outsole, and smooth leather interiors to offer your foot support and comfort throughout the day. This classic wing tip design from Dr. Comfort provides a quality orthopedic shoes that you won't want to take off.

    $ 138.95
    In Stock
  • $ 144.95

    The Venture collection offers the ultimate in comfort and function without compromising on style. It also exceeds SATRA and MARK II slip-resistant standards for dry, wet and oily surfaces. These classic shoes are ideal for casual or dress wear. Durability and comfort come to mind with the Venture Classic Strap. The full grain leather uppers...

    $ 144.95
    In Stock
  • $ 119.95

    A great men's dress shoe for foot conditions like, high instep/cavus/swelling, pronated/flat foot, bunions, hammertoes, and partial foot. The London also can accommodate AFOs and custom inserts. A5500 approved footwear.

    $ 119.95
    In Stock
  • $ 144.95

    Set in sleek leather, the Apex Lexington Loafer's classic penny saver band and low, tonal moc-toe stitching deliver a handsome, laidback look you'll want to rock right through the weekend and back to work.

    $ 144.95
    In Stock
Showing 1 - 60 of 82 items