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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 86 products.

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  • $ 199.95

    The Drew Trevino is a sleek styling, men's double depth comfort hi-top shoe. This style offers a premium leather upper and odor- and moisture-resistant Drilex® lining. The Opanka construction provides a shoe that will last and is a lightweight boot. The tempered steel shank gives you support and stability and the two removable footbeds allow you to adjust...

    $ 199.95
    In Stock
  • $ 179.95

    The Mansfield II is not only a stylish men's shoe but also has more than a few key features when looking for an ultra lightweight comfortable dress or casual shoe. The removable insoles allow for insertion of your own orthotics. The steel shank system provides stability. The outsole and rocker bottom feature provide the foot with ease while in motion....

    $ 179.95
    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
  • $ 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
  • $ 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
  • $ 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
  • $ 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
  • $ 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
  • $ 109.95

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

    $ 109.95
    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 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
  • $ 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
  • $ 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
  • $ 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
  • $ 99.95

    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.    

    $ 99.95
    In Stock
  • $ 119.95

    This waterproof boot combines comfort, weatherproof, and sophistication in one. The soft faux fur lining is gentle on your feet while the twin zippers on either side allows you to easily slide your feet in the boot. A classic design with comfort - the Troy is the perfect fall/winter boot.

    $ 119.95
    In Stock
  • $ 134.99

    The Canton from Drew Shoe is a casual dress shoe that has therapeutic foot health benefits and a sleek style. You will be able to adjust the fit just to your liking with the adjustable Velcro® strap and removable inserts. The inserts make this dress shoe a double depth shoe and can be taken out to accommodate for custom orthotics. Additional features of...

    $ 134.99
    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
  • $ 57.39

    Stay comfortable and dry this season with the Propet Truman. The supple leather uppers provide a nice clean look. Not to mention the soft faux fur lining that will feel like heaven on your feet. The sophisticated look packed with comfort features make this a go-to boot.

    $ 57.39
    In Stock
  • $ 53.79

    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.

    $ 53.79
    In Stock
  • $ 114.95

    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...

    $ 114.95
    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
  • $ 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
  • $ 57.39

    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...

    $ 57.39
    In Stock
  • $ 71.79

    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...

    $ 71.79
    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
  • $ 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
  • $ 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
  • $ 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
  • $ 119.95

    The Mt. Emey 2012 is a men's orthopedic strap shoe with a slip-resistant outsole. The wide entry opening and removable insole accommodates AFOs and a variety of foot conditions. The hook and loop velcro strap make these shoes easy to fasten securely when putting on and easy to undo when taking the shoes off. With the quality leather uppers and...

    $ 119.95
    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
  • $ 199.95

    For guys who want a stylish casual shoe with therapeutic benefits turn to the Park by Drew. Showcasing a sleek and classic design, you'd never know it is therapeutically beneficial! This handsome derby features double Depth, a firm heel counter and leather linings help provide all-day comfort.   

    $ 199.95
    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
  • $ 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
  • $ 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
  • $ 119.95

    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. 

    $ 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
  • $ 62.99

    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...

    $ 62.99
    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
  • $ 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
  • $ 139.99

    The Bryan from Drew Shoe comes in durable and smooth suede leather and has two removable insoles to accommodate for custom orthotics and a variety of foot problems. 

    $ 139.99
    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
  • $ 148.76 $185.95 test123 -20%

    A men's orthopedic dress shoe with a classic wingtip oxford design and made with the finest leather. Its therapeutic offerings are not compromised with two removable insoles for added and double depth, tempered steel shank, and a firm heel counter to give you support and stability - plus all-day comfort. HCPCS Code A5500

    $ 148.76 $185.95 -20%
    Reduced price!
    Product available with different options
  • $ 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
  • $ 57.39

    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...

    $ 57.39
    In Stock
  • $ 179.95

    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...

    $ 179.95
    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
  • $ 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
  • $ 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
  • $ 89.95

    Protect your feet in comfort and style. The smooth leather upper works with trousers or jeans, and the breathable mesh lining pulls moisture away from your feet, keeping them cool and dry. A high traction rubber sole gives you a strong grip on any surface. The padded tweed collar adds a unique flair with extra comfort at the ankle. A modern, classic...

    $ 89.95
    In Stock
  • $ 129.95

    Need a shoe where the sole can be modified to your specifications? The 708-L offers a symmetrical cut-line so a custom sole can be added for a variety of foot conditions and needs. The interior of the shoe has two removable inserts for extra space or orthotic accommodations. The quality leather uppers and seamless lining make for a durable shoe that will...

    $ 129.95
    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
  • $ 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
  • $ 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
  • $ 149.95

    A Drew Shoe favorite because of its therapeutic benefits and sleek look that will have you experiencing comfort in style. Available in dark brown and black this shoe comes in double depth for a custom fit. The firm heel counter, durable leather linings, and lightweight outsole work to create the quality you would expect from a Drew Shoe. HCPCS Code A5500

    $ 149.95
    Product available with different options
  • $ 134.99

    The Dakota is perfect for the man on the go in need of functional style. Featuring a functional zipper, hidden depth and sleek Opanka construction, and two removable footbeds.

    $ 134.99
    In Stock
  • $ 146.99

    Classic and comfortable, the Fairfield by Drew is a timeless silhouette that will never go out of style. This men's slip-on has a genuine leather upper and looks great with your favorite pair of slacks, or denim for a more casual look.

    $ 146.99
    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
  • $ 144.95

    You can wear these new Apex Lexington Moc Toe Oxford Men with Dress Pants, Khaki's or Jeans. This Oxford is designed to combine classic, refined styling with Apex's unmatched comfort and customization. Built to feel like the Apex Athletic shoe, no one will know how good your feet feel as they admire them. 

    $ 144.95
    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
Showing 1 - 60 of 86 items