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Men's Orthopedic & Diabetic Boots

Whether you need men's boots for style or work, you must always consider comfort as one of your priorities when selecting footwear. With our selection of men's orthopedic boots, you can expect quality and comfort that lasts. Choosing a high value pair of men's orthopedic/diabetic boots can have a huge impact on your daily life. Let's face it - living with foot pain is no joke.

The selection below offers solutions to a variety of foot conditions such as bunions, hammertoes, edema, and more. Plus, our boots feature stability and mid-foot support to help alleviate lower body pains associated with foot problems. Browse our variety of boots from chukka boots to steel toe work boots - an ideal selection of boots for every occasion.

BootsThere are 64 products.

per page
  • $ 154.95

    Men's boots designed for charcot foot. The boot features a bowed out design at the arch to accommodate for foot conditions associated with charcot. The uppers are made of soft leather material and feature removable, heat-moldable inserts. For added comfort, there is a padded collar and a seamless vamp lining. The speed lace system makes it convenient to...

    $ 154.95
    In Stock
  • $ 139.95

    An OSHA-approved men's low top composite toe work boot that is rugged enough for the most extreme occupations. The leather/canvas uppers are durable to last you many work days. Designed with added depth feature and a removable insole, these shoes can accommodate a variety of foot conditions including, AFO and orthotic accommodation, swelling, arthritic...

    $ 139.95
    In Stock
  • $ 149.95

    Slip on style and comfort in the Jason men’s high top Chelsea boot. With durable weather-resistant uppers and dual side stretch goring, you can expect more out of the Jason. The EVO compound footbed and rubber outsole keep this shoe lightweight and supporting you all day. Enjoy each step in the Jason!

    $ 149.95
    Product available with different options
  • $ 154.95

    Mt. Emey Men's 503-C Adjustable Strap Charcot Boot provides comfort to those suffering from edema, bunions, hammertoes, severely swollen feet (edema), and charcot. The 8” shaft height of the shoe provides extra support for the foot and ankle. This shoe is very soft and great for sensitive feet. Apis Men's 503-C Adjustable Strap Boot is also A5500 SADMERC...

    $ 154.95
    In Stock
  • $ 129.95

    Work in comfort in the Calgary! This men's durable work boot is made with water-resistant full grain leather uppers. Its lining is breathable, soft fabric lining and features a padded tongue and collar for your therapeutic benefit. Plus, get more room in the toe box for foot conditions like hammertoes, bunions, or swelling. The rugged welt-like...

    $ 129.95
    In Stock
  • $ 179.95

    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®...

    $ 179.95
    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
  • $ 89.95

    Hike to your full potential in the Traverse. This men's comfort hiking boot can get you through diverse terrain and extreme temperatures and climates. The waterproof knit mesh uppers and TPU toe cap keeps your feet dry and makes for a dry hiking experience. The EVA midsole and high traction rubber outsole provide you with stability and a...

    $ 89.95
    In Stock
  • $ 104.95

    A 4" shaft composite toe work boot that offers the clean, sleek look with the protection you need to get the job done safely. The Seeley Hi features a leather/mesh upper combo for breathability. Plus, a removable high-density open cell foam puncture-resistant footbed for cushion, support, and protection. The outsole is made of slip-resistant rubber...

    $ 104.95
    In Stock
  • $ 129.95

    With a hiking boot style in mind when designing this high-top composite toe work shoe, the New Balance 989 was made for functionality and comfort. The 989 provides ankle support and protection for the industrial worker needing the safety and support in work environment. It's durable full grain leather in the front and breathable mesh synthetic in the back...

    $ 129.95
    In Stock
  • $ 269.95

    The Rockford boot for men creates its own category as a truly unique comfort boot. The Drew Rockford men's comfort boot is the ideal work boot and everyday boot for men. Hit the great outdoors in the unbeatable comfort of Drew's Rockford boot.  

    $ 269.95
    In Stock
  • $ 159.95

    A hip high top sneaker that promotes foot health. From its breathable "V" perforation on the quarter to the podiatrist designed Orthaheel insoles, you will treat your feet right. The inserts help with foot conditions like over-pronation and plantar fasciitis by aligning your feet in their natural position. A high top casual sneaker perfect for a...

    $ 159.95
    In Stock
  • $ 114.95

    ​A versatile boot that can be worn with your work attire or casual clothing. Use for casual wear or hiking trails and expect comfort that lasts all day with the lightweight, cushioned EVA midsole. Plus, you can use with your custom orthotics since this boot has a removable footbed. And never worry about excessive moisture with the Sealtex waterproof...

    $ 114.95
    In Stock
  • $ 139.95

    Enjoy exceptional comfort and protection with Orthofeet's Boots for Men. They are lightweight and have plenty of comfort-enhancing features that offer great walking experience. Orthofeet crafts these boots for men with advanced athletic shoe technology, offering anatomical orthotic support, excellent cushioning, extra room and comfort detailing. 

    $ 139.95
    In Stock
  • $ 139.95

    Orthofeet Glacier Gorge Men’s Strap boots offer anatomical arch support, non-binding relaxed fit, and maximum protection against pressure points. The Gel orthotic-insole along with the ergonomic, cushioning sole soften step, enhance stability, and facilitate natural foot motion. The deep toe box design allows the foot to relax and spread out naturally for...

    $ 139.95
    In Stock
  • $ 189.95

    Enter a room with confidence in the Chelsea boot. It's bold, classic ankle-high boot styling with dual side goring give you the adjustability and look you desire. The premium soft leather uppers or dark taupe suede exude sophistication and finesse. The removable leather foot bed feels great but can be replaced with your own orthotic. Slip these on and we...

    $ 189.95
    In Stock
  • $ 84.95

    Get ready to hit the trails in comfort in these boots that are built to last. The molded counter support, waterproof uppers, and stable outsole contribute to the overall performance by increasing traction and durability. Additional comfort features include a padded tongue and collar, plus an EVA midsole. 

    $ 84.95
    In Stock
  • $ 129.95

    Stylish men's boot made by Apis. These boots are part of the Men's Comfort Collection and are just the right boot to accommodate a number of foot conditions such as AFO's, hammer toes, bunions, moderate pronated feet (flat foot) and moderate to severe high instep swelling.

    $ 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
  • $ 99.95

    For hiking, casual strolls, work, and more, the Propét Cliff Walker Low Strap is ready for the challenge. It's weather-resistant leather uppers combined with the Sealtex waterproof bootie construction make this a tough and durable shoe. The dual hook and loop closure make for a secure fit while being easy on-and-off. Enjoy the outdoors in the...

    $ 99.95
    In Stock
  • $ 84.95

    The Propet Lance shoe features a waxed Nubuck finish with nice detailed stitching. The shoe is made of an EVA midsole with rubber inserts to improve traction. You will love this shoe is it is not only extremely comfortable but also comes in three different width options: Medium, X Wide, and XX Wide. 

    $ 84.95
    In Stock
  • $ 79.95

    A low-top hiking boot that can be worn casually or for outdoor activities. The waterproof construction will keep your feet dry and the outsole tread provides high-traction functionality for ultimate grip. A comfortable hiking boot with high quality construction and comfort and support where its needed for all-day wear.

    $ 79.95
    In Stock
  • $ 99.95

    The Propet Blizzard Mid Lace Winter Boot has everything you need to stay warm and protected in chilly weather.

    $ 99.95
    In Stock
  • $ 239.95

    Trek for men has all the therapeutic benefits of a Drew Shoe, in a men's boot designed with waterproofing inside and out. The lightweight boot also offers oil resistance and slip-resistance in a non-marking rubber lug sole. Drew Trek shoes protects the feet from the outside elements while an oblique toe, steel shank and firm heel counters add to the...

    $ 239.95
    In Stock
  • $ 148.95

    A boot for all seasons, Jackson Hook & Loop features a water-resistant upper, leather collar lining, and moisture-wicking Trek-Dry vamp lining. The blucher style and three adjustable hook & loop straps allow for an adjustable fit to accommodate all foot types.

    $ 148.95
    In Stock
  • $ 129.95

    Men's Apis Casual Boots 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
  • $ 148.95

    The Jackson boot from Oasis is made of quality genuine full grain leather and a Trek-Dry® fabric that has been given an anti-microbial treatment to enhance its moisture absorption. Comes with pre-molded inserts that include a pair of removable spacers allowing for internal extra depth for the foot. F.C.T. Technology combines thermoplastic heel cup with a...

    $ 148.95
    In Stock
  • $ 119.95

    A classically designed chukka dress boot - made for formal occasions. It's supple full grain leather uppers and shock absorbent soles help stay soft on your feet while being durable. Available in widths up to men's XXW(5E) and sizes 15. Look great and feel even better with the Propét Grady!

    $ 119.95
    In Stock
  • $ 91.95

    A perfect easy-in, easy-out shoe for the cold weather. A low-top boot that you can keep by the door and be ready-to-go quickly. When heading back in, you can easily slide off. During wear, you can be sure that your feet stay dry and comfortable with the waterproof Scotchgard leather upper and moldable rubber toe. Be ready this season with comfort and...

    $ 91.95
    In Stock
  • $ 169.95

    A double-depth shoe that can be used for work or casual wear. With its added depth, this shoe accommodates for custom and extra-thick orthotics and extreme foot conditions. This is the lower-cut version of another Drew shoe, the Rockford boot. Additional features include water-resistant upper and linings and slip resistance. An everyday shoe that can...

    $ 169.95
    In Stock
  • $ 114.95

    Stay protected and comfortable with this durable constructed composite toe work boot. The waterproof construction and leather uppers make this a trusted footwear choice for even the most toughest of jobs. The removable footbed allows for foot orthotic accommodations and the high traction rubber outsole keep you stable. Let the Shield Walker be your work...

    $ 114.95
    In Stock
  • $ 94.95

    A versatile men's low-top shoe can be used for hiking or casual wear. Modeled after the popular Cliff Walker boot, this style comes with all the great design and features you love. From it's waterproof construction and weather-resistant leather uppers, you can do it all in this shoe. Be nimble on your feet with lightweight EVA mid-soles and high...

    $ 94.95
    In Stock
  • $ 159.95

    Support the natural contours of your foot with the Apex Ambulator Biomechanical Triple-Strap Work Boot. This boot is often recommended for those with diabetes, arthritis or anyone looking for supreme comfort.  

    $ 159.95
    In Stock
  • $ 159.95

    Apex Ambulator Biomechanical 6-Inch Lace-Up Work Boot has seven-eyelet lacing for easy on/off and a snug fit. This boot is often recommended for those with diabetes, arthritis or anyone looking for supreme comfort.

    $ 159.95
    In Stock
  • $ 179.95

    The most comfortable boot we've found. Big Easy combines a one-piece hook and loop fasteners with a sleek boot design. It's easy to wear, durable and comfortable. Two removable insoles allow for customization. The shoe's extended medial heel stabilizer reduces heel slippage and the boot top provides additional support.

    $ 179.95
    In Stock
  • $ 99.95

    A protective, composite toe low-top shoe - designed to keep you protected even during the toughest tasks. A top choice in low-top work shoes where you need toe protection and comfort. The durable, weather-resistant leather uppers and removable footbed have you covered in durability and adjustability for custom orthotics. Work lighter in the Shield...

    $ 99.95
    In Stock
  • $ 199.95

    Hit the trails with this durable Rugged Canyon Hiker by Drew! It features a genuine leather upper that is waterproof, laces for a great fit, padded collar, tongue and insole for superior support. Stay sure on your feet with Canyon's slip-resistant outsole.  

    $ 199.95
    In Stock
  • $ 114.95

    A perfect strap winter boot constructed to endure the wet and cold. The weather-resistant leather uppers and Sealtex waterproof bootie construction will keep your feet dry so you can keep going. The boot features three hook and loop straps and a padded, mesh-lined collar and ultra-soft, warm interior. Stay light, warm, and stable with the Cliff...

    $ 114.95
    In Stock
  • $ 109.95

    The dual-strap version of the Cliff Walker lace boot comes with the same great features of a removable footbed and waterproof material. A lightweight boot with a hook and loop strap closure and a durable outsole to grab the ground with each step for traction and support. The Cliff Walker Strap's sleek design and easy-entry strap feature make this a great...

    $ 109.95
    In Stock
  • $ 129.95

    A men's high-top athletic shoe that is lightweight and accommodating for a variety of foot conditions. Three Velcro® straps make for an easy closure while keeping the foot secure in the shoe - but just as easy to remove when unfastened. Broad entrance and extra room at the toe box for the comfort and satisfaction you are looking for from an athletic shoe.

    $ 129.95
    In Stock
  • $ 114.95

    A dress boot that features waterproof, supple leather uppers. The soft leather allows flexibility where you need it. The faux fur lining is soft on your feet and the single adjustable strap allows for more room in the entry area to easily get your foot inside the boot. A sophisticated look with a classic design, packed with plenty of comfort to keep you...

    $ 114.95
    In Stock
  • $ 154.95

    Apis Men's 503 Adjustable Strap Boot provide comfort to those suffering from edema, bunions, hammertoes, and severely swollen feet. The 8” height of the shoe provides extra support for the foot and ankle. This shoe is very soft and great for sensitive feet. Apis Men's 503 Adjustable Strap Boot is also A5500 SADMERC approved as a diabetic shoe.

    $ 154.95
    In Stock
  • $ 154.95

    Men's Boots from Apis Footwear made with genuine uppers & lining. These boots are ideal for moderate to severe foot problems such as pronated/flat foot, AFO's, bunions, hammer toes, and swelling. 

    $ 154.95
    In Stock
  • $ 138.95

    A lightweight hiking or work boot from Dr. Comfort with a unique no-tie elastic lacing and Velcro closure. The Ranger is your go-to boot for the next hiking adventure or outdoor excursion. It can also be used as a durable, rugged work boot. Designed to keep your feet comfortable during every wear. From the padded heel and tongue to the...

    $ 138.95
    In Stock
  • $ 157.95

    The Dr. Comfort Boss is an orthopedic lightweight work boot with a padded collar for added comfort. A boot designed for the hard working man that needs footwear support and comfort throughout the day. This orthopedic work boot offers a tough high abrasion, oil resistant outsole. Available in Black or Chestnut.

    $ 157.95
    In Stock
  • $ 144.95

    The Apex Sierra Trail Running hiking shoe offers a variety of features to provide support and keep your feet healthy. It highly breathable from the advanced technology advanced uppers and a soft, padded collars to prevent blisters. There are two removable inserts to accommodate for custom orthotics and arch support inserts. The EVA outsole provides rear...

    $ 144.95
    In Stock
  • $ 68.97 $114.95 test123 -40%

    Stay comfortable and dry this season with the Propet Truman. The supple leather uppers give your feet the comfort they need. 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.

    $ 68.97 $114.95 -40%
    Reduced price!
    In Stock
  • $ 134.95

    Let your feet spread out in the Hunter Hiking Boots. The wide toe box design allows your feet to spread out naturally for added comfort. The mesh and sueded combo allow your feet to breath while out in nature. Plus, the D-ring lacing system makes it easy to fasten to your feet for the perfect fit. The padded collar provides cushion around the ankles and...

    $ 134.95
    Product available with different options
  • $ 129.95

    Added-depth comfort boots that offer therapeutic benefits and some extra room for orthotics, AFOs, or internal modifications. The mesh and genuine leather uppers provide breathability while the high top feature provides ankle stability and support. The solid injected EVA midsole makes for a lightweight shoe, while the rubber outsole...

    $ 129.95
    In Stock
  • $ 139.95

    A hiking high top boots with plenty of orthopedic features to accommodate a variety of foot conditions. The symmetrical cut-line on the outsole make it easy to custom modify to your specification. With the two removable layers of inserts, you can remove one for some extra space or take both out to better accommodate for custom orthotics or AFOs. The...

    $ 139.95
    In Stock
  • $ 164.95

    A composite toe work boot for men made to keep you comfortable throughout the work day. The padded collar and leather/canvas uppers provided added comfort and durability. The removable insert and added depth accommodate custom orthotics or offer extra room for a variety of foot conditions. A great solution for your foot care needs.

    $ 164.95
    In Stock
  • $ 167.95

    A solid orthopedic steel toe work boot from Dr. Comfort with a padded collar for added comfort. This rugged work boot is lightweight with a tough high abrasion, oil resistant outsole. A perfect solution preventing discomfort while working hard on your feet.

    $ 167.95
    In Stock
  • $ 175.95

    Show off your rugged good looks while keeping in complete comfort in the Tucson boot from Drew Shoes. Its lustrous leather upper has a rich grainy texture and will look so handsome with its traditional lace-up front that no one will know that they were made to accommodate orthotics, and have enough padding on the insole, heel collar, and tongue to cushion...

    $ 175.95
    In Stock
  • $ 159.95

    The APEX Hudson Chukka Boot therapeutic shoe provides comfort and style for both casual or dress settings. This footwear designed to help you feel great on your feet while looking good while you are in them. A classic design featuring a whole lot of comfort!

    $ 159.95
    In Stock
  • $ 139.95

    A quality comfort hiking boot that features soft, tumbled leather uppers that helps to reduce friction and provide more flexibility. Enjoy even more comfort with the padded suede collar for added ankle protection and comfort. The AM5605 also features ultimate traction and stability with the durable high grip lug outsole. Hike the trails or take the...

    $ 139.95
    In Stock
  • $ 114.95

    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 much more comfort - the Troy is the perfect fall/winter boot.

    $ 114.95
    In Stock
  • $ 219.95

    A peak for men has all the therapeutic benefits of a Drew Shoe, in a men's ankle boot designed with waterproofing inside and out! The lightweight boot also offers oil resistance and slip-resistance in a non-marking rubber lug sole. 

    $ 219.95
    In Stock
Showing 1 - 60 of 64 items