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Diabetic & Orthopedic Dress Shoes For Women

We offer comfort women's dress shoes, including high heels, flats, kitten heels, and more - for all formal occasions. Some of our dress styles offer a low heel and wide toe box to reduce friction and rubbing and help with foot conditions like bunions. You can be a fashionista without being uncomfortable, our selection has all the stylish and trendy comfort shoes without compromising on foot support. Browse our brands of women's comfort dress shoes!

DressThere are 183 products.

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  • $ 149.95

    The Drew Bouquet shoe has it all! The Bouquet has removable insoles to allow for insertion of your own orthotics and across the forefoot flap, enjoy the convenient dual side Velcro® closure which helps for easy entry into shoe. Lightweight and sturdy, the Bouquet is surely a favorite.

    $ 149.95
    In Stock
  • $ 109.99

    The Heidi dress shoe is stunning. The Heidi comes in Black Diamond, Silver Iridescent Glitter, or Black Microtouch fabric. Enjoy the padded footbed and quality fabric and leathers made throughout Ros Hommerson’s Evening Wear collection. With a swing or salsa dancing style design, these dress shoes work with all types of formal wear.

    $ 109.99
    In Stock
  • $ 124.99

    The Drew London II Wedge is a casual slip-on shoe that offers lots of comfort features for unbeatable all-day comfort. Double depth with two removable insoles creates space for custom orthotics or simply some extra toe room.

    $ 124.99
    In Stock
  • $ 159.95

    When it comes to therapeutic shoes, style often takes a back seat to function, but with the Drew Rose Mary Janes you won't have to sacrifice either. These simple comfort shoes are designed with Drew's Plus Fitting System which incorporates two removable, moldable, dual-density PU footbeds for added double depth. 

    $ 159.95
    In Stock
  • $ 132.99

    Enjoy a romantic dinner with your darling in this beautiful pair of Mary Jane casual shoes that give you the custom fit you need with two removable inserts for added and double depth. The stylish look works well with a number of different outfits and provides you with a stable wear with it's tempered steel shank.

    $ 132.99
    In Stock
  • $ 119.95

    A beautifully designed mary jane style shoe with detailed cut-outs on a supple leather upper. The flexible leather provides some give for your feet during wear. The adjustable strap allows you to securely fit the shoe to your feet. This shoe also features a Drilex lining to wick away moisture to help keep your shoes fresh and prevent odors. All this...

    $ 119.95
    In Stock
  • $ 129.99

    This Apis Women's Mary Jane dress shoe is part of the Women's Comfort Collection series designed to accommodate moderate high instep/swelling, pronated/flat foot, & bunions. Also accommodates severe hammer toes, partial foot, and AFO's. Closure is a velcro strap.

    $ 129.99
    In Stock
  • $ 84.95

    The sweetest little Mary Jane shoe around. Check out the Mary Ellen full grain leather shoes. These shoes feature double insoles for double depth and added custom ability. Remove both insoles to allow for your own custom orthotics or AFO accommodation. The Mary Ellen is approved for reimbursement under the Medicare Therapeutic Shoes for Persons with...

    $ 84.95
    In Stock
  • $ 29.99

    The Propet Diana Strap Women's Stretchable Shoe is a stylish dress shoe that provides you with all day comfort and a healthy solution to common foot pains. This shoe has two removable footbeds. Diana is a comfortable and handsome casual shoe with a bicycle toe and hook-and-loop instep strap.  

    $ 29.99
    In Stock
  • $ 129.99

    Comfort blends perfectly with fashion in this women's dress shoe. Wear this buckle-closure pump all day without the typical aches and pains. This shoe is also one of the few dress shoes with removable insoles and breathable, full leather linings. 

    $ 129.99
    In Stock
  • $ 139.99

    The Heather Drew® Shoe does a great job of combining style and comfort while providing that much needed arch support. Take a stroll in the park or head to the coffee shop in these perfectly cute mary jane shoes that are a must have for every gals wardrobe.

    $ 139.99
    In Stock
  • $ 109.99

    If you're looking for a comfortable shoe for an elegant occasion, the Ros Hommerson Tawnie Pump is the complete package wrapped up in a neat little bow. Premium quality leather upper meets a patent toe cap and feminine bow detailing in the upper. 1-inch chunky heel adds stable height. In the interior, Drilex lining wicks away moisture while the padded...

    $ 109.99
    In Stock
  • $ 134.99

    You'll love the ease and comfort of the fisherman-style Ginger, which features clean lines in the strappy upper and a simple hook-and-loop closure. Designed with Drew's proprietary Plus Fitting System, it has two removable insoles that provide for double the added depth and the perfect fit you can even insert your own custom orthotics.

    $ 134.99
    In Stock
  • $ 139.95

    Women's Vionic, Josie Low Heel Pumps These kitten heels are a sleek and flattering choice Leather upper Slip-on style for an easy on and off Manmade linings Molded, cushioned footbed with biomechanic contours and a layer of foam added to the metatarsal dome padding to support and cushion the foot Deep heel cup and enhanced forefoot contour for added...

    $ 139.95
    In Stock
  • $ 99.95

    One step into this shoe and you'll feel like you're walking on clouds. Great-looking crackled leathers make Ros Hommerson® Ronnie slip on the most requested one in the industry. These Ros Hommerson shoes define quality, comfort, and style.

    $ 99.95
    In Stock
  • $ 124.95

    Orthofeet Celina Women's mary jane shoes 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.

    $ 124.95
    In Stock
  • $ 84.99 $99.99 test123 -15%

    Enjoy your next night out in the Ros Hommerson® Pearl. Pearl is dressy, opened toed sling that features an adjustable heel strap. This women's dress pump is crafted with a foam-cushioned footbed and flexible leather sole to keep you comfortable throughout the day.

    $ 84.99 $99.99 -15%
    Reduced price!
    In Stock
  • $ 119.95

    A t-strap women's dress shoe features a swirl button design at the toe area. The uppers are made of soft leather and the linings are a soft leather material. The insole can be removed to accommodate braces and orthotics or keep them in for therapeutic relief. A cute women's dress flat style with durability and comfort. Look and feel great in the Paris!

    $ 119.95
    In Stock
  • $ 79.95

    The Miriam sandal is perfect for those looking for a truly customizable fit in their sandal. The uppers feature stretchy straps for those who experience slight swelling of the foot when walking. The footbed is ultra-comfortable as it is made using a generous amount of padding. The small grommets add a unique look to the shoe. Wear with long dresses,...

    $ 79.95
    In Stock
  • $ 52.99

    A classic strap loafer design with luxurious soft leather uppers. Get around smoothly with the Autumn women's loafers.  The removable high-density open cell insole provides exceptional arch support and allows for breathability during wear. The insole can be removed as well for your own inserts. With the light and flexible...

    $ 52.99
    In Stock
  • $ 99.99

    The Ros Hommerson® Helen shoe is made from the finest fabrics on the market and offers elastic stretch in the upper for a premium fit. This sleek slip-on offers drilex® lining and foam padding in the footbed. Helen by Ros Hommerson® is extremely lightweight yet the quality and comfort are unmatched in the industry. 1.75" heel.

    $ 99.99
    In Stock
  • $ 139.99

    The Drew Genoa is a casual, everyday shoe packed with all the comfort features Drew is famous for. The adjustable single-strap hook and loop fastener in this timeless Mary-Jane style offers maximum adjustability for a customized fit. The Drew Genoa goes great with any outfit, for any occasion.

    $ 139.99
    In Stock
  • $ 99.99

    The Jada ballet flat captures a classic style with comfort and durability. Features removable, moldable, dual-density insole with shock absorption and a firm heel counter that accomodates prescribed orthotics.  

    $ 99.99
    In Stock
  • $ 109.99

    The Twilight dress shoe features a classic design and a smart bow adornment on the top of the shoe.  Enjoy the removable padded footbed and foot-flattering design. The 1” heel height works great for those who need just a small pep in their step. Made with quality materials and flexible rubber sole, these dress flats do not disappoint.  

    $ 109.99
    In Stock
  • $ 69.99

    The Mackenzie sandal is similar to the Miriam and the Mellow. All feature a comfortable footbed due to the generous padding built into the sandal. The Mackenzie sandal features a beautiful beaded detail on the uppers. Enjoy a 1” heel height for a little pep in your step. Wear with skirts, shorts, or even boyfriend jeans cuffed at the ankle.

    $ 69.99
    In Stock
  • $ 144.95

    We love the Janice! It's a great looking therapeutic shoe that doesn't compromise on protection. The Janice also has a roomy toe box design and an advanced outsole for shock absorption and resilience.   

    $ 144.95
    In Stock
  • $ 129.99

    A women's oxford wingtip design gives the Rome a classic look while providing flexible fitting with its two removable footbeds. Enjoy the added comfort of the Rome with its padded tongue and collar, which also helps reduce heel slippage. Made to provide relief for a variety of foot conditions, walk in comfort with this classically-designed style!

    $ 129.99
    In Stock
  • $ 129.95

    Orthofeet new shoes offer the "slip-on" look with the comfort of adjustable strap shoes. The shoes feature hook and loop straps that provide a wide opening and facilitate getting in and out of the shoe. The original middle strap can replaced with a longer strap, which comes with the shoe, offering a perfect fit for feet with higher instep

    $ 129.95
    In Stock
  • $ 144.95

    An intricate perforated slip-on design with hook-and-loop strap for adjustability, the Regina delivers style. Its full-grain leather upper and soft fabric linings wick moisture away from the foot and help keep feet dry.  

    $ 144.95
    In Stock
  • $ 119.95

    The Karat is the dress shoe that you have been waiting for. The footbed is removable! The uppers are elasticized to enhance the fit of the shoe. Wear with slacks or skinny jeans or a pencil skirt. Wear with your favorite dress on date night. The polished look of the Karat goes with so many outfits. These dress shoes are truly versatile.

    $ 119.95
    In Stock
  • $ 119.95

    a women's casual dress shoe designed for foot conditions like hammertoes, swelling (edema), arthritis and more. The upper stretch material on the vamp of the shoe help reduce rubbing on the top side of the foot, thus helping prevent sores and ulcers. The Surefit Lima is a perfect solution for those in need of foot protection and looking for a classic...

    $ 119.95
    In Stock
  • $ 114.95

    A modern, sleek design with a unique strap and buckle adornment. The zipper on the inside of the boot allow for easy entry and the full-grain leather upper create a durable boot that will last. Inside the boot has a latex-cushioned insole and Nylex lining for additional support and comfort.

    $ 114.95
    In Stock
  • $ 129.5

    The Orthofeet Maya 2" heels are biomechanically engineered with Orthofeet’s innovative Bioheel Technology comfort features that are not found in any other high heel. Bioheels’ Ortho-Cushion® technology allows you to walk comfortably without the discomfort, which is common with regular high heels. This unique heel features a embellished vamp...

    $ 129.5
    In Stock
  • $ 129.5

    The Orthofeet Lilly 2" heels is part of the Bioheel line offering a better way to wear heels. The Bioheel collection is biomechanically engineered to allow comfort while walking in heels and the ability to adjust the support at the arch and the space in the shoe to prevent heel slippage. The classically designed...

    $ 129.5
    Product available with different options
  • $ 99.99

    The Tempt is a classy and beautiful dress shoe great for evening wear. Enjoy the padded footbed and quality fabric and leathers made throughout Ros Hommerson’s Evening Wear collection. With the minimal heel height, you’ll be light on your feet all evening.  

    $ 99.99
    In Stock
  • $ 109.95

    The Kitty dress shoe is packed full of elegant style. The Kitty dress shoe is also a stretch pump making them ultra-comfortable to wear. Check out the elasticized topline! The footbed is also removable. Enjoy the most comfortable 2” dress shoe you’re going to find.

    $ 109.95
    In Stock
  • $ 58.99

    An elegant comfort boot with a unique tweed fabric accent that makes for a modern design. Easily slip on-and-off this boot with the full inside zipper and enjoy the comfort inside with the Nylex lining and latex-cushioned insole. This boot also includes a buckle for aesthetics and sophistication. A great ankle bootie for the fall and winter seasons!

    $ 58.99
    In Stock
  • $ 139.95

    The Magnolia features the Plus Fitting System two removable footbeds for added and double depth. Removable ULTRON footbed with Drilex Topcover. Ultra lightweight polyurethane slip-resistant outsole. Extended medial heel stabilizer. Tempered steel shank. Drilex lining with AEGIS Microbe Shield. Soft, foam-padded collar. Accommodates prescribed orthotics.

    $ 139.95
    In Stock
  • $ 139

    New to the Casual Comfort Collection is the Cara, a classic style perfect for any occasion. The Cara chukka boot is a popular style that has a suede leather upper, extra depth (A5500) and is made of durable, full-grain suede leather with stylish appeal. Available in black and brown.

    $ 139
    In Stock
  • $ 139.99

    Pamper your feet in the Drew Hannah. This style comes with convenient stretch gore panels for easy on and off and two removable footbeds to allow more room in the shoe to accommodate custom orthotics. Features a nice sturdy steel shank for added arch support and overall stability. The cross-design element and fine detailed stitching add to the stylish...

    $ 139.99
    In Stock
  • $ 139.99

    Pamper your feet in the Drew Metro. This style comes with a convenient side zipper closure and two removable footbeds to allow more room in the shoe to accommodate custom orthotics. Features a nice sturdy steel shank for added arch support and overall stability. The perforated cutouts add to the stylish look and also allow substantial breathability....

    $ 139.99
    In Stock
  • $ 179.95

    Drew Kool boots combine the softness of Drew's most popular comfort shoes with long-lasting, all-purpose durable leather and suede combination. On the inside, these orthotic boots contain one of the best, supportive insoles in the world, while on the outside, they have the durability to fit an active lifestyle. The water-resistant construction allows your...

    $ 179.95
    In Stock
  • $ 89.95

    The Tina dress shoe features a classic design and cutouts for added breathability.  Enjoy the padded footbed and quality fabric and leathers made throughout Ros Hommerson’s Evening dress shoe collection. The 1” heel height works great for those who need just a small pep in their step. You’ll love these flattering and feminine dress shoes.

    $ 89.95
    In Stock
  • $ 159.95

    A modern version of the classic Mary Jane style shoe, the Buttercup features an extra adjustable strap at the heel to reduce heel slippage and provide a better fit. The adjustable strap at the instep comes with a strap extender to allow for even more room. Also, inside the shoe is a soft spandex lining to help eliminate friction during wear. The outsole...

    $ 159.95
    In Stock
  • $ 144.95

    A clean and classic look complements the therapeutic comfort of the Apex Linda monk-strap shoe. Featuring an upper of full grain leather, this women's monk shoe is part of the Petals collection of ultra-lightweight comfort footwear. An instep strap with hook-and-loop closure allows for quick on/off while accommodating, snug fit. 

    $ 144.95
    In Stock
  • $ 129.95

    A trendy tassled mule available with suede nubuck uppers. The Vionic Reagan will be the dress shoe that is talked about this season. Dress with style and comfort in suede uppers all on top of a leather stacked heel. 

    $ 129.95
    In Stock
  • $ 144.95

    The Ambulator Biomechanical Mary Jane is designed with comfort in mind with features such as rocker soles, removable comfort orthotics and soft pigskin leather linings.

    $ 144.95
    In Stock
  • $ 99.95

    A slip-resistant occupational slide shoe that is designed to provide you comfort when you are on your feet for prolong periods. An easy slide in or out to get going in the morning or take off after a long day. Enjoy the removable footbed which allows for insertion of custom orthotics. The Jana comes in a variety of widths including Medium, Wide, and...

    $ 99.95
    In Stock
  • $ 129.5

    The Orthofeet Marina 2" heel features biomechanically engineered comfort with its Bioheel Technology design. The Bioheel Technology helps with adjustability with arch support and space in the shoe to prevent heel slippage. The elastic goring and velcro strap across the shoe help secure the foot while providing the perfect fit. A clean,...

    $ 129.5
    In Stock
  • $ 119.95

    The Cozy features a unique twist on a ballet style shoe. The cross-straps across the front allow the ultimate in flexibility while the fully cushioned footbed soothes your feet while walking. These shoes are perfect for those with an active lifestyle. Slip them on and head to your favorite park or book store. You’ll love these super cute comfy shoes.

    $ 119.95
    In Stock
  • $ 139

    Beautiful details and rich finishes adorn our women's Lu Lu shoes. The Merry Jane style features a full top grain leather upper which creates luxurious looks for casual or dress. Lateral strap self-adjusts with a contact closure for a perfect fit. 

    $ 139
    In Stock
  • $ 109.99

    The Tango dress shoe features a modern twist on a classic design with the asymmetrical patent design and textured print leather on the top of the shoe.  Enjoy the removable padded footbed and foot-flattering design. The 1” heel height works great for those who need just a small pep in their step. Made with quality materials and flexible rubber sole, these...

    $ 109.99
    In Stock
  • $ 119.95

    Slip into a casual but classy flat with the Vionic Minna flat. Flexible and lightweight, this chic flat is crafted with premium leather and rubber outsole for a comfortable wear.

    $ 119.95
    In Stock
  • $ 136.99

    The Drew shoe Endeavor is not only stylish but comes with great arch support and a light-weight insole making them great for those who need a little more stability out of their shoes. Those who overpronate may find this shoe beneficial to their wardrobe. The uppers are made with a quality leather and the removable footbed allows for custom orthotic...

    $ 136.99
    In Stock
  • $ 99.99

    Unique and made from the finest materials, this sleek slip-on offers soft lining and a foam padded footbed. Features an oversized bow for additional personality and style.

    $ 99.99
    In Stock
  • $ 99.99

    You’ll feel lucky when you wear the Lucky! Enjoy the padded footbed and quality fabric and leathers made throughout Ros Hommerson’s Evening Wear collection. Made with silver iridescent glitter or black microtouch fabric, you’ll appreciate the sexy design of these dress shoes. So, grab your Lucky shoes and head to the nearest casino or go salsa dancing. Go...

    $ 99.99
    In Stock
Showing 1 - 60 of 183 items