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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 181 products.

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  • $ 134.95

    Comfort all-around in the criss-cross mary jane Orchid! Quality construction and materials and the classic design make this the everyday footwear choice. The criss-cross straps allow for the perfect adjustable fit and providing a larger opening for a variety of foot shapes. This mary jane is gentle on your feet with its soft leather uppers and spandex...

    $ 134.95
    In Stock
  • $ 149.95

    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...

    $ 149.95
    In Stock
  • $ 89.95

    Design flair gives this classic Mary Jane a modern look. The soft leather upper is lined in full-grain leather, with an extra-cushioned, removable poly insole and micro-fiber sock lining. Rubber inserts provide extra traction for an overall comfort package that you can walk around in all day.  

    $ 89.95
    In Stock
  • $ 79.95

    We are rating this sandal 5 stars for the most comfortable footbed. This dressy sandal is versatile and styled to give it an easy day or evening look. The 2 strap textured leather upper is accented with metal ornament capped straps for a little glamour. Enjoy easy walking with micro-fiber lined footbed, and a poly outsole that absorbs shock, reduces...

    $ 79.95
    In Stock
  • $ 122.95

    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.

    $ 122.95
    In Stock
  • $ 149.95

    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.

    $ 149.95
    In Stock
  • $ 149.95

    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.

    $ 149.95
    In Stock
  • $ 149.95

    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. 

    $ 149.95
    In Stock
  • $ 129.95

    A classic dress slip-on that charms and dazzles. The Treasure truly is a treasure for your feet with its ultra lightweight sole and uppers. Plus, a removable padded insole that provides all-day comfort. All decorated with a ornament and metal trim. Enhance your wardrobe with these elegant Treasure!

    $ 129.95
    In Stock
  • $ 129.95

    You won't want to pass up this versatile women's dress mary jane flat . The Danish brings functional features with a chic design. The stretch single strap is a perfect solution for a comfortable fit. The comfort does not stop there, with the lightweight and flexible outsole to make getting around a breeze. Plus, the padded footbed is one you will...

    $ 129.95
    In Stock
  • $ 129.95

    Comfort chic describes the Donut to a T. The Donut offers exceptional comfort for casual dress wear. The outsole is lightweight and flexible for a pleasant experience during wear. The dual stretch goring at the top allows for a perfect fit. Plus, the padded insole will help you keep going throughout the day. All the comfort features are paired with...

    $ 129.95
    In Stock
  • $ 99.95

    For the casual chic woman who likes versatility, the Harissa is a new twist on a classic. The open-toe sandal will look beautiful with a dress, jeans or a pair of shorts. The leather or natural cork uppers have five adjustable hook-and-loop straps for optimal support and adjustability. With the style in place, these sandals kick comfort to the next level,...

    $ 99.95
    In Stock
  • $ 149.95

    For the woman who loves classic style with a current edge, the Astrid is reimagined retro. This platform wedge is available in some of the season's most essential colorways. The suede uppers offer adjustable hook-and-loop straps for a custom fit, and a durable rubber outsole. The 3.0” platform heel is biomechanically designed to hug your arches, and...

    $ 149.95
    In Stock
  • $ 139.95

    A versatile sandal is a favorite for pairing with skirts, jeans, or even shorts. The Anna is an irresistibly feminine and daring espadrille wedge. The premium Nappa leather upper has an adjustable ankle strap with metal buckle, 2.5” heel, and scalloped edge detail. The jute-wrapped wedge heel has a rubber sole for stable walking.

    $ 139.95
    In Stock
  • $ 149.95

    Nothing sets off a summer dress or a great pair of jeans better than the perfect sandal. The Stephany is a classic and sexy open-toe sandal with Nappa leather upper, adjustable 3/4" strap, metal buckle detail and daring scalloped edge trim. The 2.5” jute-wrapped wedge heel has a rubber sole for stable walking.

    $ 149.95
    Product available with different options
  • $ 139.95

    Combine comfort with style in this sleek leather or kid suede upper with a classic kitten heel and adjustable strap. With a 1.93” heel and on-trend pointed toe, they are the perfect finish for a dress or a pair of slacks. The German rubber soles provide durability while the deep heel cup gives you unmatched support.

    $ 139.95
    In Stock
  • $ 139.95

    Make a statement of taste and glamour with a kid suede pump in a versatile style that will fit your looks at work or when you’re stepping out. The elastic trim and rubber sole give you excellent comfort, and the two-inch heel is just the right height for a transitional shoe. With Vio-Motion Technology designed to hug your arches, this is a special...

    $ 139.95
    Product available with different options
  • $ 99.95

    This classic shaped pump offers anything but classic style that truly makes it stand out from the rest. The Nappa leather upper with patent leather capped toe and 2” heel make this an edgy look from every angle. The removable microfiber footbed is a lightweight source of extra cushion, and Vio-Motion Technology hugs your arches to keep you comfortable.

    $ 99.95
    In Stock
  • $ 119.95

    What’s more timeless in fashion than a pair of cute flats? The Desiree is a fun and flirty ballet flat that works perfectly with jeans, slacks, or a dress. No matter your style, the quilted Nappa leather upper with patent leather toe cap are a perfect balance of classic and contemporary. 

    $ 119.95
    Product available with different options
  • $ 139.95

    For a smart look that fits any style, the Savannah flat is a winner. Contemporary colors and stitching make this a match for any outfit, and the perfectly versatile design easily takes you from business wear to weekend casual. Available in Leather or Vionic’s exclusive Savannah Suede, the comfort is unsurpassed with removable cushioned EVA insoles.

    $ 139.95
    In Stock
  • $ 149.95

    For the women with distinctive style, the Vionic women’s Evelyn Derby shoe is a perfect fit. The nubuck leather upper with ribbon laces is classic look that gives a woman singular style for any occasion. The clean lines and one-inch heel make it an understated but elegant accessory that pair well with any fabric for dressing up or keeping it casual.

    $ 149.95
    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
  • $ 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
  • $ 79.95

    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...

    $ 79.95
    In Stock
  • $ 189.95

    An ankle boot that is versatile and stylish. Made in either weather resistant suede or weather-resistant leather uppers and comes with a 2.4" heel that boasts confidence. The side tassel zipper makes for a beautiful detail as well as easy closure and a secure fit. Inside the boot is a supportive insole that contains a deep heel cup and contoured...

    $ 189.95
    In Stock
  • $ 129.5

    Comfortable and pizzazz are not words used together often with shoes - until now! The Orthofeet Emma offers a chic look with a biomechanical design to have you look great and feel even better. The wide 2" heel provides more stability and the medial inside zipper allows for easy entry. The outside goring allows for some stretch when walking and a...

    $ 129.5
    In Stock
  • $ 149.95

    Height and stability are merged into a stylish solution. The Tawny platform wedge offers some elevation while maintaining stability. The 3" platform is paired with suede straps and an adjustable buckle at the ankle for a secure, comfortable fit. The open air feel from the straps is great for warm summer days. Plus, the built-in footbed has a...

    $ 149.95
    In Stock
  • $ 149.95

    Look your best this summer with the Ariel Wedge sandal! This jute-wrapped espadrille wedge is available in three fun colors (Cherry, Black, or Nude). Plus, the style features an adjustable buckle at the ankle for a comfortable fit and a wide, perforated strap at the toe for breathability and style. The built-in footbed design cradles your foot to...

    $ 149.95
    In Stock
  • $ 137.95

    Soft on your feet and durable on the pavement. The Mallory offers an easy slip-on/slip-off wear while providing rigid shank in the mid-sole for arch support and stability. Plus, the roomy toe box and minimal seamlines give your feet exceptional comfort and prevents unnecessary rubbing which can cause skin irritation. Perfect for those with foot conditions...

    $ 137.95
    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
  • $ 129.95

    The Shoenanigan casual shoe is the perfect slip on shoe made with supple leather and a stretch gore on the center strap. Enjoy the removable cushioned insole which allows for a custom fit. Additionally, the Shoenanigan casual shoe comes in 5 width options for those needing a perfect fit. Wear with long skirts or pants cuffed at the ankle.

    $ 129.95
    In Stock
  • $ 109.95

    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...

    $ 109.95
    In Stock
  • $ 129.95

    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.  

    $ 129.95
    In Stock
  • $ 129.95

    The Tootsie dress shoe features a classic and breathable design.  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, these dress flats will have your feet smiling in no time.

    $ 129.95
    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
  • $ 109.95

    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.

    $ 109.95
    In Stock
  • $ 93.46 $109.95 test123 -15%

    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’s and head to the nearest casino or go salsa dancing. Go...

    $ 93.46 $109.95 -15%
    Reduced price!
    In Stock
  • $ 109.95

    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.  

    $ 109.95
    In Stock
  • $ 129.95

    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.

    $ 129.95
    In Stock
  • $ 129.95

    The Kiki mary jane style dress shoe hits all the marks for fashion and functionality. The footbed is removable! Get ready to dance to your favorite song in the Kiki. Wear with slacks or skinny jeans or a pencil skirt. Wear with your favorite dress on date night. The dainty look of the Kiki works with so many styles. So, grab your Kiki’s and go have fun!

    $ 129.95
    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
  • $ 79.95

    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.

    $ 79.95
    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
  • $ 89.95

    The Wish sandal will have you wishing on a star they came in more colors! It’s perfect for a night out with your favorite person or even wear to the office with a pair of slacks. Enjoy a 2” heel height and the padded memory foam footbed for an extra comfortable fit. You’ll love this beautiful yet flexible sandal.

    $ 89.95
    In Stock
  • $ 129.95

    The Vandy sandal is made with a snake print upper for an extra spicy look. The open toed feature is a nice touch and the adjustable back strap works great for added customization. The 1.25” heel height is great for those looking for a small addition to their heel height. Wear with your favorite little black dress or even a pair of boyfriend jeans. You’ll...

    $ 129.95
    In Stock
  • $ 129.95

    The Vacay sandals are perfectly designed for those looking for a cute yet functional style sandal. Enjoy the open toe feature and the adjustable sling-back strap at the ankle. The detailed stitching across the top adds a sophisticated look to the sandal. Wear with shorts, a long skirt or short skirt, or even boyfriend jeans.

    $ 129.95
    In Stock
  • $ 129.95

    The Voluptuous sandal features a dressy style with a little buckle adornment for added pizzazz. Enjoy the comfortable footbed and soft leather as well as the modest heel height of 1.25”. The wedge design makes these sandals great for wearing with long dresses, shorts, or even boyfriend jeans.

    $ 129.95
    In Stock
  • $ 129.95

    The Venture sandal features the perfect blend of chic and comfort. Enjoy the open toe design and the sling-back adjustable strap at the ankle. The fabric instep offers support and comfort for all day wear. Take a short stroll to your favorite coffee shop in these beautiful sling-back sandals.

    $ 129.95
    In Stock
  • $ 129.95

    The Virtual dress sandal is well made and pretty. Enjoy the sling-back adjustable strap at the heel and the stretch straps at the ankle. The lower heel height of 1.25” gives you just enough height to feel dainty without compromising on comfort. Wear them with a long skirt or dress or an old pair of boyfriend jeans cuffed at the ankle.

    $ 129.95
    In Stock
  • $ 129.95

    The Va Va Voom slide dress sandal is the perfect dress sandal for those looking for a shorter heel in their shoe. The soft suede leather uppers enhance the delicate look of the cross-strap design of the shoe. Wear on a summer day with a long skirt or dress or an old pair of boyfriend jeans cuffed at the ankle. The classic look of these sandals will have...

    $ 129.95
    In Stock
  • $ 74.95

    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...

    $ 74.95
    In Stock
  • $ 94.95

    Cute and slip resistant, the Jessica is perfect for the lady on her feet all day. A great occupational shoe for comfort and functionality. Enjoy the removable footbed which allows for insertion of custom orthotics. The Jessica comes in a variety of widths including Medium, Wide, and Extra Wide.

    $ 94.95
    In Stock
  • $ 89.95

    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...

    $ 89.95
    In Stock
  • $ 119.95

    A slim look and perfect design, we cannot decide which of the fabulous colors is best. The Vionic Gem Delilah comes in a stunning navy blue, rich mocha, and a classic black color. Wear them with denim or a skirt and head to a book club meeting. They are comfy and cute, what more can we hope for in a shoe? 

    $ 119.95
    In Stock
  • $ 149.95

    Look at these beautiful suede clogs! The Vionic Day Kacie clog is stunning. Featuring three fabulous colors: rich toffee, bright cherry, and classic black, these clogs can go with just about any outfit. Wear with flowing linen pants and a cropped shirt or pair with jean shorts. Have fun!

    $ 149.95
    In Stock
  • $ 119.95

    The spring style you have been looking for is here! The Coralina is a slingback espadrille wedge that goes beyond just looks. Its biomechanically designed foot bed supports your feet that promotes natural lower body alignment. The jute-wrapped wedge gives a earthy look and will be sure to heads. Be ready for the warmer days in the Coralina.

    $ 119.95
    In Stock
  • $ 139.95

    A dress shoe on a block heel with a sling back closure; someone pinch me! The Vionic Plaza Nareen is so special with its straight toe design and quality suede uppers. The outsole is made of German rubber and the deep heel cup and enhanced forefoot contour provide the comfort and stability you're looking for. These dress shoes pack in features and...

    $ 139.95
    In Stock
  • $ 149.95

    Dress for success in the Kaia! You will feel great in the Kaia with its stacked 3.1" heel height while offering a supportive deep heel cup and arch-hugging insole. The open heel and peep toe give the Kaia a unique styling that is sought after in this category. Be your best self in the Kaia!

    $ 149.95
    In Stock
Showing 1 - 60 of 181 items