Black FridayDealsBuying guidesBrandsStoresTermsPrivacydeal.ai apps

© Deal.ai Inc.

Deal.ai › Dr. Comfort
Dr. Comfort
Dr. Comfort Wing Men's Therapeutic Diabetic Dress Shoe

Dr. Comfort Wing Men's Therapeutic Diabetic Dress Shoe

4.3· 27 ratings

Best price now

$109.00at PoshmarkObserved at 10:53 PM

32% under what the other stores charge

Compared across 4 stores. Prices are checked against each store and labelled with when.

Visit Poshmark

Ask our shopping agent

Enter to send, Shift+Enter for a new line

Our take on the Dr. Comfort Wing Men's Therapeutic Diabetic Dress Shoe

The Dr. Comfort Wing is a men's leather lace-up dress shoe built as a therapeutic diabetic shoe, with a roomy toe box and removable insole. It pairs a dressy wingtip look with the deeper, wider fit that medical footwear needs. As of November 3, 2026, the best new price is $109.00 at Poshmark, with 4 stores selling it new.

Best forMen with diabetes or sensitive feet who need a dress shoeWide or extra-wide feetWeddings and formal eventsAll-day wear at work
Pros
  • Leather upper in dress wingtip style
  • Roomy toe box for diabetic and wide feet
  • Removable insole fits custom orthotics
  • Lace-up closure for adjustable fit
  • Comes in chestnut and black
Cons
  • Limited color choices
  • Dress styling, not a casual sneaker
  • Sizing runs wide, so fit needs checking
  • Fewer ratings than mainstream shoes

Dr. Comfort Wing Men's Therapeutic Diabetic Dress Shoe prices at every store

  • PoshmarkNew

    In stock

    $109.00Observed at 10:53 PM
    Visit store
  • Ames WalkerNew

    In stock

    $160.00Observed at 10:53 PM
    Visit store
  • OrthoticShop.comNew

    In stock

    $181.00Observed at 10:53 PM
    Visit store
  • American Quality Health ProductsNew

    Availability unknown

    $122.99Observed at 10:53 PM
    Visit store

Also available at

  • Flow Feet Orthopedic ShoesCheck price at Flow Feet Orthopedic Shoes
  • DT FootwearCheck price at DT Footwear

Dr. Comfort Wing Men's Therapeutic Diabetic Dress Shoe price history

Lowest price we've seen: $109.00 on Nov 4 at Poshmark. Tracked across 6 stores since Nov 4.

What reviewers say

Owners rate it 4.3 out of 5 across 27 ratings. Buyers with wide, sensitive feet tend to be the most satisfied.

Pros
  • Comfort for wide and diabetic feet
  • Dressy look that hides the therapeutic build
  • Room for orthotics
Cons
  • Fit can run large
  • Limited color options

Specifications

Dress Color
Chestnut, Black
Dress Fabric
Leather
Dress Closure
Lace-up
Shoe Type
Dress shoes, Dress, Boots

Questions and answers

Is the Dr. Comfort Wing worth it?
If you need a dress shoe that fits wide, sensitive feet, it is one of the few leather wingtips built for that. At $109.00 at Poshmark as of November 3, 2026, it costs less than most therapeutic dress shoes.
Does it fit orthotics?
Yes. The insole is removable, so you can swap in a custom orthotic. Check the depth first if your orthotic is thick.
How does the sizing run?
The Wing is built on a wide last and many buyers find it runs large. Measure your foot and consider going down a half size.
What colors does it come in?
Chestnut and black, both in leather. That covers most formal and business dress needs.
When is it cheapest?
The lowest new price seen is $109.00 at Poshmark as of November 3, 2026. Watch for markdowns on older colorways.
Where is the Dr. Comfort Wing Men's Therapeutic Diabetic Dress Shoe cheapest?
At Poshmark, for $109.00, 32% under what the other stores charge, as of our latest check.
What do buyers say about the Dr. Comfort Wing Men's Therapeutic Diabetic Dress Shoe?
Rated 4.3 out of 5 from 27 ratings.
Where can I buy the Dr. Comfort Wing Men's Therapeutic Diabetic Dress Shoe?
6 stores we checked sell it, including Poshmark, American Quality Health Products, Ames Walker, OrthoticShop.com, Flow Feet Orthopedic Shoes.

More from Dr. Comfort

  • D
    Dr. Comfort Justin Casual Dress Shoe
    Dr. Comfort Justin Casual Dress Shoe
  • D
    Dr. Comfort Men's Therapeutic Diabetic Shoes
    Dr. Comfort Men's Therapeutic Diabetic Shoes
  • D
    Dr. Comfort Men's Athletic Diabetic Sneakers
    Dr. Comfort Men's Athletic Diabetic Sneakers
  • D
    Dr. Comfort Women's Therapeutic Diabetic Shoes
    Dr. Comfort Women's Therapeutic Diabetic Shoes
  • D
    Dr. Comfort Gordon Diabetic Shoes
    Dr. Comfort Gordon Diabetic Shoes
  • D
    Dr. Comfort Men's Endurance Plus Diabetic Shoes
    Dr. Comfort Men's Endurance Plus Diabetic Shoes
  • D
    Dr. Comfort Refresh Diabetic Shoes
    Dr. Comfort Refresh Diabetic Shoes
  • D
    Dr. Comfort Men's Endurance Diabetic Shoes
    Dr. Comfort Men's Endurance Diabetic Shoes
All Dr. Comfort deals and products →