Best Dress Shoes for Flat Feet: Feel Comfortable and Stay Stylish

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by  Karlton Miko Tyack | Last Updated: 
best dress shoes for flat feet - Thursday Boots Cavalier, Amberjack Loafer & a flat foot vector

If you have flat feet, you know you have particular footwear needs. You risk soreness, ankle pain, and long-term discomfort if you don’t meet these needs.

Unfortunately, many function-forward models are more orthotic than stylish.

Get the best of both worlds with our five best dress shoes for flat feet.

Best Overall
  • Innovative comfort technology gives arch support, cushion, and follows your natural movement
  • Design is both contemporary and classic, offering great versatility
  • Flexible outsole offers wide range of motion, while heel cup provides security
Best on a Budget
  • Leather-covered open-cell foam footbed combines comfortable breathability with structure
  • Leather sole with injected rubber is resilient and lithe
  • Excellent shape and size for those with extra wide feet
Great Value
  • Shape-forming footbed accommodates to flat feet for comfort and structure
  • Steel shank provides balance and support
  • High level of hand craftsmanship and supple calfskin leather offer impressive value
Most Comfortable
  • Heat-activated arch support tailors itself to your specific level of foot flatness
  • Sheepskin lining is durable but soft
  • Combination of heel support and flexibility
Best Chelsea Boot
  • Shock absorbing insole protects uneven terrain
  • Cork bed midsole supports all arch types
  • Goodyear welt construction ensures longevity

You may not know it, but there are a lot of benefits to having flat feet.

I’ve heard that folks with more horizontally-inclined feet can have enhanced balance or stability, and that with training, might be able to propel faster.

Flat feet are nothing to be ashamed of. 

However, they do make finding a suitable dress shoe a bit more difficult. The formal footwear market seems more dominantly aimed at the well-arched set.

If you’re fat footed and are sick of dress shoes causing you ankle pain, check out this round-up.

How Did I Come Up With My List?

As someone who wears dress shoes to work every day but spends more time running around concrete floors than sitting at a desk, I’ve studied, worn, and kept up to date with all of the footwear comfort technologies.

Using that knowledge, I consulted colleagues with flat feet and spoke with shoe experts, particularly those specializing in support and comfort, regarding almost 100 highly-rated models on the market.

I deep-dove into reviews on websites, trade publications, and commercial publications and stomped around shoe stores throughout the city wearing different models.

This round-up is a result of those weeks (but really years) of hands-on research. Each pick excels in a specific category, and I start with the best overall.

Arch Support and Comfortable Construction – These Are The Best Dress Shoes for Flat Feet 

Best Overall: Cole Haan Washington Grand Laser Wing Oxford

When I covered the Cole Haan Washington Grand Laser Wing Oxford in our most comfortable dress shoes round-up, I called it the dress shoe of the future. Part of it has to do with its innovative style, but this shoe isn’t all bark and no bite. Its comfort features are truly sophisticated.

It has Cole Haan’s special Grand.OS technology and anatomically-designed EVA footbed. This partnership balances arch support with cushion and heel-to-toe support that follows the movement of your foot.

This gives your flat feet the structure they need while providing softness and comfort.

Meanwhile, the leather outsoles are engineered to adapt to and mimic your foot’s natural motion when walking or running. Sometimes, shoes developed for flat feet are overly structured, but all your bases are covered since this outsole reduces fatigue.

And, of course, it’s a cool-looking shoe that isn’t overly trendy. The minimalist, perforated design has a contemporary vibe, but the slim, classical silhouette can blend in with any traditional suit and tie.

What I Like

  • The anatomical footbed and Cole Haan’s in-house comfort technology balance arch support with cushioning while accommodating to your foot’s natural movement when you walk or run.
  • The classic silhouette and contemporary details are distinct yet versatile.
  • The flexible outsole works with the secure rubber heel cup, partnering support with motion.

What I Don’t Like

  • This shoe runs a bit narrow. If you have wider feet, you’ll just have a more substantial break-in period. But bare with it—you’ll get there.

What Do Other Reviewers Say?

This shoe gets a lot of praise from reviewers with flat feet for how customized the comfort features are. Many claim that some overly-structured shoes give them the support they need but can sometimes tire out your foot sooner than you’d like. It’s like standing straight with perfect posture for too long.

There are some complaints about how narrow the shoe is, though users also report that the tightness goes away after the shoe is completely broken in.

The Verdict

Cole Haan’s Washington Grand Laser Wingtip provides the arch support needed for flat feet and has several features that ensure energy return to balance out the structure. The sophisticated comfort technologies accommodate your foot shape and movement, making this fatigue-reducing shoe perfect for work or play.

Style-wise, it’s a truly unique design. The wingtip visual is achieved using contemporary perforation, giving it a distinct character but all the adaptability you want from an oxford dress shoe.

Best Overall
Cole Haan Washington Grand Laser Wingtip

Cole Haan combines traditional craft with contemporary technology in the form of the Washington Grand Laser Wingtips. The proprietary cushioning system on this sleek dress shoe provides comfort, arch support, and mimics the natural movement of your feet.

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Best on a Budget: Florsheim Salerno Wingtip Oxford

With the Salerno Wingtip, Florsheim serves up a supportive and comfortable oxford by cleverly partnering up basic, tried-and-true shoe functions.

First, the footbed has Ortholite cushioning, a high-rebound and responsive foam. This material also has an open-cell construction, meaning it isn’t so dense that it makes the inside of the shoe unbreathable. In fact, this helps balance insulation and airflow.

When your feet are flat, the last thing you want is your shoe overheating and expanding them.

Second, this footbed is lined with leather, which helps with foot conforming.

And finally, the rubber injected leather outsoles create resilient comfort right out of the box and provide impact resistance. 

Sure, these features might be more elementary than the ones in the previous Cole Haan model, but this shoe is also several fractions of the cost, and does the trick just fine.

What I Like

  • The open-cell foam footbed is highly responsive and provides breathable support and rebound.
  • Between the leather lining and temperature-regulating sole layers, this shoe helps prevent overheating which causes your foot to expand.
  • The durable outsole has injected rubber taps, offering even more comfort and impact resistance.

What I Don’t Like

  • This is definitely a budget shoe with its cemented construction and non-full-grain leather upper. It won’t last you forever, which is okay considering the price. However, just know that the upper will start to crack when it’s on its way out.

What Do Other Reviewers Say?

Many reviewers are flat footed men who also happen to be wide footed. They’re grateful that the toe box is reasonably sized, which means the arch support isn’t affected by an overly squeezed foot.

A few reviewers also mention that this shoe runs large and that you should size down a half.

The Verdict

The Florsheim Salerno Wingtip Oxford is an effective choice if you’re on a budget or have wide feet.

Its simple yet effective construction provides support and temperature regulation, while the wide toe box accommodates feet of all widths.

The Salerno is also a good option if you only wear dress shoes occasionally. The budget construction won’t catch up to it as quickly.

Best on a Budget
Florsheim Salerno

The Florsheim Salernos are bang-for-buck cap-toe Oxfords that go all the way up to size 18s, with extra wide options too. They’re also equipped with comfort and support features that big and tall men often need.

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Great Value: Beckett Simonon Cohen Loafer

When your flat feet have subjected you to so many uncomfortable experiences with different dress shoe models, I understand that your instinct might be to look for softness and delicate builds.

However, you need a level of rigidity and tons of stability. That’s something a good steel shank can provide, and that’s what the Becket Simonon Cohen loafer has. It may just be a thin steel strip, but it properly distributes your foot’s weight and pressure, which a flat foot doesn’t naturally do as well when it’s in a dress shoe.

Fortunately, this structure is balanced out by a Vachetta leather lining, which regulates temperature, absorbs sweat, and controls odors, as well as a Blake-stitched construction. It’s still resoleable like a Goodyear welted shoe, but is much more flexible.

What I Like

  • With its full-grain leather upper and handcrafted build, this shoe offers a lot of quality for its price.
  • The steel shank works with the Blake-stitched construction and Vachetta interior to balance rigid support with comfort and temperature control.
  • The SBR heel cap provides impact resistance and traction, making this shoe easy to walk around in.

What I Don’t Like

  • On one hand, I love Beckett Simonon’s small batch model because it allows them to offer premium shoes at below-market prices. On the other hand, it can take over a month to ship.

What Do Other Reviewers Say?

Reviewers love the effective support the Cohen provides, especially for flat feet, and its versatile and high-quality design.

You can wear this shoe with jeans or a suit, and the supple full-grain leather is vivid in every colorway, and will patinate handsomely over time.

The Verdict

Thanks to its stable steel shank and series of comfort features, the Beckett Simonon Cohen is a supportive loafer for flat feet.

And thanks to the brand’s small batch business model, you get a handmade, hand-waxed, full-grain leather dress shoe at a fraction of what it would cost if middlemen and retailers were involved.

Best on a Budget
Beckett Simonon Cohen Loafer

With their smooth saddle and slight taper, the Beckett Simonon Cohen Loafers are elegant and unstuffy. You can wear them with anything, and their handcrafted full-grain leather construction offers unique value.

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Most Comfortable: Amberjack Loafer

The Amberjack Loafer is an adaptable minimalist shoe with an array of comfort and support features conducive to flat feet or anyone needing extra arch support.

This is because the midsole is equipped with heat-activated arch support. It might take a minute of walking for you to feel the support, but once it’s there, it’s specific to your exact arch—or lack of it. Whether you have extremely flat feet or just moderately flat ones, this shoe gives you custom comfort and support. 

Still, the soft sheepskin lining, the padded ankle, and the memory foam insole ensure this shoe is comfortable right out of the box.

This foam insole is pretty special. It’s super thick in the heel area, offering the kind of heel support you get from a hiking boot. Since it tapers towards the toe though, you also have the flexibility of a trainer.

What I Like

  • The heat-activated arch support conforms to any level of foot flatness.
  • The insole’s thick heel and flexible body, combine the best of boot functionality with sneaker functionality.
  • The minimal loafer design is versatile, regardless of which of the several colorways you go for.

What I Don’t Like

  • The lip digs into your front ankle at first, however this isn’t too bad because it just takes one wear for it to start to soften.

What Do Other Reviewers Say?

Reviewers absolutely rave about how immediately comfortable this shoe is. Few have reported any break-in period.

The only potential negative has to do with the fact that there aren’t any half sizes for the larger sizes. Reviewers mention sizing down to get a good fit, but that this situation will indeed require a break-in period. Half sizes cease from size 13 and up.

The Verdict

The Amberjack Loafer’s customized arch support is perfect for flat feet of every level. On top of that, several comfort features, like its sheepskin lining, innovative insole, and athletic TPU blended outsole, make this shoe easy to walk and stand in for hours at a time.

Most Comfortable
Amberjack Loafer

Amberjack’s Loafer is equipped with the brand’s heat activated arch support and a flexible yet boot-like heel support. Comfortable out of the box, this shoe is perfect for long periods of standing or walking.

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Best Chelsea Boot: Thursday Boots Cavalier Chelsea Boot 

The Thursday Boots Cavalier boasts two important protection and comfort features for flat feet.

The midsole is made from cork, which, when combined with the leather lining, will mold to support any arch type. Of course, this includes those with flat feet.

Meanwhile, the insole is shock absorbing. This means the arch support you’ve developed from wearing this boot won’t be knocked off course even if you’re walking on uneven terrain.

And since this is a Chelsea boot, its simple aesthetic fits into a range of personal style. Another great practical feature? It’s Goodyear welted, meaning this shoe will last you years into decades if you’re good to it.

What I Like

  • The shock absorbing insole and cork bed midsole provide comfort and protection for all arch types.
  • The Goodyear welt construction ensures longevity and water resistance.
  • The minimalist upper is adaptable and can be worn with any non-athletic outfit, whether formal or casual.

What I Don’t Like

  • The robust Goodyear welting and high-quality leather mean that this shoe will need a substantial break in period.

What Do Other Reviewers Say?

Several reviewers claim that the Cavalier is one of the most comfortable boots they’ve ever worn. Moreover, many love how flexible the elastic panel gorings are. It makes this shoe easy to slip on and off, which is highly convenient when you’re in a hurry.

The Verdict

The Thursday Boots Cavalier Chelsea Boot is an effectively supportive shoe for flat feet thanks to its cork-bed midsole and fully lined leather interior. With its Goodyear welt construction and shock absorbing insole, it’s also as protective and durable as it’s stylish and versatile.

Thursday Boots Cavalier Chelsea Boot

The Thursday Boots Cavalier Chelsea is a minimalist and adaptable boot. It’s made of full-grain leather and has a cork bed midsole supporting a wide range of arch types.

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What to Look for In Dress Shoes for Flat Feet

Good Arch Support

Of course, the most important feature you want out of dress shoes is arch support. If you have flat feet, you don’t have natural arches, making your feet more susceptible to stress during acceleration and direction changes.

Arch support makes up for this lack of structure, thereby keeping soreness and ankle pain at bay.

Comfortable Fit

All the support in the world isn’t going to make up for a lack of comfort. Make sure you get your dress shoe size correct, ideally using a Brannock, which we discuss here. Otherwise, your flat feet will be taken care of, but your toes might be squished, or your heel might be slipping.

Supportive Insoles (or Removable Ones)

Good insoles can help with fatigue reduction. Sometimes, shoes with too much support can cause your feet to get prematurely tired. Again, it’s like standing up straight for too long.

If the insoles aren’t adequate, at least go for shoes with removable ones, so that you can replace them with ones that meet your specific needs.

Adequate Width

If a shoe doesn’t have the adequate width, it can squeeze a bit more arch into your foot or flatten it out more than it already is. Either way, this isn’t good because it affects the arch support that’s in place, and it affects the way any foot conforming material will mold.

Choose the right width to ensure you get the exact arch support you need and the comfort you want.

Justice for the Flat Footed

The Cole Haan Washington Grand Laser Wing Oxford is the best overall pick, thanks to its innovative support and comfort technology, as well as its innovative looks.

If you’re on a budget, the Florsheim Salerno Wingtip Oxford has simple yet effective features that serve flat feet. Meanwhile, the Beckett Simonon Cohen Loafer offers excellent value due to the company’s small batch business model.

The Amberjack Loafer supports flat feet while providing a high level of sophisticated comfort, while the Thursday Boots Cavalier Chelsea accommodates flat feet while protecting them from impact as well.

Our Top Pick
Cole Haan Washington Grand Laser Wingtip

Cole Haan combines traditional craft with contemporary technology in the form of the Washington Grand Laser Wingtips. The proprietary cushioning system on this sleek dress shoe provides comfort, arch support, and mimics the natural movement of your feet.

Check Price on Amazon
If you click this link and make a purchase, we earn a commission at no additional cost to you.


What are flat feet?

Flat feet are those with little to no arch. If you have flat feet, this means the inner sides of your feet are flush against the ground when you’re standing up.

What type of shoe is best for flat feet?

Flat feet need shoes with good arch support, as well as the right size, width, and cushioning. If you require a dress shoe, go for something like the Cole Haan Washington Grand Laser, with plenty of support and innovative comfort features.

Should flat feet wear wide shoes?

The width of your foot, more than its flatness, affects whether or not you should wear wide or narrow shoes. However, if you have flat feet, it’s important to choose the right width and size, as these elements may affect the shoe’s arch support.

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