Most Comfortable Dress Shoes

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Dress shoes have a notorious reputation for being uncomfortable and even painful. Typically, these shoes are reserved for wearing at a formal event or on a special occasion.

Today, however, with the need to have more than just one use, shoes are more versatile. Dress shoes are now a common sight for both men and women at the office.

They are the go-to pair of shoes for many professionals, and some even use their dress shoes as part of their out-of-office casual wear. This is made possible by the availability of different styles of comfortable dress shoes on the market.

Yes, it’s easy to find dress shoes that do not cause pain, but many people still don’t know the basics of looking for the most comfortable dress shoes. To help you out, here are some warning signs that your current shoes need to be replaced with a better fitting pair.

  • Unsightly creasing at odd places is a big warning sign that you are wearing an ill-fitting pair of dress shoes. Creasing happens when the foot bends in an unnatural way to follow the shape of the shoe. This can cause a lot of pain and blistering if you continue to wear them.
  • Flopping feet and constant tripping are two signs that your shoes are too big for you. A good quality pair of dress shoes should feel like a natural extension of your feet and not a unique addition that you constantly trip on.
  • The shape of the shoe does not match your feet is a clear indication that you need new shoes. The balls of your feet, which are the widest part, should be able to fit perfectly into the broadest part of the shoe without any pinching or pain.

How to tell if the shoe fits

After you have determined that the current shoes you are wearing are not the correct size for your feet, the next challenge begins. Everyone has been through the struggle of choosing out a new pair of shoes, and it’s always hard to tell if you’re getting the right fit or not until you actually get to wear them for a full day! By then, it’s too late to return.

Here are some tips to keep in mind to help you purchase the correct size dress shoes that are comfortable to wear the entire day. With these tips, you’ll be able to make the right choice from day one.

Buy shoes that are closest to the shape of your feet

This is very helpful as a pair of shoes that have the same or a similar form to your feet will have a better and more comfortable fit. Think about it this way. If your toes are very wide and flat, you won’t want to buy a pointed shoe. A pointed shoe is unlikely to feel comfortable on your feet because they will squeeze your toes inward, and that will cause pain and blisters. Instead, try to choose shoes which mimic your feet shape.

Measure your feet regularly

Although you already know the general size of your feet, it also helps to measure them again before buying a new pair of shoes. Both adult and children’s feet size’s can change over time, and by getting the most current measurement, you will be sure to buy shoes that are the right size.

If you aren’t sure how to measure your feet, you can order a foot measuring tool online or simply use a ruler. Shoe sizes aren’t hard to figure out once you know the length of your foot. Having detailed information will help ensure that you can order the right size from any brand.

Consider the size of both feet

Each foot has a different size. It may not be a big difference, but your larger foot will feel the tightness and the pinching if you choose to follow the sizing of the smaller foot. This can lead to a lot of pain and discomfort for one foot, which is almost as bad as both feet hurting.

For that reason, most people choose to buy shoes which fit their larger foot better than their smaller foot. If the difference between your feet is extreme, you may want to consider buying two pairs of shoes and wearing two different sizes at once to get the best fit on both of your feet.

Buy shoes in the afternoon

Your feet tend to expand during the day. Buying shoes in the morning could lead to buying the wrong size as it gets tighter inside the shoes as your feet get wider during the day.

You will also want to consider the weather. If it’s very humid or very dry out, the width of your feet could differ as well. It’s not a bad idea to shop when your feet are a little bit wider than usual as this will help you find a pair of shoes that can handle the typical and persistent changes that your feet will go through.

Consider extended sizes

People with wide feet often struggle to find a good pair of dress shoes because most shoes are made for narrow to standard feet widths. If you have wide feet, don’t forget to ask about extended sizes that cater to your wide feet. This will make a massive difference in your comfort while wearing the shoes.

And don’t be ashamed to ask for wide or otherwise extended sizes!

You would be surprised at how many people should be wearing a wide size but instead squeeze their feet into a narrow width shoe because they don’t realize how big of a difference it would make. What’s wrong with getting a shoe that fits you perfectly? Ask about that wide shoe and give it a try!

Try your shoes on with socks

The final test for a dress shoe’s comfort is the sock test. People, especially men, typically use socks when they wear dress shoes, so trying on shoes with socks will give you a better idea on the fit.

If they are still comfortable after trying them on with your usual socks, they’re a winner and have the potential of being your new pair of go-to dress shoes.

And don’t be ashamed to ask for wide or otherwise extended sizes! You would be surprised at how many people should be wearing a wide size but instead squeeze their feet into a narrow width shoe because they don’t realize how big of a difference it would make. What’s wrong with getting a shoe that fits you perfectly? Ask about that wide shoe and give it a try!

Pay close attention to the materials used

High-quality materials used to create your shoes means they will last longer. You want to ensure that any shoe you buy has the right materials on the right parts, and you also want to be sure that the stitching is very good.

Check for the quality before buying to ensure that your shoes don’t disintegrate after just a few uses. There’s nothing worse than loving the fit of a pair of shoes only to discover that they are not durable. You can avoid this by guessing the durability of a shoe before you buy it.

Consider removable insoles

Insoles are the most significant contributors to a dress shoe’s comfort level. Shoes that have removable insoles can allow you to put in a custom one that is perfect for your needs. If it’s possible to get shoes that feature removable and customizable insoles, go for them. It will change your dress shoe experience for the better.

If a shoe that you like doesn’t seem to offer a removable insole, don’t panic! It might be possible to rip out the existing sole. If the shoe has enough room inside, you might even be able to add your own sole on top of the existing sole without causing any pain.

For those that already have insoles they love wearing, we recommend bringing these with you when you go shoe shopping. Though it might feel a little bit weird, trying on shoes with these insoles will help you find a better final fit in the long run.

Top 5 Amazing Dress Shoes for Men and Women

Every so often, you need to update your wardrobe, especially if you’re working at an office. Being underdressed at the workplace is considered a major faux pas, which is where dress shoes come into play. Having the right kind of shoes to match your outfit can transform your entire look.

If you want to look more confident and professional at work, here are suggestions for good and comfortable dress shoes that are perfect for office wear.

Rockport Men’s Margin Oxford

Rockport Men's Margin Oxford,Black,11 M US

Men aren’t as picky or attentive toward their footwear compared to women. Even for special and formal events, men don’t spend hours looking for a pair of shoes that specifically match their outfit for the night.

The secret that allows men to do this is found in their closet: the right kind of dress shoes. Dress shoes are very versatile and they can be used for just about any occasion.

This is why men don’t fret or struggle when a formal event follows after office hours because their shoes are often appropriate for both occasions.

This review will cover the Rockport Men’s Margin Oxford as your go-to dress shoe option. Learn more about its different features as well as its pros and cons to see if this pair will complete your wardrobe.


  • Leather material
  • Imported
  • Synthetic material used for sole
  • 1.25” heel
  • Casual and understated
  • Plain-toed
  • Free returns for size and color exchanges
  • Optimum balance between comfort and style
  • Flexible in all direction
  • Encourages natural walking motion
  • Stable and sturdy
  • Available in extended sizes
  • Comfortable cushioned footbed


  • Perfectly comfortable
  • Does not disappoint wearers
  • Versatile style and design
  • Great for office and casual wear
  • Soft heels
  • Easy to clean plain soles
  • Durable, lasts years even with constant use
  • Removable cushion insoles
  • Made with high-quality materials
  • Lightweight and sturdy


  • Size chart is only 90% accurate
  • Not great for wide feet
  • Heel height can be too high for some
  • Heel can cause pain after prolonged use
  • Custom cushion insoles cost extra


The Rockport Men’s Margin Oxford is a wonderful option for a moderately priced pair of dress shoes. They are worth considering if you’re in the market for a new and sturdy pair that are both stylish and comfortable.

ECCO Men’s Helsinki Cap-Toe Oxford Dress Shoes

ECCO Men's Helsinki Cap-Toe Oxford Dress Shoe,Black,43 (US Men's 9-9.5) M

All working professionals should have at least one pair of dress shoes for work. The problem with many formal shoes is that they are specifically worn for special occasions and are kept in the closet until the next event.

This means the shoes are not used to their full potential and usually end up wearing out without being worn. This is where sensible dress shoes that are comfortable enough to be worn for casual occasions and formal events alike come in handy.

One such pair of dress shoes are the ECCO Men’s Helsinki Cap-Toe Oxford Dress Shoes which we will discuss in this short review.


  • Leather material
  • Imported
  • Rubber soles
  • Shoes are square-toes
  • Blind-eyelet lacing with tonal stitching and cap toe
  • Breathable lining
  • Absorbs moisture
  • Keeps feet odorless and dry
  • Removable insoles are covered with leather
  • Great grip and traction
  • One-component polyurethane, direct-injected outsoles
  • Rubberized outsoles melted into leather to create watertight seal


  • Very comfortable
  • Little tread wearing
  • Lasts years
  • Durable and reliable
  • Brand has a loyal following
  • Designed for wide-set feet
  • Watertight sealed
  • Easily dries
  • Stays odorless
  • Removable insoles leave room for custom cushioning
  • Lightweight and easy to walk in
  • Stylish and versatile design
  • Perfect for office and casual wear


  • A bit expensive
  • Requires a break-in period
  • Some discomfort is common during the break-in period


The ECCO Men’s Helsinki Cap-Toe Oxford Dress Shoes is a wonderful choice for dress shoes. Although they are a little pricey, they’re worth the investment because of their durable design these shoes should last you for many years.

Dansko Women’s Lulu Mary Jane Flat

Dansko Women's Lulu Mary Jane Flat, Khaki Nubuck, 37 EU/6.5-7 M US

Women who work in an office often find themselves struggling to find the right kind of footwear. There are a lot of things to consider when choosing shoes for the workplace.

The best combination for office shoes are those that are stylish, of the appropriate height, and most of all, comfortable. It may seem odd and inappropriate to wear flats to work, but with the right kind of flat dress shoes, you’ll never have to struggle wearing absurdly high heels while at the office again.

If you want to start wearing flats at the office without looking too casual or matronly, this review of the Dansko Women’s Lulu Mary Jane Flat will give you a better idea of what the most comfortable dress shoes offer the modern day woman.


  • Leather material
  • Imported
  • Soles made with synthetic material
  • 1.75” heels and 0.75” platforms
  • Round-toe
  • Hook and loop closure mechanism
  • Wide ankle straps
  • Removable Polyurethane cushioned foot bed
  • Modern and stylish design
  • Provides excellent arch support
  • Promotes foot, leg, and back health
  • Designed and constructed for the modern working woman


  • Allows wearer to stand and stay on their feet longer
  • Super comfortable with zero to minimal pain after wearing
  • Soft, cushy, and supportive cushioned foot bed
  • Stylish and chic
  • Perfect for office and casual wear
  • Very affordable
  • Recommended by women of all ages and occupations
  • Combines comfort and style perfectly
  • Optimal women’s footwear
  • Go to pair of dress shoes
  • Excellent arch support with extra cushioning


  • Not the best dress shoes for wide feet
  • Requires a break-in period
  • Velcro straps may cause stocking tearing
  • Women with thin ankles will struggle with the large strap
  • More expensive than other brands


Once you try on a pair of Dansko Women’s Lulu Mary Jane Flats, your world will change. It provides the perfect balance of comfort, style, and chic that makes it the perfect pair for work and casual wear. Plus, it can match almost any outfit you have in your wardrobe.

Earth Women’s Wanderlust Dress Pump

Earth Women's Wanderlust Dress Pump, Size: 9 Width: B Color Pewter

Back in the day, women had to choose between style and comfort when it came to the proper pair of dress shoes. Today, there are more choices available and you don’t necessarily have to wear flats to stay comfortable during office hours.

There is now a good variety of stylish, yet comfortable dress shoes that are office appropriate, as well as good enough to wear for a casual night out on the town.

One good choice for sensible dress shoes is the Earth Women’s Wanderlust Dress Pump. This review will give you a good insight on this pair’s pros, cons, and its features that make it a comfortable choice to wear the entire day.


  • Made of calf skin leather
  • Imported product
  • Synthetic soles
  • 1.75” heels
  • Multi-density cushioning for optimum comfort
  • Latex/PU material used for cushioning foam
  • Latex material used for arch support
  • Adjustable buckle for a secure fit
  • Comes with a peek-a-boo T-strap
  • Unique and interesting design
  • TR outsoles are durable and flexible
  • Excellent heel traction
  • Padded appropriately, absorbs and displaces shock


  • Eliminates sore and tired feet problems
  • Amazing arch support
  • Cushy and soft insoles
  • No pain or pressure, even when used the entire day
  • Cute and classy design
  • Perfect for office and casual wear
  • No break-in period required
  • Stays securely fastened on feet
  • No pinching or blistering
  • Versatile and sensible dress pumps
  • Excellent grip and traction


  • Extra cushioning layers can make the shoes tight 
  • Best for women with narrow and normal feet
  • Cushioning is not removable


Most women can benefit from having at least one pair of Earth Women’s Wanderlust Dress Pump in their closet. They are versatile and reliable, making them a great go-to pair for any occasion.

Dockers Men’s Gordon Cap-Toe Oxford

Dockers Men’s Gordon Leather Oxford Dress Shoe,Black,9 M US

Having at least one pair of dress shoes helps a man get ready for the office or for a formal occasion. The problem with most dress shoe brands is their outrageous prices.

Although they are very versatile and can be used for just about any occasion, not everyone has the extra dollars to spare for footwear. This is why finding a good pair of dress shoes that are both affordable and durable is a must for all working professionals.

A great option to consider when you’re looking for comfortable dress shoes is the Dockers Men’s Gordon Cap-Toe Oxford. Learn more about these quality dress shoes in this review to see if they are worth buying for your everyday office footwear.


  • Made of leather
  • Imported dress shoes
  • Rubberized soles
  • 1” heel
  • Low-top from arch shaft measurement
  • Padded collar and cap toe for comfort
  • Practical and stylish design
  • Polished full grain leather material used for upper
  • 4 eyelets for up-front laces
  • Finished stitching is refined
  • Insoles have a perforated cushioning with a moisture-wick leather lining
  • Midsoles are lightweight, flexible, and durable
  • Excellent traction provided by rubber outsoles
  • Delivers all-day comfort and style


  • Very affordable
  • Made of high-quality leather
  • Does not wrinkle or develop strange wear marks
  • Durable and lasts a long time, even with constant use
  • Little effort results in a remarkable shine
  • Semi-gloss finish gives it a classy and clean look
  • Single-piece soles do not easily develop holes
  • Makes wearers feel comfortable and confident
  • Perfect for office desk jobs and field work
  • Excellent traction even on wet and slippery surfaces
  • Very short break-in period


  • Laces can get frayed
  • Some discomfort during break-in period
  • Considered as a “low-budget” dress shoe


For men who want to look and walk more confidently without spending too much on a new pair of dress shoes, the Dockers Men’s Gordon Cap-Toe Oxford is an excellent choice.

They are very affordable, and yet made with high-quality materials that are durable. They are also neutral enough to be worn for any formal or semi-formal occasion.

Five More Great Shoes for Men and Women

While those five shoes were our top choices, we know that not everyone is going to find their perfect pair by looking at just those options. Here are five more great pairs of shoes that you can choose from if you are looking for the best and most comfortable dress shoes.

Calvin Klein Men's Brodie Oxford Shoe

Calvin Klein Men's Brodie Oxford,Black,11.5 M US

One of our other favorite pairs of shoes is the Calvin Klein Men's Brodie Oxford Shoe. These shoes have a very classic appearance that makes them a functional yet stylish choice for many different types of occasions.

Not only do these shoes look great, but they’re also very comfortable! You can wear them for very long periods without feeling any pain, and that is a key factor when you want to get the most functional shoes.

The shoes themselves also give you an excellent lift when you wear them which can make any man feel great. Who doesn’t love to be just a little bit taller when they head out for the day? With these sensible shoes, you’ll be ready to take on the world.

These Brodie Oxford shoes are also very durable. The stitching is strong and unlikely to fray, and the bottoms won’t split from the sole easily. You are sure to get your money’s worth out of these shoes thanks to their extended durability rating.


  • 12 different color and leather finishes
  • 100% leather
  • Imported materials
  • Synthetic sole
  • From reliable and popular brand Calvin Klein
  • Classic design
  • Soft Nappa leather
  • Rounded square toe
  • Lace-up closure
  • Large sizes from 14M to 16M
  • Width from 7W to 16W
  • Flexible construction


  • Cushioned foam insole
  • Comfortable to wear all day
  • Durable construction
  • Look sleek and refined
  • Easy to polish
  • Many sizes and widths available
  • Can be worn daily
  • Soft upper feeling
  • Short break-in period


  • Leather isn’t the most expensive
  • The area around laces needs extra break-in time
  • Run slightly small


Overall, the Calvin Klein Men's Brodie Oxford Shoe is a fantastic choice for a man who wants a classic looking shoe that can work with an everyday look. Even if you’re on your feet all day long, these shoes are comfortable enough to be able to get through the day without any pain or frustration.


Bruno Marc Men's Urban Suede Oxfords Shoes

Bruno Marc Men's URBAN-08 Black Suede Leather Lace up Oxfords Shoes - 13 M US

The Bruno Marc Men's Urban Suede Leather Lace Up Oxfords Shoes is another great option for men who are looking for a shoe that can work with a casual look for the office or a night on the town with their friends. No matter how you style these oxford shoes, they’re going to look great.

While Bruno Marc isn’t the most well-known brand on the market, they are known for making high-quality shoes in many modern and appealing styles. This style, in particular, is in trend. The suede leather finish helps them to stand out from other pairs of oxfords currently on the market.

There are 15 different colors of suede and leather available, so you can choose the color that will best fit with your current wardrobe. At their price point, you might even be able to get more than one pair to add to your closet so that you can match many different outfits with ease. Additionally, the man-made sole on these shoes is very durable and will stand up even if you are wearing them every single day.


  • 15 different colors
  • Suede leather
  • Man-made sole
  • One-inch heel
  • 0.5” platform
  • Plain-toe oxford
  • Lace up closure
  • Flexible sole
  • Breathable lining
  • Grip rubber sole
  • Bruno Marc brand quality


  • True-to-size fit
  • Nice looking design
  • Many colors options available
  • A good price point for quality
  • Decent durability
  • Good for semi-formal occasions
  • Comfortable from day one


  • Some colors bleed
  • Slight chemical smell
  • Inside lining not as durable as outside
  • Color fades quickly


These are a great option for a man who is looking for a comfortable shoe that can work for semi-formal and casual occasions. They’re a particularly good choice for everyone who is looking for something that isn’t your traditional shiny leather finish. The unique suede finish stands out when compared with other oxford shoes!


Rocket Dog Women's Memories Ballet Flat

Rocket Dog Women's Memories Ballet Flat,Black,6.5 M US

Now, let’s talk about some shoes for women! The Rocket Dog Women's Memories Ballet Flat is one of the most classic and well-loved ballet flats for women who want a comfortable shoe that they can wear all day long. Whether you’re headed to a formal event or you simply want something cute and comfortable to wear out, these are the right shoes for you.

The thing that most people notice about these Rocket Dog flats is their characteristic pleated design at the front. As these shoes have been popular for several years, that design has become very well-known. Even though they’re an older design, the shoe is just as famous now in terms of style and trend as it was when the shoe was first released.

Also, Rocket Dog has continually improved this shoe to be better and better each time that they produce it. This ballet flat is easy to wear, stays on your foot well, and is super comfortable. Basically, it’s the ultimate ballet flat!


  • 100% polyester
  • Classic design
  • Reliable name brand
  • Shaft about 2.25” from the arch
  • Slip-on ballet flat
  • Four colors available
  • Many sizes available
  • The bottom sole is hard with a fabric finish


  • Comfortable enough
  • Cute design
  • Don’t need time to break in
  • True-to-size
  • Available in half sizes
  • Four unique colors
  • Easy to wear for many types of events


  • Slightly shiny
  • Not great for walking very long distances
  • Absorb smell easily


The Rocket Dog Women's Memories Ballet Flat has a super cute and popular design, and there’s a good reason for that! The ballet flat is comfortable enough to wear in the office all day, but we recommend choosing something else if you plan on walking any long distances. For looking cute, though, it’s definitely a great choice!


Top Moda Women's DS-6 Wedge Sandals

Top Moda Ds-6 Wedges Sandals, Black Pu, 9

When you’re ready for summer shoes that can keep up with you, the Top Moda Women's Ds-6 Wedge Sandals is a great choice! Not only do these sandals look incredible and give you great lines, they also make your feet feel incredible while you are wearing them.

Most women know that wearing a wedge sandal is always more comfortable than wearing a heel, and that definitely holds true with these shoes. Wedges give your feet more support while you are walking, so you can keep going for longer without feeling much discomfort.

These shoes blend an exceptional level of support with trendy and fashionable design options. That means you can feel comfortable while also looking great, and that is what every woman knows is the most important balance to strike in a shoe!

These shoes are great for outdoor summer events, days in the office, or simply going out of town. Their simple yet striking style ensures that you’ll feel like you have the best shoes ever while you are wearing them.


  • Wedge design
  • Four unique color and design options
  • Multiple sizes available
  • Synthetic sole
  • Lightweight
  • Platform about one-inch high
  • Quality construction
  • Beaded details
  • Zip closure at back


  • Super cute design
  • Convenient zipper at the ankle
  • Easy to walk in
  • Comfortable to wear for long periods
  • Multiple neutral colors available
  • Material has some natural stretch
  • Can break-in for a more comfortable fit
  • Durable soles


  • Slightly tight around ankles
  • Run a little large
  • Some durability issues with stitching
  • Insoles are a little hard


The Top Moda Women's DS-6 Wedge Sandals is a very great choice for those who are looking for a functional summer shoe that won’t hurt their feet after just a few minutes of wear. These shoes, despite their height, are very comfortable to wear thanks to the sponge-like wedge. The shape of these shoes makes them a very smart choice for many women!


MVE Women's Low Block Heel Dress Shoe

MVE Shoes Chunky Block Heel Dress Sandal Over Toe & Ankle Wrap Strap, Black NB 7

These pump sandal heels from MVE Shoes feature a very sturdy and comfortable-to-wear block heel. But are they going to be the most comfortable dress shoe option for you to wear?

Block heels like these are going to provide a very sturdy base, and the block on this one is extensive. When wearing these low block sandals, you’ll find that you can balance very easily.

With this balance, you can walk more confidently, even if you don’t have much experience wearing high heels. The lower height will help you a lot!

This shoe is available in different colors and height options. There is a lower heel version that functions more like a formal or casual sandal, and there is also a higher heel option that can be a bit fancier for when you’re wearing a dress to a formal occasion, or you want to make a more significant impact with your look.

The MVE Women’s Block Heels work for many different types of outfits. Whether you’re trying to put together something casual or a more formal outfit, you can style these shoes in a way that is going to be very impressive.


  • 30 different color and heel height options
  • Size ranges from five to 11 with some common half sizes
  • Strap around ankle
  • Low block heel
  • True to size
  • Sandal-style toe opening
  • 100% vegan
  • Synthetic materials


  • Very cute design
  • Two heel options can fit anyone’s needs
  • Many color options
  • Great value
  • Durable heels
  • Comfortable
  • Work for both formal and casual events


  • Ankle strap a bit too loose
  • Stiff material takes longer to break in
  • Run slightly narrow


These shoes are a great option if you love the idea of heels, but you aren’t as great at walking in them. Even if you have no experience in heels, the low block heel style of these sandal pumps make it easy to walk with confidence.

Plus, they look great in every color variation! No matter what event you’re getting ready for, these are a great summer option.



When searching for dress shoes that are very comfortable to wear for an extended period, it’s all about getting the right size that fits your feet.

The pair of shoes that we would recommend to men as the most comfortable is the Rockport Men’s Margin Oxford. For women, we love the MVE Women's Low Block Heel Dress Shoe because it can be great for anyone, no matter what their experience with heels is. Plus, you can get them in different colors and heel heights.

It is a myth that all dress shoes are painful, because there are so many comfortable and stylish shoes available. Get the right size for your feet, and never feel the pain of wearing dress shoes ever again.


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