Most Comfortable Dress Shoes

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Dress shoes have a notorious reputation for being uncomfortable and even painful. Normally, these shoes are reserved for wearing at a formal event or at 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 an odd 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 widest 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.

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.

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 shape to your feet will have a better and more comfortable fit.

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.

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.

Buy shoes in the afternoon

Your feet have the tendency 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.

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 normal 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 huge difference in your comfort while wearing the shoes.

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.

Pay close attention to the materials used

High-quality materials used to create your shoes means they will last longer. Check for the quality before buying to ensure that your shoes don’t disintegrate after just a few uses.

Consider removable insoles

Insoles are the biggest 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.

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.

Features

  • 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

Pros

  • 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

Cons

  • 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

Verdict

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.

Features

  • 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

Pros

  • 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

Cons

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

Verdict

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.

Features

  • 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

Pros

  • 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

Cons

  • 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

Verdict

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.

Features

  • 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

Pros

  • 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

Cons

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

Verdict

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.

Features

  • 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

Pros

  • 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

Cons

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

Verdict

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.

Conclusion

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.

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.