Best Dress Shoes for Special Events & Occasions Reviewed
You build your outfits from the shoes up – the right pair of dress shoes can not only make or break your outfit, but can determine whether you end the day happily, or with sore feet. From work to formal occasions, and even to slightly more casual wear, dress shoes can compliment any outfit, and learning how to pair them is an essential skill for any modern man. While they may seem like an easy style concept to grasp, they can be quite complex; it is important to take the time to understand them, and know how to seamlessly incorporate them into your wardrobe.
When you think of dress shoes the first style that will come to your mind is probably the Oxford, and although the most popular, they are not always what is best suited for you. Access your shoe closet and see what it is you’re lacking; if you do not have a solid, quality pair of leather oxfords then by all means you should invest in a pair, but keep in mind they are not the only style.
- Magnanni Dante
- Patent Leather
- Frye Jones
- Goodyear Welted
- Bruno Marc New York
- Padded Upper
Chelsea boots are becoming more and more popular and are very versatile making them a great staple piece to own. If you find you will be wearing those more often than others, that is the shoe you should be splurging on. A nice pair of oxfords are nice, however if you work from home and only find yourself going to events or weddings once a year or so, really spending hard earned money on a pair of handcrafted dress shoes will not be worth it. Find the perfect pair that best fits into your life and you will be happy you did.
Most people wish to get quality footwear that looks great, but selection can be a major problem since not everyone knows the factors needing to be considered. The main aim of this write-up is to enlighten every stylish man and woman out there on how to select the best dress shoes. Tips for comfort, durability, affordability advantages and disadvantages will be highlighted below so that we can all get a great picture of the ideal footwear for those big occasions you prioritize.
10 Best Dress Shoes
1. Magnanni Dante
These shoes have a patent leather upper, as well as a leather cushioned footbed that feels absolutely amazing under your feet. It's comfortable and breathable, which means that you can wear these shoes without having to worry about dealing with any type of pain once you take them off.
Dress shoes are known for being way firmer and more uncomfortable to wear than typical everyday footwear. And while you may want to go with a foam or rubber outsole, some occasions require something a bit more elegant. Even though the outsole on these shoes is made out of leather, they still provide plenty of flexibility so as not to constrict your foot's movements while walking.
Cost and Value
A good pair of dress shoes is worth investing in, and the Dante by Magnanni is definitely an investment. With a price tag that is much higher than almost all other shoes on this list, you may wonder whether they're worth the splurge. Still, once you see these in person, and once you've put them on, you will never want to wear anything else.
- Patent Leather Upper
- Plain Toe
- Leather Footbed
- Leather Outsole
- Handmade in Spain
- Hefty Price Tag
- Not for Everyday Wear
2. Frye Jones
There is nothing better than knowing you are spending money on an item that you will get plenty of wear out of and that will last. Frye boots look stylish with absolutely any outfit, and can be worn anywhere, but don’t fret that they will deteriorate over time, they are crafted with a rich leather that will only look better as time goes on.
There are some items that everyone needs in their closet, to have on hand at all times; dress boots are one of them. When the colder months start approaching and you want a little more protection and warmth, these boots will be what you reach for. Depending on how often you wear them, one pair is really all you need, so why not invest in the best.
Cost and Value
When you think of quality shoes and boots, Frye is a brand that almost always comes to mind. They are a brand known for producing products that will last for years and years to come, while still looking in great shape. These may be one of the most expensive pairs of shoes on this list, but in the long run from the amount of wear you will get out of these, it is very worth it.
- Leather Outsole
- Leather Lined
- Wears Nicely Over Time
- Pull Tab on Heel
- Minimal Grip on Sole
- Outsole Isn’t Water-Friendly
3. Calvin Klein Bram Diamond
Unlike the typical all one textured leather dress shoes, these have a little bit something extra to make them stand out, but only subtly. The rich textured pattern makes these oxfords look expensive and high quality which is never a bad thing.
Standing on your feet all day can be exhausting enough as it is, make that even worse by having your feet be in pain. The addition of a soft, comfortable footbed means you can go from meeting to meeting without thinking twice about your aching feet.
Cost and Value
Calvin Klein is a very well known brand and known for producing high-quality products, so it’s no wonder these oxfords are not the most affordable on the list. They are some of the most unique looking though and are well worth the money if you are looking to invest in dress shoes.
- Cap Toe
- Padded Footbed
- Stacked Heel
- Rubber Sole
- Little Arch Support
- Hard Leather in Toe Area
4. Ecco Helsinki Cap-Toe
These shoes feature some of the most forward technology in dress shoes, with their focus being on breathability and comfort. Made to prevent bacteria and odor overgrowth, these shoes ensure good air circulation, which means that your feet will be comfortable, whether it’s hot or cold outside.
Shock Absorbing Outsole
The polyurethane outsole of these shoes was made to feature plenty of shock absorption, which makes these shoes perfect for prolonged wear. A removable insole is added for even more comfort, but can be substituted with your own orthotics should you need them.
Cost and Value
Ranking slightly above average on this list when it comes to price, the ECCO Helsinki cap toe shoes are a good choice for those prone to sweaty feet, or who tend to do a lot of standing and walking. With plenty of cool features to make these shoes more comfortable, you’ll definitely want to wear these shoes as often as possible.
- Leather Lining
- High Quality Materials
- Lacks Height in the Heel
- Not as Durable as Other ECCO Shoes
5. Clarks Tilden Walk
This pair of shoes has a lace up closure, but for the sake of comfort, an added elastic slit has been added, ensuring that you feel comfortable while wearing these shoes. The padded leather upper is soft and will fit most foot shapes.
In addition to a soft synthetic sole, these shoes also offer an Ortholite footbed which is cushioned and has excellent moisture wicking properties. This means that your shoes won’t develop odors, even with longtime wear.
Cost or Value
This pair of shoes is one of the three most affordable items on this list. Considering its sophisticated looks and high levels of comfort, you will definitely love wearing these both to the office as well as to more formal occasions.
- Leather Upper
- Synthetic Sole
- Ortholite Footbed
- May Fit Narrow
- Heel Can Be Problematic for Some Users
6. Dockers Agent Slip-On
The best part about these shoes is the full grain leather upper that is not only protective and durable but has also been burnished to give it a unique look. These shoes will mold to your feet and will develop a warmer, richer color with time that will be unique to you.
All Motion Comfort™ Technology
These shoes are made to be comfortable out of the box, requiring no break in period. You will definitely love the soft, flexible outsole that features generous cushioning that will bring relief to your hard-working feet.
Cost and Value
These shoes are a good choice for those who want a pair of dress shoes but are not looking to go with something too fancy. These shoes will work well both with a suit as well as with jeans, and they’re comfortable enough to be your work shoes. With a price that is around average, you’ll definitely appreciate the Dockers Agent Slip-on.
- Easy On and Off
- Thick Cushioned Outsole
- Comfortable Insole
- Stylish Stitching
- Full Grain Leather Upper
- May Appear Big on Feet
- Outsole Wears Quickly
7. Bruno Marc New York Oxford
One of the best things about this pair of shoes is that it comes in a great variety of designs and colors. With the last of the shoe being the same for all these options, you can rest assured that you will be getting the same level of comfort and quality, regardless of the decorative options you choose.
Genuine Leather Upper
These shoes feature a genuine leather upper that has been padded in order to provide you with high levels of comfort. Additionally, the insole is lined as well, so that you get a nice feeling all around.
Cost and Value
These shoes come at an unbeatable price, which is hard to believe, seeing that they are made out of genuine leather, feature a Goodyear Welt, and are comfortable for wear. Although they may not be a good option for everyday wear, they’re our top choice for shoes you only plan on wearing once in a while.
- Perforated Leather
- Secure Lace
- Color Selection
- Formal Look
- Padded Upper
- Not Breathable for Warmer Months
- Will Show Signs of Wear
8. Clarks Bostonian Bolton
These shoes are a slip-on which means that you won’t have to bother with laces. Simply put them on and off, and you’ll be ready in record time.
High Quality Upper
Made with a genuine leather upper and a lightweight EVA foam outsole, these shoes are a great choice for anyone. Whether you want to wear them to the office, as everyday shoes or on special occasions, you are bound to appreciate the padded collar and cushioned insole on these dress shoes.
Cost and Value
These shoes rank low on this list when it comes to price, and are a great option for almost anyone. Offering a wide variety of sizes, and coming in two width options, almost anyone will be able to find the perfect fit with this pair of shoes.
- Long Lasting Comfort
- Fits like a Glove
- Simple Style
- Easy On and Off
- Padded Collar
- Thin Soles
- Crease Easily
9. Timberland EK Brook Park
Standing on your feet all day can be a pain, literally. Ensuring you have the proper cushioning in whichever shoe you decide to wear that day is crucial to preventing foot pain, and possible injuries. Timberland not only has a leather lined footbed, it is also made with their anti-fatigue technology to provide you with comfort and support without the need for additional insoles.
Environmentally friendly shoes are a big plus and can make you feel better about your purchase especially if it is a slight splurge. These boots are carefully lined with 100% recycled herringbone to wick away moisture all day and keep your feet dry and cool.
Cost and Value
One of the more expensive pairs of shoes on this list due to the quality and the name brand. The brand name tends to always up the price of a product, and although it can mean its a better-constructed shoe than others, that isn't always the case. These Timberland boots look stylish and fit well, but there are other similar dress boots on the list at a lower cost.
- Gripstick Sole
- Two Eyelets
- Pull Tab on Heel
- Comfort Technology
- Requires a Break-In Period
- No Padding in Ankle Area
10. Dockers Moritz Wingtip
In addition to being made with genuine leather, these shoes have some hidden features as well in order to provide you with a maximum level of comfort. One of these is the hidden padding in the collar, which will prevent these shoes from creating problems in the ankle area.
Both the leather upper and the rubber outsole on these shoes are flexible, allowing your foot to freely move, without any constraint. That’s what makes these shoes an excellent option for all-day wear.
Cost and Value
Ranking below average on this list when it comes to cost, the Dockers Moritz is an excellent choice for anyone who is a fan of the brand. If you are searching for a good pair of shoes that will serve you well, then these are a great choice.
- Cushioned Insole
- Breathable Fabric
- Ages Well
- Wingtip Design
- May Wear Out Quickly
- Colors Differ From Images on Website
Dress shoes are an investment piece and should be carefully picked so that you are truly getting the best quality, and a style that will suit your life. As versatile as some styles may be, the classic dress shoe has a specific purpose and should be used for that. Look at materials, and details and understand how those can drastically change a shoe. Regardless of how subtle a detail may appear to be, it is there for a reason and will change the overall look.
Durability is not a key factor when it comes to dress shoes, however, some are definitely more tough than others and that is where materials come into play. Materials play a large part in changing the elegance of a shoe, the most formal by far being patent leather. Although patent leather looks the sleekest and formal, they are relatively fragile and should not be worn on an everyday basis due to how easily they will crease. If you are looking for an everyday dress shoe consider the loafer or Chelsea boot, both classy in their own ways and very easy to wear.
There are plenty of brands producing new and exciting dress shoes every day, which makes it difficult to pick just one pair, but it also is great for having so many options. Instead of you having to research and keep up with all of the trends, we have done it for you, making it a breeze for you to look stylish at your next upcoming event. This list of the 10 best dress shoes narrows down what it is that makes a dress shoe worth investing in, and how to easily wear them.
Criteria Used to Evaluate the Best Dress Shoes
One of the most important things you want out of a pair of dress shoes is a quality make. Not only will this greatly contribute to their appearance, but it will also ensure that you get a comfortable pair of shoes that will last you plenty of time. Although high-quality shoes will often feature a hefty price tag, you might find that an initial investment can pay off with years of use.
The best dress shoes cost more than an average pair of footwear for more reasons. One of these is the use of the best materials (usually leather) which will perform better and look better than most synthetic ones. Unless you are in the market for vegan footwear, try to invest in premium leather shoes which will look amazing, mold to your feet to create the perfect fit, last a lifetime and will get better and more comfortable with age.
The highest quality dress shoes are usually handmade, which not only contributes to the fact that they are unique but also leaves you with a product which is of a better quality due to higher levels of quality control. Although machine sewed shoes can be great as well, handmade shoes are sure to set you apart in a crowd.
Most dress shoes are made of leather, and there are four types which are most commonly found in quality dress shoes. All of these are good options, but note that each has its own unique characteristics and advantages that will make a difference in how the shoes behave and fit.
- Patent – By far the most formal, and most commonly worn type of leather. Often paired with a tuxedo, patent leather dress shoes should be a special occasion type of shoe only. Although you might see them in less formal settings nowadays, note that patent leather creases easily, so it is best to save these shoes for special occasions only.
- Smooth – The most common when it comes to leather dress shoes, and the easiest to clean and shine. Due to the lack of pebbling, you are working with a completely smooth surface and therefore these are a great option for more frequent wear.
- Full Grain – Made from the most durable part of the hide, full grain leather is resilient and can even be worn in the rain. It will also age beautifully and last you a lifetime.
- Top Grain – Similar to full grain, however, the pebbling has been smoothed out to give a softer appearance to the shoe. It is the second most durable leather and great for everyday use.
When it comes to dress shoes, it is important to take the time to really consider all the features before making a purchase. This way, you are going to get a pair of dress shoes that will last a lifetime, especially if you opt for an investment piece. High quality shoes that you can rely on, although they require a bigger initial investment, pay off their value through durability and the fact that you won’t have to purchase new shoes every so often.
Whether you are going to work, a wedding, or any other formal event, you will want to match your shoes and suit to reflect the best possible image that you have to offer the world. A good pair of dress shoes can effortlessly tie your entire outfit together, under the condition that you choose the correct styling. There are several dress shoe styles, and although most look great on their own, there are a few rules that you will have to follow when matching them with an outfit.
- Oxford – The most common style of dress shoe, this closed lace design gives a sleek and elegant appearance to the shoe, so a nice pair of black oxfords should be your go to for a formal event. This style of shoe, which originated from Scotland may also be referred to as a Balmoral, and can be made in any type of leather, but opt for patent if you want the most formal look.
- Loafer – These slip on shoes may be less formal than others, however, they offer extreme comfort, and if the fit is just right they can become a go to shoe for more casual business meetings. As of lately, Gucci has made a large name for themselves in regards to the loafer, by making them a formal shoe worn frequently by celebrities.
- Chelsea Boot – Comfortable and effortlessly chic, these slip on boots are extremely versatile and add that extra something to any outfit. Of course, they are not as formal as a patent loafer, Chelsea boots are ideal for dressing up a more casual outfit and seamlessly taking you from day to night. Don’t be scared to really dress them up and go to a formal event, you will stand out and look stylish.
- Chukka Boot – A more casual boot than the Chelsea, these ankle boots are made from two pieces of leather and have a specific amount of eyelets, generally three. Chukka Boots are often made in various colors and styles, however, stick with brown, tan or black and avoid crepe soles if you are going for a more fancy look.
There are so many styles to choose from, and although it may be intimidating at first, assessing your wardrobe and what it is lacking is the first step towards purchasing the perfect pair of dress shoes. Think about each of these styles and how much use they would get if you were to buy them – do you frequent formal events often, or do you prefer something that will work in a more casual setting as well? A good rule of thumb is to always have a smooth leather pair of Oxfords on hand, so that you can dress them up or down as needed.
When it comes to dress boots, keep in mind that these do fall more on the casual side and therefore are much more versatile in your everyday life. You can never go wrong with a good quality pair of Chelsea boots, these will last forever and will become your go to shoe when looking for the perfect something to spice up your skinny jeans and leather jacket.
When deciding to invest in a new pair of dress shoes pay attention to the details and know that although similar, each pair you come across will be unique in its own way. Dress shoes are very complex and come in many different shapes and sizes. One of the key things that makes dress shoes stand out from each other is the toe design. Though not everyone will notice the toe, it can decide whether a pair of shoes is suitable for a certain occasion. The four most common toe styles when it comes to dress shoes are:
- Plain Toe – Simple and elegant, this is a classic style you can’t go wrong with. It will be featured on the most sleek and formal dress shoes, so a pair of Oxford shoes with a plain toe are a great choice of dress shoes.
- Cap Toe – This extra piece of leather stitched on to the toe makes a pair of shoes less formal and a bit more versatile. Appropriate for formal occasions if styled correctly, a cap toe should mostly be worn in a business setting.
- Wingtip – When looking down at the shoe you will see a “W” shape at the toe. This makes the shoes less formal, and more appropriate for casual wear. Depending on the rest of your outfit, the wingtip can be a great stylistic choice.
- Split toe – Also known as the apron toe, there is a seam that runs down the middle of the shoe. More common in casual shoes, this style is not considered to be formal at all.
Details are everything when it comes to picking the proper pair of shoes. They can completely change the look of your outfit, and can even make a pair of shoes inappropriate for certain occasions. Small details like these can make a large difference, so take the time to choose the best option for you.
A rule to always remember is your dress shoes should have a rounded toe, never square. One of the first things people look at after your overall appearance and outfit is your shoes, and whether or not they go with your outfit and are nice quality. It’s been said you dress from the shoes up, so keep that in mind the next time you even consider trying on that pair of squared toe dress shoes.
The outsole of your shoes makes a huge difference in their function and style. Not only will it affect the quality of your shoes, but it will also determine how the shoes feel on your feet. There are a few types of soles most commonly used in dress shoes and they all offer different things.
- Single Leather – The most common and sophisticated choice, the single leather sole allows for a very sleek look. Although nice looking, it does not offer much support and can be slippery, especially when wet.
- Double Leather – Most commonly seen on more casual styles of boots, this offers much more protection and warmth but takes away any sleek appearance from the shoe.
- Crepe – Often seen on the chukka boot, this type of rubber sole is lightweight, however, can wear down quickly and does not give off the appearance of expensive.
- Rubber – Not the most formal, however rubber soles provide excellent traction and can be great in colder months when the ground is wet, and you do not want to wear your leather soled shoes.
When it comes to dress shoes, one of the most important things is fit. Unlike other styles of shoes where there is some wiggle room when it comes to sizing, if your dress shoes do not fit perfectly they will wear in all of the wrong places. Dress shoes are made to fit close to your foot, and eventually, after plenty of wear, they will mold to the shape of your foot. Ideally, this will make them feel like a second skin. If you are not feeling as comfortable as possible in your shoes, here are some key things to check for:
- Creasing where there shouldn’t be. If you notice creasing, especially in the front of the shoe (toe area), your shoes are probably bending in ways they shouldn’t. This will affect the last of your shoes.
- You find yourself tying your shoes as tight as you can. The eyelets on your shoes should create an “V” shape from the bottom upwards when tied properly. They shouldn’t be miles apart because you are tying them too loosely, or touching for a tighter fit.
- Your heel slips out of the back of the shoe. Your entire foot should feel comfortably snug in the shoe, although there should be space for it be not feel constricted, your foot should not be moving around, especially out of the shoe.
- They feel too tight right away. Dress shoes do require a break-in period and may not feel the most comfortable off the bat, but they should not feel too tight. Leather will stretch over time, but don’t expect your shoes to grow a full size.
Dress shoes have caps in the front and back of the shoe which serve to keep their shape, and to give you some added stability. If you find that the heel caps are giving you any discomfort – either by rubbing or being too stiff – this means that the fit of the shoes is not perfect. Always take the time to assess how your feet feel in your new dress shoes, and be aware of every part of the shoe and how it feels against your feet.
With styles such as the loafer, you are slipping these shoes onto your feet, so there is no room for adjustment if they do not fit properly immediately. Ensure that it fits your foot properly throughout, and that your foot is not slipping around or coming out of the shoe. Because you are pulling them on to your feet every time you wear them, you risk them stretching out, especially in the back. Lace up shoes, on the other hand, allow for a bit more adjustability, which may be a better option for some users.
You may think that buying the right shoe is simple; get the same size as all of your other shoes. That is very wrong and you will quickly find that out when it comes to dress shoes. Not only does the size of your feet vary throughout the day from swelling, your left and right feet are also not the exact same size to begin with. This can go unnoticed for your entire life if you constantly wear runners, or shoes where it does not make a large difference. When it comes to dress shoes however, some are tailored made for your specific feet, so knowing exactly what your size is will guarantee the perfect fit.
Frequently Asked Questions
Q: Should I be shining my shoes?
A: If you have a nice pair of dress shoes you wear frequently, than yes the best way to ensure they stay looking nice is to shine them. It’s a relatively quick process and not very expensive but it will prolong the life of your shoes by a lot and keep them looking new.
Q: Should dress shoes be an item I splurge on?
A: Yes and no. Everyone should have a pair of dress shoes in their closet that are high quality, and that time and time again when an event comes up in their life, they can reach for knowing they will do their job. These do not necessarily need to be handmade, Italian leather shoes, but they should be somewhat of an investment piece that you know fit you like a glove. If those happen to be from a less expensive store, that is okay, just find what works best and feels good to you.
Q: Which type of dress shoe is the most versatile?
A: The classic smooth leather oxford is the most versatile formal dress shoe, and can seamlessly go from work to a wedding. However, if you want a casual, versatile dress shoe the Chelsea boot is a must-have in your closet and will blend right into your wardrobe.
Q: How does sizing work?
A: It is very important to take the time to properly size your feet when it comes to dress shoes. Unlike other types of shoes where wiggle room makes no difference, dress shoes will feel completely off if they are not the exact size of your feet. Remember that both feet are not the exact same size, and your feet do swell throughout the day, that is why although expensive, buying handcrafted shoes, tailored to your feet will be very worth it in the long run.
Q: How many pairs of dress shoes should I own?
A: That is completely dependant on how often you find yourself reaching for dress shoes on a day to day business. If you work in a business setting, two pairs of everyday leather oxfords will probably be enough, if they are more so just for formal events in your life, one great quality pair of dress shoes can be all you need.
Q: Do dress shoes need to be broken in?
A: Unlike some shoes like runners, dress shoes will be relatively stiff right out of the box and will require you to wear them in. It is not the most comfortable process, however, it should not take long, and before you know it you should find your shoes fit like a glove and give you no irritation. If there is pinching, and severe rubbing on certain parts of your feet, consider that you perhaps did not purchase the proper size.