Best Dress Shoes for Special Events & Occasions

Your outfit starts from the shoes up, and can make or break what it is you’re wearing. From work, to a special event in your life, it is essential to have the right types of shoes and know exactly how to pair them. Dress shoes may seem like an easy style concept to grasp but 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.

Last Updated: May 20, 2017
By Tierney Lloyd:

The newest update features 15 of the best dress shoes available today. Ranging from formal to more business casual, there is sure to be a pair for you to incorporate into your wardrobe and everyday life. A Criteria for Evaluation and FAQ section have been added to help explain everything there is to know about dress shoes, and go over which ones to buy, and how to properly maintain them.

Featured Recommendations

Magnanni Colo Oxford
  • Magnanni Colo Oxford
  • 4.9 out of 5
    Our rating
  • Made in Spain
  • Price: See Here
 
Frye Jones Chelsea Boot
  • Frye Jones Chelsea Boot
  • 4.9 out of 5
    Our rating
  • Goodyear Welted
  • Price: See Here
 
Calvin Klein Bram Diamond
  • Calvin Klein Bram Diamond
  • 4.5 out of 5
    Our rating
  • Derby Lacing
  • Price: See Here

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.

 

15 Best Dress Shoes

 

1. Magnanni Colo Oxford

For over 50 Magnanni has been producing some of the most high quality men’s footwear in Spain. From their hand crafted detailing and unique and elegant designs, these shoes are made in a family owned factory ensuring time and love is being put into every pair of shoes. If you are on the market for a new pair of timeless, elegant dress shoes look no further.
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Bologna Technique
At times called sacchetto, this technique focuses on creating superb quality shoes with an immense level of comfort. By wrapping the upper all the way around and stitching it directly to the sole you are left with a very flexible and comfortable shoe. However, like most quality items, they can be very delicate in the sense that the leather, and the shoe should be well taken care of. Try not to expose these shoes to harsh weather conditions, and clean them often to maintain their beautiful appearance.

Elegant
Everything about this dress shoes is elegant, from where they are made in Spain, to the way they are crafted with some of the finest craftsmanship and materials, these dress shoes are worth the investment. Wear these to work, to weddings and any occasion you could possibly think of, these shoes will quickly become a classic staple that you will have forever.

Cost and Value
The Magnanni oxfords are the most expensive pair of shoes on this list, and therefore they are definitely more of an investment piece. Although pricey, they are worth it if you are looking to truly invest in a classic pair of well made dress shoes. These are a pair of shoes you will have in your closet forever, and that will only continue to look better with age, with the proper care.
Pros
  • Made in Spain
  • Leather
  • Cushioned Footbed
  • Hand Finished Details
  • Flexible
Cons

Fit a Little Big

2. Frye Jones Chelsea Boot

These boots are a staple in any closet, the rich leather wears beautifully over time and although they look rather simplistic, they add the perfect stylish touch to any outfit. A great boot to not only wear to work or in a professional way, but on nights out or a nice dinner as well, the styling options are endless, and will have you reaching for these all year round.
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Better with Age
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.

Staple Piece
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.
Pros
  • Leather Outsole
  • Leather Lined
  • Wears Nicely Over Time
  • Stylish
  • Pull Tab on Heel
Cons

Minimal Grip on Sole

3. Calvin Klein Bram Diamond

Look exceptionally stylish in these unique oxford shoes that look incredible with a nice pair of dress pants. With a silky smooth leather and diamond textured pattern these shoes will make you a stand out in any business meeting.
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Textured Pattern
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.

Padded Footbed
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.
Pros
  • Leather
  • Cap Toe
  • Padded Footbed
  • Stacked Heel
  • Rubber Sole
Cons

Little Arch Support

4. Deer Stags Wingtip Oxford

4. Deer Stags Wingtip Oxford
The shoes look very sophisticated and handsome; the ace boy’s wingtip is a stylish alternative to everyday shoes. Day-long comfort of the feet is guaranteed because of the presence of a direct outsole which is light in weight and EVA insole socks.
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Comfort/Stability
The shoes are human made, with imported leather and synthetic sole to give you a long-lasting comfort and style anytime any day.

Quality/Durability
A perfect dress shoe that fits well and looks incredibly classy. Very high end it and offers excellent quality and long lasting durability.

Cost or Value
The cost of this shoe is on the small side; doesn’t cost much and definitely worth the price.
Pros
  • Adjustable Closure
  • Leather Upper
  • Lightweight
  • Cushioned Outsole
  • Mesh Lining
Cons
  • May Run Large

5. Bostonian Ipswich Lace-Up

5. Bostonian Ipswich Lace-Up
This pair of shoes is a square toe oxford shoe which is made in the USA or imported with blind eyelets and low stacked heel.
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Comfort/Stability
This laced up shoe has an exceptional comfort details that augment the sharp look of this classic oxford from Boston.

Quality/Durability
It is made of a synthetic and rubber sole with flexlite style. It is very comfortable and almost no break in.

Cost or Value
This pair costs well above average, it is a bit costly compare to other shoes but affordable for classy men who desire great comfort. It has a lower price available on select options and also has a free return on some sizes and colors.
Pros
  • Sleek Design
  • Comfortable
  • Breathable
  • Easy On and Off
Cons
  • Low Quality Soles

6. Clarks Tilden Walk

6. Clarks Tilden Walk
This Oxford Tilden Walk leather shoe made by Clarks which is a light but stable shoe. It is a lovely and great formal shoe that keeps feet looking sharp from 9-to-5 (and beyond). These shoes are so narrow at the ball and toe of the foot, and they don't break in wider. It is of excellent craftsmanship with no imperfections, and it is ideal for formal or semi-formal (office) occasions.
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Comfort/Stability
The expandable slit on the upper (Breathable leather uppers) makes it easy to fit even large foot and very comfortable compared to other similar shoes.

Quality/Durability
It has a synthetic sole, finely ribbed rubber dress sole for comfort and traction which makes it the best out of all of the currently listed top rated shoes.

Cost or Value
It is a very cheap shoe in comparison with other of the same design as the price range is average, compared to inflated. It maintains its value for as long as possible.
Pros
  • Leather Upper
  • Breathable
  • Flexible
  • Synthetic Sole
Cons
  • May Fit Narrow

7. Bruno Marc New York

7. Bruno Marc New York
This footwear is a nicely made smooth classic brogue wingtip lace leather lined perforated dress shoe. Because of its sleekness, it makes it a perfect fit for business outings. It is made from high-quality leather, soft leather lining a very nicely cut non-skid sole. It is readily made available in different colors and sizes.
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Comfort/Stability
This shoe is a classic piece for men because it offers breathability due to the perforated leather dress and also comfort because of its soft leather cushion footbed lining on the inside.

Quality/Durability
The leather material of this classic shoe is of high-quality man-made material, and the wooden heel and non-skid outsole provide flexibility thus allowing durability for this shoe.

Cost or Value
No regrets buying this shoe because its price range is reasonably and averagely cheap when compared to its value like the quality, comfort durability it gives the user.
Pros
  • Perforated Leather
  • Secure Lace
  • Color Selection
  • Formal Look
Cons
  • Not Breathable for Warmer Months

8. Dockers Agent Slip-On

8. Dockers Agent Slip-On
This is an adorable male agent slip-on produced by Dockers to fit your exclusive dress sense. This fabulous footwear is a nicely cut well-styled overlay quality leather upper part that shows the masculinity of the shoe with a soft cushion latex footbed, a well-padded collar to protect the ankle and a synthetic sole with heel measure of about 2cm.
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Comfort/Stability
The upper part of this Dockers slip on loafers made from a synthetic Leather and also with soft cushion latex footbed that then provides the users with the comfort and stability.

Quality/Durability
This shoe is very dependable due to its synthetic rubber sole that allows the individual to be confident of using for an extended period.

Cost or Value
An excellent choice to add to your cart of footwears because the price is reasonable and in the average range.
Pros
  • Easy On and Off
  • Thick Cushioned Outsole
  • Comfortable Insole
  • Stylish Stitching
Cons
  • May Appear Big on Feet

9. Bostonian Bolton Slip On

9. Bostonian Bolton Slip On
The shoe comes with a conventional but sleek design. It has a sneaker-like design and polished leather that makes it proper for casual outings, while it is still being sharp enough for formal/office use.
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Comfort/Stability
This multipurpose slip-on shoe with an upper region of full-grain leather and subtle stitching will give you a perfect signature fashion look. Its padded collar and elastic goring will guarantee you total comfort on a daily basis.

Quality/Durability
The shoe is made with imported genuine leather, a synthetic sole and leather loafer feature with double needle stitching and square toe.

Cost or Value
The price of the shoe is quite affordable and reasonable when you consider its durability and technology, you would be glad you bought this shoe.
Pros
  • Long Lasting Comfort
  • Fits like a Glove
  • Simple Style
  • Easy On and Off
Cons
  • Thin Soles

10. Ecco Helsinki Cap-Toe

10. Ecco Helsinki Cap-Toe
This shoe features a sock lining which absorbs moisture and makes feet not only dry but also odor free all day long. Its comfort fiber system and insole covered with leather offers cushioned support.
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Comfort/Stability
The leather of this classic cap-toe style pair of shoes is of very rich material. The shoe is also watertight sealed at the upper part because a rubber-made outsole was melted onto this part.

Quality/Durability
These shoes are made with top of the line leather and outsole to offer users a long lasting comfort and durability, with its removable leather covered insole and injected solid poly-urethane bottom sole with a shock point for traction.

Cost or Value
The price of the shoe is a little bit on the high side, but it is relatively affordable when you consider its durability, the shoe is a guarantee for money well spent.
Pros
  • Leather Lining
  • Breathable
  • High Quality Materials
  • Durable
  • Supportive
Cons
  • Lacks Height in the Heel

11. Timberland EK Brook Park

11. Timberland EK Brook Park
These boots are great for everyday use but can easily be dressed up with a nice pair of pants depending on where your night may take you. Made of full grain genuine leather and 100% recycled materials to make the lining, time was really spent to ensure the best quality product. Featuring Timberlands anti-fatigue technology you will be sure to feel pain free all day and night.
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Comfort Technology
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.

Recycled Materials
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.
Pros
  • Leather
  • Gripstick Sole
  • Two Eyelets
  • Pull Tab on Heel
  • Comfort Technology
Cons

Requires a Break-In Period

12. Florsheim Riva Slip-On

12. Florsheim Riva Slip-On
Made with genuine leather and hand sewn detailing, these slip on shoes give you the comfortable convenience you’re looking for while still being extremely fashionable and classy. The classic loafer style looks great paired with dress pants, jeans, khakis and anything in between, making them a breeze to style. If you are heading out on a business trip and can only take a few pairs of shoes, these should be one of them.
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Slip On
Say goodbye to having to sit down and carefully take the time to tie your shoes just right, nothing makes life easier than the convenience of slip on shoes. You never have to worry about laces coming untied, or the laces being too tight again because these easily slide onto your feet, and stay comfortable put all day.

Airport Friendly
We have all been there; struggling to take off our shoes to get through airport security, and then feeling rushed to get them back on before the next person comes through. These loafers take that struggle away by being made without a metal shank you can breeze through security. The lightweight, flexibility of these shoes also make them great for frequent travelers who want to feel and look great while on the go.

Cost and Value
Somewhat pricier than other similar styles, but well worth it considering the quality of these loafers. These shoes scream not only style but convenience as well, from being able to quickly slip them on, to not having to remove them through airport security. Florsheim loafers are a staple piece to have and are not ones that will ever go out of style
Pros
  • Leather
  • Color Selection
  • Easy On and Off
  • Airport Friendly
  • Hand Sewn
  • No Break In Period
Cons

Sizing May be Off Between Right and Left Shoe

13. Steve Madden Jimmer

13. Steve Madden Jimmer
A brand that speaks for itself when it comes to quality products; Steve Madden made no exception when it came to these Jimmer oxfords. Made with rich leather and added details like stitching and the wing tip to make them stand out, these dress shoes can be dressed up or down and are perfect for pairing with any business casual look.
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Versatile
A pair of shoes that can go from day to night make life so much easier. You don't want to have to bring a change of shoes with you and change into them before heading to a nice event, so finding a quality pair of dress shoes that look great wherever you go are not easy to find, but when you do don’t miss out.

Stand Out Detailing
It is always nice to have a subtle statement piece on hand, a pair of shoes that perhaps stand out amongst the rest of yours but in a classic and stylish way. These oxfords are that shoe; with the rich tan leather and wing tip on the toe, these smalls details really add something special to your everyday dress shoes, and makes these a beautiful pair to have.

Cost and Value
Reasonably priced considering the brand name and the quality you will be receiving, although they take a little bit of time to break-in, once they do they will fit you like a glove, and quickly become your go to pair of dress shoes.
Pros
  • Leather
  • Synthetic Sole
  • Handmade Upper
  • Fabric Lining
Cons

Short Break-In Period

14. Viotti Oxford

14. Viotti Oxford
Whether you are going to work, a wedding or any fun occasion in your life, choose to make a statement in these colorful, satin oxfords. Made with high quality materials and a soft inner lining these oxfords are a definite fashion statement, and will get you compliments all night long.
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Color Selection
The Viotti oxfords are bright and fun, yet stylish and sophisticated and are the perfect thing to help spice up any outfit. You’ll be sure to make an entrance in any colored pair while still looking classy and put together.

Plush Lining
Made to feel like a sneaker with the soft inner lining, yet look like a sleek and stylish dress shoe. These oxfords are the perfect addition to any closet because of how great they look, but they also feel great as well, and will leave your feet feeling great, even after a full night of dancing.

Cost and Value
Some of the most affordable, yet comfortable and stylish shoes on this list. They stand out amongst the rest of the dress shoes not only because of their fabulous price tag, but their fabulous look as well. These are definitely not an everyday shoe, but they are a must have to have on hand.
Pros
  • Color Range
  • Plush Inner Lining
  • Satin Fiber Panels
  • Patent Upper
  • Blocked Heel
Cons

Run a Little Small

15. Dockers Moritz Wingtip

15. Dockers Moritz Wingtip
The shoe comes with an updated classic wingtip style with supple burnished leather to give you great comfort and flexibility. The Dockers brand is the quintessential source for casual, authentic and stylish apparel.
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Comfort/Stability
The shoes are tailored to offer great cushion and comfort to the feet. You can never get tired wearing them all day long.

Quality/Durability
The Dockers wingtip shoe is made with imported leather, rubber sole and it features a brogue-perforated seam and blind-eyelet lacing.

Cost or Value
The shoe is quite affordable and relatively on the cheap side when you consider its features and functions.
Pros
  • Cushioned Insole
  • Breathable Fabric
  • Ages Well
  • Wingtip Design
  • Stylish
Cons
  • May Wear Out Quickly

 

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 most sleek 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 everyday, 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 15 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

 

Quality

You may think you are able to tell the quality of a shoe by just looking, and although expensive, fine quality shoes should look the part; there are many factors behind the scenes that go into creating the perfect dress shoe. How it’s made being number one.

Nothing matches the quality and comfort of a good pair of handmade shoes, and although you will definitely find a much larger price tag attached to a pair of them, they are better in every way. Starting with the leather used to create them – a pair of inexpensive, regular dress shoes, are often made of synthetic materials and will not last multiple wears. Premium leather not only looks much classier, it molds to your feet to create the perfect fit, and will last a lifetime, only getting better with age.

The craftsmen who create handmade shoes spend the time carefully and masterfully building each part. This may take more time, but you are left with a shoe that is noticeably higher quality. Companies that create dress shoes in large quantities are using machines to do so, and although easier to get your hands on and much more affordable, true quality is being compromised.

There are four most common types of leather used in making quality dress shoes and although they are all good quality, wearing different types can completely change up the look of your outfit. From the most formal, to more versatile here are how materials can make a huge difference.

  • Patent – By far the most formal, and most commonly worn with a tuxedo, patent leather dress shoes should be a special occasion type of shoe only. They have started to be worn in less formal settings, however because of how easy it is for the leather to crease, it is not recommended to wear them often.
  • 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 durable and okay to be worn in the rain, it will also age beautifully with time 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, if you are able to, try to take the time and find the perfect pair, and invest in them. Quality is a huge factor, and it will always be better to invest in a pair of shoes that will last you a lifetime, rather than continually having to repurchase low quality shoes. Look at where the shoes were made, how and with what materials, these will all be factors in the cost, and if you know what to look for you will end of with the perfect pair.

Styles

Whether you are going to work, a wedding, or any special occasion that requires you to dress up, after picking out your suit the next, and might I say even more important step, is putting on that perfect pair of dress shoes. The ones that effortlessly tie your entire outfit together and make people think you just walked off an Armani runway. It’s not the easiest step and knowing which pair of shoes compliments your outfit the best can be difficult so let’s familiarize ourselves with the top dress shoe styles.

  • 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 nice 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 no-laced 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, accessing your wardrobe and what it is lacking is the first step, then think about how each of these shoes will fit into your wardrobe (if they even will) and how much use they will get. Depending on the actual amount of formal event you attend, a pair of patent leather oxfords are probably not necessary. A nice smooth leathered pair on the other hand, are the perfect addition to any closet and will be something you find yourself reaching for more often than not.

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.

Details

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 key thing that makes one pair stand out from the other is the toe design. Something many people may not even notice, but a feature that can really change the appearance of the shoe, and with what outfits it should be worn. The four most common toe styles when it comes to dress shoes are:

  • Plain Toe –  The most simplistic yet classic and elegant style, this plain, sleek and most formal design is often seen on a pair of oxfords and is the most common style.
  • Cap Toe – This extra piece of leather stitched on to the toe makes a pair of shoes less formal, making them more versatile than other. Although when styled correctly they can be made to look formal, they are worn more so by business men.
  • Wingtip – When looking down at the shoe you will see a “W” shape at the toe, this additional stitching makes a shoe much less formal and are a more relaxed choice. Depending on where you are going, Wingtip shoes can be quite versatile.
  • 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 that will best fit your lifestyle. It may seem like an easy task to go out and purchase a pair of dress shoes, however much more thought should go into your decision. The smallest details can make the largest difference, and it is important to know what those are.

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 sole is a detail that should never be missed, this will not only affect the overall quality of the shoe, but the feel of it as well. 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.

Fit

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 essentially molding to the shape of your feet to 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.) This means your shoes are bending in ways they shouldn’t when you walk. This can really affect the quality of the shoe, and how long they will last.
  • You find yourself tying your shoes as tight as you can. The eyelets should create an almost “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 not that much, look for a snug fit.

Dress shoes have caps in the front and back of the shoe, although these are great for keeping the shape of the shoe, and providing you with stability, heel caps tend to be quite stiff and can cause discomfort and irritation if the fit is not perfect. Always take the time to access 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 properly throughout, and 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, a lot quickly than oxford style shoes that need to be laced.

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.

FAQ

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.

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