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Best Dress Shoes for Special Events & Occasions Reviewed

last updated Nov 15, 2018

You build your outfits from the shoes up - the right pair of footwear can not only make or break your outfit, but can determine whether you end the day happily, or with sore feet. From work to special occasions, and even to slightly more casual wear, formal footwear 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.

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 ones 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 option for you. 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.

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Products Evaluated
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Products Evaluated
Last Updated:
By Ana Rockov:

The latest update to this article replaces one item with a higher quality product, ensuring that the list is always reflective of the best dress shoes available for purchase. Additionally, more criteria has been added, and the entire article was updated in terms of appearance, making it easier to find all the important info you need for a successful shopping experience.

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1
The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
98
Materials
99%
Style
96%
Advanced Features
98%
Fit
99%
Price Comparison Last Updated (20.11.18)
$328.00
2
The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
97.8
Materials
98%
Style
99%
Advanced Features
97%
Fit
97%
Price Comparison Last Updated (20.11.18)
$299.00
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The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
96.8
Materials
97%
Style
96%
Advanced Features
99%
Fit
95%
Price Comparison Last Updated (20.11.18)
$154.95
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The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
94
Materials
95%
Style
90%
Advanced Features
95%
Fit
96%
Price Comparison Last Updated (20.11.18)
$93.95
5
The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
92.8
Materials
92%
Style
93%
Advanced Features
94%
Fit
92%
Price Comparison Last Updated (20.11.18)
$55.44
6
The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
91.3
Materials
91%
Style
96%
Advanced Features
89%
Fit
89%
Price Comparison Last Updated (20.11.18)
$53.99
7
The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
89
Materials
93%
Style
87%
Advanced Features
86%
Fit
90%
Price Comparison Last Updated (20.11.18)
$59.95
8
The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
87.8
Materials
88%
Style
88%
Advanced Features
84%
Fit
91%
Price Comparison Last Updated (20.11.18)
$37.47
9
The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
85.3
Materials
85%
Style
84%
Advanced Features
95%
Fit
77%
Price Comparison Last Updated (20.11.18)
$59.95
10
The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
84
Materials
86%
Style
77%
Advanced Features
79%
Fit
94%
Price Comparison Last Updated (20.11.18)
$94.50
In Depth Review Top 10
  • Frye Jones
  • Magnanni Dante
  • Johnston & Murphy Conard
  • Ecco Helsinki Cap-Toe
  • Calvin Klein Bram Diamond
  • Clarks Tilden Walk
  • Dockers Agent Slip-On
  • Clarks Bostonian Bolton
  • Dockers Moritz Wingtip
  • Timberland EK Brook Park
Table of contents
  • Criteria Used for Evaluation
  • Other Factors to Consider
  • Frequently Asked Questions
  • Sources

Top 10 Dress Shoes

1. Frye Jones

The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
98
Frye Jones
Materials
99
Style
96
Advanced Features
98
Fit
99
best offer for today
$328.00
Pros:

Leather Outsole

Leather Lined

Wears Nicely Over Time

Elastic Gore

Pull Tab on Heel

Cons:

Minimal Grip on Sole

Outsole Isn’t Water-Friendly

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; formal 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 footwear in general, 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 on this list, but in the long run from the amount of wear you will get out of these, it is very worth it.

2. Magnanni Dante

The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
97.8
Magnanni Dante
Materials
98
Style
99
Advanced Features
97
Fit
97
best offer for today
$299.00
Pros:

Patent Leather Upper

Plain Toe

Leather Footbed

Leather Outsole

Handmade in Spain

Cons:

Hefty Price Tag

Not for Everyday Wear

These formal patent leather shoes by Magnanni are a pair of premium quality fashion staple ones that are going to take your style to the next level. If you're looking for a pair that will be unparalleled in comfort and quality, then this is definitely the pair for you. Handmade in Spain, these look so good that they definitely justify the price tag they come with.

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All Leather
They 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 them without having to worry about dealing with any type of pain once you take them off.

Flexible Outsole
In general, they 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 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 is worth investing in, and the Dante by Magnanni is definitely an investment. With a price tag that is much higher than almost any other pair 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.

3. Johnston & Murphy Conard

The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
96.8
Johnston & Murphy Conard
Materials
97
Style
96
Advanced Features
99
Fit
95
best offer for today
$154.95
Pros:

Hand Burnished Italian Leather Upper

Sturdy Buckles

Cushioned Footbed

Rubber Outsole

Stacked Heel

Cons:

Runs Narrow

Monk straps have become increasingly popular in the last couple of years, mainly because they offer a refreshing look that's still greatly formal, and works well with almost any outfit - from sleek suit, to skinny jeans. This model by Johnston & Murphy is premium quality option for those who like to make good investments in life. Nonetheless, the Conard also comes in a cap toe, plain toe, wingtip and single monk strap option, just in case you prefer to stay away from lots of buckles.

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Italian Leather Upper
When it comes to leather, you can't get much better than that which comes from tanneries in Italy. Hand burnished and featuring some of the best done broguing money can buy, the Conard truly is an excellent choice. The closure features two sturdy buckles that'll allow you to find the perfect fit, while the leather itself is soft enough to mold to your feet for a pair of monk straps you'll be wearing for years to come.

Cushioned Footbed
Formal footwear is often uncomfortable, as any woman will be glad to say (those heels are a killer). But flat styles can also be uncomfortable to walk, stand or dance in for prolonged periods of time, so a cushioned footbed is a most welcome addition, ensuring a higher level of support and shock absorption, lowering the level of fatigue you feel at the end of the day. If you're planning on wearing these to a wedding, you should expect a bit less swelling than you'd get from your regular, stiff pair of Oxfords.

Cost and Value
With a price that's average compared to the other items on this list, the Conard can be considered a steal. Not only is it highly fashionable, well made, and durable, but it's also a versatile pair of footwear that'll work at the office, at the club, formal gatherings, as well as casual outings and dates. You'll definitely impress in this pair of monk straps, all you have to do is choose one color option.

4. Ecco Helsinki Cap-Toe

The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
94
Ecco Helsinki Cap-Toe
Materials
95
Style
90
Advanced Features
95
Fit
96
best offer for today
$93.95
Pros:

Leather Lining

Breathable

High Quality Materials

Durable

Supportive

Cons:

Lacks Height in the Heel

Not as Durable as Other ECCO Models

ECCO is a brand which focuses on providing their users with comfortable, shock absorbing footwear that looks nice and is pleasant for everyday wear. The Helsinki Cap Toe is no different and is a stylish option that will look amazing, whatever you decide to wear it with. Featuring a full grain leather upper and featuring unique ECCO comfort technologies, this is one of our top choices.

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Highly Breathable
These ones feature some of the most forward technology, with their focus being on breathability and comfort. Made to prevent bacteria and odor overgrowth, they ensure good air circulation, which means that your feet will be comfortable, whether it’s hot or cold outside.

Shock Absorbing Outsole
Their polyurethane outsole was made to feature plenty of shock absorption, which makes them 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 model is 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 them more comfortable, you’ll definitely want to wear them as often as possible.

5. Calvin Klein Bram Diamond

The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
92.8
Calvin Klein Bram Diamond
Materials
92
Style
93
Advanced Features
94
Fit
92
best offer for today
$55.44
Pros:

Leather

Cap Toe

Padded Footbed

Stacked Heel

Rubber Sole

Cons:

Little Arch Support

Hard Leather in Toe Area

With a subtle update to the classic design, the Calvin Klein Bram Diamond is an excellent choice if you want to get something less ordinary. You will look exceptionally stylish in these unique Oxfords that look incredible with a nice pair of pants. With a silky smooth leather and diamond textured pattern they will make you a stand out in any business meeting.

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Textured Pattern
Unlike the typical all one textured leather ones, 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.

6. Clarks Tilden Walk

The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
91.3
Clarks Tilden Walk
Materials
91
Style
96
Advanced Features
89
Fit
89
best offer for today
$53.99
Pros:

Leather Upper

Breathable

Flexible

Synthetic Sole

Ortholite Footbed

Cons:

May Fit Narrow

Heel Can Be Problematic for Some Users

This pair of Oxford shoes by Clarks is an excellent choice for those looking for an affordable option. With a leather upper and plenty of comfort features, these will feel great on your feet after a solid 8 hour work day, and you won’t dread the special occasions when you have to put these on. And what’s best - they also come in a wide fitting for those who need a bit more room in their footwear.

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Comfort Features
They have a lace up closure, but for the sake of comfort, an added elastic slit has been added, ensuring that you feel comfortable while wearing them. The padded leather upper is soft and will fit most foot shapes.

Ortholite Footbed
In addition to a soft synthetic sole, they also offer an Ortholite footbed which is cushioned and has excellent moisture wicking properties. This means that they won’t develop odors, even with longtime wear.

Cost or Value
This pair 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 special occasions.

7. Dockers Agent Slip-On

The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
89
Dockers Agent Slip-On
Materials
93
Style
87
Advanced Features
86
Fit
90
best offer for today
$59.95
Pros:

Easy On and Off

Thick Cushioned Outsole

Comfortable Insole

Stylish Stitching

Full Grain Leather Upper

Cons:

May Appear Big on Feet

Outsole Wears Quickly

If you’re looking for a slip-on style, then the Agent by Dockers is a great choice. Not only do they look good, but they’re made with a quality leather upper and a softly cushioned latex footbed. A padded collar and synthetic sole contribute to the overall feeling of comfort you will get with them, while the heel measures about 2cm, which is the perfect heel height according to foot health specialists.

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Full Grain Leather Upper
The best part about them is the full grain leather upper that is not only protective and durable but has also been burnished to give it a unique look. They will mold to your feet and will develop a warmer, richer color with time that will be unique to you.

All Motion Comfort™ Technology
They 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
A good choice for those who need a formal pair but are not looking to go with something too fancy. They will work well both with a suit as well as with jeans, and they’re comfortable enough to wear to work. With a price that is around average, you’ll definitely appreciate the Dockers Agent Slip-on.

8. Clarks Bostonian Bolton

The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
87.8
Clarks Bostonian Bolton
Materials
88
Style
88
Advanced Features
84
Fit
91
best offer for today
$37.47
Pros:

Long Lasting Comfort

Fits Like a Glove

Simple Style

Easy On and Off

Padded Collar

Cons:

Thin Soles

Crease Easily

This pair of loafers offers a sleek design that will easily transition from day to night wear and will look great with most outfits. If you’re a fan of Clarks which are known for their quality and comfortable footwear, then the Bostonian Bolton may be a great option for you. You’ll especially like the fact that these are very lightweight, something that can’t be said of most other models on this list.

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Slip-On Style
These are slip-ons 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, they are a great choice for anyone. Whether you want to wear them to the office, as everyday footwear or on special occasions, you are bound to appreciate their padded collar and cushioned insole.

Cost and Value
They 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.

9. Dockers Moritz Wingtip

The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
85.3
Dockers Moritz Wingtip
Materials
85
Style
84
Advanced Features
95
Fit
77
best offer for today
$59.95
Pros:

Cushioned Insole

Breathable Fabric

Ages Well

Wingtip Design

Stylish

Cons:

May Wear Out Quickly

Colors Differ From Images on Website

The Moritz Wingtip by Dockers is made with a supple burnished leather upper that offers excellent comfort and flexibility. With a rubber outsole that is stable and comfortable, you can wear them anywhere. Available in both black and brown, the Moritz can be worn with any of your favorite suits or outfits.

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Hidden Comfort Features
In addition to being made with genuine leather, these ones 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 them from creating problems in the ankle area.

Flexible
Both the leather upper and the rubber outsole are flexible, allowing your foot to freely move, without any constraint. That’s what makes them 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 that will serve you well, then these are a great choice.

10. Timberland EK Brook Park

The rating is based on the average rating (1-100) from all the criteria in which we rated this product.
84
Timberland EK Brook Park
Materials
86
Style
77
Advanced Features
79
Fit
94
best offer for today
$94.50
Pros:

Leather

Gripstick Sole

Two Eyelets

Pull Tab on Heel

Comfort Technology

Cons:

Requires a Break-In Period

No Padding in Ankle Area

These chukka 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 with 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 options 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 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 boots on the list at a lower cost.

Criteria Used for Evaluation

Materials

One of the most important things you want out of your pair is a quality make. Not only will this greatly contribute to their appearance, but it will also ensure that you get a comfortable pair that will last you plenty of time. Although high-quality ones will often feature a hefty price tag, you might find that an initial investment can pay off with years of use.

The best brands 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 a pair of premium leather ones 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 products 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 footwear can be great as well, handmade ones are sure to set you apart in a crowd.

Most are made of leather, and there are four types which are most commonly found in quality models. All of these are good options, but note that each has its own unique characteristics and advantages that will make a difference in how they behave and fit.

  • Patent - By far the dressiest, and most commonly worn type of leather. Often paired with a tuxedo, patent leather should be a special occasion type of shoe only. Although you might see them in more informal settings nowadays, note that patent leather creases easily, so it is best to save these for special occasions only.
  • Smooth - The most common when it comes to leather options, 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.
  •  

    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 that will last a lifetime, especially if you opt for an investment piece. High quality footwear 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 ones every so often.

    Style

    Whether you are going to work, a wedding, or any other ceremony, you will want to match your footwear and suit to reflect the best possible image that you have to offer the world. A good pair can effortlessly tie your entire outfit together, under the condition that you choose the correct styling. There are several 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, 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 classier 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 sleekest look.
  • Loafer - These slip-on ones may be more informal 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 dressy 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 choose them to 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. 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 style them up or down as needed.

    When it comes to 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.

    Advanced Features

    When deciding to invest in a new pair pay attention to the details and know that although similar, each pair you come across will be unique in its own way. They are very complex and come in many different shapes and sizes. One of the key things that makes them stand out from each other is the toe design. Though not everyone will notice the toe, it can decide whether a pair is suitable for a certain occasion. The four most common toe styles are:

  • Plain Toe -  Simple and elegant, this is a classic style you can’t go wrong with. It will be featured on the sleekest models, so a pair of Oxfords with a plain toe are a great choice.
  • Cap Toe - This extra piece of leather stitched on to the toe makes a pair 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 them 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 footwear, this style is not considered to be formal at all.
  •  

    Details are everything when it comes to picking the proper pair. They can completely change the look of your outfit, and can even make a pair 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 they should have a rounded toe, never square. One of the first things people look at after your overall appearance and outfit is what you're wearing on your feet, and whether or not they go with your outfit and are nice quality. It’s been said you plan your outfit from the toes up, so keep that in mind the next time you even consider trying on that pair of squared toes.

    The outsole of your footwear makes a huge difference in their function and style. Not only will it affect its quality, but it will also determine how the pair feels on your feet. There are a few types of soles most commonly used 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 ones.
  • Fit

    One of the most important things is fit. Unlike other styles of footwear where there is some wiggle room when it comes to sizing, if your special pair doesn't fit perfectly it will wear in all of the wrong places. These 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, 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), they are probably bending in ways they shouldn’t. This will affect how long they last.
  • You find yourself tying them as tight as you can - The eyelets 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 - They 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 them to grow a full size.
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    Most 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 their fit is not perfect. Always take the time to assess how your feet feel in your new pair, 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 them 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 ones, 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 footwear. That is very wrong and you will quickly find that out! 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 trainers where it does not make a large difference. When it comes to dressier footwear however, some are tailored made for your specific feet, so knowing exactly what your size is will guarantee the perfect fit.

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    Dress Shoes And Suits

    If you're headed to work, office causal, or a bit more stylish business attire is easily accomplished by wearing your favorite dress shoes with slacks, khakis, sometimes even jeans.
    However, if you find yourself headed out for the evening to a more polished event, having a suit handy is the way to go. Investing in one suit that is tailor made just for your build and shape not only leaves you looking amazing, but allows you to feel comfortable in your own skin, and hold your head high.
    If you've not yet found the perfect suit, visit your local tailor and have a chat with them. If they can't find you something you love, they can certainly recommend where to go!

    Oxfords Or Derbys

    When checking into selecting your new style of dress shoes, a few basics to remember about oxfords and derbys.
    Oxfords are signature style closed lace system shoes, where the vamp is sewn atop the quarters. When you lace together the quarters, they can come close enough to touch. Usually considered a more elegant style of footwear, it was used by those in uniform since long ago.
    Derbys are a more relaxed fit, with and open lace system. This gives the shoe the appearance of being slightly less formal than the oxford.

    Other Factors to Consider

    Value

    As with most other footwear, you can expect a high price tag to go with a well-made pair of formal shoes. However, with dress styles, this can be even more pronounced, with some brands even going as high as 4-figure prices. To some, this may seen completely crazy, but others will be happy to make an initial investment and own a product that will last a lifetime.

    However, if your budget is not quite there yet, you should definitely opt for a combination of affordability and quality, based on how you plan on wearing your newly purchased footwear. If you need something to wear once, that will likely be sitting in the back of your closet for the next ten years, then there's definitely no need to splurge. But, if you want to wear these regularly, or want to have a stunning pair of Oxfords to wear on special occasions, then a higher cost may be justified.

    Definitely be aware of the fact that price and quality are not always related. A better way to determine if a product is worth the investment is to check the materials used in the making process, inspect the stitching, check the fit and read customer reviews. These should give you a good idea of whether the purchase will work well for you, or if you should move on to something else.

    Durability

    Another factor that has a lot to do with the materials and construction of a pair of shoes, the durability will greatly depend on the quality of the make. Nonetheless, you will definitely want to go with something that won't wear out after just a few hours of wear.

    The top products featured in this article are all made with the best leather money can buy, and you can expect them to hold up to wear well. But how any footwear ages will also greatly depend on how you use it. We would advise agains wearing fancy shoes in foul weather. You should also take care of how you store it, making sure it's in a dry and well ventilated space.

    If your footwear got wet, you will need to dry it thoroughly, and maybe even use some conditioning products to lessen the damage. Last but not least, do not wash leather items with too much water (or in the washing machine). Instead, take the time to care for it properly, and you'll find that it'll last you much longer that way.

    Support

    For those who work in a formal setting, a good pair of dress footwear will mean everyday wear, sometimes even for longer than 8 hours. If you suffer from any preexisting foot health conditions such as flat feet, plantar fasciitis, bunions, or other types of sensitivity, you'll definitely need more than just the regular flat leather sole.

    Some of the models listed above feature some type of support features, most often found in the arch and heel area. Some will have an insole that can be removed and replaced with a custom orthotic, and this is a definite advantage for achieving the best possible support.

    But, if the model you like does not have any of these features, you may still be able to get away with it. In that case, we would recommend checking whether a supportive insole will fit. If yes, that's great. If not, then you might want to try and get a half size larger to accommodate the additional material in the shoe.

    Shock Absorption

    If you walk a lot, you probably know how much your heel, knees, hips and back can suffer from the continuous shock that travels up your legs with every foot landing. Luckily, a number of manufacturers are taking this into consideration when making their products, applying technological advancements that were reserved for athletic footwear for a long time.

    Today, you can purchase formal footwear with just as much shock absorbing properties as those found in running sneakers. Brands such as ECCO and Cole Haan are including excellent cushioning systems that are located in the heel, dispersing the force that is created on impact, and helping the foot cope with it better.

    While these styles may cost a bit more upfront, they are a great choice for those who need something truly comfortable on an everyday basis, and can even do a great deal in preventing future podiatric problems.

    Frequently Asked Questions

    q: Should I be shining them?
    a:

    If you have a nice pair 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 their life by a lot and keep them looking new.

    q: Should these be an item I splurge on?
    a:

    Yes and no. Everyone should have a pair 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 ones, 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 is the most versatile?
    a:

    The classic smooth leather oxford is the most versatile, and can seamlessly go from work to a wedding. However, if you want a casual option, 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. Unlike other types of footwear where wiggle room makes no difference, dress ones 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 ones, tailored to your feet will be very worth it in the long run.

    q: How many pairs should I own?
    a:

    That is completely dependent on how often you find yourself reaching for them 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 can be all you need.

    q: Do they need to be broken in?
    a:

    Unlike some other footwear, like runners, these 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 them 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.