Best Derby Shoes Reviewed & Rated

Shoe styles have expanded over the years to include more trendy and comfortable day-to-day footwear.  And even more so when we start to look at sports shoes and beach-wear.  But the derby shoe with its open lace structure and classic design is one of everyone’s favorites.  

Derby Shoes - black shoes

The derby shoe is a very versatile style and can be casual/business casual, business, semi-formal or formal depending on its features.  Start with the classic open lacing system of a traditional derby and add a durable sole and some color, and you have a great casual shoe paired with jeans or khakis for around town or business casual.  Change it up a little with some additional stitching, perhaps a cap toe and some smooth leather and your derby will take you to the office paired with slacks or a suit.  Add some detailing or adjust the heel height and you can change the occasion and purpose for wearing the shoe.  

Last Updated: November 9, 2017
By Darcy G:

The recent update to the 10 Best Derby Shoes reflects the criteria used to evaluate derby shoes and how to make your shoes more comfortable. You will also find additional information about shoe lining. Also added are some frequently asked questions about how to care for your derby shoes.

Featured Recommendations

Bruno Marc Urban
  • Bruno Marc Urban
  • 4.7 out of 5
    Our rating
  • suede upper
  • Price: See Here
Rockport Ellington
  • Rockport Ellington
  • 4.5 out of 5
    Our rating
  • Block heel
  • Price: See Here
Bostonian Kinnon
  • Bostonian Kinnon
  • 4.5 out of 5
    Our rating
  • Synthetic sole
  • Price: See Here

And comfort is always important no matter where or when you wear a shoe.  It’s important to check the cushion, flexibility and stability features of the shoe to make sure it meets what you are looking for.  Some derby’s in this list have special features to keep your feet cool and dry, and some focus more on stability and durability.  Other derby’s have a sense of flair and adventure while others are more subtly elegant. Take a look at these derby’s and think about which features are most important to you as you narrow down your decision to buy.  


10 Best Derby Shoes


1. Bruno Marc Urban

This fresh look on a classic derby style makes it a top pick for a business casual or casual event. The open lacing system, suede finish and heel blend the classic with the contemporary. And the sturdy comfort of the Urban will keep you going on those long days on your feet. With many colors to choose from, you will find one or two to fit your lifestyle.
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Contemporary Casual
This look takes can take you to the office on business casual day or around town for all of your activities. The basic design paired with a variety of colors adds style to your wardrobe without being too busy.

Stylish Charm
With a basic style but in a textured suede, these shoes appeal to people in all walks of life. They go with just jeans, pants and just about any seasonal wear to top it off.

Cost and Value
The Urban is a great value for your money. With so many styles and colors, there is something for everyone. You can even pick up more than one at this price!
  • Casual and stylish
  • Luxury look in many colors
  • Classic derby open lacing to adjust to your foot
  • Manmade outsole for slippage control
  • Quick break-in period
  • Consider a suede or nubuck protector
  • Some say run they large

2. Rockport Ellington

This classic derby is perfect for casual business wear. It’s sleek and subtle with enough detail to make it interesting without being overstated. The open lacing system has a versatile fit and allows you to adjust the snugness to your comfort and foot shape. The Ellington’s waterproof insole keeps your feet dry on those damp days. This is a great all-around shoe that goes with any look.
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The Rockport has a patented air circulation feature that is designed move air within the shoe and keep your feet cool and comfortable in all situations.

Stability Control
With a thicker sole and tread, and specially designed outsoles to support your natural walking motion, the Ellington gives you the stability and flexibility you are looking for.

Cost and Value
For a quality dressier shoe that breathes and keeps your feet dry, the Ellington is a decent buy for the price. A dressier show will cost you a little more but worth it for a quality look and feel.
  • Versatile for dress or business casual
  • Flexible after break-in period
  • Waterproof insole
  • Stability and traction control
  • Extended sizes and widths
  • Only available in 2 colors
  • 2 week break-in period

3. Dr. Martens Original 8053

This shoe has more of a casual, classic look for around town activities. With a thicker, rubber sole and low heel, the Original 8053 is a go-to shoe for those dress down days when you are on your feet. The cushioned footbed and traditional lacing keep your feet comfortable for hours. The Original 8053 also has a non-slip sole in those slippery situations.
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Classic Durability
Dr. Martens are built to last and these are no exception. The premium leather upper holds up to your day-to-day activities, and the thick sole is attached to the upper with the goodyear welt for long-lasting flexibility.

After that initial breaking in period, the Original 8053 is known for comfort. The traditional lacing lets you tighten and loosen the fit as needed, and the cushioned footbed absorbs impact as you walk.

Cost and Value
Dr Martens are a great bargain when you look at the longevity and durability of this shoe. They look great and are built to last.
  • Durable lasting footwear
  • Soft leather upper for flexibility
  • Breathable lining
  • Air cushioned sole for comfort
  • Traction tread for a non-slip grip
  • Break-in period

4. Clarks Tilden

4. Clarks Tilden
The Tilden has a polished sophisticated look without being too formal, perfect for the office, business casual or when you want to be a little less casual. It’s stretch panel and open lacing system provides maximum adjustability. The Tilden’s cushioned insoles provide extra comfort and wicks away moisture to keep feet dry and comfortable.
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While the Tilden looks stylish and is great for the office, it has the expected Clark’s comfort features the company is known for. The cushioned insole reduces the impact of being on your feet, and the elastic panel in the upper stretches for those small adjustments you need during the day.

Polished Style
This shoe looks right at home in the office or at a semi-formal event. The Tilden goes with suits, dress pants and even a dressy pair of jeans. The cap toe and double stitching gives the shoe a little detail without being overdone.

Cost and Value
The Tilden gives you great value at a good price. Getting this comfortable business and business casual shoe in a basic color is money well spent.
  • Long lasting comfort
  • Dressy for the office and semi-formal events
  • Insole controls moisture
  • Minimal break-in period
  • Light tread to control slips
  • No removable insole
  • A little narrow

5. Calvin Klein Bram Diamond

5. Calvin Klein Bram Diamond
The Bram Diamond is a sophisticated derby shoe that takes you through business and semi-formal events alike. This shoe appeals to those who want something a little out of the ordinary with its textured stylings. Comfort details make this a great choice when you have to be on your feet longer than usual.
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Uniquely Sophisticated
With smooth leather on the cap toe and quarter and diamond textured leather on the vamp, the Bram Diamond adds a noticeable flair to your ensemble. The stacked heel and finished laces complete the look of prestige and sophistication.

Comfortable Style
The Bram Diamond has an open lacing system for getting the correct adjustment for your foot. It’s padded footbed and rubber sole absorbs shock and keeps your feet comfortable and the partial leather lining protects against unwanted chafing as you walk.

Cost and Value
This dressy shoe is a little pricier, but is still a good value for your money. It adds flair to your wardrobe and keeps your feet comfy when you have to be on your feet.
  • Quality, interesting leather upper
  • Padded footbed for all-day comfort
  • Partial leather lining for durability
  • Rubber sole to limit slipping
  • Short break-in period
  • Runs long / long toe box
  • Limited color choices

6. Bostonian Kinnon

6. Bostonian Kinnon
The Bostonian Kinnon derby shoes is a well-made classic dress shoe. It’s professional-looking shine takes you to the office and business events later in the day. The subtle appearance will complement your professional look. It’s durable features combined with a padded footbed designed to keep your feet cool all day.
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Classic Silhouette
This shoe has the classic derby silhouette with a cap toe for to add visual appeal. A one-inch stacked heel adds to the classic look along with the rounded toe makes this shoe a good choice for your business wear.

Comfort for Extended Wear
The Bostonian Kinnon is lightweight and gives you all day comfort with a specially designed footbed to cushion and breath. The rubber sole gives you extra comfort when you are on your feet.

Cost and Value
This shoe is a great general dress shoe for those occasional semi-formal events. Some colors and sizes vary in price, but it is a bargain for your dress up days.
  • Looks like a very expensive shoe
  • Textured rubber sole for stability
  • Flexible and light
  • Short break-in period
  • Comfortable padded insole
  • Some say runs narrow
  • May have a high sided fit for some

7. Allen Edmonds Ashton

7. Allen Edmonds Ashton
With a sturdier look and a deeper footwell, this shoe goes well with business casual and casual weekend looks. This stylish shoe is great for custom orthotics or use the Ashton’s insole to keep your feet comfy. And the luxurious look and quality of this shoe will make you feel pampered all day long.
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Quality Casual
The Ashton is stylish without being formal. You can see the quality in the raised stitching and leather upper. And everyone appreciates a casual shoe with a simple, burnished leather.

Durability and Reusability
When you find that favorite shoe, it feels like we found a new friend. And with a removable footbed and depth to accommodate a custom orthotic, you want to keep it as long as possible. The welt on this shoe allows it to be resoled so you can extend the life of the Ashton.

Cost and Value
One of the most expensive on the list, but very well made and gives you the extra room whether you have a custom orthotic or just need more space in your shoe.
  • Burnished leather upper
  • Removable footbed
  • Welt constructed to keep out moisture
  • Made to last
  • Rubber sole for stability
  • Price
  • Too deep for some

8. Cole Haan Carter Grand

8. Cole Haan Carter Grand
The Carter Grand is a great shoe for semi-formal attire and to wear to the office. The buffed leather and gives this shoe a quality sheen that pairs with your business and special event attire. It’s lightweight cushioning and outsole and provides flexibility without sacrificing durability.
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The Carter Grand is lighter than most business and semi-formal footwear, and your feet will appreciate the lighter shoe. Its proprietary cushioning foam is thinner than typical cushioning without sacrificing comfort. They have re-engineered the shank and part of the outsole to make this shoe even lighter.

The engineers at Cole Haan have worked to make this shoe more flexible. They improved on the upper, liner and outsole to help the shoe move well with your feet.

Cost and Value
This cost of this shoe is higher than several on this list. For a comfortable dress shoe with detailed tooling and a classy look, it still is a decent deal.
  • Improved cushioning
  • Leather lined leather upper for flexibility
  • All around lighter construction
  • Classic style
  • Unique color option
  • May squeak before breaking in

9. Magnanni Colo

9. Magnanni Colo
The sleek, timeless design of the Magnanni Colo has the classic derby shoe look. With its streamlined appeal, this shoe goes to semi-formal events and into the evening.
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These shoes are classically designed with expert craftsmanship and attention to detail. The hand detailing and fine leather adds to the exquisite look and feel of this shoe.

Flexible Construction
The Magnanni Colo is engineered to be flexible. The upper is wrapped around to be attached directly to the sole to achieve maximum flexibility.

Cost and Value
Another of the most expensive on the list, this shoe is made of the highest quality materials inside and out as well as hand-finished details. If you are looking for a luxury shoe, this is the one.
  • Sleek, subtle elegant look
  • Agile and flexible to move with your foot
  • Finest quality materials
  • Hand detailing and design
  • Good selection of large sizes
  • Price
  • Runs large

10. Viotti Formal

10. Viotti Formal
The Viotti Formal is just that – a derby with an open lace system that is perfect for your fun dress up occasions. It comes in a variety of bright colors to take your next ensemble to the next level. With their fun look and snazzy shape, they are sure to please.
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Fun Colors and Fabric
The imported silk Viotti will stand out in a crowd with their color choices of red, blue, gold or silver. They also come in the more subtle black, white or grey. A fun striped pattern and metal tip make these shoes a showstopper.

Lots of Compliments
Since these shoes are so unique people will notice them immediately. You will get lots of compliments on these shoes because of their brilliant color, striped pattern and grand look.

Cost and Value
Great value for the cost of a fun, dress shoe for the occasional formal event. It’s sure to get you noticed at the next party.
  • Lots of color choices
  • Great striped pattern
  • Goes great with special occasion attire
  • Unique look for a festive experience
  • Some say the metal tip has come loose

Now that you’ve read through the top 10 of our picks for the best derby shoes around, think about what you are looking for in a derby, how often will you wear it and which places you will go in your Derbys.  If you are looking for an occasional dress shoe, you may be able to sacrifice a little comfort for a lower price tag.  But if you wear your derbys several times a week and are on your feet most of the day, you may find benefit in spending a little more for a longer lasting, more comfortable shoe.  Wherever your derby’s take you, there is a pair waiting for you that fits your needs and your lifestyle.


Criteria Used to Evaluate the Best Derby Shoes


Visual Appearance

Since most people try on a shoe based on its visual appearance and then determine whether it is comfortable or not, first we looked at the overall aesthetics and type of material for our top picks.

When you choose your derby, think about where you will wear them most often.  Casual outings with family and friends, to the office where the dress code is a little more formal, or even to a semi-formal affair are all things to consider when finding a derby shoe.

Leather or a quality, flexible synthetic is typically the choice for a dress shoe.  Synthetics tend to be lighter and breathe better than leather, and with the right construction can hold up just as well as leather to wet conditions.  Suede has a more casual look and with weatherproofing, can stand a bit of moisture.  All look nice and have a place in your wardrobe.

Options for different colors and styles were also considered as most people have some variety in their wardrobe.  Many of our choices are in basic black or brown/dark tan, but there a few with more pizazz and contrast.  All of our derby shoe top picks have a heel that adds a bit of formality to your look.  

Style was also considered because a little stitching, texture and contrast makes your shoes more interesting without being over-stated.  The cap toe shoe adds some formality to your foot-ware, while a shoe textured uppers adds depth, and a shoe with broughing (perforations) adds interest and makes your shoe slightly less formal regardless of the toe style.  


Many people are on their feet all day, or possibly are not used to wearing a more dressy shoe.  So, the next criteria for picking the top 10 was the comfort.  The various ways our picks provide comfort are equally important as the appearance of the shoe.  There are several ways our top picks met the comfort criteria.  First, we looked for a cushioned or specialized insole/footbed to absorb shock and provide a better fit for your shoes.  A little cushioning and moisture wicking properties to keep your feet dry goes a long way to keeping your feet comfortable.

We also looked at the outsole of the shoe for stability and traction control.  Almost all of the shoes on the list have some level of tread on the sole of the shoe to avoid slipping and sliding.  And many of the shoes have at least a partial rubber sole and some also have a rubber heel for additional stability.  

Other comfort items you will find in our top picks are the break-in period for the various derbys.  It’s important to know that for the shoes that have a longer break-in period, take your time and wear them gradually until they are broken in and formed to your foot.  After that break-in period, you derbys will be ready to keep your feet comfortable.  

Derby vs Oxford

Both the derby and the oxford are a dressier shoe.  However, the oxford is typically considered more dressy and formal than the derby.  The derby can be identified by an open lacing system, where you can see the flap underneath the laces, where the oxford is a closed laced system where you can’t see the flap.  While the level of detail on the shoe can make it more or less formal, the oxford with the closed lace system is considered a more elegant, formal shoe.

Shoe Lining

Most shoes have lining to cover the seams for a comfortable experience and to extend the life of your shoes.  Leather lining is soft, lets your foot breathe and absorbs moisture well.  But, it adds extra weight to the shoe.  Fabric is more commonly used for lining due to its lower cost.  But be aware that while some fabrics breath and absorb moisture better than others, they don’t breathe or absorb moisture as well as leather.  

To care for your shoe lining and extend the life of your shoe, give your shoes time to air out before wearing them again as the moisture from your foot is absorbed into the lining and other materials in your shoes.  For best results, store your shoes on a shoe tree to maintain their shape, prevent odors and aid in drying your shoes.  

How to Make Your Shoes More Comfortable

Shoes, like your feet, come in many different depths and widths.  Make sure that you get a shoe that is the correct depth and width for your foot.  If you have a shallow foot or have a pair that are too deep for your feet, you may want to use inserts such as tongue pads or heel inserts to gt a better fit.  However, the best approach is to get a shoe that works for your foot shape.

If your shoes are too tight, you may choose to stretch them to make them more comfortable.  But be careful not to stretch them too much.  An overly loose shoe is almost as uncomfortable as a too tight shoe.  Trying on shoes in the afternoon or evening when your feet may have become a little swollen during the day may help you get a better fit that will last all day.  And make sure you have enough room in your shoe.  Try to keep a thumbs width of distance from your longest toe to the end of your shoe.  This gives your foot enough room to move when you walk.



Frequently Asked Questions

Q:  How Can I Tell if it’s A Derby?

A:  Both the derby and the oxford are a dressier shoe.  However, the derby is typically considered less formal.  The derby can be identified by an open lacing system, where you can see the flap underneath the laces when they are tied.  This is especially helpful when you need to adjust the tightness of your shoes throughout the day.  The oxford is a closed lace system where you can’t see the flap.  While the level of detail on the shoe can make it more or less formal, the oxford with the closed lace system is considered a more elegant, formal shoe.

Q:  When Should I Wear a Derby Shoe?

A:  Derby shoes are versatile, depending on the style, material, and details of the shoe.  So your derbys can be more casual, such as a suede, for those weekend and non-business occasions.  Or fit right in for a day at the office or even take you to a semi-formal event.   

Q:  How do I Clean My Derby Shoes?

A:  It is important to periodically clean, polish and condition or re-treat your investment to keep them looking great and extend their wearability.  

For all types of shoes, you may want to remove the laces to get dust and grime from around the eyelets. And take a look at the laces.  If they are dirty either wash them or replace them.  

  1. To clean leather derby shoes, start with a quality shoe brush.  One made with horsehair is considered the best.  Use it to remove dirt, grime or other materials from the leather, around the eyelets and other parts of your shoe.  If there is dirt ingrained in the leather, clean it with a leather cleaner or saddle soap, water and a soft sponge.  Let them completely air dry before you move on to conditioning.   When your shoes are dry, apply a leather conditioner according to the product directions.  You will probably need to let your shoes dry again after conditioning.  Then you can apply polish and buff your shoes to the desired shine.
  2. To clean suede derby shoes, make sure your shoes are dry and clean them with a suede brush.  Carefully brush the suede in one direction to remove dirt and raise the nap.  You may want to use a suede eraser to remove stains left behind after brushing.  Apply a coat of suede protector on your derbys.  Make sure to follow the product instructions.
Q:  How Can I Make my Derbys last longer?

A:  Make sure to clean them regularly and try to alternate pairs of shoes each day.  Give your shoes time to air out before wearing them again as the moisture from your foot is absorbed into the lining and other materials in your shoes.  For best results, store your shoes on a shoe tree to maintain their shape, prevent odors and aid in drying your shoes.  

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