10 Tips for Buying the Right Pair of Dress Shoes

For decades, dress shoes have been considered an essential part of a man’s wardrobe. In fact, the right pair of shoes can make or break your whole ensemble.

Sadly, it seems many men are losing the ways of their grandfathers and treat their dress shoes as an afterthought. It’s time to fix that, and the first step is buying the right dress shoes. This arguably one of the most important and fulfilling purchases a man should make if they care about their style.

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1. Define Exactly What is a “Dress Shoe”

The first step to buying dress shoes is clarifying what qualifies to be called a dress shoe. First, let’s define what a dress shoe is not: It’s not a sneaker, hyper-casual shoe style, or any style of footwear that exposes your feet.

Simply put, a dress shoe is usually worn at more formal events, special occasions, or at work as part of a formal dress code. So the first step to buying the right pair of dressing shoes is determining where you want to wear them and if they’re the appropriate footwear for that setting.

2. Always Have Your Feet Measured

The next time you walk into a store to buy a pair of dress shoes, have your feet measured, even if you’re confident about your size. Our feet can change shape over time, and it is not uncommon to end up with the wrong size. This is especially important if you have a preference for online shopping. 

Access to a greater range of quality shoes at highly competitive prices provides flexibility and convenience up to the point the shoe doesn’t fit. So make sure to get your size right. A well-fitting pair of shoes should enclose snuggly around the middle of your foot without feeling tight.

3. Don’t Go Cheap

Many men make the mistake of assuming the best strategy is saving money and buying a few pairs of cheap (and subsequently lower quality) dress shoes. They look fine in the beginning, but after frequent wear, they deteriorate quickly, and in just a year, the sole falls apart, and you need to get new ones.

This will happen even faster if you wear them more frequently. On the other hand, better quality (definitely costlier) ones with proper care will potentially serve you for years to come—a textbook definition of a good return on investment. 

4. How Much Should You Spend on Dress Shoes Then?

Whether you will wear them once a year or every day, if you want long-lasting, quality dress shoes from a reputable brand, expect to spend at least $300.

Nothing speaks class and manly elegance than a classy and superb quality pair of dress shoes. Be ready for compliments from strangers, coworkers, women, and possibly a few backhanded comments by envious male friends.

On the other hand, cheap leather dress shoes don’t age gracefully and look terrible over time. Examples of reputable brands that offer quality dress shoes in this price range include Meermin Oxford, Loake, and Allen Edmonds.

Remember, this is only the entry-level in the world of higher quality shoes, with Bespoke Shoes costing north of a thousand dollars. More on that later.

5. Stay Away from Synthetic Leather

Also commonly known as faux leather, pleather, or man-made leather, synthetic leather, is made from polyvinyl chloride (PVC) and polyurethane(PU leather.) Sheets of these two polymers are heat-stamped with an artificial leather grain to make them look like leather. Large quantities of these polymers can be easily produced at a low cost, making extremely cheap faux leather shoe flood the market. 

On the other hand, genuine leather shoes are made from animal hide that has been processed without artificial intervention. These will cost more but last a lot longer actually, look better with age, and will breath more (very beneficial if you suffer from sweaty feet).

6. If You Have the Money Consider Luxury Bespoke Footwear

Sometimes the rack just won’t do. That’s when you navigate to the world of bespoke footwear, also known as ‘custom’ or ‘made-to-order’. A genuinely bespoke process involves a custom shoemaker getting to know you and your style and having an in-depth discussion about precisely what kind of shoes to make, customizable right down to the toe shape.

The amount of time and perfection is the reason why top luxury bespoke shoe brands have clients on months or years-long waitlists. Handmade bespoke shoes, a pair from luxury brand George Cleverley, will cost between $3,000 and $5,000.

bespoke dress shoes
Credit: Bespoke Unit

7. Know What Shoe Style Fits your Foot’s Shape

There are more than 50 men shoe styles, the most common dress shoe styles being: Oxfords, Monk Straps, Penny Loafers, Brogues, and Derby. Even then, not all types will be appropriate for you. Different shoe styles are better suited for different foot shapes.

People with high insteps or wide feet will feel a better fit with an open lace shoe like Derby, while those who need a snugger fit should go for a closed lace shoe, such as the Oxford.

8. Closed Lace vs. Open Lace Shoes

This is must-know information for any man who ever plans to buy dress shoes. But first, let’s quickly define two shoe anatomy terms.

  • Vamp-the part of the shoe that covers the front portion and sides of the foot
  • Quarters-the part of the shoe that meets the vamp mid-foot and wraps around the heel.

Open-laced shoes have the quarters sewn on top of the vamp, and closed-laced shoes have the vamp sewn on top of the quarters. Some men find open lace shoes to be more comfortable. They can allow for more space for expansion (that’s why they are better for people with wide feet). On the other hand, closed laces shies are more formal.

closed vs open lace shoes

9. Avoid Glued Soles

There are two main types of sole stitching: Blake Stitch and Goodyear Welt. The most popular is the Goodyear Welt method, whereby the sole of the shoe is stitched to a strip of leather (the “welt”), and then the welt is stitched to the upper of the shoe for sturdy but flexible sole attachment. 

One great advantage with this method is the ease of resoling when the sole wears out, adding years to the lifespan of a well-cared-for pair. In the Blake Stitch method, the sole is simply stitched directly to the upper for a lighter, sleeker, but less durable shoe. Both approaches result in a quality shoe. 

However, at all costs, stay away from glued soles. This is a cheap, inferior way of making shoes. That will quickly leave you complaining once your shoe’s upper separates from the sole. 

Credit: The Adult Man

10. What If I Can Only Have One Pair Of Dress Shoes?

If you could only have one pair of dress shoes, they should be closed-laced with minimal brogueing (decoration) and be black (most versatile color). For example, a pair of black oxford shoes will see you through any formal event from black tie, weddings to job interviews. And better still, you can dress it down with a pair of denim or khaki and a sports jacket for a more casual setting.


  • Henry Killingsworth

    I appreciate the advice you shared about having your feet measured when purchasing dress shoes. I need to get some dress shoes. If the shoes don’t fit me properly, I can always find a service that will adjust the size for me. http://www.expertshoeandluggagerepair.com

  • Rosemarynix

    The only way too go is quality and real…

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