13 Tips for Shopping for Dress Shoes

Once upon a time, acquiring a pair of new shoes was as simple as going to the mall with your mother. You'd spend an afternoon trying on a few pairs of colorful kicks with velcro straps, each embellished with a superhero logo. It didn't matter if they matched your outfit—sometimes, they even lit up!

If only adulthood were that simple.

Perhaps this is the first time you're looking into buying dress shoes, or maybe you have a few pairs you don't love. You want to look polished and feel confident at work or special events. What's the difference between brown and cognac, anyway?

We've created this guide to help you understand your dress shoe options so shopping won't feel like a struggle. Read on to explore our 13 tips for choosing and buying shoes like a pro.

1. Start With a Versatile Shoe

Shoes are a status symbol. Just as your Spiderman sneakers marked your dominance on the playground, your dress shoes help you exert yourself in the working world. Your first inclination might be to choose something unique to help you stand out.

Instead, we recommend beginning with a simpler, more versatile shoe. You'll wear a more versatile shoe more often, as it will go with more outfits. Comfortable shoes, such as leather dress shoes, tend to get softer the more you wear them.

When your shoes match your ensemble, they're less likely to attract the wrong attention. If your shoes are too distinctive, people will notice each time you wear them.

Begin with a neutral shade such as brown, and avoid patent leather and embellishments until you've built up a more extensive collection.

2. Prioritize Quality

The golden rule for every garment you purchase should be "quality over price." This goes double for anything you wear on your feet all day. Your dress shoes form the foundation for your body, and a low-quality pair can cause pain and health complications.

If you don't physically fall apart, your low-quality shoes will. Poor-quality leather lacks durability and will begin to scuff and appear drab. A poorly constructed sole will crack, fall apart, or disintegrate.

A pair of shoes made with higher quality materials is an investment, as those shoes will last longer, even after repeated wear. Plus, a cobbler can repair a well-constructed shoe. If you bring a cheap shoe to a shoe repair shop, they'll most likely advise you to buy something new.

Are you unsure if the shoes you're considering are high-quality? Look for fine, durable leather and handcrafted construction.

3. A Brand That Stands by Its Quality

Before you take out your credit card and invest in that new pair of comfortable shoes, ask if the brand offers a quality guarantee. Likewise, check in about a return policy.

A brand that will willingly take back a faulty pair is a good sign. It means they believe in their product and stand by its quality and construction. If a brand is defensive and makes you jump through hoops for a refund, they might be trying to hide something.

The truth of the matter is the more liberal a brand is about its quality guarantee, the less likely you are to need it.

4. Square Toes Are Out

What pops into your mind when you hear the word "fancy?" Often, we conjure images of impractical attire, such as boxy, square-toed dress shoes. Not only are square-toed shoes out of fashion, but they're impractical and often poorly constructed.

The most fashionable contemporary men's dress shoes feature a rounded or tapered toe. The silhouette is sleeker and more in line with current trends. You're also less likely to trip over your own feet, which is always a better look!

All that to say, you don't need to dress like a 1930s businessman to command respect in your new shoes!

5. Consider Shopping on Sale

We understand that a high-quality pair of dress shoes is an investment and that not everyone is in a position to take a risk on a big-ticket product. If you play your cards right, you can buy a great pair of shoes on sale.

This is a great option for your first everyday pair, as they'll help you understand what you like about the style, fit, construction, and comfort level. That information will come in handy when you're ready to buy your next favorite pair.

6. Measure Your Feet at Home

As a child, your shoe size seemed to increase every few weeks. As an adult, we expect our shoe size to remain pretty stable.

Believe it or not, our feet do tend to change as we age. They may not grow in length, but they can become wider as ligaments begin to relax. The shape of your foot plays a significant role in choosing the ideal size for your new shoes.

When shopping for quality leather shoes, measuring your feet at home can help ensure nothing has changed. Leather becomes more comfortable over time but does not always stretch. If your shoe doesn't fit when you try it on, it probably won't fit later, so get those measurements right!

7. Consult Online Sizing Charts

In the clothing world, men's sizes tend to be fairly standard. They refer directly to the measurements used to construct the clothing. Shoes don't always play by the same rules.

While you can assume sizing will be consistent within a brand, always study sizing charts when switching to a new manufacturer. One brand's size seven may be another brand's size eight, and you don't want to get stuck with an ill-fitting pair.

In the event that your new shoes don't fit, a generous return policy comes in handy, so shop boldly!

8. Know Your Styles

Many different types of shoes come under the umbrella of "men's dress shoes." Shopping is easier when you can use the right vernacular to ask for what you want.

Look into the following styles:

  • Oxford
  • Derby
  • Brogue
  • Monk strap
  • Loafer
  • Chukka
  • Chelsea Boot

Each style has a different shape and gives off a distinct impression. The most versatile style on the list is the oxford, which you can dress up or down.

9. Keep Texture in Mind

Just as dress shoes don't come in a single style, leather shoes don't come in a single texture. The texture of the leather informs the finish of the shoe. In other words, do you want something shiny, matte, soft, or bumpy?

You'll see the following terms used to describe leather texture:

  • Patent
  • Smooth
  • Full grain
  • Top grain
  • Pebble grain

You're unlikely to wear a pair of patent leather shoes on a casual date or a pair of pebble-grain shoes to a wedding. Your everyday dress shoes will likely be smooth and somewhat matte, like the everyday styles carried by Gatsby.

10. Consider Color

If you're starting with a single pair of dress shoes, color matters. You want something versatile that goes with your regular color palette. When deciding which color shoe to choose, start in your own closet and take note of the shades you find there.

As a general rule, always pair black shoes with a black suit. Navy blue and light gray suits can pair well with any color shoe.

Furthermore, many colors subtly imply a level of formality. Black shoes tend to be the most formal. Brown shoes are great for everyday wear, while alternate browns (like burgundy or oxblood) are more casual and creative.

11. Comfort Is Critical

Depending on your daily style, your dress shoes might become a wardrobe staple. If that's the case, and you'll be on your feet all day, it's wise to prioritize comfort when choosing your shoes. Orthopedic dress shoes are just as stylish as traditionally constructed shoes but offer more support for busy professionals.

These shoes are often slip-resistant, which makes them safe and appropriate for all settings. Consider prioritizing breathability, too. Moisture in your shoes leads to discomfort, and a breathable design prevents issues.

12. Choose Your Formality Level

When choosing shoes, men often fall in love with the details. Be aware that, as a general rule, the level of detail often makes a shoe more or less casual. The fewer details on your shoe, the more formal it appears.

13. It's Okay to Ask

If you're shopping for shoes specifically for an event, it's appropriate to ask the organizers what style they think might be appropriate. Nobody expects you to become an expert overnight. Find out what other attendees will be wearing and try to match their style.

With that said, you might fall in love with the effortless, upscale style of your new shoes!

Find Your Next Great Pair of Dress Shoes at Gatsby

Clearly, a lot goes into finding the perfect pair of unique, versatile dress shoes. The process gets easier when you start with a handcrafted, high-quality brand like Gatsby. Every shoe in our collection is stylish, comfortable, and casual, and you really can't go wrong.

Every pair in the Gatsby collection includes a quality guarantee so that you can feel confident about your purchase. We're so certain you'll love your new shoes that we'll issue a full refund if you don't fall in love. Start your search by browsing Gatsby's collection online today.

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