Whether you prefer quality over quantity or just want to treat yourself, a $500 budget can offer you some of the best dress shoes available. Here you can expect hand craftsmanship and constructions made to last decades.

We got frugal and tested dozens of shoes to find the Best Men’s Dress Shoes Under $500:

  1. Oxford Shoes: Allen Edmonds Fifth Avenue Cap-Toe
  2. Brogue Shoes: Allen Edmonds Strandmok
  3. Comfortable Oxford: Wolf & Shepherd Close Cap Toe
  4. Comfortable Brogue: Wolf & Shepherd: Senna Wingtip
  5. Handmade Brogue: Maglieriapelle Pamukkale
  6. Monkstrap: Johnston & Murphy Fielden
  7. Wholecut Shoe: Paul Parkman Brown Oxfords
  8. Comfortable Boot: Wolf & Shepherd Breakaway

See anything you like? Just use the links above to jump ahead. Alternatively, scroll down to see them all! Furthermore, we’ll touch on the premium features you can expect from high-quality shoes on a $500 budget.

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Quick Buyer’s Guide

If you want to jump right in and find the best shoes according to style, use the Quick Buy Guide below to head straight to the retailers. Alternatively, scroll down to learn more about them individually.

Oxford Shoes

Allen Edmonds Fifth Avenue Oxford Shoes

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Brogue Shoes

Allen Edmonds Strandmok Brogues

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Comfortable

Wolf & Shepherd Closer Cap Toe Oxford Shoe

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Wingtip

Senna Wingtip Brown Comfortable Dress Shoes

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Handmade Brogue

Maglieriapelle handmade & Painted Pamukkale Brogue Shoes

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Monk Strap

Johnston & Murphy Fielden Monkstrap

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Wholecut

Paul Parkman Handmade Wholecut Shoes

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Dress Boot

Wolf & Shepherd Breakaway Boots Feature

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What Are The Best Men’s Dress Shoes Under $500?

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1. Allen Edmonds Fifth Avenue Cap-Toe [Premium Oxfords]

Allen Edmonds Fifth Avenue Oxford Shoes
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Overview

Allen Edmonds is an American brand often synonymous with quality and prestige. As such, it’s no surprise to find several of their creations on this list. We’re very fond of their premium Oxfords that feature a classic balmoral cap toe with a touch of broguing, which gives an elegant finish.

How To Wear

Ideal for both business professional and formal needs, you can wear these shoes with a suit but even take them for an evening out in cocktail attire. Whatever your suit style, they’ll blend right in.

Best Colors

You can choose between either black or light brown shoes in this style. If these are your first pair or your needs are more formal, we’d opt for the black. However, brown is a great option for a less formal and slightly more casual shoe.

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2. Allen Edmonds Strandmok [Brogue Shoes]

Allen Edmonds Strandmok Brogues
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Overview

Another shoe from Allen Edmonds, we absolutely adore these brogues. They’re incredibly stylish and feature a Goodyear welt as well as very eye-catching rust-red Dianite soles.

How To Wear

What we love the most about these brogues is their level or sheer versatility. It’s rare to find a shoe that can be worn for almost any occasion, but these work just as well with chinos as a three-piece suit. Whether it’s for a business casual working environment or lavish cocktail events, these are perfect.

Best Colors

Although they’re only available in a single style, you benefit from the colourful style for maximum versatility. With a vintage-style brown leather upper, tan welt and rust red soles, there are a number of options for pair them.

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3. Wolf & Shepherd Closer [Comfortable Oxford]

Wolf & Shepherd Closer Cap Toe Oxford Shoe
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Overview

Having claimed to have created the world’s most comfortable dress shoe, we were excited to see what the hype was all about. We weren’t disappointed and left very impressed with the construction quality, style and premium styling.

How To Wear

A formal shoe of a similar ilk to the Allen Edmonds Fifth Avenue, these look fantastic with a suit. They’re perfect for any dress code above and beyond business professional. However, if you’re looking for something more versatile that offers the same experience, we’d suggest the Senna Wingtips below.

Best Colors

Nevertheless, if you still want a traditional Oxford shoe with a cap toe but that’s a little more casual, you can opt for either a maple brown or honey tan colour. Otherwise, for the most classic style with a suit, black can’t be beaten.

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4. Wolf & Shepherd Senna [Comfortable Brogue]

Senna Wingtip Brown Comfortable Dress Shoes
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Overview

If you want to enjoy the same comfortable experience from Wolf & Shepherd but prefer more casual and ornate brogues, then these are what you’re looking for. Streamlined and elegant, these are truly beautiful shoes indeed.

How To Wear

As they’re blind brogues without a toe medallion, they’re still quite formal. This means that they can be quite versatile and worn with either suits or even casual chinos and a sport jacket.

Best Colors

As with the Oxfords, they’re available in black, maple mid-brown or honey tan. We love the lighter honey tan as it looks stunning with a suit as well as more casual attire.

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5. Maglieriapelle Pamukkale [Handmade Brogue]

Maglieriapelle handmade & Painted Pamukkale Brogue Shoes
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Overview

A unique and ambitious brand, Maglieriapelle is based in Istanbul, Turkey, and crafts beautifully painted handmade shoes. Their small team create some of the most eye-catching designs that are surprisingly affordable given the work involved and the Pamukkale is their flagship brogue.

How To Wear

Given the hand-painted finish, these are somewhat less formal than the other models on this list. However, they can be successfully worn with a natural, earthy tones to bring out the patina’s deep brush strokes.

Best Colors

These are only available in brown but each shoe they make is unique as they’re hand-painted!

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6. Johnston & Murphy Fielden [Monkstrap Shoes]

Johnston & Murphy Fielden Monkstrap
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Overview

As part of their “Handcrafted In Italy” collection, the Fielden range is one of Johnston & Murphy’s most prestigious offerings. Usually a brand that dominates the mid-priced market, they’ve excelled at crafting a stunning monkstrap.

How To Wear

The hand-stained and burnished Italian calfskin leather offers deep textures that are contrasted by smooth and embossed finishes. Depending on the colour you choose, they can either be excellent formal shoes for business professional attire or more casual in nature.

Best Colors

We’re quite fond of the textured hues found on the cognac brown, which is great for casual occasions. However, you can also pick the black for a more understated shade that’s perfect for formal-wear.

7. Paul Parkman Hand-Painted Oxford [Wholecut]

Paul Parkman Handmade Wholecut Shoes
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Overview

Like Maglieriapelle mentioned above, Paul Parkman are a better known brand with a reputation for eccentric yet elegant footwear. These beautiful wholecut shoes feature subtle broguing details and a unique hand-painted patina.

How To Wear

Thanks to the wholecut design, these can be worn quite formally. Meanwhile, the brown colour allows them to be worn casually too. We would recommend that these fall into a more business casual dress code but can be pushed up with a fashion-forward suit.

Best Colors

Paul Parkman offer a wide selection of colours yet each model has its own. If you’re looking for something more sombre or even livelier, head to their site to explore the variety.

8. Wolf & Shepherd Breakaway [Comfortable Boot]

Wolf & Shepherd Breakaway Boots Feature
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Overview

You may have noticed with the entries above that we’re rather fond of Wolf & Shepherd. If you’re equally fond of boots, then you simply have to try the Breakaway! They’re considerably lighter than most dress boots and feature a thick cushion and spongy EVA heel.

How To Wear

Although we’ve listed them as business casual, they’re remarkably understated thanks to the low-profile sole and easy to wear with a suit. We often wear them casually too and find that they’re among the most versatile boots that we own.

Best Colours

The photo above shows the cognac colour. However, you can buy them in honey tan or black too. Nevertheless, we have a preference for the cognac’s versatility.

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What To Expect From $500 Dress Shoes

allen edmonds shoe boxWhen pulling the trigger on $500, you’re making a significant investment. Therefore, it’s of no surprise that you have certain expectations when parting with a fair amount of hard-earned cash.

Whilst $100 offer some decent performance on a budget, $500 should be in an entirely different league. Here, you should expect high-quality materials as well as shoes that last decades rather than years .

In the following section, we’ll be exploring the features that you should expect from the best $500 dress shoes.

Goodyear Welt

Goodyear-Welt-Shoe-Construction-Graphic

First and foremost, you should accept nothing less than a Goodyear welt. If you don’t know what this means, welting is the technique used for attaching the sole to the bottom of the shoe.

Cheaper shoes tend to resort to a quick and easy technique called “cementing” where the sole is fused using a special adhesive. However, these tend to last one or two years at best.

Meanwhile, the mid-range welting technique is known as the “Blake Stitch”. This process involves actually stitching the sole to the shoe, which makes it somewhat more durable. However, it’s not as labour-intensive as the Goodyear welt, which means that although it’s less expensive, it’s not as robust.

Finally, the Goodyear welt is the oldest technique where the shoe is stitched to the sole in multiple steps. It earned its name when Charles Goodyear invented a machine in 1869 that made this somewhat quicker to do.

Overall, a Goodyear welt is more robust than any other technique so your shoes are unlikely to fall apart. Furthermore, they’re designed in such a way that virtually any cobbler can resole the shoe an almost unlimited number of times.

They’re also more waterproof as the greater number of stitches creates a better seal that still breathes naturally.

Of course there are other types of welting that exist that are less common. However, the Goodyear welt is the most famous and for good reason. If you want to learn more about welting, you can refer to our dedicated shoe construction guide.

Prime Leather Upper Grades

Varied Color Horween Leather RollsYour shoes’ leather quality is always important but it becomes fundamental when purchasing high-quality shoes. When forking out such a large sum, you should expect that your shoes are made of the best possible materials.

As much as the term “genuine leather” may sound reassuring, there are many different types of leather, which each have their own individual grades. You’ll hear a lot about full-grain leather, which is a type of top-grain leather.

Overall, top-grain leather comes from the hide’s outer layer. Here, the fibres are densely packed, which means that the leather is stronger and more durable. The best areas are closer to the spine where the animal’s skin was the tightest. As you move further out, the leather features more veins and blemishes.

However, even top-grain leather consists of three grades, which each have five subgrades of their own too. From this moment on, it can get quite confusing.

Nevertheless, remember that a hide will typically provide the leather for around seven pairs of shoes. To save money, factories will use a combination of different parts and their corresponding grades to maximise their costs.

Yet when buying premium leather shoes, you want them to be made from only the very best sections. Furthermore, you don’t want it to be a mix where lower-grades are used in unseen areas like the vamp.

Whilst this is hard to check when buying online, you can visually inspect the leather when you have it. Good-quality leather should be tight and free of any blemishes or wrinkles. Similarly, both shoes should be identical. If they’re not, the factory may have used different grades for each shoe.

Quality Soles

Allen Edmonds Dalton Wingtip Brogue Boot Dianite SoleRubber is a popular material for shoe soles and whilst there are some of excellent quality, it can vary greatly. For instance, we love Dainite soles, which appear on most of Allen Edmonds’ shoes.

Their studded rubber soles have been made in the United Kingdom since 1894. They offer superior cushioning, hard-wearing durability as well as stylish designs.

However, leather soles are equally common for dress shoes. For some people, this is a desirable trait but rubber has been gaining traction over the years. The advantage of leather soles is that the natural materials breathes better for the feet.

Nevertheless, it tends to require more maintenance and it’s recommended to add rubber reinforcements as they can wear down quite quickly. Some brands offer leather soles with reinforced leather sections to make them last longer.

Finally, stacked leather heels are another desirable trait even if the shoes feature have a rubber finish. A simply chunk of rubber on the heel is cheaper and easier to make. However, it isn’t as attractive and may give too much bounce.

Therefore, ensure that the heel consists of high-quality stacked leather rather than artificial materials that give off the same effect. Whilst this stacked leather heels are pricier, they’re more comfortable and indicate superior quality.

Handmade In A 1st World Country

Leather storage for bags and suitcasesSimilarly, premium shoes should retailed at their prices not only because of the materials used, but the labour involved too. When a pair of shoes are sold for around the $500 price point, you’d hope that some of the manufacturing process was undertaken by hand.

Nevertheless, a lot of techniques have been largely mechanised since the industrial revolution. However, many others since then have been automated even further than that.

Therefore, you should check what form of hand-craftsmanship was involved in making the shoes and expect that the majority involved traditional techniques.

Although it may sound superficial at first glance, it’s also ideal that the shoes are made in a 1st world country. Whilst there are many proficient craftsman and women in other countries around the world, the workers’ rights are not quite as protected.

Similarly, the working conditions tend to be quite poor and sometimes outright deprived. As such, when investing into premium shoes, you want to be funding skilled artisans rather than supporting exploitative factory working conditions.

Finally, the quality control in larger factories tends to be lower than in smaller workshops. If you turn to lower-scale operations, you’ll increase your chances of purchasing a labour of love rather than just a commodity.

What Next?

Whilst it’s tempting to grab a pair of shoes at around $100 to $300, remember that the manufacturers are able to sell these shoes at such a price for a reason. Although you can obtain some decent shoes for this price, a higher budget can give you a pair of shoes that will last decades.

However, feel free to check out some of our other shoe guides with other budget considerations before you pull the trigger:

Best Dress Shoes Under $500 Guide
Reviewed by Terry C., on .
"Beautiful shoes that I'm proud to wear! From the construction to the design and comfort, these are great and will last me forever!"
Rating: 5.0 ★★★★★

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