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.

brown allen edmonds brogues

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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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