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:
- Oxford Shoes: Allen Edmonds Fifth Avenue Cap-Toe
- Brogue Shoes: Allen Edmonds Strandmok
- Comfortable Oxford: Wolf & Shepherd Close Cap Toe
- Handmade Brogue: Maglieriapelle Pamukkale
- Monkstrap: Johnston & Murphy Fielden
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.
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.
In This Guide
Other Shoe Budgets
Other Dress Shoe Guides
Recommended Shoe Guides
- Style: Oxford Shoe
- Formality: Business Professional
- Pricing: $425 [Buy From Allen Edmonds]
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.
Also Featured In
- Style: Brogues
- Formality: Varies
- Pricing: $345 [Buy From Allen Edmonds]
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.
Also Featured In
- Style: Oxford Shoes
- Formality: Business Professional
- Pricing: $380 [Buy From Wolf & Shepherd]
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.
Also Featured In
- Style: Brogue
- Formality: Business Professional
- Pricing: $495 [Buy From Maglieriapelle]
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!
Also Featured In
- Style: Monkstrap
- Formality: Business Professional
- Pricing: $399 [Buy From Johnston & Murphy]
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.
What To Expect From $500 Dress Shoes
When 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
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
Your 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.