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Get Your Shoe Game on Point: Best Dress Shoes for Men Under $500

Most men know to some degree what a man’s dress shoe is; for most it’s just ‘the smart ones’, for others it’s ‘the expensive ones’ and for nearly all of us it’s the ones which we don’t wear very often and when we do we can’t wait to take them off because they’re so uncomfortable.

All of these descriptions are right, but they don’t have to be the exhaustive list of criteria to describe men’s dress shoes. While they are indeed smart, they don’t have to break the bank, and even though they’re not going to be as comfy as your Flyknits, they don’t need to give you blisters or be a chore.

dress shoes for men

Why you need dress shoes

One of the reasons men have these issues with dress shoes is that they don’t know why they need a good pair. That will change after you read this article. You need a good pair of dress shoes for three reasons: 

  • One; a good pair means you only need to buy one pair every decade or maybe more. Good shoes, from a quality brand, made of strong leather will last a long time and will end up being very comfortable.
  •  Two, a good pair of shoes is a sign of a responsible and confident man. Women often look at a man’s shoes to help them draw some inference as to whether they see him as suitable partner. So not only is a good pair of dress shoes an investment into the future of your finances, but it is an investment in your ability to attract the right women. Think of it like this; good quality shoes equals a greater chance with a stand up gal.
  • Finally; purchasing a good pair of shoes means you aren’t going to get as much foot pain and blisters. The shoes are more purposefully made with more knowledge and often years in the shoe game, meaning they know how to create quality products for men’s feet.

How to choose the right dress shoe for you

Now that you know why you need a dress shoe, let see how you can have the right dress shoe. How does one go about choosing a decent pair of dress shoes? There a few things to consider. You need to think about durability, because if so, you will want to stay away from trending fashion, as that won’t be there forever. Instead it’s better to opt for classic styles which will always be stylish; the derbies and Oxford’s are best for this.

Something else to think about is how multi-purpose you will want them to be. By this I mean, do you want them for work, for funerals/weddings, parties and everything else combined, or do you just want them for a few or one occassion. If you want your dress shoes to service every possible scenario then the colour will matter greatly.

Black shoes will probably be your best bet; some weddings are black tie, funerals often require an all-black attire, and opting for the in-trend tan wingtips will be cool for a party but not for some offices and events already mentioned.

Now that the groundwork has been laid, let’s look at the best option in each style of dress shoe.

The Best Dress Shoes for Men Under $500​


Oxford’s, known as Bal-type shoes in the US, found their origin in Scotland and Ireland and were at that point called Balmorals (after the castle in Scotland), but were soon appropriated and made popular by students at Oxford University in 1800.

These shoes have evolved over time from the Oxonian, a boot from which they were derived, into the quintessential dress shoe. The simplicity and understated nature of the shoe lends itself to all formal occasions and is perhaps the best option to purchase for multiple purposes.

The Shoe for the Unpretentious Man: Aldo- Carlus Oxford ($125)

Aldo Carlus Oxford

This shoe is a perfect example of how much you can get for your money. At only $125, this 100% leather oxford is ideal for the penny-pincher and wannabe fashionista alike.

The shoe boasts a decent style and while not pushing the boat out in terms of design, it does everything you need from a formal shoe.

If you are one of those blokes who begrudgingly wear dress shoes only when you have to, then this non-fussy option is probably a good choice.

Another benefit of this shoe is the rubber heels; while these don’t last as long as their wooden counterparts, their comfort levels are certainly graded higher.

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While the monkstrap has been around for a long time, it does occasionally fall out of fashion, meaning that the long-term thinkers out there may want to give this one a miss. However, if you are into your trends and always want to be wearing the latest styles then a monk shoe is ideal.

The shoe is laceless and is fastened onto your foot with a buckle, which is known as the monk strap. Due to the constant ebb and flow which is ‘trend’ in the fashion world, you might as well go all out with one of these shoes, perhaps stacking the trend by making it suede or brogue.

For the New Age Gent: Church-Lisbon Monk Suede Shoe ($420)

Church-Lisbon Monk Suede Shoe

Churches are without a doubt one of the best brands of shoe you could ever purchase. The brand was established in 1873 by Thomas Church and his three sons, and ever since then they have been producing incredible shoes.

This particular shoe is made out of the finest suede and is constructed in England by shoemakers with decades of experience. A block heel and silver-toned metal complete the beauty of the piece. An elegant shoe designed for the fashion forward and classy among you.

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The Derby shoe, also known as a Gibson, or if you are American; a Blucher. This option was popularised in the 1850s by hunters, but by the early twentieth century it had become a common ‘town shoe’. These days the Derby, characterised by its open lacing (the opposite of an oxford), has become the line on which formal and informal shoes tread.

While you can rock an awesome suit with a pair of Derbies, you can also combine them with some jeans and t-shirt for a relaxed stroll through town. All in all, the derby is the ultimate all-rounder.

For the High Roller: Paul Smith-Robin Derby Shoes ($235)

Paul Smith-Robin Derby Shoes

If you are looking to get your hands on a piece of British sartorial heritage, then Paul Smith is the way to go. Founded in Nottingham in 1970, Paul Smith has been a leader in the class and modest fashion of Britain, but has done it in an incredibly unique way; combining classy fashion with vibrant colours and kooky designs.

This shoe represents decades of honed and perfected English craftsmanship. For the quality and style of the shoe, the price is very reasonable.

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Brogues are one of the most informal versions of dress shoe, finding their foundations in the countryside, yet they remain a mainstay of current fashion, often being found in tan and other variants of a brownish hue.

Brogue is perfect for parties and more relaxed formalities, they work well with light coloured chinos and jeans, and if you are hell-bent on wearing a suit, a pair of tan brogues works perfectly with a light grey suit.

For the Fashionista: Grenson-Dylan Leather Wingtip Brogues ($380)

Grenson-Dylan Leather Wingtip Brogues

Grenson is another Brit on the list; classic, heritage and high-quality. The brand which stretches all the way back to 1866 where Grenson started it’s long journey of impeccable design and extraordinary shoes. These particular brogues continue that long-standing tradition of excellence by using a new lightweight design to develop a slimmer look.

The burnished toe cap and wooden heels add to the feel of English class. If you want to put together a killer outfit, get a pair of straight light blue jeans and a crisp white cotton shirt, match a belt to the brogue and finish it off with a bright pair of socks.

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This slip on shoe is often worn for comfort and ease of use. The lazier and most informal dress shoe has grown in the fashion world in the last 5 years with the tassel loafer making a triumphant resurgence to the glossy pages of fashion mags.

The loafer which was introduced by a London company (the English certainly do a lot of shoe stuff) called Wildsmith Shoes in the nineteenth century and was actually designed for George VI (a king of England) as a house shoe.

Now that all sounds pretty regal and pompous, but the modern day loafer has found itself donned mainly alongside slim trousers and the mega hip cliques of fashion. If you like jumping on trends, jump on this one. One tip; don’t wear socks with the shoe.

For the Laid Back Man: Grenson-Grayson Tasselled Loafer ($310)

Grenson-Grayson Tasselled Loafer

Another Grenson (because they’re awesome). This Grenson is the most casual shoe on the list; however this doesn’t mean that it wouldn’t look great with a light grey suit or a pale-blue number.

​Shoes like this work well with smart casual garments and if you work at a more relaxed and style-conscious company then with a single button slim fit suit.

The outstanding benefit of wearing shoes like loafers is just how comfy they are; often made out of a softer leather, the shoes don’t hurt you anywhere near as much when you break them in, if at all.​

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Whether you want a pair of dress shoes to fight off the nagging of your wife, who ‘just wants you to look nice’, or because you want to take pride in your footwear, you can now see that there is an option for everyone.

Biggest tip; try them on and don’t be afraid to send them back a few times until it’s the right fit. Your feet will thank you later.

Written by Terrence Kennedy

Terrence Kennedy is the man’s man on a journey to self-discovery. A traveler, extreme sports aficionado, an observant wanderer, a DIY-Know-How, an ultimate outsider and a documentarist of culture, sex, dating, relationship, fashion, style and gentleman's etiquette. He has learned a lot through his escapades, and is happy to pass that knowledge on to you.