Sometimes we want to wear shoes that walk the fine line between dressy and casual. However, this can be quite challenging as even the business casual dress code is quite subjective and can vary between different environments. So what are our options in terms of casual yet smart footwear?

We’ve looked back through our reviews and collections to assemble the ultimate list of the Best Casual Dress Shoes For Men:

  1. Beckett Simonon Leonard
  2. Allen Edmonds Strandmok
  3. Aurélien Driving Shoe
  4. Beckett Simonon Cohen
  5. Ace Marks Hugo
  6. Maglieriapelle Cunda
  7. Wolf & Shepherd Breakaway Boot
  8. Beckett Simonon Lopez
  9. Trickers Stow Boot
  10. Taft The Saint Boot

Scroll down to read it all or use the links above to jump ahead.

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What Are The Best Casual Dress Shoes For Men?

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1. Beckett Simonon Leonard

Beckett Simonon Leonard Single Monk Strap Shoes

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Ethically crafted in Beckett Simonon’s workshop in Bogota, Colombia, the Leonard is made with premium Argentinian full-grain calfskin. The shoe is constructed with a Blake stitch and features a wholecut vachette lining for extra comfort.

We love the smooth finish with the subtle buckle detail. As a result, the shoes are very easy to wear casually but are also versatile enough for more formal occasions.

Thanks to a group made-to-order business order, the shoes offer exceptional value for money and you pick up a pair for just $170 with our code “BU20“.

"An exceptional specimen of single monk strap shoes that effortlessly bridges the gap between formal and casual footwear."
Bespoke Unit Rating: ★★★★★

2. Allen Edmonds Strandmok

Allen Edmonds Strandmok Brogues
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Bespoke Unit’s Charles-Philippe adores these brogues and often comes back to them for a variety of occasions. Made with a Goodyear welt and featuring stylish red Dainite soles, they’re wonderfully outgoing and comfortable brogues.

These are probably the most versatile brogues that we have worn. Thanks to the stylish blend of colours, they can be worn quite formally but also as a casual shoe. Whether you’re wearing jeans or chinos, they’ll compliment the overall look.

Although only available in a single colour, the shoe features such a level of complexity that it becomes so versatile. The uppers are a shade of brown leather with a distressed effect, which gives a vintage finish. Meanwhile, a red Dainite style offers a splash of colour whilst the tan welt provides contrast.

3. Aurélien Suede Italian Driving Shoe

Aurélien Suede Leather Sole Detail
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Even as a casual option, it may be pushing the limits by referring to a suede driver as a dress shoe. Nevertheless, Aurélien’s Italian loafers are a great option to consider if you want to wear something that is as close to casual as possible.

If you were to choose a suede leather loafer, we would highly recommend Aurélien’s Italian-made driving shoes. Thanks to the unique oil treatment, they’re supple comfortable to wear.

As driving shoes, they’re also very practical and great for running on errands thanks to the well-made pebbled soles. Whether you’re behind the wheel or not, they look great and offer a loose and comfortable fit.

4. Beckett Simonon Cohen

Beckett Simonon Cohen Penny Loafer On Wall

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A more formal alternative to Aurélien above, Beckett Simonon’s classic penny loafer is far more versatile and more acceptable when worn for dressy occasions. These shoes are manufactured at the same workshop while using the same techniques and materials as the Leonard above.

They’re also available in a variety of colourways, which will significantly change their level of formality. While the tan shoes pictured above are the most casual, dark colours will render them more appropriate for more “serious” wear.

5. Ace Marks Hugo

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Blucher boots are a great option if you’re looking for versatile footwear that can be worn for different occasions. Thanks to their sleek and elegant contours, Ace Mark’s Hugo is probably one of the best specimens that you can consider.

As mentioned above, darker colours will render them more formal. Meanwhile, a paler boot will be a great casual option that offers a premium flair. The premium construction and leathers used are indicative of its Italian craftsmanship. Indeed, they’re lined with calfskin with a full-grain upper.

6. Maglieriapelle Cunda Tassel Loafer

Maglieriapelle handmade Cunda Tassel Loafers
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You’ll often hear brands claim that their shoes are handmade. However, in most cases, this only consists of some of the stitching whereas most of the assembly will resort to machinery.

Maglieriapelle is an Italian-inspired Turkish brand that doesn’t compromise on craftsmanship. Indeed, the shoes are entirely made by hand! The results speak for themselves and the shoes are finished with a dazzling hand-painted patina that reveals mesmerising brush strokes and depth.

Tassel loafers are an excellent casual option that offers both class and sophistication. The Cunda by Maglieriapelle is a great example of how its sleek design and profile can be worn to retain an element of elegance.

7. Wolf & Shepherd Breakaway Boot

Wolf & Shepherd Breakaway Boots Close Up
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As with hand craftsmanship, a lot of manufacturers love to boast about the comfort of their footwear. However, most aren’t quite as cosy as they claim. Nevertheless, Wolf & Shepherd is a brand where comfort is the foundation of its DNA.

Launched in 2014, Wolf & Shepherd shoes were inspired by athletic footwear technology. Following years of critical acclaim, the brand has now introduced a plethora of different shoe designs. One of favourites is the Breakaway boot.

A classic blutcher boot on the outside, they’re made with EVA heels, memory foam footbeds, and a lightweight PhoenixTECH rubber sole. As a result, they carefully brace the feet and don’t have much weight. Therefore, they can be worn for hours without causing aches or tiredness.

8. Beckett Simonon Lopez

Beckett Simonon Lopez Boots

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At Bespoke Unit, we’re very fond of Chukka boots in general. However,Beckett Simonon has drawn inspiration from WWI heritage style to produce an elegant alternative.

The design is sleek with refined stitching details. The Lopez boot also features a rubber sole for added traction and durability. If you want a dressier alternative to the very casual chukka, here’s our first choice.

As you will have seen, we’ve mentioned Beckett Simonon shoes multiple times in this list. Indeed, their construction is admirable and they offer excellent value for money.

9. Trickers Stow Boot

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Trickers is a celebrated English shoe brand that has been operating in Northampton since 1829. On its 160th anniversary, Prince Charles visited the factory to award the historical shoemaker with a Royal Warrant.

Indeed, Trickers is often credited with having created the first men’s country boot. This heritage lives on as the stow boot, which is made in England using 260 different processes including a traditional Goodyear storm welt, and Dainite rubber soles.

Although very premium, the Stow Boot is the ultimate example of a casual boot that has become dressier over time. Therefore, if you’re looking to wear a heritage style that’s versatile for both casual and semi-formal wear, the Stow Boot is an excellent option.

10. Taft The Saint Boot

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Taft is celebrated for its rebellious and wild designs that are a little more outlandish and contemporary that many traditional brands. We’re particularly fond of the Saint boot, which is made from hand-woven leather that results in fascinating details.

Given the cost of hand-weaving leather, the Saint is constructed using a Blake stitch in order to ensure that its price is consistent with the brand. Nevertheless, the Blake stitch still offers excellent durability and function for many years.

If you want a versatile boot with a dressy construction and a casual flair, the Saint is something that will certainly turn heads!

What Are Casual Dress Shoes?

Trevor Guilday On Railroad With Leather Chukka BootsAs we highlighted in this guide’s introduction, casual dress shoes walk the fine line between two very broad dress codes. In fact, the term may sound like something of an oxymoron as dress shoes are traditionally perceived as anything but casual.

However, there are times when you might be looking for a more relaxed style of dress shoe that lets you tone things down a bit. This might be because you’re seeking to fulfil a business casual dress code or you may simply want a more stylish shoe to wear casually.

Overall, a casual dress shoe features a conventional yet relatively informal shoe design. Meanwhile, the materials used are perceived as less formal yet still very high-end.

As a general rule of thumb, a casual dress shoe is something that you’d struggle to wear with a suit but would pair nicely with jeans. For instance, black Oxford shoes look great with any sort of formal wear but would appear totally out of place with denim.

Furthermore, the colour of the shoe plays an important role in its level of formality. Whilst dark colours considered the most formal with black at the top, they become more casual as they get lighter.

Casual Dress Shoe Styles

Allen Edmonds Strandmok Brogues With Jeans & ChinosOf course, not all dress shoe styles are strictly casual or formal and there are a lot of factors that come into play. However, here’s a non-exhaustive scale from formal to casual to give you an idea:

  • Brogue Shoes: Featuring a closed-throat lacing system like Oxfords, Brogue shoes are rendered more casual thanks to various ornamentation such as toe medallions, pinking and perfing.
  • Derby Shoes: Also known as Bluchers, Derby Shoes are the most formal casual dress shoe style. Often confused with Oxfords, they feature an open rather than closed-throat lacing system.
  • Loafers: The largest and most inclusive group of casual dress shoe, loafers are convenient and comfortable yet quite stylish. Consider varieties such as Venetian loafers, penny loafers, tassel loafers and bit loafers.

Other potentially casual styles include monkstrap shoes or even brogue variants such as Longwings and saddle shoes. Nevertheless, a lot of this can depend on other considerations such as their materials and colour.

Furthermore, although a lot of dress boot styles are growing in popularity, they’re traditionally considered more casual than formal. This is because boots were originally a type of utilitarian footwear.

Best Casual Dress Shoe Materials

Green Pants With Grey Suede BroguesAs suggested above, the type of material used to construct a shoe style can profoundly change its formality. Types of leather such as patent, calfskin and full-grain are considered the most formal. However, with the exception of patent leather, they’re still casual if made into a casual shoe style.

Meanwhile, other types of leather such as pebbled, suede or Nubuck will render an otherwise formal shoe into something that’s much more casual. Furthermore, casual dress codes can open doors to other non-leather materials.

For example, materials such as canvas aren’t viable in dressier situations but add an extra touch of flair to casual shoes. They can even be used to complement leather features with certain styles like saddle shoes.

Best Casual Dress Shoe Colours

red white and blue saddle shoeAlthough very casual shoes can come in a variety of bright colours such as red, yellow, orange or purple, they will rapidly lose their dressiness. However, there are exceptions, which are slightly less unorthodox. For instance, white, dark blue and sand are conventional enough to still be a casual dress shoe.

However, the best casual dress colours are usually shades of brown. Overall, tan is the most versatile and casual dress shoe colour. Nevertheless, you could go for a traditional mid or dark brown so the shoes could be worn more formally.

Otherwise, you could instead seek out browns that come with a hint of dark red such as Oxblood, burgundy or even Cordovan. These are very versatile colours that offer a pop of colour without becoming too casual.

What Next?

Now that you have read about the best casual dress shoes for men, consider checking out some of our other related guides.

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