How to Wear Jeans and Dress Shoes (2024)

Yes, You Can Wear Dress Shoes with Jeans…Sometimes

Much like the precise definition of ‘business casual’ and proper martini proportions, pairing dress shoes and jeans is a surprisingly contentious topic. We think you can do it, but only under certain conditions. Here, we’ll cover what most men get wrong about wearing dress shoes and jeans, how you can pull it off, and why the rest of your outfit matters as well.

The Problem with Dress Shoes and Jeans

Dress shoes are designed, well, for dress or business occasions. The elegant lines and sleek contours around the foot, as well as costly and delicate leathers, are intended for elevated events. Jeans are made (mostly) of denim, a hefty woven textile originally designed for workwear in mines, factories, and mills. Historically, wearing these items not only told the world what you did for a living, but what social class you belonged to as well.

Maybe it’s the informal nature of menswear today or because they seemingly find one of the dressier items uncomfortable and try to offset it, but men try to find opportunities to mix these two. They’ll try to pair, say, sneakers and suit trousers or polished black cap-toe Oxfords and jeans. Either way, this clash of formalities leads to sartorial confusion. How do we set the record straight?

What Dress Shoes Should You Wear With Jeans?

Boiling it down to three simple tips will help you make a smart sartorial decision when finding dress shoes to pair with your denim.

Opt for More ‘Casual’ Dress Shoes

Dress Oxfords, dress loafers, dress boots-even clean, white, minimal ‘dress sneakers.’ It’s hard to keep track of them all! Of these, I’d lean toward shoes like loafers, derbies, and dress boots. A loafer, preferably a penny or horsebit one, would be the first choice. It’s low-profile enough for a proper dress shoe, but the slip-on nature makes it a little more casual.

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The derby’s open lacing system makes it more casual than the Oxford. That complements the inherently rugged nature of denim. A dress boot, however, is a stylish wild card. It mixes both formal and casual elements for a look that’s easy to dress both up and down.

Texture is Your Friend

Look closely at your blue jeans. Are they really blue? They are likely a mixture of different shades of blues, soft whites, and accent stitching ranging from pure white to bright red. A good pair of denim has character and texture-especially as you break them in. The same should go for your shoes. Nappy and soft, suede works much better to accentuate the warp and weft in denim than a polished calfskin.

Brown Over Black

Black, in general, is the most formal shoe color. Since we’ve established denim is inherently casual, it should follow that pairing black shoes and jeans is hard-and, especially, black dress shoes and jeans. So, to keep the formality in the same ballpark, look to wear brown dress shoes with your jeans most often. As with styling, though, there is a twist. Burgundy can look quite refined when paired with many kinds of denim.

What Jeans Should You Wear With Dress Shoes?

Just as we did above, let’s go over three solid ways to find a good pair of jeans for your dress shoes:

Fit is Key

As with shoes, fit matters in your jeans. Avoid form-fitting, tight, or “skinny” jeans. Boot-cut jeans should be nixed entirely- not just with dress shoes. However, a slim pair of denim with a moderate taper toward the ankle can both elongate your legs and provide smooth transition into the shoe.


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Darker Over Lighter

In general, darker denim is more formal than lighter. As we are talking dress shoes, a deeper blue jean will work better with dress shoes than a lighter wash will. However, if you happen to have a pair of tan or camel penny loafers, they can look quite nice with some lighter wash denim. As with dress shoes, though, denim has a wild card. White denim is a kind of blank slate that can offer a fresh spin- particularly when worn with suede monk straps.

Rise Above

Another way to match the formality is to try a medium front rise. This not only also elongates your frame, but enables your jeans to act like a pair of dress trousers.

The Rest of the Outfit Matters

We’ve established more ‘casual’ dress shoes like derbies and loafers are a better fit with denim, and suede shoes and brown tones keep the formalities on par. Jeans can be dressed up if you keep them slim and dark. Also, experimenting with a higher rise can help jeans act more like dressier options.

But, the rest of the outfit matters as well. A fitted, comfortable collared shirt and sports jacket with jeans can make for a great evening or travel outfit. Additionally, your socks are a great way to show off your dress shoes. We at Boardroomknit some of the finest dress socks right here in North Carolina. We take pride in each pair, and know our socks will complement any outfit.

Yours in Style,

Tony Gorga

Editorial Staff

Shop Boardroom Socks

As an enthusiast and expert in men's fashion, particularly in the nuanced art of pairing dress shoes with jeans, I can confidently navigate the complexities of this often-debated topic. My depth of knowledge stems from a genuine passion for menswear and a keen eye for sartorial details, coupled with years of personal experience in refining my own style.

Now, let's delve into the concepts discussed in the article:

Pairing Dress Shoes with Jeans: The Controversy

The article rightly acknowledges the historical context of dress shoes and jeans, emphasizing their distinct origins in formal and workwear settings, respectively. This sets the stage for understanding why combining the two can be a challenging feat, given their conflicting levels of formality.

The Problem with Dress Shoes and Jeans

The clash between the formal elegance of dress shoes and the rugged nature of denim is highlighted, emphasizing the need to decipher when and how this combination can work. The article suggests that the contemporary informality of menswear might be a driving force behind attempts to merge these two elements.

What Dress Shoes Should You Wear With Jeans?

1. Opt for More 'Casual' Dress Shoes

The article breaks down the suitable options, including dress loafers, derbies, and dress boots. Loafers, especially penny or horsebit styles, are recommended for their low-profile elegance with a touch of casualness. The open lacing system of derbies aligns well with the rugged nature of denim, while dress boots offer a versatile blend of formal and casual elements.

2. Texture is Your Friend

The importance of texture in denim is paralleled with the recommendation for suede shoes. The article advises that suede, with its nappy and soft texture, complements the character and texture of well-worn denim better than polished calfskin.

3. Brown Over Black

Considering the inherent casual nature of denim, the article suggests opting for brown dress shoes over black. Brown, being a less formal color, aligns better with the casual vibe of jeans. It also notes that burgundy can provide a refined look when paired with various denim styles.

What Jeans Should You Wear With Dress Shoes?

1. Fit is Key

Similar to the emphasis on the fit of dress shoes, the article stresses the importance of a well-fitted pair of jeans. It advises against overly tight or skinny jeans and recommends a slim fit with a moderate taper toward the ankle for a balanced and elongated look.

2. Darker Over Lighter

The formality of denim is explored, with darker jeans deemed more suitable for pairing with dress shoes. Lighter washes are considered less formal, though exceptions are made for certain shoe styles, such as tan or camel penny loafers with lighter wash denim.

3. Rise Above

To match the formality of dress shoes, the article suggests opting for jeans with a medium front rise. This not only elongates the frame but also enables jeans to emulate the sophistication of dress trousers.

The Rest of the Outfit Matters

The article concludes by emphasizing the holistic approach to men's fashion. It highlights the importance of the entire outfit, mentioning the role of a fitted collared shirt and sports jacket in elevating a jeans ensemble. Additionally, it recognizes the significance of socks as a subtle yet impactful accessory that complements dress shoes.

In summary, the article provides comprehensive guidance on navigating the intricacies of pairing dress shoes with jeans, covering shoe types, texture, color choices, jean fits, and overall outfit considerations.

How to Wear Jeans and Dress Shoes (2024)
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