by Editorial Staff April 18, 2022

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.

compilation of men wearing jeans with derby dress shoes


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.


wear tapered jeans with dress shoes


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 Boardroom knit 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



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Editorial Staff
Editorial Staff

Our editorial staff is comprised of menswear experts dedicated to providing you with helpful information. Sharing everything from style tips to sock care instructions, these gentlemen are a wealth of knowledge for both our customers and the Boardroom Socks team.



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