How to Wear Dress Shoes With Jeans (And Look Great While Doing So)

This pairing looks great when done right.

I’m a big fan of wearing dress shoes with jeans. Maybe it’s a UK thing. Plenty of bars and clubs don’t let you in if you’re wearing sneakers, which means generations of men get used to wearing leather shoes with their jeans for nights out.

Having said that, there are ways of doing it that work better than others. Boots and dress shoes with casual details are more likely to work. While you’ll struggle to get away with a pair of black patent oxfords.

Can You Wear Dress Shoes With Jeans?

Simple answer, absolutely. In many cases, dress shoes look great with shoes. The complex answer is that it depends on what you mean by a dress shoe and the type of dress shoe you have in mind, not to mention the kind of jeans you want to pair them with.

Here is a deeper look at some of the subtleties of this complex fashion dilemma.

How to Wear Dress Shoes With Jeans: Six Easy to Follow Tips

Choose Your Dress Shoes Carefully

Black Sweater gray blazer jeans
The Brdwlk

Dress shoes can mean anything from highly-polished black oxfords to tan brogues or tasseled loafers. You can even include Chelsea boots and chukka boots in the definition. This means you have a ton of choices to go with. Personally, I’d avoid wearing jeans with dress shoes that sit at the most formal end of the spectrum. But loafers, brogues, and chukka boots will fit into your outfit seamlessly.

The Color of Your Dress Shoe Matters

Black jeans black shoes
The Brdwlk

Mid-brown dress shoes are the easiest to dress down and they go great with blue jeans. While black shoes work best with black or dark gray jeans. High-shine or patent shoes should be avoided in most cases.

Choose Your Jeans Color Carefully

Tan brogues jeans
Brodie Viessers

When paring jeans with dress shoes, go for jeans at the smarter end of the spectrum. Black jeans are the safest bet but dark shades of blue work well too. Try to avoid aggressive fading or rips, although it can work if you really lean into it. It can also work if your dress shoes are intentionally casual. For example, it’s common for people to wear suede Chelsea boots with faded jeans.

Choose Your Jeans Fit Carefully

Brown shoes brown socks black pants

The fit of your jeans also plays a big part in whether your outfit will work. Basically, you’re aiming to avoid the material bunching up on top of the shoes. Skinny jeans or slim jeans work best in my opinion as the tighter fit means there’s less material to bunch up. Straight jeans can work as long as they are cropped at the ankle. If your jeans are too long, you can always turn them up to get the fit right.

Read next: Check out all my favorite skinny jeans

Match Your Outfit

Outfits that pair dress shoes with jeans typically run from smart casual to semi-formal. This means you have plenty of options for what to wear. Smart sweaters, shirts, blazers, and jackets can all work well depending on the type of jeans and shoes you choose. The key is to match the outfit to the jeans and shoes. If your shoes are at the more formal end of the spectrum, the rest of your outfit will have to match.

Chunkier Shoes Work Well

Skinny Jeans Smart Shoes
Photo by Zahir Namane on Unsplash

Chunkier dress shoes work well with the rugged look that jeans bring. Go for a pair of shoes with a thick sole and a wide toe box rather than a pair of pointy shoes. That’s because the thinner shoes risk being overwhelmed by the rest of your outfit. You could even go for a pair with an oversized sole for a modern look.

Socks or No Socks?

Black jeans, dress shoes, no socks

Traditionalists won’t like it, but not wearing socks with dress shoes and jeans can look good. The key is to do it intentionally: wear slim-fitting cropped jeans that show part of your ankle. And while we’re talking about socks, you can also experiment with different colors and patterns to add a little extra to your outfit.

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Duncan Elder

Duncan is the founder and editor-in-chief of The Boardwalk. He's a menswear writer who has spent the last 15 years developing his own sense of style, which lies at the cross-section of mid-noughties indie and Uniqlo-inspired minimalism.

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