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How to Wear Dress Shoes With Jeans: 12 Rules for Men

It’s easy to think that as a professional man it’s easy to dress, but when you get into it, there are a lot of things to consider. One such consideration is wearing dress shoes with jeans. It sounds like a strange combination, but if you follow our advice, you can pull it off like a champ!

Dress Shoe with Jeans

Threading this particular needle and keeping all the moving parts working in tandem to achieve a look of casual elegance doesn’t require much, but if you go out there without a plan, then you’re going to be found wanting by women, business partners, fashion mavens, and those who know how to put together a snappy ensemble. When you’re ready for the ultimate in business casual, all you need is this guide to wearing a pair of dress shoes with jeans.

1. Always Wear Socks

Always Wear Socks With Formal Shoes

First off, a lot of guys try to go completely sockless when they go for this look and it is a failure each time. You’re not wearing a pair of boat shoes. You’re trying to enhance your casual look to include more style, not less. Wearing no socks, or no-show socks says one thing: I put on whatever shoes happened to be closest. It speaks of sloth and laziness which negates the look entirely.

2. Rule of Socks: No Black, No White

Gleaming white socks are little better than going sockless, as they declare in sterling ivory splendor: I just grabbed whatever was at the top of my drawer! This isn’t a pick-up basketball game, so leave the white tube or crew socks out of the rotation.

Pure black socks go too far in the other direction. They claim you wanted to dress nicely, but your slacks were in the laundry, so you went with jeans. Black is too formal, while white is too casual.

The answer here is to go with a pattern. Frankly, bright neon pink is better than choosing white or black, because it says you had to make a choice to put those on. Go splashy, have fun, be ridiculous, just don’t make it look like you went with the basic options.

3. Get the Right Jean Cut

Blue Denim Jeans with Proper Shoes

A set of smart shoes doesn’t work with just any cut of jeans. If you go with a relaxed or loose-cut pair of jeans, they’re going to be too blousy. Dress shoes make your feet appear smaller, which means you need to mitigate how much fabric spills out over them. Get a pair of slim-fitting or regular-fit jeans. You want them to be close at the waist and hips with minimal puffing down the legs.

Boot-cut jeans aren’t great, but if you’re going with a higher dress boot, you might be able to pull it off. Use with caution.

4. Jean Color Requirements

Darker is almost always better when you’re looking to pair dress shoes with jeans. Indigo tends to be ideal, with navy and black going neck and neck for a spot in second place. Since such shoes tend to be darker, the lighter your jeans are, the more your footwear looks out of place.

5. Make Your Shoes Contrast

Wearing Jeans With Brown Shoes

You never want to be wearing a pair of black jeans with black shoes, because it then looks like you’re trying to match them. A minimal amount of contrast is necessary to land this look. Camel shoes or a rich brown go with almost any jeans, particularly those in the lighter set. Since you should be going dark with your jeans, black shoes can be questionable. Just make sure they aren’t too close in color to the bottom of your jeans and you’ll walk out a winner.

Check out our complete guide to matching clothes.

6. Jeans to Avoid

Dirty Jeans With Good Shoes

Do not even try to pull off the distressed jeans look, those with holes, or battered gear you just wore to the dog park. As with socks, the worse your jeans look, the more it seems like your shoes were an afterthought, not an intentional maneuver.

Here’s a visual guide to 40 types of jeans to help you out.

7. Don the Proper Shirt

From the soles of your feet to your waist, you’ve gone to the trouble of telling two different tales. The shirt is what is going to help tie these together. A hoodie, a tee-shirt, or a jersey sides with the jeans and will drag you into the purely casual tier. A polo is the least you can do, with a dress shirt highly preferred. Untuck it if you want to prove you’re off the clock.

Related Reading: Best Men’s Dress Shirts

8. Consider a Jacket

Wearing Jeans with a Jacket

Generally speaking, a jacket is the ultimate way to top off the formal shoes and jeans attire choice. Wearing a sport coat with jeans proves you’re paying attention to what you wear, and if it blends with your shirt and shoes, then you’ve just managed to combine all the disparate aspects, just like a man of style should. Have a scotch, winner.

9. Simplify Your Accessories

The jeans say you’re not trying too hard, and your accessories should tell the same story. As using a sweatshirt pushes you too deep into casual territory, throwing on cufflinks, a pocket square, a tie with clip, a vest, and a hat can suddenly drag you too far into the boardroom world, making the jeans look like a mistake. You should have a belt that matches your shoes, and hats are rarely a mistake with this look. Pocket squares should be kept to the barest minimum if used at all. Ties should be casual, usually woven with a square base, or left off entirely.

This is highly dependent on the person, so play around with different bits and bobs until you’re sure you’ve found the right balance of smooth and playful.

10. Buy for Your Build

Dress for Your Size

As stated above, dress shoes are going to make your feet seem smaller, which can kill this whole guise for bigger chaps. Slimming down the jeans helps, but you might also need to bulk up the shoes as best you can. Consider going a size larger if necessary so as to avoid looking like you have mincing little feet being hidden by jeans. Cuffing your jeans can help with this, should you have the length to do so. Consult a tailor if all else fails.

11. Reduce the Shine

Whatever else you do, avoid having shoes that sparkle like they’ve been spit-shined and polished while your drill instructor stands over you. When you combine dress shoes with jeans, you’re aiming at semi-casual, so don’t turn your feet into a high-powered luncheon while your legs are looking for a stool at the pub. They need to flow together to create a complete look. The more your shoes and jeans seem to be at odds, the more you look like a tacky sot.

12. Choose Your Shoes Wisely

Formal Shoes

In addition to knowing the right color combination of jeans and shoes, getting your style right is half the battle. Oxford shoes are mostly overkill, as are wingtips. Loafers can be perfect with the right set of smashing, patterned socks, and monk straps are absolute killers that tend to also look bulky. Brogues and derbies can make the grade, particularly if you wear them with a cuff. A matte finish is generally the way to go, or a brushed rather than truly shiny polish that glows instead of sparkles.

Recommended Dress Shoes to Pair with Jeans

So now that you know what to do, how will you execute your sartorial plan? Will you dig those old formal shoes you bought for a funeral out of the closet, hoping to hop into a fly business casual? Or will you put your money where your mouth is, and invest in a proper pair of modern shoes?

The choice is ultimately yours, but keep in mind that comparison shopping can suck. That’s why we’ve done some of the legwork for you, with these three outstanding men’s formalshoes:

Velasca – Spazzacamin

Velasca - Spazzacamin

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The Spazzacamin classic black leather shoes by Velasca are a fantastic pairing with jeans. Velasca combined design elements of brogues and Derbys to create their Spazzacamin shoe.

An ideal shoe for both formal or casual ensembles, the full-grain leather Spazzacamin has a durable Vibram rubber sole. If you’re only to have one smart shoe in your collection, then you can’t go wrong with a classic black leather pair. Velasca also created the Spazzacamin in smooth calf leather and suede calf leather for alternative looks. 

The low-cut design will sit stylishly under jeans or formal pant legs. 

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MYRQVIST – Smogen Black Calf

MYRQVIST - Smogen Black Calf Loafers

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Laces aren’t for everyone, and if you’re looking for a more streamlined shoe, a penny loafer will be just it. 

MYRQVIST designed their Smogen apron fronted penny loafers in four classic colors to suit all trouser patterns and styles. You can dress their simple yet incredibly smart design up or down to compliment any occasion.

The company crafted the shoes from full-grain calf leather and finished the heel caps with leather board. They wanted their shoes to be durable and comfortable, lasting their wearers for years to come.

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Lennertson – The Brawler in Brown

Lennertson - The Brawler Brow Dress Shoes

On the hunt for a full coverage yet straightforward dress shoe? Well, the Lennertson The Brawler in Brown’s could be the ones for you. 

Lennertson designed The Brawler with a minimal pattern, so your eyes are drawn to the shoe’s distinctive shape. The medium to dark brown leather has a slightly red undertone that makes the shoes look rugged. An excellent match for formal or casual events. 

The company uses high-quality European leather to create shoes that are built to last. Lennertson included a cork footbed that molds to your specific shoe shape for ultimate comfort over time. Also available in black, The Brawlers are a classic shoe that’ll never go out of style.

Conclusion

Now that you’ve got the basics covered, it’s up to you to assemble a style that is uniquely you. Knowing the rules gives you leeway to break them–so long as it’s purposeful and you put the appropriate amount of thought into your outfit.

Do you have any other insights on how to wear dress shoes with jeans that we might include in a future update? Drop us a comment below!

2 comments
  1. Thank you for writing this article. Many men are attempting the dress shoe and no sock look and it looks silly every time. A high water skinny suit, dress shoes, and no socks is the ultimate fail. Thanks again and I’ll be sure to share with every male that I know.