How To Pair Dress Shoes With Jeans (2024)

While dress shoes and jeans are on opposite sides of the formality scale, they can actually be paired together in a number of different varieties of stylish outfits–so long as a few key criteria are kept in mind. Here’s our guide to wearing them well!

You may be unsure of how to properly style yourself when wearing dress shoes and jeans, but it is more than possible to pull off wearing them together while maintaining some personality and a sense of professionalism. However, simply choosing any dress shoes with any jeans you might happen to have in your closet won’t work. There are a few key things to look out for to make sure that your end result looks clean-cut and effortless.

Jeans: Choose The Right Style, Fit & Color

Correct Style

The style of the jeans that we’re going to be looking for are clean-cut, timeless, preferably in a dark wash. A few dress shoes to consider wearing with these jeans would be derbies, monk straps, loafers, or even brogues. Desert boots or chukka boots could also be considered for more casual occasions.

Correct Fit

First and foremost, the jeans should properly fit the wearer’s body type. Learn what jeans flatter you best by checking our guide here.

Correct Color

The goal is to make sure that the colors of the shoes and jeans that you choose don’t detract from the rest of your outfit. We really want to make sure that the color of both the dress shoes and the jeans will complement one another so it’s very important to select a very versatile color of the shoe and very neutral or dark color in your jeans.

Style, Fit & Color Mistakes for Denim & Dress Shoes

Inconsistent Style

Regarding style, the incorrect way to go about doing this would be to wear jeans that are inconsistent with the style of your shoes. For example, wearing jeans in a modern style but dress shoes that happen to look much more classic. This causes an onlooker to believe that some elements of your outfit might have been an afterthought, as the styles do not complement one another.

You really want to avoid jeans that are distressed and highly embellished. Jeans that have overtly large pockets or even pocket details. Also, try to avoid jeans that have very large pronounced contrast stitching. It might seem obvious but we also really want to avoid wearing patent leather evening dress shoes or even some kind of a hybrid shoe. These are pretty popular right now but this will detract from the rest of the outfit.

Incorrect Fit

It’s important to avoid ill-fitting and flattering jeans that are either too loose or far too tight. Wearing jeans that are too short or far too long is also incorrect. You should also avoid jeans that are going to sit too low on your waistline. This will become an issue when you start tucking in your shirt and wearing a belt. If you’re not wearing a sport coat or a sweater to cover your waistline, you might notice that your untucked shirt might become exposed rather quickly.

Incorrect Color

Try to avoid jeans and non-neutral colors with a lot of fading or whiskering over the thigh and/or seat area. It’s very important to stay consistent with the general style of your outfit. If you don’t, certain elements of your outfit will stand out for all the wrong reasons. We want to make sure that you remain as the focus. The clothing is here to compliment you, not absorb all the attention.

Common Misconceptions of the Dress Shirt & Jeans Combination

Myth #1: Dress shoes work with and elevate any jeans.

Wearing any style of jeans in and outfit and just elevate its style with a pair of dress shoes would not work. In fact, this is not accurate. Just because a pair of shoes is listed as dress shoes doesn’t indicate that they should be worn with that particular outfit and in the same way, not all jeans will work for all situations, personalities, or body types.

Do your best to stay away from boot cut jeans and instead, look for a pair that is as tapered as your body type will allow. The lack of excess fabric found in your jeans will in fact give your outfit a very clean finish unless however, you are a very muscular man with larger legs in which case you may need to look for a more regular fit.

Myth #2: You should wear short and narrow jeans (like a hipster) to look stylish.

As mentioned earlier, a slim fit is ideal but in fact, you should only wear things as slim as your body type will allow. Don’t follow trends, but pay attention to what is really flattering for your physique.

Myth #3: Shoes that look like dress shoes will always work.

Actually, it’s very important that you invest in as good of a pair of dress shoes as you can afford as opposed to getting faux leather or plastic looking shoes that might be coming from a fast-fashion brand. A majority of your outfit with jeans may lean more casual, so wearing good quality leather shoes will help raise the standard of your entire outfit.

Outfit Ideas for Dress Shoes & Jeans

1. Sport Coat and Dress Shirt

This is one of the most popular combinations men wear. If you have proper fitting sport coat options at your disposal, this outfit will be fairly simple to put together. The key here is to make sure that the color selection is accurate and that the patterns, whether that be found in your shirt your pocket square, or your jacket are complementing one another and not competing.

2. Turtleneck and Sport Coat

This outfit is also fairly simple to pull off but is best suited for a colder season. If you currently don’t own any turtlenecks, I would recommend that you start looking for some in neutral colors in either merino wool or a cashmere blend. Try to find some that are also not too bulky because it’s important to maintain some sense of freedom of movement underneath your sport coat.

3. Sweater and Dress Shirt

The dark wash jeans you’re wearing are going to pair nicely with a variety of different sweater colors. The simplest way to pull off this outfit is to start out with solid colored sweaters. This is going to look great over both pattern or solid colored shirts. Try to steer clear of sweaters that are too bulky. If you don’t plan on wearing a sport coat with this outfit, try looking for a shawl-collared sweater as well.

Bonus Tips

Here a few extra tips to make sure that your experience wearing jeans with your dress shoes goes off without a hitch.

1. Don’t Go Sockless

The noses of the entire world will thank you, but seriously, without the ability to breathe your feet will begin to smell and sweat and can possibly ruin the interior of your shoes. It’s not a good thing. At the very least, throw on a pair of no-show socks and keep your sweaty feet at bay.

2. Don’t Wear A Solid Black or White Socks

The white socks will look quite distracting and almost as though they are missing their sneaker counterparts while wearing black socks might look too formal or dressy with this outfit with jeans. Instead, start by looking for a unique color and or pattern to add some life to your ankles. For some great sock options, check out the Fort Belvedere shop here.

3. Try To Add Some Contrast

It’s important to remember that a little contrast can actually go a long way. With your dress shoes, it’s best to opt for a shade of brown as that’s going to offer you the most versatility. When it comes to other shoe colors, you can consider blue, gray, and many others but a shade of brown will offer you the most options.

4. Accessorize Your Outfit

To add more personality into your dress shoes and jeans outfit combination, you can always add a classic watch, a signet ring, a pocket square, or even a signature scent.

Conclusion

Even though many believe they don’t dit well together, you can absolutely wear dress shoes with your jeans. However, there are some things to avoid to make sure that your entire outfit looks effortless and timeless. Also, remember that not all dress shoes are going to look good with all jeans. The dress shoes should complement and not compete with the rest of your outfit.

Would you wear dress shoes and jeans in a single outfit? Is it a stylish pairing overall? Let us know your thoughts in the comments section!

Outfit Rundown

I’m wearing a tan and white plaid sport coat along with a burgundy sweater over a white dress shirt and then I’m pairing that with a really unique burgundy paisley print pocket square from Fort Belvedere. I’m pairing that against a dark wash indigo slim fit denim and some suede leather dress shoes. I’m also wearing a navy blue and burgundy shadow stripe Fort Belvedere pair of socks as well to finish off the entire look and to tie in nicely with the Fort Belvedere pocket square and my burgundy sweater. I could wear this entire outfit with a pair of dark brown, suede chukka boots as well.