How to Dress Up Denim with Dress Shoes

How to Dress Up Denim with Dress Shoes

Let’s face it: jeans are better than what they used to be. Just a generation ago—iconic denim pants we all know and love started off as workwear for miners and factory workers—denim was still seen as only appropriate in casual settings. 1 Now, having expanded its domain from grunge concerts to garden parties, denim is more versatile than ever.

With denim clothing of all stripes becoming more commonplace in upscale settings, it’s important to pair it with the appropriate footwear, and choosing the right shoes is the key to toeing the fine line between a casual and elevated look.

Even still, you may be asking yourself “can you wear dress shoes with jeans?”

The answer is a resounding yes. This will be your definitive guide to wearing jeans with dress shoes.

Stronger: The Power of Dress Shoes

The specific pairing of dress shoes with jeans is a powerful combination. Denim, having been strongly associated with “casual” for so long, lends breeziness and ease to an otherwise dressy look. When paired with tasteful dress shoes, the right pair of jeans just screams chill but chic.

Sounds simple, right?

However, there’s a little more to it than just throwing on an old pair of ripped baggy jeans and any old heels. Some styles of shoes complement some jeans more than others. For example, straight leg jeans might look better with a penny loafer shoe style while classic blue jeans might work best with a more casual shoe style. We’ll go into these nuances in-depth further down.

You’re the Best Around: Top Shoe Styles for Denim

Dress shoe styles that work well with denim fall into a few broad categories:

  • Oxford shoes – A truly classic shoe style, the oxford shoe on its own is a classy and timeless option, but still neutral enough to pair with most styles of jeans.2 Try a style like the Alfina Oxford with a skinny jean or with rolled cuffs to show off a little ankle.
  • Loafers – Another undeniable classic, loafers add polish and shine to any outfit with a special ability to level up a denim look.3 Whether you go for a classic penny loafer or a more modern platform loafer like the Uptown Loafer, this shoe style works great with a straight, blue or black jean. 
  • Boots – They’re made for walkin’, and they’re also the most obvious choice to pair with denim—for good reason. A dress boot will pair especially well with (surprise) a boot-cut style of jeans.
  • Heels – We hear your incredulity already. “Heels with jeans?” It’s not only possible, but it’s an absolutely elegant choice to heighten your outfit (in more ways than one). While they might be a more formal shoe choice, they add a touch of sophistication to both dress pants and denim jeans alike.

Higher Ground: Adding Height with Dress Shoes

Heels and jeans can easily complement one another. The look just requires you to step up your stylistic creativity. That added height—paired with the comfort of a well-fitting pair of jeans—can be one of your staples.

Heeled Boots

Choosing a heeled boot or bootie is the easiest way to get a boost while wearing denim. As a bonus, an ankle boot with a heel, worn along with blue jeans and a white cardigan or dress shirt is a beloved autumn look.

Pointed Toe Heels

Usually associated with formal occasions, a pointed toe heel, such as the Perris Slingback Heel, can take any denim piece to a more elegant place. This style of heel most complements a flared-bottom or straight-cut style of jeans.

Heeled Sandals

For a great summer choice, pair a heeled sandal, such as the Chardonnay Heeled Sandal, with skinny jeans for a universally beloved warm-weather look.

Cool for the Summer: Dress Sneakers with Denim

Emphasizing both the “cool” and “casual” in “casual-chic” is easy with a dress sneaker. Jeans and sneakers have both come a long way, starting casual and evolving into something you’d see on both the boardwalk and in the boardroom. Either way you’d prefer to spend your time, you can always choose sneakers to pump up your choice of pants.

Consider Going Laceless

A slip-on style, like the Uptown Loafer, without visible laces is the perfect mid-point between a sneaker and a loafer. The simple silhouette and ease of use make a slip-on sneaker an excellent pairing for a skinny jean. Think of it like a slightly dressed down loafer.

The Colour and the Shape: Matching Shoes and Denim

So far, we’ve outlined the types of dress shoes that take denim from a casual choice to a chic statement. All of these shoes, however, come in a variety of colors, which adds another layer of choice.

A general rule of thumb for determining the best dress shoes to wear with jeans is to keep them neutral. Dress shoe colors and tones like white, gray, black, and brown are almost always your best bet whether you’re picking an oxford or a boot. White shoes especially make a deep blue jean pop.

If you do want to add a pop of color to your footwear, then a strapped heel is a great option to consider. The reduced surface area of a strappy heeled sandal or similar shoe makes a pop of color a welcome addition to an outfit without causing any clashing. 4


Any Way You Want It: Dress Shoes for Every Occasion

Have you ever showed up to a social event and, upon arriving, thought to yourself “I’m way too overdressed for this?” You’re not alone. Pairing jeans and smart casual dress shoes correctly can make this dilemma a problem of the past.

Stepped-Up Casual

The perfect style for a picnic in the park or last minute brunch plans. Whether it’s a dressy sneaker with a plain straight cut jean or oxfords and ripped skinny jeans, a dress shoe takes a casual, comfortable weekend look and elevates it to a slightly higher level.

Casual Chic

Casual chic splits the difference between fully casual and full-blown workwear. In this category, you’d find a wide spectrum of outfits including women’s boots (with or without a heel), oxfords, or slip-on sneakers. With enough creativity, any shoe with the right jeans can result in a chic, yet casual look.

Dressed-up Denim

A well-pressed pair of straight leg jeans with a dress shoe is an elegant enough look to bring to the workplace.5 Heels, flats, and loafers are the best choices to complete this look and present a professional image.

Rolling in the Deep: Showcasing Dress Shoes with Rolled Jeans

When you’re wearing a particularly stylish dress shoe, you naturally want to show it off. Rolling and cuffing your jeans is done expressly to display your tasteful footwear. 6

You can choose between a simple single roll, a double roll, or a tightly rolled cuff, depending on the fit of your jeans. A looser or longer pant leg might need a tight roll, but skinny jeans may be well suited by a simple single fold.

The cuffed look goes especially well with a low-cut shoe like an oxford or slip-on sneaker, or anything that shows a little ankle already. The cuffed jean leg emphasizes that little pop of skin.

Kinds of Blue: Dress Shoes for Skinny, Straight, and Bootcut Jeans

Not all jeans are created equal. Whether the year’s fashion trends favor skinny jeans or mom jeans, there’s a compatible shoe style out there.

Skinny Jeans

The slim fit of this trendy pair of pants is well-served by an oxford shoe, a flat, or a heel—the idea is to emphasize the snug fit at the lower shin by showing a bit of ankle.

Straight Jeans

A straight jean’s more relaxed fit makes it the prime candidate for cuffing. This style looks lovely with a chunky loafer, or even a dress sneaker such as the Galia Sneaker.

Bootcut Jeans

Bootcut jeans live up to their namesake by looking great with—you guessed it— boots . While boots are versatile and could theoretically go with any style of jeans, bootcut jeans are made expressly for this pairing.

Mom Jeans & Boyfriend Jeans

Some argue these are the jeans of the future. Some of the hottest, trendiest threads out there right now, these loose-fitting yet flattering jeans also pair well with dress sneakers or low-cut boots.


The dark horse of the denim world. Wearing overalls brings you back to the rustic roots of the world-famous indigo-dyed cotton-based fabric. Overalls most obviously pair well with boots, but a laced dress sneaker look with overalls is currently “in vogue.”

Dress Up Your Denim with Vionic

The 2020s are shaping up to be a denim decade. This one fabric is ubiquitous enough to wardrobe both social Saturday nights and meetings on Monday mornings. This means that accessorizing denim is one of the most important fashion skills of the current age.

At Vionic, we provide a selection of dress shoes, dress sneakers, and boots wide enough to provide a foundation for any outfit, denim or otherwise. Shop for oxfords, loafers, slip-on sneakers, women’s heels, and anything else you need to make your jeans outfit pop. Many of our shoes are podiatrist-approved, carrying the American Podiatric Medical Association Seal of Acceptance.

Use these tips when you’re browsing the dozens of stylish dress sneakers, loafers, heels, boots, and more that Vionic offers to make sure your favorite pair of jeans never have to stand alone.




  1. “Jeans: The History of Everyone’s.” Thirteen.
  2. “How to Wear Oxford Shoes.” Her Style Code. Updated 10 April, 2023.
  3. Eggenberger, Maxine. “Jeans and Loafers.” Who What Wear. 23 April, 2023.
  4. “Shoes to Wear with Jeans.” Shoe Tease.
  5. Segran, Elizabeth. “Wear Jeans to Work in 2023.” Fast Company. 3 January, 2023 .
  6. “How to Cuff Jeans.” Master Class. Updated 10 February, 2022.

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