How to Wear Dress Shoes With Jeans the Right Way

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by  Karlton Miko Tyack | Last Updated: 
how to wear dress shoes with jeans - mens jeans & monk strap shoes

There’s nothing like pulling off a good high-low combination when you’re putting an outfit together.

I think that’s why it feels so good to wear sneakers with a suit. Well, that and the whole comfort factor.

It’s admittedly more confusing to navigate the reverse of this, though. I’m talking about wearing dress shoes with a casual outfit—specifically, with jeans.

If you can pull it off, though, you can really level up some casual combos. Here’s how to do it.

How to Wear Dress Shoes With Jeans: Style Rules to Remember

1. Black Dress Shoes Are Tricky (but Not Impossible) to Pull Off With Jeans

Black dress shoes are the most formal dress shoes. So, they’re inherently difficult to pull off with jeans. My advice? Unless you’re a young, trendy TikTok influencer, avoid pairing black dress shoes with oversized blue jeans (more on this later).

You can, however, wear black leather dress shoes with dark, straight-fit jeans. The more the jeans look like chinos, the better. Charcoal and black selvedge denim are ideal since they naturally look less casual than blue jeans. The lighter the wash, the less aligned with the shoe’s aesthetic.

If you can add another piece of formality to the outfit to bring balance, say a blazer or a dress shirt, even better. Basically, you can temper the mismatch of the shoe style and pant style using colors and silhouette.

Context matters too. So, if you go for a more casual dress shoe, especially one with hardware, it can visually register as boot-like. A square-toe triple monk strap, for example, has enough hardware on it that it wouldn’t look out of place with blue jeans (though you might want to top the outfit off with a tonal leather jacket).

Which brings me to my next point.

2. Dress Shoe Style Matters Just As Much As Color

Not all dress shoes are highly formal. The more detail there is on the shoe, the more casual it is, and the easier it is to wear with jeans.

Hardware not only adds detail to the shoe’s upper, but it’s also reminiscent of workwear. That’s why a monk strap is easier to wear with jeans than a plain-toe oxford the more buckles the better. The same goes for horsebit loafers.

Other dress shoes with extra detail and topography include brogues and derbies.

On the other end of the spectrum, the cleaner and more minimal the upper, the dressier it looks. Wholecut oxfords and opera pumps are some of the most formal dress shoes you can wear. Other features that make a shoe look dressy include a thin, tapered silhouette and a pointed toe.

And, of course, black is more formal than brown.

So, a brown square-toe monk strap, a suede cognac horsebit loafer, or a highly-brogued chestnut derby would all pair appropriately with blue jeans. A black opera pump or a pointy Italian loafer? Not so much.

Penny loafers are pretty universal. Most brown penny loafers can go with most well-fitted jeans.

3. The Style and Fit of Your Jeans Is Crucial

No matter how you style it, there are just some denim pant silhouettes that simply won’t work with dress shoes. Here’s a quick list of do’s and don’ts.

Wear these jean styles with dress shoes:

  • Straight leg, a consistent width from the hip to the ankle.
  • Slim straight. It’s roomier in the thigh and gradually narrows towards the ankle. This is arguably the best choice because it has a similar silhouette to a dress pant.
  • Slim fit is a middle-ground between straight leg and skinny.

These jean fits do not work with dress shoes:

  • Boot cut. This fit is tighter in the thighs then flares out slightly to make room for boots. Dress shoes would look far too delicate paired with this.
  • Relaxed, a roomier version of the straight leg. It’s basically just too casual to wear with dress shoes.
  • Oversized or baggy. The only context I could see this working in is if it were some subversive high-fashion thing.

There are two jean fits that I’d call conditional:

  1. Tapered. Tapered jeans are a bit like slim straights. They’re roomier in the thigh and narrow towards the ankle, but are much more dramatic. If the contrast between the thigh area and the ankle area is major, you’ll just look like you’re wearing cinched-hem joggers or MC Hammer pants. If that’s the case, avoid pairing it with dress shoes.

    If the taper is more gradual, similar to that of a slim straight, you can consider dress shoes.
  2. Skinny jeans are just really tight, close-to-body denim pants. There’s no rule that says you can’t pair them with dress shoes since trousers can be skinny too, but it’s definitely a look.

4. Darker Jeans Pair Better with Dress Shoes, Generally

I already mentioned that the best jeans to wear with black dress shoes are black or charcoal ones. This goes for any color dress shoe, really.

And even if you’re going for brown shoes that partner well with blue jeans, the darker the wash, the better. I’d say that the lightest you can safely go with blue jeans is a medium wash, which is the standard blue tone.

Ironically, you can wear dress shoes with white jeans because they’re so visually close to chinos. This is definitely a summer look, though.

5. It’s All About The Correct Proportions

And, of course, you always have to think about your proportions and how your body carries the different shoe shapes and jean fits. It’s particularly important when you’re doing something relatively unconventional, like pairing dress shoes with casual pants.

For thinner-fitting jeans, go for narrower shoes. Let’s say you do want to wear skinny jeans with dress shoes. Don’t go for a clunky square-toe brogue. A highly-tapered oxford would be more flattering. 

Be careful with this dynamic if you have really thin legs and large feet too. It can result in a clown shoe effect. A cap-toe oxford or a slightly slim penny loafer might be a better choice.

Similarly, if you have big, strong legs, then you’ll probably go for the straight cut. Don’t wear this with a highly-tapered dress shoe. Instead, go for some brogues or a round-toe monk strap.

Outfit Ideas for Styling Dress Shoes and Jeans

Outfit 1 – Black and Blue

By going for a darker blue jean in a slim fit, their base outfits invoke the natural relationship between black and navy in the formal dress realm. The turtleneck further cinches the dressiness.

Then, the gent on the left leans harder into the casual side by finishing his outfit off with a leather jacket that matches his shoes. Meanwhile, the gent on the right goes for a black suit jacket, leaning harder into the formal components of their base outfit.

Outfit 2- Smart Casual

This outfit takes a full suit and makes it smart casual by replacing the trousers with jeans. This works for two reasons. 

First, the jeans are a darker wash, giving the combination a broken suit vibe. Second, he goes for sockless monk strap shoes, the hardware of which matches the workwear vibes of the denim.

Outfit 3- Textures and Tassels

What’s great about this outfit is how he incorporates patterns and textures into an otherwise classy silhouette. The check vest is a statement piece but one that’s relatively understated since it falls into the entire combination’s color palette.

This texturing makes the tassel loafers fit organically into the mix, which he spotlights by cuffing his jeans and wearing tonal socks.

Outfit 4- Elevated Casual

This clever lad goes hard with the denim on denim but creates a visual separation between his jacket and his pants by choosing subtly contrasting colors. In fact, his pants are closer in tone to his black oxfords, which makes that combination more natural. 

And how is he pulling off these relaxed fit jeans? Well, the dark wash is part of it, but the high hems make them look neater, with cleaner lines.

Outfit 5- Effortlessly Balanced

This outfit is so well coordinated, and yet it could’ve taken him all but ten seconds to put together. He’s basically just in a t-shirt and jeans, which his tonal loafers would’ve looked fine with alone. But by throwing on that unbuttoned double-breasted blazer, he brings a perfect balance to the look.

Mastering the Dress Shoe & Jeans Combination

Again, pairing suit trousers with sneakers is so much easier than trying to wear dress shoes with jeans.

That being the case, if you can master just one or two of these rules, you’d be on your way to having an arsenal of high-low combinations in your back pocket.

I think the most important thing to remember is to go for darker jeans with cleaner fits, and to go for less formal dress shoes with more details.

From there, everything else will fall into place with practice.

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