How to Wear Dress Shoes with Jeans and Still Look Stylish

By Jack Prenter / November 26, 2017
Leather Shoes with Denim

Finding the balance between smart and casual can be difficult, especially when your day might consist of an office job, a visit to a bar and eventually perhaps even a nightclub. Mixing dress shoes with jeans is a great way to turn an otherwise casual outfit into one that you can wear in a variety of circumstances.

Choosing the Right Jeans

The most important variable in making this outfit work is picking a pair of jeans that are going to go well with a pair of dress shoes that are inherently smarter than your jeans. The key is to avoid jeans that are overly casual.

Dress shoes are one of the most formal types of footwear and therefore you need to avoid matching them with jeans that are too casual. This mismatch generally looks odd and out of place, rather than planned and effectively mixed.

Indigo Men's Jeans

Jeans from Boohoo

The most formal jeans are going to have a tailored fit, not overly slim but certainly not baggy. They should be cut in the same way as you would with a pair of suit pants, well-fitting along the thigh and tailored down to the ankle but not tight.

Slim jeans can be worn, but this is going to give a more modern look that is generally only going to work with less formal dress shoes like loafers. On the other hand, skinny jeans are too tight and therefore casual to work with any style of dress shoe.

Color is also tremendously important, certain washes feel more professional than others. Indigo and perhaps even black jeans are the most formal and work best with dress shoes, whereas blue and light wash jeans look too casual when next to leather dress shoes.

It should go without saying that distressed and ripped jeans should never be worn with dress shoes, this was more common in the early 2000’s and it looked out of place. If you’re going to match a traditionally casual garment with smart shoes, you want to try and minimize the difference in formality between them as much as possible.

Choosing the Right Dress Shoes

Just as it’s important to pick the right jeans, you also need to choose a pair of dress shoes that are going to look right with a casual denim. Fortunately, you have some flexibility.

The most common dress shoes that you will see matched to jeans are brown leathers, usually brogues or capped shoes. Brown is significantly more casual than black and that means that they usually go better with jeans.

But that’s not to say that you can’t wear black dress shoes with jeans, you just need to do so only with the most formal, dark, tailored jeans that you own. On the other hand, because brown leather is more casual they look great with a much wider range of jeans.

Brogues are a simple choice, but you might also consider monk straps or loafers, both of which give a more relaxed feel to your outfit, perfect for informal events and parties.

Matching Shoes and Jeans

When you’re trying to match shoes with jeans you should start from the item that you already own and don’t want to replace. If you love your jeans then you should try and find a pair of shoes that match them and vice versa.

Jeans too baggy for shoes

Credit: Pinterest

The key to an appropriate match is primarily in the level of formality, ideally both the shoes and the jeans should be similarly formal so as to prevent them clashing. You can see in the photo above that a light blue wash jean looks out of place compared to the smart black shoes, the tailoring is also poor and that only accentuates the difference in formality making for an odd look.

On the other hand, the images below show a much closer match, with jeans that align better with the formality of the shoes that they are worn with. This makes the whole outfit look purposeful and stylish.

Monk Straps with Jeans

The Monk Strap has seen increasing popularity in the last couple years thanks to more publicity from celebrities and style experts. These shoes strike a great balance between work and play, generally being cut slim and modern, they are the perfect dress shoe for matching with denim.

Wearing brown leather monkstraps with dark blue jeans

Credit: Pinterest

With such noticeable straps you should opt for a shoe that isn’t overly detailed, this will help to prevent the shoe from clashing too much with jeans which are relatively plain. Similarly, because of their stylish and modern cut you should choose a pair of jeans that are well tailored and slim at the ankle.

Chunky jeans that flow over the top of your shoes and gather at the ankle are going to clash with just a sleek style of footwear. You’ll also notice that by wearing a denim with a tighter ankle you can show off more of the straps, a key feature that makes this footwear so beautiful.

A tailored or slim fit is ideal for Monk Strap shoes but the color of denim is going to depend on the color of the shoes. If you opt for black, the only color that can match that formality is a deep indigo. On the other hand, brown shoes open up a little more flexibility and you could opt for a blue wash instead. However, darker washes are generally going to look best with all styles of formal dress shoes.

Brogues with Jeans

Brogues, one of the most formal styles of footwear and an all-time classic that is unlikely to ever go out of fashion. Brogues are all about the detailing, they usually have elaborate patterns along the length of the shoe and the last thing that you want to do is to cover that up with an oversized jean.

However, that doesn’t mean that you need to opt for a slim or skinny jean. In fact, because of the formality of brogues it’s often best to stick to a straight leg denim that has a good sized cuff which you can roll up. Doing this will reveal the lighter inside of the denim, creating a nice color transition between the brogue and the jean. It also allows the cuff to sit on-top of the shoe, accentuating the details on the footwear.

Although you can certainly find brogues in black, they are most commonly available in tan and mahogany shades. These brown colors add a little informality to them, making them a great choice for pairing with denim. Brogues are going to look best with darker shades of denim, indigos, dark navy washes and even black or charcoal.

Loafers with Jeans

Once the weather starts to warm up it might not be appropriate to wear heavier footwear like brogues or monk straps, this is when loafers are ideal. They are still relatively formal, but they can be worn without socks and this can help to keep your feet cool during the summer.

Dark brown loafers with pin-rolled jeans

Stefano Tinti / Shutterstock.com

Loafers are traditionally made out of either leather or suede, for the sake of this article we are looking at dress shoes and therefore we will only be consider leather loafers. Suede is incredibly casual and would be better suited to light wash jeans, but they aren’t really ‘dress shoes’.

The most common way to combine jeans and leather loafers is to go without socks and then leave a noticeable gap between your footwear and the denim. The reason for this is because loafers are cut low and having your jeans gather around them can look sloppy, unlike how it would look with brogues.

Instead, the cut lends itself to a European look, no socks and turned-up jeans to leave some skin on-show.

With this in mind, you can wear a tremendous range of jean colors, everything from light blue washes through to indigo and even black. This look is informal and that gives you more flexibility with the type of jeans.

However, distressed and ripped jeans and likely to still look out of place next to leather shoes. Look for well tailored jeans that are comfortable through the thigh but slim past the knee towards the ankle. This cut of jean prevents any bunching around the ankle and makes turning-up the ends of your jeans easier and cleaner.

Select the Rest of Your Outfit Appropriately

Now that you’ve picked out a matching pair of dress shoes and jeans it’s important that you ensure that the rest of your outfit matches your bottom half. Some of the more common mistakes that men make are with the formality of their shirts, jackets and the socks that they wear.

If you’re going to wear socks, which most men should do unless they are wearing loafers, you need to pick a pair that are going to match your jeans and the formality of your footwear. White tube socks aren’t the right answer, despite how frequently guys seem to wear them with dress shoes.

Instead, you can simplify the problem by choosing socks that are the same color as your jeans and just one shade darker. For example, if you wear indigo jeans you could opt for a very dark navy or a black. With blue jeans you might opt for navy or dark blue socks. Wearing darker socks helps to make your jeans ‘pop’ and simultaneously hides your socks by making them less obvious.

When it comes to your upper body you need to be careful, you want to pick a shirt that looks good next to jeans but that doesn’t conflict with the formality of your shoes. Generally, t-shirts aren’t going to work, they are too informal and while they look good with jeans they are going to be out of place with leather dress shoes.

Instead, a less informal choice could be a long-sleeved henley shirt. Again, the shirt that you pick will depend on your footwear, for some a henley might be far too informal to wear with brogues, but it might look appropriate with leather loafers.

If in doubt, a great option is the Oxford shirt, a thicker material that doesn’t have the same sheen look that most dress shirts do. Most of them will also have button-down collars which are more casual than dress shirts and also a breast pocket. Oxford Cloth Button-Down shirts or OCBD for short, should be a staple in every mans wardrobe, they are tremendously versatile as well as being comfortable and warm during the evening.

Presumably your jeans will be in a shade of blue or indigo, which makes a white shirt an obvious choice. But that’s not to say that other colors can’t work, navy and even pale blue shirts can look handsome, especially if you’re going for an office casual look.

To finish off the outfit you should opt for a second top layer, either a blazer or a coat, which serves a functional purpose of keeping you warm but also makes the outfit more interesting. Black trench coats are always a great look, as is a thick grey peacoat, but the best choice might just be a well tailored blazer in a solid color like navy or beige.

Each of these three options strikes a good balance between formality and fun, giving you the ability to take the layer off or put it back on depending on your environment.

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