Are Dress Sneakers for Men Timeless, or Just a Trend?

The dress sneaker has really been making waves in menswear as of late; really staking its place as a good option for casual, 21st Century footwear, and even though we’re fans of classic style, we acknowledge that clothing evolves, so is the dress sneaker a timeless piece of men’s style or just a trend?

It should come as no surprise that the world we live in now is a lot more casual than it used to be. While there are undoubtedly styles that last from decade to decade, history has also shown us that certain clothing items can be a victim of trends of fashion as well. Let’s look at dress sneakers and see if they have the ability to stay or if they gotta go.

What Is a Dress Sneaker?

So, why do we have to clarify? Well, “sneakers” is a really large umbrella term, and there are many different types – some work well for some occasions and others do not. Sneakers – or as my friend across the pond, Jack, calls them, “trainers” – really have their roots in athletics. So, even though men used to wear sneakers for specifically athletic purposes, like playing tennis, they’ve evolved and become more functional today.

And, overall, in the world of sneakers you could really break them down into three groups. There’s the footwear that’s used for actual physical exercise, there’s footwear that only makes you want to sweat financially, and then, finally, there’s the dress sneaker.

The dress sneaker is a nice cross between a more formal dress shoe and an athletic shoe. Or, if you’re gonna put it in a more light-hearted way, these aren’t the shoes that your grandpa wore, and it’s not the shoes that you go to the gym in – which is why people like them.

What Makes Them Smart?

If you take a look at these types of shoes, you’ll start to see why we call them “dress sneakers” and, as you’ll quickly notice, the devil really is in the details. They have a comparatively slim sole. It’s not chunky or distracting like on a pair of running shoes. They have flat laces in a horizontal bar style, unlike the casual crisscross laces or Velcro fastenings found in other sneakers. They’re typically constructed from finer materials that are associated with dress shoes, such as quality leather, and they possess an elegant last shape that hugs your foot, instead of obscuring it.

There’s also color to consider, too, as traditionally athletic shoes have brighter, louder colors. Dress sneakers typically have a more muted monochromatic color palette, but occasionally, you’ll get weird choices like this one. But, most of the time, you’ll find dress sneakers in really nice, muted, classic menswear shades.

So, if you take a pair of traditional sneakers and you put them in a classic colorway, why do dress sneakers still look smarter? Really, the difference is in the design details. A monochromatic pair of athletic shoes still boasts a lot of distracting things – panels, elements, and logos that break up the profile of the shoe. Whereas, if you take a similar color dress sneaker, they look a lot more sleek and smart because the last and the shape itself is the design. They don’t have any fussy paneling, stitching, mesh, or logos, which throw off the look. And after all, history shows us that there really is a winning design formula for a dress sneaker. 

Although dress sneakers have really come into prominence in the last few years, thanks to brands like Common Projects, if you look at their design, it’s really modeled after historic sneakers like the Converse High Top. So, what you see here is effectively a shoe with a derby construction, albeit with an elongated lacing system, and that configuration is mirrored in dress sneakers.

So, it’s clear to see that the design of the dress sneaker really isn’t anything new. So, what makes a Common Project more elegant and put together than a Converse High Top? Typically, a dress sneaker is finished all in one material versus the Converse All-Star’s combination of different materials.

The other big difference is obviously the design as the low-cut Common Project really looks a lot sleeker and smarter versus the high-top nature of the Converse All-Star. And in case you were wondering, if you decide to get a high-top version of a dress sneaker, it’s more casual. They simply look too close to a classic high-top basketball sneaker than a smart shoe.

Also, one quick thing to point out, it’s important to note that a dress sneaker is not one of these frankenshoes. We’ve talked about these types of shoes before but – spoiler alert – they’re not for us. Don’t wear them.

The big difference between a dress sneaker and a Frankenshoe is that a Frankenshoe is trying to do two things at once. Because the Frankenshoe is trying to do two things at once, it really doesn’t do any of them well. It tries to trick you into thinking that it’s a fancy wing tip or a brogue, whereas the dress sneaker, knows what it is – it’s a dress sneaker. It’s not trying to be anything else.

Do they fit into a classic wardrobe?

So, since you’re a viewer of the Gentleman’s Gazette, I’m going to take a guess that you’re a lover of classic style just like us. And, as we all know, Raphael he’s on a wholea nother level. Honestly, for many years, sneakers and classic style haven’t mixed well. So, I get that it can be difficult to consider a dress sneaker for your wardrobe, especially if you like blazers over Balenciagas.

The overall trick with a dress sneaker is just to keep things casual. Without a doubt, the dress sneaker can be considered in the same footwear category as boat shoes or a casual loafer. So, clothing items that would be a perfect pairing would be things like denim, chinos, sweaters, and polo shirts – maybe an OCBD. All these things are things that you would consider in smart casual. Also, keep in mind that you can wear the classic dress sneaker with a pair of shorts and a polo shirt easily as well.

There might be a debate about whether or not dress sneakers are appropriate for business casual or office settings. And, if you want to know more about business casual and dress codes, we got you covered.

As we all know, business casual has the tendency to mean one thing to someone, and it’s something completely different to another. Since our guides tend to have a more classic influence and inspiration, you’ll notice that we don’t recommend dress sneakers for the business casual dress code. To us, business casual is all about erring on the side of caution and being more dressed up than dressed down.

One other thing to note, despite what all the magazines and influencers say, sneakers really don’t look good with a suit. I’m sure you’ve seen this look a thousand times already and, honestly, you will more in the future. If you just ask for our take, the T-shirt, suit, and sneakers just isn’t a look for us. After all, dress sneakers and sneakers, in general, are supposed to be more of leisure footwear and really shouldn’t be combined with fine tailoring.

So, why does this look get so much attention then? The reason we think that this look gets so much popularity is because of the high level of contrast that it achieves. After all, you have a suit that’s one color and one pattern, and you contrast it with a really bright, white sneaker. And while we have guides about combining ensembles for you, overall, we think the best shoe for this sort of situation is a white buck.

As you can see, the idea of combining bright footwear with a smart outfit really isn’t a new one. What these gentlemen understand, however, is that a white sneaker or a dress sneaker really shouldn’t be combined with a full suit.

So, like a pair of white bucks, the highest that a pair of white dress sneakers could go on the formality scale would be a combination outfit with a jacket and a different pair of trousers. And if you want to get the balance of things right, so the whole outfit is harmonious, it really comes down to the details.

Make sure that you pick a jacket that isn’t overall structured or, I would go as far to say, not structured at all, and avoid double-breasted jackets as they tend to be more formal. You really want to stick to a relaxed vibe here, so I’d stick to more casual fabrics, such as corduroy, cotton, linen, flannel, and things like that. Overall, fine worsteds just create too much of a clash in formality.

Death of The Dress Shoe?

So, it’s safe to say that the dress sneaker has become a major player in the menswear scene. And, although we’ve previously addressed the decline of the classic dress shoe, does this mean that they’re on their way out? Absolutely not.

The important thing to remember is that style evolves over time. I mean, after all, if it didn’t, we’d all be wearing loincloths. A perfect example of how classic style has evolved is looking at the classic, black, cap-toe Oxford. This is perhaps best known as the “classic dress shoe.”

Around the 1800s, the footwear choice for men was a pair of boots. So, whether you were doing hard manual labor or walking the streets of London, the menswear choice was a boot. And, as you might be able to tell from this picture, these things must take an eternity to lace up, so that’s when the Oxonian shoe hit universities. It became really popular because it was a lot less fussy. 

So, effectively, a similar look was achieved with less overall effort and more comfort. I used this example to show you the interesting parallel between dress sneakers and dress shoes. Just as the Oxford shoe provided men a new way to dress smart in the 1800s, the dress sneaker is doing the same today.

Plus, don’t forget that the Oxford shoe was originally seen as the casual way to dress, much like the dress sneaker today. And it’s weird to consider that, at some point in time, a shoe like that was considered casual.

Timeless or Trend?

So, given everything that we’ve discussed today and our short little history lesson, we have to ask: Are dress sneakers timeless or a trend?

In this case, we feel like they have a very high potential to remain timeless, and, of course, there are going to be those who feel like sneakers have absolutely no place in classic menswear. And that’s fine. After all, we’re allowed to have our likes and our dislikes.

The overall rise of dress sneakers seems to follow an established pattern of success, and that’s a good thing because it just allows wardrobes to be more varied. And, as you might have noticed, different members of our Gentleman’s Gazette team have different takes on style. Some of them like to be more formally dressed, and others like myself like to be more casual. 

Take Preston, for example; we know that he’s always sharply dressed, even when he’s in bed. Around the office, we always joke that Preston would never wear sneakers. As long as I’ve known Preston, he’s always worn loafers or a dress shoe to the office and, of course, always has a hat. But, sometimes people surprise you.

When noted sneaker maker, Crown Northampton, reached out and wanted to send us some shoes, Preston decided to pick a cordovan leather sneaker. And, of course, this post is 100% not sponsored. Crown Northampton just happened to send some shoes over, and it was perfect timing for this post.

So, by picking a timeless color and a sole that isn’t too distracting, Preston was able to pick up a pair that he could incorporate into his own wardrobe. And I’ve heard that he’s been pleasantly surprised with them, he finds them very comfortable.

So, did you think we were going to say that dress sneakers were timeless or a trend? And after you heard our thoughts, do you agree with us? Do you disagree? I want to hear your thoughts in the comments below.

Outfit Rundown

It’s been getting hot here in Minneapolis, so I’ve been wearing some warm weather attire which goes perfectly well with dress sneakers.

I’m wearing a polo shirt with a floral pattern. It has a really interesting collar. It’s one piece with one button, and it was made for me by Yeossal.

I’m also wearing a pair of classic navy, chino shorts. These are from Vineyard Vines. I love them because, for a guy built like me, they fit my legs. I’m wearing them with a brown, woven, leather belt, which is perfect for the summer.

My shoes are a pair of classic white leather dress sneakers from Beckett Simonon. I really love these even though they’re quite tired. I need to get a new pair and upgrade. But they’re so comfortable, I wear them anyway and try to keep them as clean as I can.

And you might be looking at my feet saying, “Wow! That’s gross! He’s wearing his sneakers with no socks.” That’s where you’re wrong. I’m wearing a pair of gray and blue polka dot no-show socks from Fort Belvedere.

These are a prototype of some cool things coming. If you’re interested in picking up any socks or any other Fort Belvedere products, check out the shop here.