The Best Dress Shoes for Boys

Most boys aren’t keen on dressing up. It’s just a fact. But if they do manage to wrangle themselves into a fancy outfit (whether it be a suit and tie or just something casual), it’s all too rewarding for the parents. And what ultimately brings the outfit together is a nice pair of dress shoes. Yes, we’ve all seen torn and tattered sneakers accompanying a pair of slacks, but that style lacks the charm and subtlety that can be brought forth with the right pair of Oxford’s. So without further ado, let’s explore the best dress shoes and find out which ones are perfectly tailored for young boys.

Deer Stags Ace Wing-Tip Dress Shoes

Stylish, Comfortable & Perfect For All Kids

These manmade wingtip dress shoes from Deer Stags will leave your son feeling confident and comfortable.
Best Overall

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The right pair of dress shoes can unlock a level of confidence in young boys. You’ll see the transformation the moment you slip into these wingtips from Deer Stags. Emitting class and a high level of fashion ingenuity, these shoes automatically bump every outfit up to the next level. And with an ample amount of comfort, these Deer Stags can easily look great when paired with a nice set of slacks or blue jeans, making them the best overall on our list.


  • 100% manmade, extra precision and detail is devoted to the quality of each pair.
  • Lightweight, and with a polyurethane outsole, they’re extremely comfortable and easy to move around in
  • Offers support without compromising style
  • Waterproof


  • They scuff easily
  • Sizing can run on the larger side

Deer Stags Gabe Lace-Up Dress Shoe

A Classic That Never Goes Out Of Style

Always fashionable, this classic dress shoe will spruce up any ensemble.
Best Classic

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When it comes to dress shoes, it’s tough to beat the classics. Some things never go out of fashion and that’s exactly the case with these Gabe Lace-Up dress shoes from Deer Stags. With its lightly padded insole and manmade outer sole, you’ll look good and feel great in these Deer Stags. The synthetic leather is also a bonus, as it won’t break the bank, and you’ll feel a little less worried about scuffs along the way.


  • 100% Synthetic leather
  • Bicycle toe and lace up front, they’re easy to put on and take off
  • Padded insole
  • Matches comfort with quality


  • They tend to run small
  • The synthetic leather can wear down rather easily

Oxford Slip-On Dress Shoes

Slip-On Shoe Perfect For School Or Play Time

These slip-on Oxford’s are perfect for any school uniform or casual outfit.
Best Slip-On

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Putting on dress shoes can sometimes be a hassle. Plus, there’s a preconceived notion that the majority of them are clunky, uncomfortable, and difficult to lace up. Well, all three of those notions are immediately debunked once you try on a pair of these Oxfords. Lace-free, these shoes glide right on thanks to the dual elastic stretch side panels. And with a classic square toe design, your feet will have just the right amount of wiggle room.


  • Lace-free, they slide right on and come off just as easily
  • Classic square toe design
  • Fits perfectly with any school uniform
  • Breathable insole and non-marking outsole


  • Synthetic leather can easily wear off around the toe
  • They have a tendency to run on the smaller side

Dadawen Lace-Up Oxford Dress Shoes

Classic Gets An Upgrade

Dadawen gives the classic Oxford dress shoe a modern-day makeover.
Flashiest Style

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Flashier than most dress shoes, this modern take on an old school Oxford classic is perfect if you’re looking for a little extra edge in your fancy footwear. Manmade patent leather with a cushioned sole, this shoe stands out amongst the crowd. With a classy style and a dapper design, this option is available in several different color patterns, so you can make your mark wherever you go.


  • Stylish design and sleek finish enables this shoe to stand out amongst the competitors
  • Although flashier than the typical Oxford, it still fits in perfectly for any special events
  • Lightweight and comfortable
  • The unique pattern on the inside adds to the individuality and charm


  • Insoles can fall out easily
  • Although they come in half-sizes, they still tend to run on the larger side

Josmo Boys Double Monk Strap Oxford Loafer

Double Strap Dress Shoe Defines Elegance

Boys' dress shoes get taken up a couple of notches with this elegant double strap Oxford from Josmo.
Most Sophisticated

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A dress shoe can subtly stand out on its own without being loud or ‘in your face’. That’s exactly what Josmo delivers with this sophisticated double strap Oxford that truly defines elegance. And with Josmo, the quality matches the design. Not only does this dress shoe look fantastic, but it also excels in comfort, too. Available in brown or black, this shoe bucks the trend and bears a mark of independence. And with its hoop-and-loop buckle, it easily slides on and off. So if class and sophistication are at the top of your list, look no further than this collection from Josmo.


  • Quality you can trust at an affordable price
  • Resonates an extra level of class and sophistication
  • Hoop-and-loop buckle allows for easy on and off
  • Manmade sole allows the shoes to be comfortable and soft


  • Narrower than most dress shoes

Frequently Asked Questions

When it comes to buying a boys’ dress shoe, does price make a difference?

Yes and no. Obviously, a name brand shoe will charge a little more, but that doesn’t ensure the quality will be any better than a shoe half its price. And let’s face it, boys are active. They’re running around scraping their knees and scuffing up their shoes in the process. They’re not focused on keeping their footwear neat and tidy, so in that sense, it’s best to go into the buying process knowing that wear and tear will be inevitable. Plus, boys tend to outgrow things quickly, especially shoes, so best to zero in ones that are more moderately priced.

Laces or no laces, which is dressier?

In this case, it’s the dealer’s choice. Both can be dressy and stand out in their own right. Of course, laces can come undone, and no one wants that when they’re walking, or heaven forbid, running. But laces can also give a little extra pop to your dress shoe. However, a slip-on certainly has its own charm and elegance. We can’t leave buckles out of the conversation. They offer up a completely different class of sophistication. But whether your preference is laces, buckles, or slip-on’s, one thing’s for sure – you’re guaranteed to look sharp in whatever dress shoe you put on.

When ordering dress shoes online, how accurate are the size charts?

We’d say this varies from brand to brand. We’ve seen some brands that naturally run on the larger side, while others may run small. With a little bit of research and scouring through customer reviews, you should be able to get a good idea of how a particular brand sizes. We found a brand that had several reviews saying the shoe usually runs about a half size too big. We considered that when ordering, and ended up with the perfect size being delivered to our front door.