The Best Shoes for Boys

by Bethany Braun-Silva

The Best Shoes for Boys
Shop Story

Boys go through shoes like, well…. boys. If you thought you had a hard time keeping up with your toddler’s growing feet, than get ready for what your big boy and preteen is about to show you: feet that seem to grow overnight! Not to mention all the wear and tear that your boy will put his shoes through. It’s likely you’ll be buying him shoes more often than not.



Best Sneakers For Boys:




  • Vans Old Skool Sneaker






Best Dress Shoes For Boys:









Best Sandals For Boys:









Best Boots For Boys:









Best Trendy Shoes For Boys:









So you’d think it would be easy to just run to your local department store and grab a pair or two. And in a perfect world, it would be that way. But these guys are growing fast and have a lot of opinions about their own style. Shoes for boys need to be cool as well as functional, and of course, support their changing bodies. Kids learn to express themselves through their clothes and footwear, so picking a shoe for your son is suddenly a bit more difficult. Luckily you’ve got lots of options when it comes to the shoes you will need for your boy.


Types of Shoes for Boys



Sneakers will take your boy from school to practice and back again and will likely be his shoe of choice for its comfort and durability. Aside from athletic shoes, you may want to invest in a slip-on sneaker to change it up a bit.


Dress shoes

While you may get a bit of resistance from your boy every time he has to wear dress shoes, there are many that are comfortable and cool enough for your little man. Chukka boots and oxfords are just a few of the styles he can choose from.



Your boy will need definitely need a pair of sandals in the summer that can he can wear at the beach or the playground. If he plays sports, flip-flops are great for the shower and athletic sandals with straps are a good choice for more physical activities.



When it’s cold or wet outside, your boy will need a pair of rain boots or snow boots. For hiking or rough terrain, a hiking boot is just the ticket.


What to Consider When Buying Boys Shoes

So in addition to checking off all the “cool” boxes, shoes need to fit, so it’s important that you get your son’s foot measured pretty regularly. You’re going to want to do it at a shoe store that has the proper measuring equipment. As parents, we often think we know our kids’ shoe size only to be quite surprised when we get to the store and the footwear don’t fit. Once you know his correct size, you’re ready for the next step. Below, we’ve rounded up some of the best shoes your boy can wear, from sneakers to sandals to smart dress shoes. Good luck, and happy shopping!

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Best Sneakers for Boys

New Balance 574


Your kid might not know what “retro” means; he just knows there’s something about these shoes that are super cool. They have an EVA cushioned footbed and a stabilizing heel cup to provide all-day, all-activity comfort. Triple-strap Velcro fasteners make these shoes a cinch to get on. Plus, all the neat color combos might inspire Dad to grab a pair for himself.

What Reviewers Are Saying:
“These are adorable, well made shoes. Great blue color and fit comfortably on my child's feet. Great for running around the playground and jumping and they hold up very well.”

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Nike Air Max 270


These shoes are super sporty and will support your little guy through any activity, be it track, soccer or anything else. It has open-weave mesh that brings flexibility to a stretchy sock-fit sneaker. The shoe, which comes in subtle but modern color combos, also has asymmetrical lacing that follows the contours of his foot to make sure it stays put

What Reviewers Are Saying:
“This is the second pair of Air Max 270 I have purchased for my son. He is 7 and can be quite hard on shoes. I must say that I am impressed with how well these shoes hold up, and he says they are the most comfortable shoes he has ever worn.”

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Vans Old Skool Sneaker


This classic sneaker may inspire your child to try his hand at skateboarding! It features a low-top design, vulcanized lace-up style with Vans signature side stripe, a round toe, padded collar for extra comfort, a smooth lining and a cushioning insole. It comes in a variety of colors, but nothing beats classic black!

What Reviewers Are Saying:
“They hold up to kids and adults.”

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Adidas X_PLR Sneaker


With soft, breathable mesh and flexible fabric, this shoe has a sock-like feel and is very comfortable for kids. It also features an OrthoLite® cushioned footbed that will support boys through the school day and well into practice. It has a grippy rubber sole for traction during any activity and comes in colors boys will love.

What Reviewers Are Saying:
“My little one loves these stylish pair of shoes. As soon as he saw them at the store, he shrieked for them and it’s been on his feet ever since we got home. He even feel asleep in them!”

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Nike Huarache Extreme Sneaker


With soft, breathable mesh and flexible fabric, this shoe has a sock-like feel and is very comfortable for kids. It also features an OrthoLite® cushioned footbed that will support boys through the school day and well into practice. It has a grippy rubber sole for traction during any activity and comes in colors boys will love.

What Reviewers Are Saying:
“My little one loves these stylish pair of shoes. As soon as he saw them at the store, he shrieked for them and it’s been on his feet ever since we got home. He even feel asleep in them!”

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Best Dress Shoes for Boys

Kenneth Cole Real Deal Chukka Boot


This shoe is made from 100% canvas, so it’s breathable and comfortable for boys to wear. Available in navy, black or brown leather, the boot look is dressy without being overly stuffy, pairs well with slacks, khakis or jeans.

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Deer Stags Kids Loafer


A classic penny loafer is a comfortable yet dressy option for boys. Ring bearers and little groomsmen will be supported by the shoe’s EVA cushioned insole and will have no problem dancing the night away. Parents will love that the shoe is easy to put on and take off, and boys can easily do so with no help.

What Reviewers Are Saying:
“My six year old loves his Deer Stags Kids Loafers, along with the several other pairs of Deer Stags shoes. They're simply the best looking, and great quality. He always gets compliments.”

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Footmates Connor Oxford


Oxfords are perfect for the most fashion forward boys. While the style is vintage, it has many contemporary touches. This royal blue leather oxford features a cushioned insole that will keep boys comfortable. Parents will love the Custom Fit System (CFS) interchangeable insole system, which provides medium and wide leather-lined insoles for a custom fit. Genius!

What Reviewers Are Saying:
“Very classy and dressy shoes with a suit. I got so many compliments on these shoes that I got for my son.”

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Tucker & Tate Little Preston Derby


This is a sharp shoe made of suede and featuring contrast stitching and a two-tone sole. It also has an adjustable hook-and-loop Velcro strap. The shoe can be dressed up or down depending on the occasion and will look just as good with jeans as it will with dress pants. It comes in a variety of neutral colors.

What Reviewers Are Saying:
“These are cute, true to size, and can be worn with dressy or casual outfits. Works great for us!”

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Florsheim Navigator JR


This classic shoes comes in a kids size and has the same great features as the adult version. It’s made of 100% genuine leather or suede and has moisture-wicking suedetec linings. Sweaty feet are no match for these dress shoes, which also have a memory foam insole for added comfort.

What Reviewers Are Saying:
“My son said these were comfortable, and I really love how they stand apart from their plastic-y peers in this product segment. I would buy again without hesitation, and probably will as his feet grows and we need another shoe for dressy occasions.”

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Best Sandals for Boys

Timberland Adventure Seeker


These water-friendly sandals will take your boy from the beach to the playground and back again. Featuring an adjustable Velcro strap, an EVA foam footbed with odor-control properties, the durable sandals will last you through the summer and beyond.

What Reviewers Are Saying:
“This is a good quality shoe, my son doesn't want to take them off. They are very comfortable and fantastic looking. I've bought 2 pair.”

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Adidas Adissage


Slides are a perfect vacation staple, as they are easy to just put on and go. Plus, boys will likely get more than one season out of them, as many athletes pair these with socks when traveling to and from practice (who knows?). They have an adjustable strap and massage nubs that make them super comfortable. They’re quick drying and have a durable rubber sole.

What Reviewers Are Saying:
“Son is 11, loves these, they are his favorite sandals ever, has worn them all summer, they have held up great, very true to size, like the adjustable fit with the Velcro.”

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Keen Newport Sandal


These sandals are the perfect shoe to help your boy along on his next adventure. The elastic cord lace and adjustable hook and loop strap allow kids to put them on and take them off by themselves. No straps or buckles involved! The quick-drying webbing is perfect for the beach, the sprinklers or jumping in puddles. The sandals, which are even great for hikes, also features Keen’s Cleansport NXT for natural odor control, a breathable mesh lining and a compression molded EVA midsole. This really is the ultimate sandal!

What Reviewers Are Saying:
“I love these shoes for my kids to wear in the summer”

“I have been purchasing Keens for my kids for the last 3-4 years. They are perfect for kids to wear outdoors because they work well in all types of conditions - we can go from sand to mountains to water and everything in between without an issue.”

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Reef Kids Ahi Sandal


This flip-flop is a great slip-on sandal and has a padded, contoured bottom that gives boys the much-needed support that other flip-flops just don’t have. The padded straps won’t dig into his feet and it comes in over 10 different colors and prints he’ll love.

What Reviewers Are Saying:
“I have bought my son several Reef sandals. They hold up, they are comfortable, and clean easily.”

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Chaco Kids Eco Tread


The straps on this sandal will allow boys to be as active as they like without worrying about losing their footwear in the process. It has a molded, supportive footbed and a rubber tread so they won’t slip or fall. It’s also eco-friendly and made from 25% recycled rubber.

What Reviewers Are Saying:
“My kids basically live in their sandals during the summer. These are easy to adjust, are comfortable and my 5 year old can put them on by himself. Highly recommend these despite the high price”

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Best Boots for Boys

Hunter Original Rain Boot


This mini version of the original Wellington boot protects him from puddles and keeps his feet and legs warm. Rainy walks to school are no match for the Hunter Original Rain Boot. It’s made from 100% rubber and is grippy enough that he won’t slip or fall while jumping in puddles. It’s handmade and durable and will last until your boy grows out of them.

What Reviewers Are Saying:
“My 9 year old son had these in a huge snow melt puddle within minutes of putting them on. Fit is true to size ( he has a narrow foot and they still fit well). They have been used daily since.”

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UGG Neumel II


Yes, it feels as cozy as it looks. The classic chukka boot gets a major UGG upgrade with plush UGGpure™ lining, which is made to feel like real shearling. It also has a slip-resistant sole and the classic suede fabrication the company is known for. The shoe is water and stain-resistant, and while it’s very warm, it’s also lightweight. It comes in black, charcoal and brown that pair well with any style of pants.

What Reviewers Are Saying:
“I’m so glad that I got these for my son because he absolutely loves them. Every time we go out he asks, ‘Mommy can I wear my uggs? They’re so comfy.”

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Littleplum Kids Hiking Boot


Tough enough for hiking but stylish enough for everyday wear, this waterproof hiking boot has an anti-skid sole that provides traction in wet and dry terrain, plus mesh panels for breathability. The high-top design provides sufficient ankle support. This boot does a lot and won’t break the bank.

What Reviewers Are Saying:
“My son adores these. He loves that they're more of a tennis shoe/snow boot hybrid. Much lighter weight than I expected. The metal claws on the bottom are a great touch too.”

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Keen Lumi Waterproof Boot


These waterproof snow boots are insulated for added warmth. In fact, they’ve been tested in -40°F weather, so your kid will be warm in any conditions. They feature elastic laces that are very easy to tighten so your boy won’t even need to take his gloves off to do so. They are sturdy and durable and have a padded interior for added comfort.

What Reviewers Are Saying:
“My boys always push back when it comes to wearing boots because they can’t run!! Not these, my twin boys were fight over who got to wear them because they were so comfy and cool.”

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The North Face Kids Hedgehog Hiker II


This cool-looking shoe looks more like a sneaker but does work like a boot. It’s waterproof and the rounded toe bumper protects your boy’s feet against the elements. It features a bungee lace-up with adjustable toggle closure, so it’s super easy for him to tighten. It has a padded insole and cushioned collar with a pull-tab heel that makes it easier to get on over thick socks.

What Reviewers Are Saying:
“Bought a pair of these Junior Hedgehog Hiker Mid for our son. The shoes are comfortable, stable, offer great protection for the feet, toes and ankle, the sole is grippy and flexible enough for hiking, running and playing outdoor.”

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Best Trendy Shoes for Boys

Stride Rite Lights Kaden


Just because your little man is growing doesn’t mean he can’t enjoy a light-up sneaker. These Stride Rite sneakers for boys have the light-up feature without looking like they’re made for babies or toddlers. They have elastic laces and an adjustable Velcro strap. The shoe is durable and breathable and features a water-repellent outer layer and memory foam insole for added comfort.

What Reviewers Are Saying:
“My very picky 7 year old put them on and loved them. The elastic laces can be pulled to make them tighter.”

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Heelys Launch Skate Shoe


As if your boy didn’t already move fast, these Heelys Skate Shoes will have him flying. The lightweight sneakers have a hidden wheel at the rear of the shoe, and when kids lift their toes up, they can glide. The wheel is removable, transforming them into trendy street shoes, but we doubt your kid will let you do that!

What Reviewers Are Saying:
“My son loves them, and I love that the wheels can be removed for normal wear. The shoe itself is well made and looks really nice.”

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Vans Kids Classic Slip On


These classic are not only comfortable but also stylish. They come in a number of different prints your boy will love, including sharks, army camo and pirate prints. This a great way to let him express himself, and you might be surprised at which ones he picks (yeah, there’s also a Demon Troll print). The canvas shoe is easy to put on and take off and has padded sides and elastic accents for an adjustable fit.

What Reviewers Are Saying:
“These are great shoes. I love the sole of the shoes. It last a very long time, and that is good because the kids are tough on them.”

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Converse Kids Chuck Taylor All Star Dinoverse


These bold shoes are sure to make a statement and feature multi-colored dinosaurs on a classic hi-top Chuck Taylor sneaker. The shoe has the famous rubber cap toe, textured toe bumper, contrast sidewall tri, and medial-side air vent holes. They also have a durable rubber sole to protect against slipping. But let’s get real: This shoe is more for fashion than function!

What Reviewers Are Saying:
“Love the design so does my son. Everyone gives him compliments and say his shoes are cute.”

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Air Jordan IV Retro Sneakers


If your son is a “sneakerhead,” then you probably already own a pair of these retro Air Jordans. The original shoe was released in 1996 and sparked an entire movement in the sneaker world. Is there a more famous sneaker? They are a splurge, so perhaps they’re best for a special occasion like a birthday. Comfortable and functional, they’ll make your little boy feel like an all star.

What Reviewers Are Saying:
“My son absolutely loves the shoes and has been playing in them all basketball season. Great fit!”