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In a previous life, you might have loved shoe shopping. But now you are in a strange new world, a place where just the idea of footwear is fraught with drama and stress. Seriously, why is it so damn hard to measure our kid’s shoe size? And as for bringing our little monsters with us to the store...forget it. That’s why we compiled this list of the absolute best shoes for toddlers, all approved by real parents with real shoe problems.

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kids shoe sizes
Twenty20

When should children start wearing shoes?

A word to the wise: There’s really no reason to add shoes to your baby registry. That’s because your kid doesn’t actually need a pair of kicks until they start walking—and even then, the American Podiatric Medical Association (APMA), says that barefoot is best at first. Walking without shoes on gives a child’s feet room to grow and develop properly. It also helps kids get their balance since they can use their toes to grip. But when your toddler starts to get more comfortable on their feet and ventures outdoors, that’s when you’ll want to invest in a good pair of shoes.

What to look out for when picking toddler shoes

Whether your kid is only just starting to take a couple of steps or is a toddling pro, you’ll want to make sure that their shoes are comfortable and flexible, while also being solid and stable. Here are some tips for shoe shopping for toddlers from Dr. Suzanne Fuchs, a foot and ankle surgeon and sports medicine specialist in Palm Beach.

  • “Toddler shoes should have a wide toe box to allow the child to freely move their toes as well as allow their toes to spread without constriction as they grip the ground to walk,” says Fuchs. “A wide toe box is also important to allow the foot to go into the shoe easily without squeezing. This helps prevent toes from curling, deformities such as hammertoes and allows the feet to develop naturally.”
  • Shoes should be lightweight, Fuchs tells us. “Heavy shoes may cause toddlers to have tired leg and foot muscles and could also cause malalignment of the spine.”
  • Sorry, friends: You may want to think twice about passing off big sister’s hand-me-downs to your tiny tot. If shoes are worn out, they likely won’t have enough structure to support your early walker’s feet. (Those fancy party shoes that she only wore once, however, are totally fair game.)

Zappos

1. Best for Wide Feet: Stride Rite Wes Sneakers

  • Value: 17/20
  • Ease of putting on/taking off: 18/20
  • Quality: 18/20
  • Aesthetics: 19/20
  • Comfort: 20/20
  • Total: 92/100
Sneakers that look sharp but won’t slow your tot down—this suede and leather number is fashionable but not flashy. Parents report that the fit is great for wider feet and the leather isn’t stiff, so no blisters for your babe and no buyer’s remorse for you. (Full disclosure: I have two small people who hate shoes, and I am a loyal Stride Rite fan. Their squishy and soft toddler sneakers have been saving my sanity for many a season.)

Buy It ($52)

Amazon

2. Best for Adventures: Timberland 6“ Classic Boots

  • Value: 18/20
  • Ease of putting on/taking off: 16/20
  • Quality: 19/20
  • Aesthetics: 20/20
  • Comfort: 18/20
  • Total: 91/100
We think this rugged classic looks good on boys and girls alike, and goes well with most any outfit. They’re also built to last forever—even the most active adventurer will outgrow them before she wears a hole in ‘em, and they have a waterproof exterior with a climate controlled lining, making them equally practical for puddle splashing and snow-day play. Despite the bigger price-tag, parents keep picking these boots for their functionality, quality and kid-tested comfort.

From $60 at Amazon

Amazon

3. Most Comfortable: See Kai Run Ryder Sneakers

  • Value: 18/20
  • Ease of putting on/taking off: 19/20
  • Quality: 18/20
  • Aesthetics: 18/20
  • Comfort: 20/20
  • Total: 93/100
We love the playful look of the Ryders, but you can also file this guy under fuss-free fashion. Awarded the seal of acceptance from the American Podiatric Medical Association (APMA), these lightweight shoes feature a soft lining and somehow manage to be both durable and flexible. They’re also a great option for kids with high arches or flat feet. (And come on, how cute is the little wagon on the side?)

$50 at Amazon

Amazon

4. Best Slipper: Norty Suede Leather Moccasins

  • Value: 18/20
  • Ease of putting on/taking off: 19/20
  • Quality: 18/20
  • Aesthetics: 18/20
  • Comfort: 19/20
  • Total: 92/100
When it comes to casual comfort, we vote mocs over Crocs. The faux-fur lining of these slip-ons is plush and plentiful, so perfect for keeping your kid’s feet warm around the house. But they also have a sturdy rubber sole, which means your toddler won’t slip on the tile floor, and you won’t have to pause and put him in “real” shoes when he wants to help you take out the trash.

From $16 at Amazon

Amazon

5. Best for Getting Muddy: See Kai Run Summit Sneaker

  • Value: 18/20
  • Ease of putting on/taking off: 19/20
  • Quality: 18/20
  • Aesthetics: 18/20
  • Comfort: 18/20
  • Total: 91/100
It’s the universal law of parenting: It doesn’t matter what the weather is doing—if there is mud somewhere then your kid will find it. These cute kicks from See Kai Run are ideal ‘get dirty’ shoes: great grip for adventure seekers plus they’re machine-washable and quick-drying. Parents also agree that these shoes go on quickly and without a struggle.

$55 at Amazon

Ten Little

6. Best Guaranteed Fit: Ten Little Everyday Original

  • Value: 18/20
  • Ease of putting on/taking off: 19/20
  • Quality: 18/20
  • Aesthetics: 19/20
  • Comfort: 19/20
  • Total: 93/100
When we signed up to be parents, no one warned us how freakin’ difficult it would be to measure our child’s shoe size. But the pros at Ten Little make the whole process easy. Answer a couple of questions and their online algorithm will recommend a healthy size in just a few clicks or they’ll mail you a free shoe fit finder. These cool shoes feature reinforced toe caps and non-skid soles, plus a range of fun colors (each pair also comes with stickers so your kid can personalize her kicks). The earthy mama in us also loves that these shoes are made from vegan leather and natural rubber.

Buy It ($39)

Polarn O. Pyret

7. Best Rain Boot: Polarn O. Pyret Waterproof Rain Boots

  • Value: 18/20
  • Ease of putting on/taking off: 16/20
  • Quality: 19/20
  • Aesthetics: 19/20
  • Comfort: 18/20
  • Total: 90/100
Splashing in puddles is a rite of passage for preschoolers everywhere, and these parent-approved, Scandinavian-made galoshes are solidly waterproof enough to protect little legs from getting drenched. To be honest, we’d buy these for the adorable frogs alone, but we’re also big fans of the 3M reflectors on the back, reinforced rear section and toe for better durability (hey, kicking up leaves can take a toll) and the handy spot inside to write your child's name. As the Swedes say, ‘there's no such thing as bad weather, only bad clothing.’

Buy It ($36)

Amazon

8. Best Flexibility: Stride Rite Soft Motion Artie Sneakers

  • Value: 17/20
  • Ease of putting on/taking off: 18/20
  • Quality: 18/20
  • Aesthetics: 17/20
  • Comfort: 19/20
  • Total: 89/100
The Soft Motion line from Stride Rite is perfect for toddlers who are walking, running and climbing with the best of them, but still relatively new to the concept of footwear. These sneakers are soft and flexible from heel to toe, but not in that I’m-a-sock-pretending-to-be-a-shoe way, and the rubber soles are thick and can take a playground beating, or a thousand. The best part? Your child won’t complain about wearing them every day, and you won’t need to buy another pair until she’s ready for the next size up.

From $18 at Amazon

Zappos

9. Most Fashionable: Saucony Jazz Hook & Loop Suede Sneakers

  • Value: 18/20
  • Ease of putting on/taking off: 20/20
  • Quality: 18/20
  • Aesthetics: 18/20
  • Comfort: 20/20
  • Total: 94/100
These live up to their jazzy name. The bold color combinations are fun, playful and definitely a hit with kids, yet not offensive to adults (so you won’t find yourself wondering if you’re wrong for wanting to explain the definition of “tacky” to a toddler). The oversized Velcro tab means you have a larger margin of error while trying to secure them to the foot of a moving target, and if you’ve ever tried to put shoes on a toddler in a hurry, you know that’s a big deal. In fact, there’s a good chance your kiddo can put these on himself, so you won’t even have to break a sweat before leaving the house.

Buy It ($35)

Amazon

10. Best Sandal: Native Unisex Charley

  • Value: 18/20
  • Ease of putting on/taking off: 19/20
  • Quality: 17/20
  • Aesthetics: 18/20
  • Comfort: 18/20
  • Total: 90/100
Maybe you’re looking forward to a warm-weather getaway, or maybe you’re merely daydreaming about summer, but if you’re searching for some very small sandals, you should check these out. The material is soft, so it won’t rub or cause discomfort, and it wipes clean in a second. Parents love the simple style: gender-neutral, cute and easy to dress up or down. Most importantly, these weren’t designed by a sadist, so there are no buckles! The Velcro closure is secure and easy to use, so you can spend more time in the sun and less time swearing under your breath.

From $17 at Amazon

Amazon

11. Best Winter Boot: Bogs Kids’ Snow Day Snow Boot

  • Value: 18/20
  • Ease of putting on/taking off: 17/20
  • Quality: 19/20
  • Aesthetics: 18/20
  • Comfort: 19/20
  • Total: 91/100
Scoop up these lightweight, non-cumbersome workhorses before the season’s first snow day, and you and your babe will be happy you did. The sole is super sturdy (meaning your toddler has all the traction she needs), the interior is fleece-lined to keep her extra warm and cozy, and the bungee-cord drawstring at the calf ensures she stays that way even after a snowball fight.

From $40 at Amazon

Amazon

12. Best Water Shoe: Native Jefferson Waterproof Slip-on

  • Value: 19/20
  • Ease of putting on/taking off: 19/20
  • Quality: 19/20
  • Aesthetics: 19/20
  • Comfort: 19/20
  • Total: 95/100
The Jefferson slip-on from Native is a thing of beauty; it might even be the perfect shoe. Somewhere between Toms and Crocs, these slip-ons score top marks for both form and function. Not clunky, not ugly, not smelly, not heavy, not ouchy—just right. So easy to slide on, an 18-month-old might be able to do it without help; so sturdy they show no signs of structural wear and tear after hitting the pavement every day on the foot of a 5-year-old. The rubber material is super easy to clean too. Our only complaint is that, no matter how awesome they are, you can’t in good conscience ask your kid to wear them in the winter.

$33 at Amazon

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