Boys High Top Sneakers(that double as Dress Shoes)

A great solution to the “these dress shoes hurt” fight I often get in with my 10 year old son is a High Top sneaker. A High Top sneaker functions as a great winter shoe that can also be worn to compliment a holiday outfit. Plus (unlike most dress shoes) High Top sneakers can be worn as everyday sneakers throughout the season, so you get more bang for your buck. High Top sneakers are practical for colder or wet days, while still being stylish. Some are even sherpa lined for extra warmth and coziness. Save yourself from the dress shoe fight and go for some cool High Top kicks instead. 

VEJA Kids Small Esplar Mid

Veja sneakers are just plain cool. Love the European look and they come in so many stylish colors, like this rich combination of olive with navy. Downside to this brand is they are pricey and not very cushioned on the insole.  Run small so size up.

Cienta Kids Shoes 95887

This slip on style by Cienta is easy and stylish. Because it doesn’t open in any way, these would not work well for wide feet. They have very flexible soles, they are lightweight with very soft leather upper. Available in 4 colors-all so well done.

Rennon High Top Sneaker UGG®

The Rennon High Top Sneaker by UGG is the perfect cold weather sneaker. Lined with the coziest sherpa, feet will stay warm and toasty on cold winter days. The double Velcro straps have a hook and loop closure which will keep the boots securly on the foot. Available in boys sizes 6-12.

See Kai Run Kids Devon (Toddler/Little Kid)

The Devon by See Kai Run is the winter sneaker that checks every box. The black suede would look great with cords for a dressier holiday look while it also has a converse like look for everyday. The bumper toe will help them stay new looking which is always a perk! Soles are flexible and lightwieght, leather is super soft and cozy sherpa lining covers the entire upper. Also available in a rich chocolate brown. Boys sizes 4-13.

Chuck Taylor® All Star® Berkshire Sneaker Boot CONVERSE

I am obsessed with this Chuck Taylor® All Star® Berkshire Sneaker Boot by Converse!! Think of this as the winter version of classic Converse high top. It is lined with lightweight fleece feeling fabric so not bulky but soft and warm. So stylish and cool, these should come in adult sizes!!

Old Soles Top Louis

The Top Lois by Old Soles is a combo boot/sneaker look. The leather is buttery soft, and insole feels like marshmallows. Love the rich chocolate brown and grey color combo. Fit is meant to be slip in, the ties can be left undone or tied to ensure a perfect fit. Available from toddler size 6 to big kid size 3.

UGG Jayes Sneaker

The Jayes sneaker by UGG is simple European looking style. The classic tie bootie is updated with a side zipper for easy in and out once you have the ties adjusted properly-so smart! The orange pop on the heel adds some fun and style, while the soft leather and squishy insole will be soft and warm and comfortable. Great everyday shoe that works for all occasions.

Did you buy one of these products?

Snap a pic, post it to Instagram, and tag @gumshoekids. Happy shopping!

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