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Winter Outfits for Boys: What to Buy for Winter 2021

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How to Put Together Cute Outfits for Boys this Season

kidpik subscription boxes are a great way to explore new fashions all from the convenience of your home!

Winter can be a tricky season to dress up boys and as parents, we want to make sure that what they are wearing during winter is functional and stylish at the same time. Proper winter clothing should be warm enough to be worn outside in cold weather and waterproof, if necessary. 

Buying winter clothes can be challenging, especially if you are a busy mom who takes care of a million other things at once! Take out the guesswork in buying clothes for every season by subscribing to kidpik. With free shipping and returns, and many options to choose from, you can get your son involved in choosing the clothing he likes and getting it conveniently delivered to your house.  

Winter clothing for boys: Helping him choose his style 

Enabling your son to make choices when it comes to his clothing will improve his confidence and make him discover his own, personal style. As parents, we want our kids to be able to make informed decisions about their clothing so that they will like what they wear. Whether it’s a classic, active, sporty, or urban style, the way your son dresses up says a lot about his personality. Once he can choose his style, he will be more confident as he goes along with everyday life. 

Letting your kid choose their style might sound intimidating but as parents, you have the power to guide them. It is not as complicated as you think it is – here are some questions that you can ask your kid to help them: 

What hobbies or sports is he interested in? 

If he can dress up as a TV, movie, or book character, who would it be? 

Are there any colors, patterns, or prints that he likes? 

Our stylists at kidpik have a great understanding when it comes to choosing winter clothing pieces that your kid will wear!  

boy in kids clothing

It’s all about the basics 

Trendy fashion pieces are always fun to wear and shop for, but when it comes to kid’s clothing, sometimes basics are better. Basic clothing will never go out of style, and you can layer it with trendy pieces that will update your kid’s outfits. When it comes to winter clothing, basic pieces should include fleece or snow jackets, snow or rain boots, flannel shirts, beanies, and mittens. For baby boys, fleece footed pajamas are great clothing options to keep the baby warm.  

If you are looking into layering clothing for winter, you can always start with a base layer and start adding a jacket or a hoodie. The best thing about layering is that you can mix and match, which results in multiple outfit options making it look like your wardrobe is new. 

boy in kids clothes

Essential winter clothing for boys 

Dressing up for winter can be challenging because you have to make sure you take into account the weather conditions and what activities your kids are doing. Here is the essential winter clothing for boys: 

T-shirts and button-down tees 

Flannel is the name of the game when it comes to winter clothing. Flannel button-down shirts are trendy and can be layered with a T-shirt underneath to make you warmer. Flannel shirts can also be dressed up or down, depending on the occasion which makes it so convenient. 

Jackets and Hoodies 

The type of jackets or hoodies that go with your kid’s winter outfit depends on the winter weather in your area. If you get a lot of snow, waterproof and snow jackets are the norm especially if you are doing outside activities. If you don’t get a lot of snow or it doesn’t get too cold in your area, a hoody will suffice. Jackets and hoodies can also be used as layering pieces and can be taken off when your kid gets too warm. 


Snow pants are ideal when you are dealing with snowy and icy conditions, this will make sure that your kid is kept warm and waterproof.  

Shoes and Accessories 

Snow boots are waterproof and can keep your kid’s feet warm, especially if you are dealing with snow and rain. Accessories such as mittens, beanies, and scarves can also add another layer of protection from the cold and a chance for your kid to show off their fashion style! 

boy in kidpik subscription clothes

Get your kidpik box today! 

With our kidpik subscription boxes, you won’t have to go to the mall to try on clothes and it takes out the guesswork when it comes to shopping for your kids. Our team of fashion experts has expertly curated all the pieces that come with the boxes – making it a fun experience not just for kids but for parents as well! 

Each box comes with 7 hand-picked clothing items that can be used to create 3 different outfits. The clothing items can be customized depending on what your kid likes or doesn’t like based on his style and preferences. The best thing about the kidpik subscription boxes is that you can try them on at the comfort of your own home and keep the clothing that you love.  

When you sign up for kidpik, your kid can take a quiz that will determine what he prefers when it comes to clothing options and his style. Each look can be unique and the results from this quiz will help our fashion experts pick out the best clothing options that fit your kid’s personality and style. 

Any parent will tell you that kids grow up too quickly and that means clothing sizes change frequently. With kidpik subscription boxes, you can easily get outfit options that will fit your kids as they grow and outfits that will change like the seasons. 

Shopping for winter clothes should be fun and your kid should be able to wear the clothes that he loves so that he will have a great time wearing them. With kidpik, your kid will surely be the trendiest kid on the block. Subscribe to kidpik today and have boy clothing delivered right outside your doorstep! 

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