5 Cool Winter Outfits for Tween Boys

This past fall I included a photo of my son and daughter wearing their first day of middle school outfits in my Tips for Parents of Students Entering Middle School post. I was surprised how popular the images were on Pinterest (and continue to be) I realized that Pinners are not only looking for outfit inspiration for themselves, but also for their children. After the success of my 5 Fall Outfits for Teen Girls post I asked my son to help me document his favorite winter wear.

Disclaimer: We live in “sunny” California where temperatures tend to be in the 50’s and 60’s during the winter. I know many of you face much colder weather where you live. These outfits would call for a few additional layers during a polar vortex…or just plain snow.

Does anyone else have a middle school aged boy who would prefer to wear athletic shorts and a t-shirt on a daily basis? Call me crazy, but I tend to think that wearing pants and long sleeves on a cold, rainy day makes a bit more sense. The mission (should you choose to accept it) is to find cold weather clothing that your son actually likes and are appropriate for chilly temperatures.

I have learned that the only way my son will wear the clothing in his closet is if he picks it out himself. Sometimes that means a trip to the mall and other times we check out the options online. Before we start shopping I take a minute to let him know what types of items he will need to include in his wardrobe. For example, when shopping for winter clothing we discussed the fact that he would need outfits that are appropriate for school, church, and a nice dinner out. He has free reign over the styles, colors and prints as long as he picks outfits appropriate for each of those activities. I encourage him to include each of the following items in his winter wardrobe:

  • athletic pants
  • cozy joggers
  • a pair of jeans
  • long sleeved t-shirt
  • sweatshirt
  • athletic shoes
  • khakis
  • collared shirt
  • sweater
  • dressier shoes
  • hooded/water proof jacket

The outfits below have been my son’s favorite looks this winter. I am thrilled that we were able to find items that reflect his personal style.

Fit Tip: My son is 12 years old, around 5′ tall and weighs approximately 90 pounds. The clothing pictured is size 12-14.

joggers and long sleeved t-shirt
jogger pants, long sleeved t-shirt, athletic shoe

This outfit is a favorite for both school and lazy Sundays spent watching football on the couch. The jogger pants are currently on sale for $24.74. We both like the fact that the zippered pockets keep valuables from unintentionally slipping out .

I was pleasantly surprised when my son picked out these taupe slim pants. The thick, sturdy material will hold up to wear and tear on the school yard and still be appropriate for attending church or a nice dinner out when paired with a collared shirt or sweatshirt. The pants are currently on sale for $24.99. The burgundy short sleeved t-shirt is a great layering piece for a warm afternoon or after working up a sweat shooting hoops. My son had to have this hoodie. The tie die print makes it stand out, but the neutral colors pair with any number of shirts.

athletic long sleeved shirt, athletic pants, athletic shoes

This is probably my sons outfit of choice on most school days. He feels comfortable playing basketball at recess in the dry fit material and I appreciate the fact that he has long pants and sleeves to keep him covered on a winter’s day. The shirt is thin enough to layer under a thick outer layer and comes in multiple colors.

tilly's boys outfit
lightweight hoodie, slim taupe pants, sneakers

The taupe shade present in the camo print hoodie pairs perfectly with the slim taupe pants. This outfit is a step-up from the athletic apparel my son typically wears, but still “cool” enough for middle school. It is something he might choose to wear for a presentation, picture day or a school dance. I personally like the look of Vans or Converse for dressier occasions (as long as they are in good condition). These sneakers are currently on sale for $39.99 and the gray color compliments a multitude of looks.

Tip: If the white rubber on your sneakers has become soiled, use a small amount of whitening toothpaste on an old toothbrush to return the rubber to its former bright white.

Where to Shop

These stores have been our go-to shopping spots for my son this year:

  • Nordstrom (shoes, athletic wear)
  • Tilly’s (t-shirts, sweatshirts, joggers, pants, swimwear, socks, underwear)
  • Zappos (shoes)
  • Crewcuts (collared shirts, basic t-shirts)
  • Nike Outlet (athletic wear, shoes)
  • Under Armour Outlet (athletic wear, athletic underwear, golf apparel)
  • Gap (denim, underwear, pajamas, shorts, basic t-shirts, sweaters)
  • Vinyard Vines (khaki shorts and pants, collared shirts, t-shirts)


  1. Karen

    February 12, 2019 at 9:22 am

    Great article! What a good model (and good sport!) your son is. ๐Ÿ˜‰

    1. Parker

      February 12, 2019 at 9:52 am

      Thank you! He surprised me a little when he agreed to let me photograph him. Just getting my kiddos to smile for everyday photos can be a feat๐Ÿ˜‚

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