Summer Wardrobe Essentials for Tween Boys

Good Morning Friends! Was anyone else a little surprised yesterday to discover that it was already July? Summer is flying by! I am excited to be celebrating the 4th of July this week. It definitely ranks among my top three holidays. I love the feeling of community at a small town parade, eating yummy BBQ, and snuggling with my family while watching fireworks. Wishing you all a very Happy 4th of July🇺🇸

This post has the summer wardrobe essentials necessary to outfit your favorite middle school boy for the months ahead or at the very least pack for your upcoming vacation. Every item is not only comfortable, but appropriate for a wide range of warm weather activities. These closet staples were all my son needed for a family trip to Washington DC, our annual Lake Tahoe vacation and everything in between. My son picked out each of these looks from Tilly’s, Macy’s, Nordstrom and Zappos. He is wearing a boy’s size large (14-16) or size 27 in all of these items.

A Pair of Hybrid Shorts

t-shirt, hybrid shorts, flipflops

These shorts will be the workhorse of every boys summer wardrobe. A neutral pair of khaki, gray or black hybrid shorts will coordinate with almost every t-shirt, polo, and button-up shirt in your closet. Hybrid shorts create a look that can be cool and casual during the day or dapper enough for a dinner out. The hybrid fabric packs well and doesn’t require an iron. These shorts are dressier than athletic shorts, but feel just as comfortable due to the soft and stretchy material. They even serve as swim trunks in a pinch. For an everyday summer look my son likes to pair these shorts with skate and surf brand t-shirts featuring summer colors and prints. Add a pair of sneakers or flip-flops to complete this cool, casual look.

A Collared Shirt

collared shirt, khaki hybrid shorts

Every boy needs at least one collared shirt in his closet (or suitcase) for when a more formal occasion presents itself. This is probably the category that my son is most particular about what he will and won’t wear. After scouring all of his favorite clothing websites, this crisp, graphic, button-up shirt met his approval. The fact that it was on sale made the choice even easier.

A Comfy Outfit

similar cotton camo-print t-shirt, cotton shorts

A comfy outfit is an essential for a long airplane ride, road trip or just lounging around once you have reached your destination. This camo-sleeved cotton t-shirt and this pair of cotton drawstring shorts has been my son’s go-to travel outfit this summer. The soft, mid-weight cotton couldn’t be cozier. I appreciate that these shorts won’t snag like some of the polyester athletic fabrics tends to do from regular wear and tear.

Athletic Wear

dri-fit training shorts, logo t-shirt, socks, athletic shoes

It wouldn’t be summer without spending time outdoors working up a sweat. This pair of dri-fi training shorts and this t-shirt are what you will typically find my son wearing most days. The lightweight material keeps him cool while shooting hoops, going on family hikes, and riding bikes with buddies on hot summer days. At least one athletic outfit always finds its way into my son’s suitcase. It works for travel days, exploring new cities on foot, or more adventurous vacation activities such as zip-lining.

A Lightweight Layer

hooded windrunner jacket

This hooded jacket is a travel and closet essential. It is currently on sale at the Nordstrom 2019 Anniversary Sale. It easily layers over a variety of outfits when the wind starts to kick up or the sun sets. The waterproof fabric and hood is a lifesaver during a mid-summer storm. Neutral colors allow it to easily pair with almost every color in a closet. The zippered pocket keep money and technology safe when on the go. Although this jacket is the perfect weight for warm weather wear, I also see my son layering this jacket over a thick hoodie on a rainy, winter day.

Summer Footwear

A pair of flip-flops, sneakers and athletic shoes are the only shoes my son needs to see him through the summer months.

My son’s prefers mid-calf socks with fun patterns whenever he is wearing closed-toed shoes. This brand is his favorite. They hold up well and come in cool designs, but can be pricey.

Shopping Tip: Did you know that Stance has an outlet store at the San Francisco Premium Outlets in Livermore? At the outlet you can buy four and get two free. The wild designs are a big hit with middle school boys and make a great gift.


Flip-flops aren’t just for the beach and pool, but can also be worn around town. I find a leather pair is the most versatile option because they can be appropriate for dressier occasions such as going to dinner or attending an outdoor celebration. These flip-flops have a padded footbed which my son claims feel like pillows under his feet when he walks.


These sneakers are great for everyday wear and when you need to dress it up a little. They are also one of my husband’s favorite pair of summer shoes. The light gray fabric and tan soles look great with all the shades of summer including neon brights and pastels. A little soap and water on a clean cloth is all it takes to wipe away ice cream drips and keep these sneakers looking brand new. They are currently on sale.

Athletic Shoes

Owning at least one pair of athletic shoes is a no-brainer. They are going to offer the best support when running, hiking, biking and playing. This pair saw us through the second half of the school year and is still going strong. I always steer my son towards gray athletic shoes because most of his athletic apparel tends to be black or navy and these coordinate well with both. They are currently on sale.

Shopping Tip: The upcoming Nordstrom Anniversary Sale (July 19 – August 4th) is always a great opportunity to find name brand athletic shoes for a more affordable price.

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