Back-to-School Shopping for Boys

Each year, I take my sons back-to-school shopping and it’s been interesting to watch their personal styles develop. My 10 year old son, N, has always had a clear idea of what he liked. It started in kindergarten when he wanted some “broken pants.” While he prefers to wear athletic gear, he’s just as comfortable with polo shirts, skinny jeans, and a fedora. Shopping for him can be challenging, though. He’s picky about his clothing and likes to find items that are somewhat unique and suit his personality. Once I had to drive to three different shoe stores to find a pair of sneakers that he liked and that none of his friends had.

This year, I went to Kohl’s (disclosure: I was provided with gift cards) to see if I could buy all of his back-to-school outfits in one place. At the store, I gave my son a budget and told him to select items he liked and meet me in the dressing room in about 20 minutes. He returned with a stack of clothing that I knew exceeded the budget.

“Did you check the prices on these items?” I asked.

“No,” he said. “I just grabbed stuff I liked.”

I shook my head and ushered into the dressing room. After several minutes of trying on clothes and eliminating items that didn’t fit properly, we got to the hard work of picking my son’s favorites. I reinforced the importance of remaining under budget as my son made his selections. He examined each item individually then paired them with other items. He replaced a few items because he realized that they were too expensive and that he could get two articles of clothing for the price of that single piece. After what felt like an eternity, made his final decisions. Here are a few of the outfits he put together:


Polo shirt by Chaps, Slim fit pants by Levi’s, Converse All-Stars


Helix shirt, Levi’s slim fit jeans, Converse All-Stars, Fedora hat.


Houston R0ckets T-Shirt by Adidas, athletic pants by New Balance, Shoes by Nike

My six year old son, X, who is going to first grade is a little easier to shop for. Although he is slowly coming into his own style, he takes his fashion cues from his older brother and me. While I’m flattered that he wants to dress like Daddy, my older son doesn’t want his little brother to copy his style.

Like other kids his age, X likes to wear Teenage Mutant Ninja Turtles or Batman T-shirts, but he also likes to get dressed up. For Father’s Day, he wore a navy blazer, jeans, loafers, oxford shirt, and tie. Later that afternoon, when I asked him if he wanted to change into something more comfortable, be said no. He told me that he wanted to wear that outfit every day. Although I’d love for him to dress like that on a daily basis, I decided to buy him outfits that were a little more practical for school. Here are a few of the outfits X and I selected:


After applying coupons and other discounts, I was able to get five full outfits for each boy, some school supplies (Kohl’s has partnered with Office Max), and a cool Batman watch for myself (my son is wearing it in the photos above) for $300. Although I still had to drive to the mall to buy some sneakers for N, I was pleased that I could get most of our back-to-school shopping done at one place. Now the hard part will be keeping the boys from wearing their new clothes before school starts.

Stay Strong,

mocha dad logo, mochadad





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About author

Frederick J. Goodall

Frederick J. Goodall is the founder of Mocha Dad - a parenting website focused on fatherhood. He is passionate about parenting and helping men to be great dads, husbands, and role models. You can contact him at or on Twitter at