As the mom of two energetic little boys, I’ve come to terms with their fashion choices, which mostly consist of an array of Minecraft shirts, Skylanders underwear, and skull-patterned socks. In the early days, I dressed my firstborn in collared shirts and plaid shorts, delighting in the preppy look. However, as he grew, his clothing style shifted to a mix of cartoon characters and video games that are rated “E” for everyone—a trend he has happily passed on to his devoted little brother. Consequently, I’ve stepped down from my role as fashion director. Or maybe I just got a bit lazy. The days of leisurely browsing the Babies”R”Us sections, marveling at tiny overalls, are now replaced by rushed trips to Target, where I grab milk along with some last-minute pajamas.
Despite all of this, one aspect of my sons’ appearance that I’ve held onto is their haircuts. From the moment my oldest was able to sit still long enough to wear a barber’s cape, I’ve cherished our trips to the barbershop. The buzzing clippers, the vintage photos of classic men’s haircuts on the walls—it’s all part of the charm. There’s something nostalgic about watching a line of boys and young men, patiently awaiting their turn, that feels like a glimpse into a simpler time.
Perhaps my fondness for barbershops stems from my own upbringing. As the eldest of four sisters, I endured homemade bowl cuts on a kitchen stool, leaving me to gaze longingly through barbershop windows, convinced they were places for boys—boys who didn’t stress about their looks. Those boys could get haircuts without fear of judgment, embracing comfort and simplicity in their style.
As I grew older, the pressure of femininity—first periods, training bras, perms, and blue eyeshadow—made me yearn for the carefree nature of boyhood. I imagined waking up one day as a boy, slipping on the first fresh T-shirt I found, and stepping out into the world ready to be judged for my coolness rather than my looks. Since I couldn’t live that dream, I decided to experience it through my sons.
I know that one day, my boys will likely have more to say about their hairstyles, but for now, their ages and lack of interest in styling gave me the upper hand. So, I confidently took my 5-year-old to the barbershop a few days ago. His hair had grown faster than usual, likely due to the summer heat, and I figured a shorter cut would be easier to manage. “Sure,” the barber said, wrapping the cape around my reluctant son. “I’ll do a No. 1 on the sides instead of a No. 2. That should last until school starts.”
Ten minutes later, after a dusting of hair was brushed off his shoulders, my son faced the mirror—his expression instantly transformed from anticipation to devastation. “Too short!” he wailed, arms crossed protectively over his head. I offered a reassuring smile to the barber while internally cringing at my son’s reaction. It was short, but not extreme—definitely not the shortest he’d ever had. Still, the drastic change from his longer style was likely a shock.
“You look amazing!” I encouraged him. “So handsome!” But he merely glowered, still shielding his head as we walked to the car. “Too short, too short, too short…” he chanted as he climbed into the backseat. “I look bald!”
I rolled my eyes through the rearview mirror. “Come on, it’s just a haircut,” I muttered.
Over the following hours, I tried various tactics to ease his distress, each one less effective than the last. “You look older,” I said. “Like you’re almost 7!”
“I look old and bald,” he retorted.
“Plenty of little boys get their hair cut this short for summer,” I reasoned.
“Not anyone I know,” he insisted.
“Daddy has really short hair,” I pointed out. “You look just like him.”
“No, I don’t,” he argued.
Finally, I admitted, “I’m sorry it turned out this short. I didn’t think you’d mind. I won’t have it cut this short again, okay? But it’ll grow back in two weeks.”
“I want to wear a hat to camp,” he demanded.
As much as I wanted to remind my 5-year-old that he was overreacting, I paused. His main concern was that everyone at camp—kids and adults alike—would tease him for being “bald.” It was challenging to explain the absurdity of his worry, but I understood how a simple haircut could spark such anxiety.
Forty-eight hours later, he still refused to leave the house without a baseball cap pulled tightly over his ears. I couldn’t help but admire his determination. “Did he keep his hat on in the pool?” I asked the camp counselor when I picked him up.
“No,” she chuckled, “but he kept his arms over his head most of the time.”
While his reaction seemed dramatic, I realized I could relate. How many times had I worried about fitting in on the first day of school? The anxiety of being judged for my outfit or hairstyle was all too familiar. My son, who usually expresses himself freely at home, was clearly struggling with the idea of standing out.
Eventually, I recognized that my assumptions about boys being carefree were simplistic and unfair. My son is proving to have a keen awareness of how he wants to present himself, and within reason, I’m ready to support that—just no ponytails or mullets, please.
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In summary, navigating the world of haircuts with my boys has opened my eyes to the emotional stakes tied to appearance. As I support their choices, I’m reminded that self-expression is important at every age—even if it comes with a side of drama.