For the past three years, I cut Toby’s hair myself. But I had no clue what I was doing! He would end up with shaggy hair and Dumb-and-Dumber bangs. Thankfully, this weekend, my friend Reagan, a hair stylist, agreed to teach me…

This is the tangled mess we were working with. I would literally cut off tangles every few days, resulting in bald patches at the back of his head!

Our handy list of tools: a blanket and clothespin to cover him up, a spray bottle of water, a comb, cutting shears and a Trader Joe’s lollipop. And we washed his hair with Honest shampoo, conditioner and used their genius conditioning mist, which detangles hair and calms cowlicks.

Reagan started by spritzing his hair with water. And I learned my first lesson: Toby didn’t like getting his hair sprayed and asked Reagan to stop—so she stopped immediately and said she could cut his hair mostly dry. “If you start off on the wrong foot with children, you can’t build back their trust,” she explained. “Scissors shape the hair more easily if it’s wet, but no worries if the kid doesn’t want to do that!”

She explained that a haircut is a collaborative effort between you and the child. “No kid’s haircut is ever perfect,” she laughed. “They’re wriggly, they’re restless, so you have to move quickly and do what you can.”

We also kept Toby entertained with the strawberry lollipop, Peppa Pig videos on my phone and lots of impromptu singing and dancing. Reagan asked him to get his wiggles out in the photo above, and it worked!

Three tips from Reagan:

1. Start around the ears because that’s when the child will be calmest. You want to be really careful around the ears, so you don’t cut them.

2. Take vertical sections (parallel to the wall, not the floor). And then cut with your scissors at a 11 o’clock angle, versus parallel to your fingers. This technique allows for mistakes, blends the hair and helps it grow in more nicely. Otherwise, if you cut parallel to your fingers, you’ll end up with one thick blunt panel.

3. You establish your lengths with the first section you cut. Then, as you start working around the head, you can take a little bit of your previous section as your guideline, so you know how short to go.

(If you’re cutting a girl’s hair, part the hair in the middle, pull everything to the back and then just cut a pretty straight line—with your scissors at 11 o’clock, like above, so it has a soft, textured line. Cut the back first, and whatever is in front of the ears and forward, you can pull straight down to the sides and connect with the back hair to make sure it’s even.)

To cut bangs, pull them straight down and cut at 11 o’clock. “Easy does it,” says Reagan. “I’d rather cut the bangs a couple times to get it right, versus accidentally cutting them too short.”

Afterward, I sprayed his cute cut with some Honest conditioning mist to keep it detangled and silky. (I actually use this on my own hair now, too!)

Meanwhile, Anton was totally entranced by his big brother. (And how awesome are those bike diapers?!! I love them so much.)

Well done, Tobes!

Do you cut your child’s hair? Any tips (or funny stories) to share? I used to cut it in the bathtub and would lean all the way over Toby to get to the other side of his head—totally treacherous!

Thank you to The Honest Company for sponsoring this post. Honest makes natural baby, bath and cleaning products, which we love and use every day for our family. How cute are their spring diapers? I love the giraffes.

Bonus for all readers: Get 30% off your first-time purchase with the code JOSAVE30 (limited to shop orders only; one per customer). Applies to U.S. and Canadian residents. Good until March 31st.

P.S. Four hair tutorials for little girls.

(Photos by Alpha Smoot for Cup of Jo. Hair tips by Reagan Baker. This post is sponsored by The Honest Company, whose mission I adore. Thank you so much for supporting the sponsors that make Cup of Jo possible.)