It’s back to school season and in the spirit of all those newly sharpened pencils and crisp clean jackets we’ll be interviewing Henry today about school, friends, wishes, fears, and San Francisco in collaboration with GapKids and this cool GapKids class of 2014 contest going on to. This age is just the sweetest. Henry still gives me huge hugs when I drop him off at school, and can’t sleep at night waiting for the tooth fairy to pay a visit,  but is starting to understand the small nuances of how the world works around him and his interaction with it. Oh, and not to mention the adorableness of their missing front teeth! Between Harper and Henry they only have one front tooth currently intact, and even that one is hanging on by a thread!

Keep reading for Henry’s in-depth interview (my favorite is what he would change if he were principal of his school and his favorite place to run around outside in underwear) and more pictures of his back to school outfit featuring clothing from Gap Kids: Graphic tee/Red puffy vest (a must have in San Francisco!)/Scout patch lunch box/Shadow western denim shirt(my favorite!)/Midtop deck sneakers/1969 Straight jeans (great fit and wash).

And stay tuned…next week we’ll interview his friend and fellow first grader, Harper.

Photography and styling by Liz Stanley. Assisted by Sara Albers. Thanks to our sweet toothless models, Henry and Harper.

What’s your full name? Henry Wayne Stanley

How old are you? 6 1/2

If you could be any age, what age would you want to be? why? I would like to be 16 so I could drive a car

What’s your favorite color? Golden or gold. They’re the same.

What’s your favorite book? The Magic Treehouse. Any of them. There are four of them.

Favorite food? Lots of foods. Pizza, brownies, dumplings, ice cream.

Anything you definitely will NOT eat? That yucky green thing with the big pit in the middle. Oh, an avocado?

What do you want to be when you grow up? why? I will want to be a police officer and then I can catch bad guys.

How do you think first grade will be different than kindergarten? It gets harder with each grade. Also my class is smaller this year.

What advice do you have for kids that are nervous about starting kindergarten? I will tell the teacher so they can help the kid know what to do. I was afraid on the first day of kindergarten and didn’t want my mom to leave.

What are you excited about in first grade? Yeah because it would be a new classroom with new stuff like maybe with desks and not tables

What’s your favorite subject in school (writing, reading, math, science, social studies, etc?) Writing words. I don’t like it at home though just at school. I don’t know why.

What’s one thing at school that you’re really good at? I’m good at sitting on the rug. I’m good at doing my journal too.

Favorite thing to play at recess? Kicking the ball on the wall and going on that spinny thing with Fountain.

If you were principal of your school what changes would you make to it? Only carrots allowed. But not for me, I get to have cake and only a tiny bit of carrot. And if you don’t eat your carrots you can’t have lunch.

What’s one thing you’ve learned to do lately that you’re proud of? Write not fancy ‘a’s’ but lowercase a’s that look regular

Do you have a best friend? What do you like about them? Yes, Fountain. He has short hair and he is crazy and I’m crazy too.

What advice do you have for kids who are nervous about making new friends at school? You should just say ‘Hi, what’s your name?’ and then you have a friend

Describe what a typical day is like for you after you come home from school? After school snack first. Then homework. Then playing. Then going out in the big city. I’m not a baby I don’t take naps.

What do you like about living in San Francisco? I like that there are cousins around and there’s my school that I really like

What don’t you like about living in San Francisco? I don’t like that there isn’t a waterpark close by

If you had three wishes what would they be? I want to have the biggest racetrack in the world, 10 billion lego sets and be batman

Can you describe your family? A baby whose 8 months old so she cries every day, a boy in 1st grade (that’s me) whose 6 1/2, a mom who does art projects with me, and a dad who is good at playing soccer and video games

Thanks Henry! I’m a huge fan of GapKids (and GapBaby as well for Edie!). So many cute things I wanted to share, here are some more favorites for boys this back to school season: stylish varsity jacket (adorable toddler modeling it below for GAP!), utility jacket (I want one in my size!), distressed straight jeans, hi-top sneakers in white

This post was sponsored by GapKids. While I was compensated to write a post about GapKids, all opinions are my own