Donald “Drawbertson” Robertson is the head of creative development at Bobbi Brown, but outside of his full-time gig, he has made a name for himself as a social media-savvy fashion illustrator,  best known for ‘gramming up a storm with fanciful drawings at his every waking moment (that you can purchase through Trendabl). And he does it all so well that he was nominated for the 2014 CFDA Fashion Instagrammer of the Year Award (our fingers are crossed!).

There’s more—in addition to parental duties as a father of five and illustrating our monthly 20th Anniversary page (found on the last page of each InStyle issue this year), Robertson has squeezed in one more venture to his overcrowded roster: designing tees for J.Crew’s kids line crewcuts. He has recently released three girls tees (all pictured above), each wonderfully whimsical, cheerfully hashtagged, and priced at $40 at jcrew.com.

Needless to say, Robertson is one busy man, but the illustrator-turned-designer took a moment to type out his answers to all of our questions about his latest project, straight from his fingertips (and if you’re reading this on mobile) to yours.

How did the collection come about?
This super nice woman Michelle Copelman (brand curator and designer for J.Crew) follows me on Instagram (@donalddrawbertson)! She called me out on the comments bar. I was away in Asia on bizness so my daughter Drue and her friend Olivia went to J. Crew to meet with her. My daughter brokered the deal—she is 18.

What was your design process like?
Michelle and Drue hashed it out! Everyone is into my giraffe character #mitford, so they ran his baby picture on one.

Why did you decide to include hashtags?
Because we met on Instagram! So #madesense.

You have so many ideas (as seen on Instagram) – how did you narrow it down to three illustrations?
J. Crew weeded it down. I couldn’t. No way.

Will you be designing a T-shirt collection for boys? Or for adults?
Yes! We are now having regular play dates! I love Mickey Drexler and Jenna Lyons. They are doing such a great job with their brand. My whole family wears it. And I have five kids!

Will this be an ongoing venture?
Hope so.

What other projects do you have in the works?
I have a big show June 21st at the Eric Firestone Gallery in East Hampton hosted by my buddy designer Lisa Perry! It’s called #highfunctioningadd.