...the artist and designer on the other side of the screen! I run this show from my cozy little home office in Lexington, Kentucky, and I consider it a privilege to welcome you to my creative space.

When you’re here, you can expect to feel encouraged, confident, and inspired to dig into your creative side. My favorite way to share what I know is through my growing library of online courses, covering everything from lettering to Procreate to oven-bake clay earrings! In between classes, there are plenty of easy tutorials and fun content to be found on my blog.

i'm kiley bennett

Hey there!

In 2013, I started a blog called Kiley in Kentucky.

This humble blog about life in Kentucky soon turned into a place to share my love of crafting and easy DIY projects. When a move to New York City took Kiley out of Kentucky in 2014, that didn't stop me.

From the desk of my receptionist job at a top-tier ad agency, I taught myself how to brush letter.

And Kiley in Kentucky turned into a blog about lettering and art and all the things I was teaching myself how to do.

in 2016, desperate to go full-time with my art, I launched an etsy shop.

And moved to Southern Illinois with my husband, where he started graduate school, and I launched my print shop. By the end of 2016, it was clear that selling products and creating logos was not my passion. So, with nothing left to lose, as a last-ditch effort to keep my failing business afloat, I launched my first online class - Love How You Letter.

Well, not quite.

I shut that Etsy Shop down, and kept creating classes. In 2018, my first book, Super Simple Hand-Lettering was published (and has since sold over 100,000 copies), I joined Skillshare as a Top Teacher, and I shifted my creative focus to surface pattern design.

and the rest is history!

today, kiley lives in kentucky.

I teach on Skillshare, produce privately hosted classes, design fabric and wallpaper and blog about easy DIY projects and home decorating and I promise, I do not refer to myself in third person in conversation!

things were about to get interesting.

So, where does that leave
me and you?

My story

I started a blog called Kiley in Kentucky and blogged about life in the south. Soon, it turned into a place to share my love of crafting and easy DIY projects. 



I moved to New York City and got hired as a receptionist at a top-tier ad agency. It was there that I taught myself how to brush letter and use Adobe Illustrator to digitize my designs and doodles. I started blogging again, this time about lettering.


Desperate to go full time with my art, I launched an Etsy Shop and moved to Southern Illinois with my husband. By the end of the year, it was clear selling products and creating logos was not my passion. So, with nothing left to lose (literally and figuratively), I launched my first online class!


By 2018, my business was running on online courses! I taught a class with Brit + Co, and I published my first book, Super Simple Hand-Lettering. I also became a Skillshare Top Teacher. This was a huge year of self-discovery and new opportunity for me. 


I began teaching myself how to sew, and my love of fabric design started to grow. I invested in education to learn the ins and outs of surface pattern design, and made a decision to pursue this new area of my business.


While creating my first fabric collection, I started working on my second book, 'Super Simple Hand-Lettered Projects' that released in May 2020. In September, I launched my first business-to-business course, Crafting Online Courses.


A year of growth for me, I took the time to evaluate what I really wanted to do and the direction I wanted to take in my career. I continued to release Skillshare classes and work on different passion projects, but took a break on any big endeavors.


Several years of hard work in developing my fabric design portfolio resulted in my first ever licensed collection! I am gearing up to re-release an updated and improved version of Crafting Online Courses, and relaunched my blog to the world! And I am just so happy to have you here ❤️


tell me more, tell me more



anywhere with a beach


The Real Housewives


to write romance novels




fabric collections. always!


helping you learn new skills


open a storefront