Letter Like a Boss – My Favorite Tutorials for Learning Lettering

I just recently reached my one-year calligraversary, and I can’t believe how much my lettering has improved. Here’s a quick before and after, if you need proof that practice pays off.
My first hand-lettered post on Instagram:

A recent hand-lettered post on Instagram:

I can't believe how quickly July flew by! #helloaugust #ipadlettering #procreatelettering

A post shared by Alexis Gentry (@alexisgentry) on

So how did I go from the first one to the second one? Where did I start? What tips and advice can I give to people who are just beginning with lettering?

The number one thing you can do to improve your lettering: practice. I have done some kind of lettering almost every single day for a year. My Camera Roll is filled with photos of lettering I’ve done with Crayola markers, Tombows, and my personal fave, an iPad Pro and Procreate. Practice makes your hand steadier, it gets you used to pressure and speed with a marker or with an Apple Pencil, and it makes you feel more confident to try out something you might have seen online. For me, practice never feels like work. I love lettering, so it’s something I do to mellow out at the end of the day or to take my mind off work during my lunch break. If you really love it, practicing all the time is easy and fun.

Okay, you know you need to practice, but you want to take it a step further and learn some new techniques. My advice: start with YouTube. Almost everything I learned about using Procreate on iPad Pro came from watching YouTube tutorials. I have lots of favorites, but here are a few I found particularly helpful…

If you’re learning lettering or design, you just have to follow every-tuesday. Teela makes some of the best tutorials of all time and her class on fontmaking opened up a whole new world for me. She also has some excellent classes on Skillshare that are definitely worth checking out if you have a membership.

Karin from ipadlettering is another amazing person you should be following on social media if you want to learn to letter on iPad Pro.

Tara from Rad & Happy has a few really good ones, including this one on some great Procreate features:

Dawn Nicole has a good one to give you a glimpse at iPad lettering with Procreate:

Ian Barnard has a great one about adding gradients and shadows:

And once you’re ready to move on to more advanced stuff like creating your own Procreate brushes, Halfapx has an awesome one that takes you through everything you need to know about making a Procreate brush:

Lastly, I would highly recommend following Grace Frösén on Instagram. Her lettering is beyond beautiful, and just watching how she creates her shapes can inspire you to give flourishing a try.

Instagram is your best friend when you’re learning lettering, so browse the #handlettering tag or check out all the great #ipadlettering you can find in that tag. And, of course, follow me @AlexisGentry.

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