Lettering: Tips for Drawing Letters


Annie Dailey


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A few months ago, I hosted a skill-share for the Design Team at Lattice on some tips for lettering. I’m a self taught letterer, with plenty of room to grow, but it’s a medium that I’ve enjoyed for many years and was thrilled to have the chance to share some of my learnings. In the spirit of that skill-share, I wanted to share some tips on the what, why, and how of lettering!

What is it?

There’s a quote from Jessica Hische, a well regarded and very talented lettering artist, that I think perfectly explains what lettering is and how it compares to other letter-based art forms. She says: “Lettering is drawing, calligraphy is writing, and type/type design is a system of letters.”

When it comes to lettering, it’s not about building a typeface or writing an essay - we’re drawing letters using shapes, curves, textures, and colors to convey a message.

Why do it?

I got into lettering many years ago as a way to reflect on my day-to-day life, capture memories, and play around with different letterforms. I was intrigued by the seemingly endless styles of letters and the incredible ways artists could transform a simple statement or word into a work of art. I’m not a particularly good writer, but I am a good drawer, and lettering allowed me to express myself using skills I already had while tapping into some of the benefits of journaling - therapeutic reflection and mindless documentation. I’ve used lettering as a way to remember places I’ve gone, spotlight silly phrases I’ve heard, and reflect on moments in culture or politics. I’m also a big fan of wordplay and lettering is a medium that welcomes a good pun :)

What I especially enjoy is the illustrative and decorative forms lettering can take. Unlike calligraphy or type design, lettering can be very free form. You don't necessarily have to follow the conventional rules of type design because it's not meant to be used as a font. You’re creating a singular piece of artwork, not writing an essay!

How I do it

There’s really no right or wrong way to develop a lettering piece - it comes down to how you like to work and the tools you use. I like to start with pencil and paper to sketch out concepts or phrasing and play around with compositions. If I’m working on something that is a bit more complicated I’ll use tracing paper to trace over my original sketch and slowly start to refine. Then I’ll scan the image to begin digitizing and refining using Illustrator, Photoshop, or Procreate on the iPad. Once I’m working digitally, I can begin experimenting with colors, textures, and effects.

Who I look to

Lettering has really grown over the years as a medium and career for a lot of artists. With access to so many tools and educational resources, it’s never been easier to learn new ways of lettering. There are also endless resources to pull from which can be really inspiring and fun to experiment with. When I start a new lettering piece, I often look to Instagram or Pinterest for inspiration. Artists like Jessica Hisch (who I quoted earlier) and Lauren Hom are not only extremely talented, but are also dedicated to sharing their process and methodology to their audience. I often look to them specifically for ideas on technique and how to create a compelling piece. Here are a handful of other artists I look to for inspiration:

Tips for Lettering

Let’s get into some quick tips for drawing your letters!

1. Use a reference

Beyond looking at other artists’ work, it can be really helpful to have a point of reference when you’re thinking about the type of letters you want to draw. I use Pinterest a lot for this purpose because there are a surprising number of accounts that share scans of type specimens. It can be useful to look at the construction of single letters and try to expand on the style rather than replicating a completed lettering piece from another artist.

2. Use simple shapes

When you start drawing your letters, consider basic letterforms used in typography such as script, serif, sans serif, and slab serif. This is where using a reference can help inform the style you want to take on. Consider the shapes that make up the letter and start with simple lines and curves. When digitizing a piece, I use the Pen Tool to refine my letters and build more complicated shapes. If you ever want to try and improve your Pen Tool skills, digital lettering can be a great way to practice and it can really open up the possibilities for how you create your piece.

3. Use space with intention

Because lettering doesn’t strictly follow traditional rules of type design, you can really play around with how letters relate to each other without needing everything to sit on the same baseline (the imaginary line where a line of text rests). Take advantage of the negative space created by letters to add interest and create a balanced composition. This can be accomplished by using different letter sizes, widths, and styles.

4. Use layout grids

When lettering a piece with multiple words, it can be challenging to have balance and hierarchy. Layout grids are essentially containers to guide you in building your composition.They can be used as strictly or loosely as you want, while helping to map out how multiple words fit together. Instead of using straight lines, like a regular block of text, you can use guides to incorporate curves, angles, and scale to the overall composition. This will help drive emphasis towards certain words and establish hierarchy in your piece. Here are a couple of examples of layout grids that I often go to as a starting point:

5. Consider hierarchy

Just as layout grids can help drive emphasis to specific words, there are other ways to establish hierarchy in your piece. Things like color, size, shape, weight, and style will not only make your lettering more engaging, it can help guide the viewer in how to read the piece.

6. Play with effects

There are a few go-to effects that I often use because they are not only fairly easy to apply, but they add nice contrast and detail to the lettering. There’s the inline effect where you add a stroke as a highlight to the inside of the letter. The drop shadow and drop line effect add dimension and contrast by bringing the letter to the forefront of the composition.

There are endless effects that can be applied to letters, and they are a great way to experiment and learn new techniques. Things like color, texture, and decoration can do a lot to make your piece truly unique!

Bonus Tip: Find something to say

Sometimes the most challenging part of lettering is deciding what to say with your letters. Fortunately, Loren Hom has built a tool to answer that question: what should I letter? It’s literally called WTF Should I Letter and it generates phrases that are lighthearted, and punny so you don’t have to. So if you ever get stuck trying to think of something to letter, this is a great resource. Happy lettering!