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Learn How to Match Fonts

with Visuals Like A Boss

Some things just go perfectly together.

Peanut butter and jelly…

Fireplace seats and a good book…

snow days and chicken noodle soup…

and the secret to great design is good pairing too.

When typography (font) is paired well with your visuals the viewer doesn’t have to stop to think about what to look at first. They can seamlessly read through the text and connect it to the image without being subconsciously distracted by the mix-match.

In today’s lesson I’m going to show you examples and tips for pairing your visuals with the right type for quicker conversions. I’ve created a video for you showing how I pair type with specific illustration styles along with the same cheat sheet that I give to my custom template clients with a list of fonts that pair well with hand-drawn illustration.

A Quick Review: The Idea of Hierarchy 

The main thing to remember is that fonts have a weight value (how hard they draw your eye) and they take up space in different ways. Here are some examples to show you the different kinds of fonts. (I expand upon this in the video below these images).

Fonts that illustrate on their own (needs minimal illustration because it already has lots of personality):

Fonts that pair well with thin inky lines (Serif and Script):

Fonts that pair well with stamped or hand-carved illustrations (handwritten, brush or distressed):

Fonts that pair well with well stamped or hand-carved illustrations (handwritten, brush or distressed):

It’s All About Balance

If you have a font that’s full of personality, pair it with minimalistic visuals (like shapes, color, and simple icons).

If you have a detailed illustration, pair it with simple easy to read fonts.

If you’re ever concerned about whether a font pairs well you can always shoot me an email or go to and see what kind of fonts were paired with similar illustrations when they showcase them in the shop. Most illustrators have some sort of text pairing suggestion with their product already.

Here’s a video where I walk through pairing fonts to help you get an idea of what to look for: 

DESIGN TIP: When in doubt, look at the lines in the illustration. Whatever thickness they are, go with that same thickness in your fonts. 

And… whatever the illustration’s mark style is (painted, hand-drawn, pencil, ink, watercolor, computer lines, etc) use the same kind of style in your fonts. You can use your font pairing cheat sheet to help you figure out how your illustration’s mark style.

Your Action Step:


Your action step is to write down the fonts you already have for your brand and find some illustrations that match it. 

If you don’t have brand fonts yet, take a look at the video and see which fonts match the feeling you want your audience to have. Start using the fonts you choose consistently so your brand can remain as one solid entity even between platforms and posts.

Happy pairing!!

The Littlest Guide Shop is all about support and education. If you are wondering what illustration can bring to a project, what branding looks like for a small business/ solopreneur or just want some support brainstorming just click the photo above.

Can I help you find something?

A Note from the Illustrator:

Did you know that my clients get access to me whenever they need advice on a typography pairing or design question? It’s one of the perks of investing in the Visual Voyage. Curious what else is included? You can check that out here.