How to make a wonky, playful font
Make a wonky font in Font by Zaweba with the Wonky preset or rotation plus a seeded random jitter, so each letter tilts differently but the same every time.

Playful fonts get their charm from letters that don't quite line up. The fastest way to make one is to tip each letter by a slightly different random amount. In Font by Zaweba the Wonky preset does this straight away, using the rotation operation with jitter: a fixed rotation of up to 45 degrees plus a random wobble of up to 30, controlled by a seed so the same font comes out every time.
What follows is a simple method, with a few touches that make a playful font look cheerful rather than messy.
Setting off on the right foot
Pick the job first. Wonky lettering is great for party invitations, children's posters, market stall signs, jam labels and birthday cards. It isn't for long paragraphs. Knowing it's for short text lets you push the effect further.
Have some real words ready to test with. A child's name, the title of an event or the name of a stall will tell you far more than the alphabet.
Building the font
Open Font by Zaweba and choose the Wonky preset. The preview shows straight away what the jitter does.
In the style stack, find the rotation operation. Adjust the jitter amount: a few degrees gives a gentle hand made feel; more makes letters tumble.
Try different seeds. The seed is a number from 1 to 99 that decides the random pattern. If one letter lands at an awkward angle, a different seed usually fixes it without lowering the jitter. Move through a few and keep the one where your test words look best.
Add a little fixed rotation if you want everything tipped the same way as well. A small amount gives a jaunty lean.
Soften it. Corner rounding makes wonky letters look friendlier, and a medium to heavy weight helps them stay readable.
Add a decoration if it suits. Stars, hearts, flowers and dots are built in, and they can be set to rotate with the stroke so they tilt with the letters.
Check the preview, name the font and export it.
Making playful look good
Keep one thing calm. If letters are rotating, keep the weight steady and the shapes simple. Too many effects at once make text hard to read.
Watch spacing. Rotated letters have corners sticking out in new places. Font redoes spacing after every change, but look at real words and use the kerning pair editor to fix and lock any pair that collides or gaps.
Remember that every copy of a letter looks the same. A font draws each character identically every time, so every e on a page shares the same tilt. That's what keeps a wonky font consistent, and it's why the choice of seed matters.
Test at small sizes. Playful fonts often end up on labels and cards, so check the bottom of the waterfall preview.
Other playful options
Rotation isn't the only route to fun. The Polka preset fills letters with dots. Pattern fills can use your own tiles drawn in the tile editor. Vertical shear and perspective give movement for posters. Combining a little of one of these with gentle jitter can be more interesting than a lot of jitter alone.
Once installed with Install for me, a playful font made in Font by Zaweba is ready to use in any program on your account, and its fixed seed means it will look just the same next year as it does today.