12 Playful Lettering Styles. Learn 12 playful lettering styles with creative examples, and tips to help you add personality and charm to your hand lettering projects.
Learn 12 Playful Lettering Styles
As a lettering artist, creating new lettering styles is one of my favorite things. I just finished submitting the content for my third book with Better Day Books (an imprint of Schiffer Books), and part of that included creating over twenty new styles.
Playful lettering is where perfection takes a back seat, and personality gets to drive. If you’ve ever wanted your words to feel more expressive, more dynamic, or just a little more you, this post is for you. I’m walking you through 12 playful lettering styles that are easy to experiment with and perfect for adding energy, whimsy, and character to any project.
NOTEWORTHY
This blog post was originally a full-year lettering challenge (2025). Now that it’s over, I’ve updated this post for those who want to learn the art of playful hand lettering. For each style in this post, you’ll find:
- Trace-to-Learn Lettering Workbook: Includes a printable PDF and optional Procreate-format worksheets. A copy of the challenge from the newsletter is included in case you missed that month’s email.
- Free Video Tutorials: There’s a video lesson on my YouTube channel for each lettering style! The full playlist is linked below.
- 7 Tips for Creating New Lettering Styles: Be sure to read this foundational post about creating new styles.
- FAQs: Be sure to read the FAQs at the end of this post for tips on creating your own styles and more!
Lettering Style Videos (YouTube) →
Lettering Style Overview
- Optimist – A bold, beveled colorblock serif with bright, dimensional energy.
- Pinky Promise – A chunky, maximalist sans serif that celebrates playful excess.
- Joie de Vivre – An ornate, flower-garden-inspired decorative serif full of romance.
- Rainy Day – A moody serif with elegant teardrop terminals.
- Cover Girl – A glossy script and serif mashup made for headline moments.
- Milk Pop – A bubbly, retro style that practically bounces off the page.
- Rockabilly – A Victorian-inspired serif with vintage flair and rebellious spirit.
- Magical Realism – A swashy sans serif with romantasy-level drama.
- Afterglow – A sweet, ribbon-inspired script with playful twists.
- Midnight – A gothic-leaning mixed serif with an enchanting edge.
- Apricity – A modern blackletter with clean lines and confidence.
- Holly Jolly – A festive slab serif that’s bold, warm, and cheerful.
Style No. 1: Optimist – A Beveled Colorblock Serif
Optimist is a bold, beveled, colorblock serif that feels bright, dimensional, and unapologetically cheerful, like sunshine built right into the letterforms.
Here’s an example of how I used this style in a finished lettering piece.
Style No. 2: Pinky Promise – A Playful Maximalist Decorative Display Style
Pinky Promise is a maximalist style that layers on the drama with chunky shapes, playful details, and just enough flair to make every word feel like a celebration.
Pinky Promise Style Workbook →
Style No. 3: Joie de Vivre – an Ornate Flower Garden Inspired Decorative Tuscan Serif
Joie de Vivre is an ornate decorative serif blooming with garden-inspired details, delicate curves, and romantic flourishes that feel straight out of a storybook.
JOIE DE VIVRE STYLE WORKBOOK →
Style No. 4: Rainy Day – A Rounded Serif with Teardrop Terminals
Rainy Day is a softly expressive serif featuring elegant teardrop terminals that add a gentle, moody charm to every stroke.
Style No. 5: Cover Girl – a 90s Magazine Cover Inspired Script + Serif Mashup Lettering Style
Inspired by the 90s & Magazine Cutout Letters. Cover Girl blends confident script with high-fashion serif accents for a headline-worthy style that feels glossy, modern, and ready for the spotlight.
Style No. 6: Milk Pop – a Playful, Bubbly Style with Retro Vibes
Style No. 6: Milk Pop – a Playful, Bubbly Style with Retro VibesInspired by Milk and Boba Tea. Milk Pop is a bubbly, retro-inspired style packed with rounded edges and nostalgic charm that practically bounces off the page.
Style No. 7: Rockabilly – a Victorian-Inspired Serif Style with Vintage Flair and a Rebellious Spirit
Rockabilly pairs Victorian elegance with a rebellious twist, combining dramatic serifs and vintage flair for a look that feels classic but never tame.
Style No. 8: Magical Realism – A Romantasy Genre Inspired Swashy Sans Serif
Magical Realism is a swashy sans serif with sweeping curves and subtle drama, inspired by romantasy worlds where every word feels spellbound.
Style No. 9: AfterGlow – A Playfully Sweet, Ribbony Script
Inspired by cottagecore vibes with a hint of Romance and Charm. Afterglow is a ribbon-like script that twists and loops with playful sweetness, as if each letter were gently tied into place.
Style No. 10: Midnight – A Bewitching Mixed Serif with Gothic Vibes
Draws its magic from the starry night sky. Midnight is a moody mixed serif with gothic undertones, sharp contrasts, and just enough mystery to feel enchanting after dark. With high-contrast strokes and subtle gothic elements, it feels both mysterious and elegant.
Style No. 11: Apricity – A Blackletter with Modern Edge
Apricity is a modern twist on classic gothic penmanship, blending the bold strokes of the Pilot Parallel pen with a softer, more playful touch that reimagines old-world calligraphy for today’s creative work.
Style No. 12: Holly Jolly – A Slab Serif with Festive Flair
Holly Jolly is a slab serif lettering style that strikes the perfect balance between tradition and playfulness. Its bold, blocky serifs give it a classic foundation, while subtle curves and decorative details add a cheerful, festive flair.
I hope these styles inspire you to loosen your grip, trust your hand, and let your letters smile a little. Play is where confidence begins.
Happy Lettering!
