Lettering for Designers: One Drop Cap Letterform at a Time

By ·Letterer and Illustrator

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or Purchase for $25

Free With Membership

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Class Project

Create a drop cap letterform for your favorite book

I've been lettering for years, working on all sorts of projects from Wes Anderson movies, to David Eggers book covers and for every lettering project the basic unit is the same: a single letter.

In this self-paced class I'll teach you my process, starting with just that - a simple and beautiful single letter in the form of a drop cap. A drop cap is the large letter that starts a chapter in a book - an artform found in manuscripts dating back 2,000 years.

What You'll Learn

I'll teach you my lettering process along with plenty of the tips and tricks I've acquired over the years. We'll cover:

  • Research. The importance of starting small and picking the right book.
  • Brainstorming. Getting ideas out of your head and onto paper.
  • Sketching.  I'll share my sketch books and sketching process and walk through how letters are designed.
  • Digitizing. Tips and tricks for Illustrator, including how to use handlebars and where to place your vector points.
  • Critiquing. How to critique your own work and get those perfect finishing touches (ahem, perfect curves). 

What You'll Do

Building off Daily Drop Cap - a project I started in September of 2009 in which I illustrated a decorative letter every day (or at least every work day) - you'll design a drop cap of your own inspired by your favorite book. 

Daily Drop Cap Project x Penguin Books

After the Daily Drop Cap project, I'm now working with Penguin Books on Penguin Drop Caps, a series of twenty-six collectible hardcover editions of fine works of literature, each featuring on its cover a specially commissioned illustrated letter of the alphabet by yours truly! A collaboration between myself and Penguin Art Director Paul Buckley, whose series design encompasses a rainbow-hued spectrum across all twenty-six books,

Penguin Drop Caps debuted with an 'A' for Jane Austen's Pride and Prejudice, a 'B' for Charlotte Brontë's Jane Eyre, and a 'C' for Willa Cather's My Ántonia, and continues with more perennial classics from Penguin.


This is an intermediate level class because prior knowledge of Adobe Illustrator is required. Students should have access to Adobe Illustrator which you can download a free trial of at Adobe.com

Level: Intermediate

Jessica Hische

Letterer and Illustrator

Jessica Hische is a letterer, illustrator, and self-described “avid internetter”. After graduating with a degree in Graphic and Interactive Design from Tyler School of Art, she worked for Headcase Design in Philadelphia before taking a position as Senior Designer at Louise Fili Ltd. While working for Louise, Jessica also maintained a busy freelance career and after two and a half years of little sleep and a lot of lettering, she left to further her freelance career and embark on several personal projects.

Jessica has become as well known for her side projects as she has for her client work. While she doesn’t consider herself a web designer, many of her personal projects are web-centric. Her project Daily Drop Cap, is probably the reason you first stumbled across Jessica’s work, and she’s created several educational micro-sites including Mom This is How Twitter Works, Should I Work for Free? and Don’t Fear the Internet (a collaborative project with Russ Maschmeyer).

Jessica’s clients include Wes Anderson, Tiffany & Co., The New York Times, Penguin Books, Target, Leo Burnett, and Wired Magazine. She’s been named a Print Magazine New Visual Artist (20 under 30), one of Forbes 30 under 30 in Art and Design, an ADC Young Gun, and a “Person to Watch” by GD USA.

She is currently serving on the Type Directors Club Board of Directors.

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    • At a Glance

    • Membership Class

      Free With Membership

      Become a member to get access to this class for only $9.95 a month. Or, purchase individually for the list price.

      Learn More

    • 12 Video Lessons
    • 6.2K Students
    • 99% Positive Reviews (82)
    • Self-Paced Online Class
    • How does an online class work?

      Classes revolve around completing a project and collaborating with fellow students to give and get feedback on your work. Use Video Lessons and the Project Guide designed by your teacher to complete your class project.

    • Do teachers give project feedback?

      Teachers design and present all class content, but Skillshare is community based around student-to-student interaction. You'll be surprised at what you learn from your classmates!

    • When does a class end?

      Never! Once enrolled, you have lifetime access to class materials. That means you can learn when and where you want. Learn at your own pace.

    See All
    Free with Membership
    or Purchase for $25

    Free With Membership

    Become a member to get access to this class for only $9.95 a month. Or, purchase individually for the list price.

    Learn More