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  • Welcome to TPK! This is your first of 2 free articles. For unlimited access to tutorials and articles, join TPK Premium for less than the cost of a latte.

    “Sleepy Hollow” Skull Halloween Card Tutorial

    October 8, 2020

    by

    Lindsey Bugbee

    Free Printables, Greeting Card Tutorials, Halloween, Intermediate Calligraphy

    Today’s Halloween card tutorial taps into the holiday spirit with excerpts from Washington Irving’s The Tale of Sleepy Hollow and a time-honored Halloween color scheme! With the help of a free printable, you’ll be well on your way to making an elegant and spooky greeting that will delight your loved ones.

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    "Sleepy Hollow" Skull Halloween Card Tutorial

    My goal with this skull-themed Halloween card is simple: make a playful yet refined seasonal greeting. I love a good skull motif (see: Frida Kahlo, Spooky Calligraphy Drills), so I decided to begin with a creepy cranium and take it from there! In today’s tutorial, I’ll show you how to make a card like this one.

    1. Print + Trace TPK’s Skull Outline

    To get started, download and print this skull outline.

    Skull Template
    You can print this out on any sort of printer paper; no need to get fancy!

    Next, place a 5″ x 7″ (127 mm x 178 mm) blank watercolor card over the skull outline printout, then place both the skull outline and the card on a light box. Go ahead and trace over the skull with a pencil. (No light box? No worries! You can read about economical light box alternatives in this article.)

    Tracing the Skull Outline
    I like to keep these blank watercolor cards on hand for convenience. It’s easy to DIY a blank card, though! Just cut a piece of watercolor paper to 10″ x 7″, (254 mm x 178 mm) then fold it in half. I prefer to use watercolor paper because — unlike cardstock — it responds well to a dip pen.

    Once you finish tracing, your card will look something like this:

    Pencil Skull

    2. Prep Your Skull for Calligraphy

    Now, use your pencil to make several wavy guidelines along the surface of your skull. These lines should be uneven, giving the skull a mummy-like quality.

    Calligraphy Prepped Skull
    Don’t worry too much about the neatness of these lines. Inconsistent letter heights will help certain words to stand out!

    3. Write Chilling Calligraphy

    Once you’ve drawn guidelines, look to the internet or your bookshelf to find Halloween-appropriate literature. I chose The Legend of Sleepy Hollow, which is a fun story by Washington Irving. It outlines the plight of Ichabod Crane, who falls victim to a practical joke. (I love Irving’s story because I’m a scaredy-cat, and the original tale is lighter than its later film adaptations!) When you’ve chosen your literature, use sumi ink and your favorite pen/nib combination to start writing spooky excerpts within your pencil guidelines.

    "Sleepy Hollow" Skull Halloween Card Tutorial
    Be sure to use plenty of calligraphy flourishes for this tutorial! For maximum visual impact, you want to fill in the skull as densely as possible.

    Continue to make your way down the skull with calligraphy. Don’t be afraid of awkward word splits or switching up lettering styles! Just do what you have to do to keep everything within the skull outline.

    "Sleepy Hollow" Skull Halloween Card Tutorial

    Once you’re finished with the calligraphy, your skull will look something like the photo below. Notice that the eye sockets, nose, and teeth remain untouched!

    "Sleepy Hollow" Skull Halloween Card Tutorial

    While you want the eyes and nose to be blank, the teeth do need a bit of TLC. I opted to fill each tooth in with two curved lines for an effect that has some Día de los Muertos flair.

    "Sleepy Hollow" Skull Halloween Card Tutorial

    4. Add Complementary Flourishes

    Black is the color of choice for Halloween, but this skull needs a bit more color to stand out! To that end, try using tangerine ink (or orange watercolor and the watercolor calligraphy technique) to add more standalone flourishes to the skull. Then, use your orange hue to write over select words.

    "Sleepy Hollow" Skull Halloween Card Tutorial
    I tried to focus on highlighting words that remind me of Halloween (darker, stars, Ichabod, misshapen, etc.).

    5. Erase Your Guidelines and Enjoy

    Once you’re satisfied with your skull and your ink has dried, use a good quality eraser to get rid of your pencil guidelines. Then, step back and admire your handiwork!

    "Sleepy Hollow" Skull Halloween Card Tutorial

    I’d recommend sending this off in a seasonal envelope like the one below! Slightly yellowed, vintage stamps (read about where to find them here) will put this Halloween snail mail duo over the top.

    12 Artistic Envelope Ideas | The Postman's Knock
    This flourished spider is from the Garden Edition calligraphy drills.

    I hope that you like this tutorial and that you modify it to suit your supplies and style! For example, you might try using a different piece of literature (Shakespeare’s “Song of Witches” comes to mind) or a different color scheme. Once you try your hand at this, I’d be thrilled to see your work on Instagram! (I love getting to look at tutorial interpretations.) You can tag me at @thepostmansknock.

    Thanks very much for reading, and have a wickedly wonderful weekend!

    Warmly,

    Lindsey's Signature | The Postman's Knock

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About the author

Hi, I’m Lindsey Bugbee, the illustrator, calligrapher, and author behind The Postman’s Knock (TPK). Since 2012, the TPK Blog has been a vibrant creative space filled with tutorials and lessons on modern calligraphy, hand lettering, and illustration. After publishing The Calligraphy Book, I wanted to elevate the quality of content even further—so I launched TPK Premium. You can join here to receive access to some of the internet’s best creative inspiration and project tutorials.

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88 responses

  1. Jalien Van Wesemael Avatar
    Jalien Van Wesemael
    October 19, 2020

    This would be amazing with the lyrics of the hocus pocus song to lure children ^^

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    1. Lindsey Bugbee Avatar
      Lindsey Bugbee
      October 27, 2020

      What a great idea!

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  2. Christa Avatar
    Christa
    October 19, 2020

    I’d like to try this on black paper with white ink!

    Log in to Reply
    1. Lindsey Bugbee Avatar
      Lindsey Bugbee
      October 27, 2020

      That’s such a cool idea 😊

      Log in to Reply
  3. Carolina M. Avatar
    Carolina M.
    October 19, 2020

    Love your work!!! It’s given me a lot of inspiration and a desire to continue learning and improving my calligraphy skills.

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    1. Lindsey Bugbee Avatar
      Lindsey Bugbee
      October 27, 2020

      Yay! I’m so happy to hear that 😊

      Log in to Reply
  4. Thi Harper Avatar
    Thi Harper
    October 19, 2020

    I’m so excited to try this! Thank you for the tutorial! 🙂

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    1. Lindsey Bugbee Avatar
      Lindsey Bugbee
      October 27, 2020

      Of course! Excited for you to try it 😊

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✍️ There’s a fresh addition to the TPK Catal ✍️ There’s a fresh addition to the TPK Catalog: The Graceful Ballerina Calligraphy Drill Worksheet 

This ballerina is unique among TPK calligraphy drills in that it’s really not that complicated. After a few simple loops, a flourished tutu, and long strokes to make the legs, you have, well, a ballerina! 🩰 The most difficult part is getting the outline right; but even that isn’t too bad because you’ve got a traceable outline included in your worksheet set.

The beauty of the flourished ballerina? She makes *anything* look elegant: cards, envelopes, gift tags, whatever. My recommendation is to feature her on your next envelope. She’ll add a “wow” factor and allow you to left-justify the address, which is always a relief (no need to bother with centering)!

To find her, visit the link in my bio, then navigate to the Blog!

#thepostmansknock #tpk #calligraphy #calligraphydrills #calligraphyworksheet #moderncalligraphy #pointedpen #pointedpencalligraphy #calligraphypractice #flourishing #flourishedart #mailart #snailmail #envelopeart #envelopecalligraphy #handlettering #creativeprocess #artistsoninstagram #balletart #ballerinadrawing #ballerinaart #inkdrawing #calligraphycommunity #stationerylove #letterwritersalliance #penandink #calligraphyinspiration #learncalligraphy #artistlife #creativeplay
✨I’ve been making these little calligraphy Chr ✨I’ve been making these little calligraphy Christmas trees for years. They’re a go-to whenever I need a quick gift tag, envelope flourish, or something festive that doesn’t require a whole afternoon.

They look fancy, but they’re really just simple strokes stacked in different patterns. Truly: once you get the rhythm down, you can make a tree in under 30 seconds. 🎄 

If you want to try them (there are six styles!), the tutorial is on the TPK Blog, and it’s called
“6 Simple Ways to Make a Calligraphy Christmas Tree.” Feel free to google it, or visit: thepostmansknock.com/6-simple-ways-to-make-a-calligraphy-christmas-tree/

It’s very beginner-friendly, video-based, and a great way to get some creativity in during a busy season. I hope you love it as much as I do. 💛

#calligraphy #moderncalligraphy #holidaycalligraphy #calligraphyart #creativelifehappylife #christmascrafts #holidaycrafts #giftwrappingideas #diychristmas #christmascards #calligraphytutorial #finetec #metallicwatercolor #papercrafts #creativepractice #thepostmansknock #holidayinspiration #blackandgold #christmasideas #holidayideas
🎁 These printable gift tags are one of my favor 🎁 These printable gift tags are one of my favorite free printables on the TPK site. Just download, print, cut them out, and — if you want to — reinforce them with a bit of cardstock.

Inside the PDF you’ll find four designs: Festive Frida, Flourished Tree, Pine Boughs, and Merry & Bright. They’re all hand-drawn, and they make even the simplest wrapping look bespoke and artistic. 🎨 

Pro tip: If you’ve got a bit of extra time, add a pop of watercolor or some gold dots; and consider mounting the tag on a contrasting piece of cardstock for extra oomph.

They’re free to download at: thepostmansknock.com/free-super-cool-hand-drawn-printable-gift-tags/ (or visit the link in my stories today). Happy holidays!

#handdrawn #gifttags #printablegifttags #freeprintables #holidayprintables #christmascrafts #holidaygifts #papercrafts #snailmailinspo #mailart #creativegiftwrapping #diyholiday #diygifttags #artistsoninstagram #illustrationartists #thepostmansknock #tpkcommunity #calligraphycommunity #stationerylove #creativecommunity
There’s something extra fun about a card that do There’s something extra fun about a card that doesn’t just open … it comes to life. ✨ This little stand-up tree might look fancy, but it’s totally approachable — relaxing to make, satisfying to embellish, and (my favorite part) it folds up perfectly to pop in the mail. 💌🎄

If you’re looking for a holiday project that feels creative and doable, this is *such* a good one. The printable template does half the work for you, and you can customize the rest with flourishes, white ink, ornaments, or whatever feels festive to you.

The full step-by-step tutorial is waiting for you on the TPK website; just head to the link in my bio and tap “Blog.” I think you’ll have as much fun making this as I did. ❤️

#calligraphy #calligraphytutorial #holidaycalligraphy #flourishedcalligraphy #moderncalligraphy #calligraphycommunity #calligraphypractice #calligraphyart #letteringcommunity #letteringart #papercraft #papercrafting #diycards #handmadecards #holidaycards #christmascards #christmascrafts #snailmail #snailmailrevolution #snailmaillove #creativecommunity #stationerylove #makersgonnamake #thepostmansknock
I love it when I can make simple pointed pen pract I love it when I can make simple pointed pen practice on cardstock ... and it magically turns into a festive card! Find instructions + a printable template for making this “Loop-de-Loop” tree in the TPK 2025 Holiday Calligraphy Worksheet set. 🎄 (Link in bio, then navigate to the Blog!)

#pointedpen #calligraphy #calligraphypractice #pointedpenpractice #holiday #christmastree #treedrawing #doodles #goldwatercolor
Every November since 2016, I’ve looked forward t Every November since 2016, I’ve looked forward to sitting down with a cup of something warm ☕️ and sketching out ideas for the TPK holiday worksheet. This year was no exception, and I think you’ll be pleased with the motifs! They’re designed to bring calm, beauty, and (sneaky) pointed pen practice to your holiday season. 🎄Visit the TPK Blog (link in bio, then navigate to Blog) for details!
The other day, I was thinking about sending out ho The other day, I was thinking about sending out holiday cards, and I immediately dismissed the thought with, “I have zero time to calligraph envelopes for those.” ✍️

... But is that true? I put it to the test for the latest article on the TPK Blog. Using some time-saving tricks I’ve learned over the years (like using a watery ink, a bouncy calligraphy style, and minimal pencil guidelines), I timed myself making three envelope concepts. Two of them took 5 minutes or less. The most time-intensive took 5 minutes, 30 seconds. The envelopes still turned out looking elegant, especially with the help of some artistic postage stamp collages. 💌

For clear step-by-step tutorials detailing how to make these envelopes and sourcing pretty postage, visit the TPK Blog (link in bio, then navigate to “Blog”)!

#snailmail #mail #calligraphy #pointedpencalligraphy #happymail #snailmailrevolution #mailbox #postage #vintagepostage
After I chose this music to accompany this reel, i After I chose this music to accompany this reel, it dawned on me: drawing a calligraphy medallion is like, well, Belle’s arc with the Beast. 

At first, it’s a bit of a weird situation. Strange shapes, questionable structure, possibly some growling (à la “YOU WILL JOIN ME FOR DINNER. That’s not a request!”) when the inevitable ink smudge happens. You keep thinking, “I’m not sure why I’m doing this ... should I hop on Felipe and gallop away?” 🐎

But something shifts as the medallion starts to come to life. And when you finish that last detail and pull back, the music swells. Light bursts from your paper like it did from Beast’s digits as he transformed into a stunningly beautiful prince. ✨ You’re practically in a ballroom celebrating, and, wait, did your furniture just turn into an adoring crowd that’s celebrating your fortitude and skill?

(And now you know how my mind works 🧠 ... I love a good metaphor, no matter how weak it may be!) 

To learn how to make a calligraphy medallion, just search for “calligraphy medallion” on the TPK site (link in bio). You’ll find both free Blog tutorials and detailed premium worksheets.

... I’ll show myself out now. 🙈

#pointedpencalligraphy #calligraphy #handwritten #pointedpen #dippen #calligraphymedallion #calligraphydrill #calligraphypractice
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