30 September Lettering Prompts: Daily Challenge!

Pumpkins, falling leaves, apple picking - summer gets all the fuss, but autumn deserves just as much attention. There’s beauty to appreciate falling down around us (cue the colorful leaves wafting down from the sky).

We’re especially here for the back-to-school vibes, which serve as a great reminder that:

  • We’ve literally learned everything we know

  • Learning can be both challenging and fun  

  • Everything requires practice 

Our September challenge is going to make practicing fun and easy for you.

Mindset: Even if it's just a doodle on a piece of scrap paper, find a tiny bit of time to practice every day.

Let's dive into your September lettering prompts!

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>> Learn how to write September in our monthly tutorial <<

Table of Contents

    30 September Hand Lettering Prompts

    Here are your September lettering prompts. Scroll past the prompts to read challenge instructions and tips!

    1. Hello, September

    2. Labor Day (September 2nd)

    3. Changing colors  

    4. Autumn loading

    5. School supplies 

    6. Harvest moon

    7. Apple cider

    8. Happy Grandparents Day (Grandparents Day, September 8th)

    9. Tea time

    10. Crisp air

    11. Always Remember (September 11th)

    12. Pens and markers

    13. Autumn awakening

    14. New books

    15. Let's learn (National Online Learning Day, September 15th) 

    16. Goldenrod

    17. Falling leaves

    18. School bus

    19. Pumpkin spice

    20. Harvesting

    21. Number 2 pencil

    22. Equinox (Autumnal Equinox, September 22nd)

    23. Football game

    24. Fall into autumn

    25. Corn maze

    26. Apple picking

    27. Acorns 

    28. Getting chilly 

    29. After my coffee (National Coffee Day, September 29th)

    30. Autumnal mood

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    List of September lettering prompts
     

    How To Join Challenge 

    Use any writing utensil and any lettering style to write the daily September prompts. If you’re new to calligraphy, a basic style such as faux calligraphy is great for beginners.

    Don't worry about perfection as you practice; these daily prompts are about repetition and building muscle memory. You succeed not by making the "perfect" composition, but by picking up the pen and writing as best you can.

    If you share on social media, tag us so we can see!! We love cheering you on.

     
    Jillian and Jordan doing daily lettering prompts

    We’re Jordan (left) and Jillian (right), and we’ll be doing the prompts right along with you!

     

    For a daily challenge reminder, join our Facebook group.

    Easy tip: Leave your brush pens, pointed pen, paper, etc. out where you can see them so that you see them every day and won't forget to practice!

    A fun way to improve your lettering is to play with new styles and tools. Here are three suggestions for this month.

    September Lettering Styles And Tools

    If you're feeling a little bored with your lettering, consider this your sign to try a new lettering style!

    Want even more inspiration? Browse the style suggestions from previous months.

    Brush Pen Lettering 

    Bring some of that “back to school” spirit of improvement to your work by revisiting the brush pen basic forms.

     
    "Equinox" calligraphy quote

    “Equinox,” prompt #22 written with Zebra Gold Brush Pen

    "Apple picking" lettering quote

    "Apple picking,” prompt #26 written with Zig Brushaables

     

    Gather a bunch of brush pen calligraphers together in a room, and everyone will be able to tell you which letter of the alphabet gives them the most trouble.

    There may be a very easy fix for those letter hang-ups! Look up your pet-peeve letter in our detailed letter-by-letter guide that shows common mistakes in every lowercase letter and how to improve them. Read it here:

    Flourishes 

    Calligraphy flourishes compliment every calligraphy style, whether you're flourishing Copperplate calligraphy or writing digital flourishes on your iPad (plus everything in between).

     
    "Goldenrod" calligraphy quote

    “Goldenrod,” prompt #16 written with a Pentel Brush Pen

     

    While part of calligraphy is a science (the angles, the uniformity, the tradition), flourishes are all art. There are some set flourishing rules, but the variations and compositions are endless.

    In our above "Goldenrod" example, you can see four different ways to flourish the same word.

    ...and this is just the tip of the iceberg!

    Learn flourishing with our free online course:

    Want feedback on your flourishing?? We have a dedicated flourishing membership that's only $7 a month and includes 2 monthly live calls!

    Color Play On iPad

    You can do ANYTHING on your iPad... which can almost make it hard to know what to focus on when you're looking to experiment. This month, let's take inspiration from autumn and play with changing colors.

     
    "Changing colors" digital lettering quote

    “Changing colors,” prompt #3 written with our Loveleigh Procreate Brush

     

    Here are two easy ways to do this:

    • Procreate color blending. Learn how to get the exact blended effect you see in our "changing colors" quote above.

    • Color-changing Procreate brush. With our free custom Procreate brush, your writing will change color based on how much pressure you apply. You can see a subtle example of this color-play in our below "September" example.

     
    September written in calligraphy
     

    September Project Ideas

    We can pull so much inspiration from nature while practicing these prompts September hand lettering prompts. Here are 3 changes to observe:

    • Color: Nature puts on its greatest show when we go from saturated cool colors to vibrant warm colors.

    • Space: New spaces open up in garden beds, on tree branches and in your home as kids go back to school.

    • Emphasis: Notice how emphasis shifts all around in both nature and our lives when we go from summer to autumn.

    Learn more about all of these elements in our composition and layout guide.

     
    "Happy Grandparents Day" hand lettering quote

    “Happy Grandparents Day,” prompt #8 written with a Tombow Fudenosuke

     

    Free Practice Sheets

    We have dozens of free worksheets that you have instant access to here at Loveleigh Loops. Each month, we highlight 3 that fit the month at hand. Here are September's practice sheets:

    • Grandma and grandpa in calligraphy. Celebrate your grandparents in honor of Grandparents Day on September 8th. Use our free worksheet to make the perfect cards! 

    • Letter Logic. Did you know that once you master the basic letterforms, you can create your own unique lettering style? Get started with our free Letter Logic worksheet (this is a piece of our paid course!). 

    • Copperplate stems (capitals). Go back to school by practicing your Copperplate capital letters with our Copperplate capital stems worksheet. 

    Click the link to download any (or all!) of these free practice sheets and get writing!

    We've also published a September video tutorial, perfect for planners or bullet journals:

    Next Steps

    Who's ready to embrace the changing season?! These hand lettering practice prompts will help you take stock of the beauty around you while improving your lettering.

    We have endless resources for you here at Loveleigh Loops, and we hope that you'll come back to visit our website and YouTube channel often!

    Join our other challenges!

    • May challenge: join

    • June challenge: join

    • July challenge: join

    • August challenge: join