September feels like a fresh page. The weather starts to change, routines shift, and small things begin to feel different. It’s the perfect month to mix calm observation with creative play.
This September Drawing Challenge gives you 30 thoughtful ideas to explore that feeling. Whether you’re a beginner, intermediate, or advanced artist, these daily ideas will help you sharpen your skills and enjoy the beauty of early fall.
Daily Prompts – September
Day 1 – A notebook or planner
Beginner: Simple closed book
Focus: Shape and proportion
Intermediate: Add pen, notes, or open pages
Focus: Use of space
Advanced: Scene of someone writing
Focus: Build a sense of routine
Day 2 – Falling leaves
Beginner: One or two leaves
Focus: Curved shapes
Intermediate: Add motion and detail
Focus: Show falling
Advanced: Leaves in a breeze
Focus: Use lines to suggest air and energy
Day 3 – A warm drink
Beginner: Mug or cup from the side
Focus: Keep it balanced
Intermediate: Add steam or shine
Focus: Show warmth
Advanced: Place it in a cozy scene
Focus: Build mood through light
Day 4 – An umbrella (open or closed)
Beginner: Top view or folded shape
Focus: Smooth curves
Intermediate: Add ribs or raindrops
Focus: Structure
Advanced: Scene with weather
Focus: Show movement or mood
Day 5 – A hallway or path
Beginner: Straight lines and space
Focus: Simple perspective
Intermediate: Add lights or doors
Focus: Guide the eye
Advanced: Scene with a person or animal
Focus: Use the path to build a story
Day 6 – Your favorite breakfast this season
Beginner: One or two food items
Focus: Clear shapes
Intermediate: Add steam, color, or texture
Focus: Show freshness
Advanced: Scene from the morning
Focus: Let light tell the story
Day 7 – Something you carry every day
Beginner: Simple shapes like keys or bags
Focus: Form and function
Intermediate: Add small details
Focus: Use and wear
Advanced: Place it in a daily scene
Focus: Let it show personality
Day 8 – A door with texture
Beginner: Rectangle with lines
Focus: Keep the shape clean
Intermediate: Add grain, cracks, or pattern
Focus: Show material
Advanced: Scene with mood or memory
Focus: Suggest age or use
Day 9 – Your favorite chair
Beginner: Basic seat with arms or legs
Focus: Structure
Intermediate: Add cushion or fabric
Focus: Texture and softness
Advanced: Someone using it
Focus: Use posture to express comfort
Day 10 – A scarf or soft fabric
Beginner: Curved, folded shape
Focus: Smooth lines
Intermediate: Add a pattern or light
Focus: Show flow
Advanced: Use in a cozy scene
Focus: Suggest warmth as a key element
Maybe you need some Clothes Drawing References: How You Get Better At Fabric Drawing
Day 11 – A window with autumn light
Beginner: Simple frame with a light shape
Focus: Straight lines and space
Intermediate: Add a shadow or soft glow
Focus: Contrast
Advanced: Scene through or around the window
Focus: Create a quiet mood
Day 12 – A stack of books
Beginner: Simple rectangles on top of each other
Focus: Balance and spacing
Intermediate: Add titles or details
Focus: Texture and form
Advanced: Place them in a lived-in scene
Focus: Let the setting tell a story
Day 13 – Your shoes after a walk
Beginner: Side view of one shoe
Focus: Keep shapes clear
Intermediate: Add dirt, laces, or wear
Focus: Use texture
Advanced: Scene with floor, bag, or setting
Focus: Show use and daily rhythm
Day 14 – A warm light source
Beginner: Candle, lamp, or window glow
Focus: Clear outline
Intermediate: Add light and shadow
Focus: Suggest warmth
Advanced: Scene with focus on light
Focus: Let light lead the eye
Day 15 – Something that helps you stay organized
Beginner: Calendar, planner, or box
Focus: Shape and spacing
Intermediate: Add writing or tools
Focus: Use of space
Advanced: Scene of daily setup
Focus: Structure with personality
Day 16 – A jacket or coat
Beginner: Front or side view
Focus: Keep proportions clear
Intermediate: Add folds or texture
Focus: Weight and flow
Advanced: Scene with someone wearing it
Focus: Use fabric to tell a mood
Day 17 – Something is changing with the season
Beginner: Leaf, sky, or object
Focus: Clear form
Intermediate: Add signs of change
Focus: Texture or light
Advanced: Scene with movement
Focus: Show time through detail
Day 18 – A view from your window
Beginner: One main object outside
Focus: Use simple shapes
Intermediate: Add background or shadows
Focus: Depth
Advanced: Full outdoor view
Focus: Tell a story through space
Take a look at this article for Landscape Drawing Ideas: Tips and Inspiration for Beginners.
Day 19 – A quiet street or sidewalk
Beginner: Simple path and trees
Focus: Perspective
Intermediate: Add shadows and objects
Focus: Use balance
Advanced: Full scene with calm feeling
Focus: Suggest time of day
Day 20 – A seasonal treat or snack
Beginner: One food item
Focus: Keep the shape clean
Intermediate: Add detail or setting
Focus: Texture
Advanced: Scene with hands or table
Focus: Build a story through taste
Day 21 – An old object you like
Beginner: Clean outline of the item
Focus: Shape and edges
Intermediate: Add signs of use
Focus: Surface and wear
Advanced: Scene from memory
Focus: Let emotion shape the drawing
Day 22 – A parked bike or scooter
Beginner: Side view with wheel lines
Focus: Structure
Intermediate: Add shadow or marks
Focus: Use of space
Advanced: Place it in a quiet setting
Focus: Stillness through detail
Day 23 – Something you wear in cooler weather
Beginner: Hat, scarf, or boots
Focus: Outline and form
Intermediate: Add folds and texture
Focus: Show material
Advanced: Use it in action
Focus: Suggest comfort
Day 24 – A backpack or bag with items
Beginner: Closed shape
Focus: Clean lines
Intermediate: Add contents or open flap
Focus: Layering
Advanced: Scene from a school or walk
Focus: Use setting to add feeling
Day 25 – A writing tool and paper
Beginner: Pencil or pen with a notebook
Focus: Size and balance
Intermediate: Add shadows or marks
Focus: Texture
Advanced: Scene in use
Focus: Tell a quiet moment
Day 26 – An autumn fruit or vegetable
Beginner: One item, like an apple or a squash
Focus: Roundness and smooth line
Intermediate: Add stem, marks, or color
Focus: Texture
Advanced: Scene with a table or a meal
Focus: Show freshness or warmth
Day 27 – A sweater or hoodie
Beginner: Front or side view
Focus: Keep the shape soft
Intermediate: Add folds, pattern, or zipper
Focus: Suggest weight
Advanced: Person wearing it
Focus: Show mood with pose
Day 28 – A corner of your home
Beginner: Pick one object and a wall
Focus: Straight lines and layout
Intermediate: Add light and shadow
Focus: Use space
Advanced: Scene that feels personal
Focus: Let it tell a story
Day 29 – A favorite fall memory
Beginner: One object from that time
Focus: Clear shape
Intermediate: Add a setting or detail
Focus: Suggest feeling
Advanced: Full memory scene
Focus: Tell the story gently
Day 30 – Your favorite sketch this month
Beginner: Redraw or color it
Focus: Add something new
Intermediate: Adjust the light or shape
Focus: Show growth
Advanced: Mix it with another idea
Focus: Build your own voice
You Finished The September Drawing Challenge – Let Change Inspire You
You watched the season shift and let your pencil follow. Every quiet moment, soft shadow, or new routine helped you grow. This month was full of practice and progress.
Keep that momentum going.
Keep the Challenge Going
→ Start the October Drawing Challenge
→ Browse all Monthly Drawing Prompts
→ Try the 52-Week Drawing Challenge
Share Your Art from September
Finished a drawing you’re proud of?
Post it on X, Pinterest, Instagram, or send it to someone by email.
Use #DrawyagerChallenge to show your art and find other artists on the same path.
