Here is a list of 100 command prompts for portrait painting, categorized by the stages of the creative process.
1. Preparation & Conceptualization
Select the subject based on a story, not just a face.Determine the one core emotion you want to capture.Choose a pose: full-face, 3/4 view, or profile.Design the lighting: Rembrandt, butterfly, loop, or side light.Plan the composition using the Rule of Thirds or a dynamic symmetry grid.Choose the format: head-and-shoulders, full-figure, or environmental portrait.Select a color palette: limited, analogous, complementary, or a Zorn palette.Prepare your canvas with a toned ground (e.g., imprimatura) in a neutral gray or umber.Create five 1-minute thumbnail sketches to test compositional ideas.Decide on the background: a solid tone, an abstract texture, or a specific location.Analyze the subject's primary facial planes (e.g., using a planes of the head model).Pose the model (or reference) to create a clear division of light and shadow.Choose your primary brushes (e.g., flats for structure, filberts for turning form).Mentally separate the subject from their likeness; focus on shapes and values.Establish the eyeline and head tilt before making a single mark.
2. The Block-In & Underpainting
Use a large brush to draw the main gesture and "big" shapes.Establish the head's basic structure (e.g., using the Loomis method).
Map the center line and the main horizontal lines (brows, nose bottom, mouth).Block in the largest shadow shapes with a single, thin value (e.g., Burnt Umber).Mass in the hair as one simple shape, ignoring individual strands.Use negative space (the background) to define the silhouette of the head and shoulders.Check all initial proportions: eye width vs. nose width, eye-to-mouth distance, etc.Establish the darkest dark and the lightest light on the canvas.Block in the clothing and shoulders as simple geometric forms.Create a monochrome underpainting (grisaille) to establish all forms.Use a "verdaccio" (greenish) underpainting for skin tones.Focus only on value, not color, for this entire stage.Squint your eyes to simplify the subject into 3-5 main value masses.Establish the large, dark shape of the eye socket (the "bed of the eye").Re-check the "big-picture" likeness from 10 feet away before proceeding.
3. Building Form & Color
Mix a "mother" skin tone: the dominant midtone of the face.Mix a "light" color family and a "shadow" color family for the skin.Observe the color temperature: are the shadows cool or warm? Are the lights cool or warm?Paint the planes of the face, starting with the midtones.Add the shadow masses, focusing on their color, not just their darkness.Add the light masses, noting where the light is most direct.Focus on the "form-turning" (terminator) edges, not just cast shadows.Observe and paint the "halftones" that bridge the light and shadow planes.Identify and paint areas of reflected light within the shadows (e.g., under the chin).Use a palette knife to apply thick, structural paint (impasto) in the light areas.Keep the shadow areas thin and transparent.Paint "through" the forms, connecting the forehead, nose, and chin with related tones.Add saturated "blood flow" colors (e.g., alizarin crimson) to the cheeks, nose, and ears.Sculpt the form of the skull, treating the features as secondary elements on that form.Step back every 10 minutes to ensure the values are still reading correctly.
4. Painting the Features (The Likeness)
Treat the eyes as spheres sitting within the sockets.Paint the sclera (whites) of the eyes as a toned gray or blue, never pure white.Paint the shadow cast by the upper eyelid onto the eyeball.Define the planes of the upper and lower eyelids.Place the iris and pupil, noting they are perfect circles (when viewed straight on).Place the "catchlight" (specular highlight) consistently in both eyes.Ensure the catchlight is the single brightest bright on the entire painting.Add the "tear duct" (caruncle) with a saturated, warm pinkish tone.Define the eyelashes as a clumpy mass, not individual, spidery hairs.Paint the nose as three main planes: a front plane and two side planes.Define the "ball" of the nose and the two "alar" (wing) cartilages.Paint the cast shadow from the nose onto the cheek, noting its shape and edge.Define the "lost and found" edge of the nose's shadow.Place the main highlight on the "corner" (plane break) of the nose, not the very tip.Paint the nostrils as dark, warm shadow shapes, not black holes.Paint the mouth as part of a cylindrical "muzzle" form, not as flat lips.Define the "five tubercles" (three on top, two on bottom) of the lips.Observe that the top lip is almost always darker (in shadow) than the bottom lip.Place the highlight on the bottom lip, which catches the light.Define the "commissure" (corners) of the mouth, blending them softly into the cheek.Paint the "parting line" between the lips as the darkest accent on the mouth.If teeth are showing, paint them as a single, grayed-down mass, not bright white.Paint the ears with less detail and softer edges than the eyes or nose.Ensure the ears are "attached" to the jaw and skull, not floating.Use the ears to "turn the head" by managing their edges and values.
5. Refining, Details, & Background
Mass in the hair's overall value and color first.Paint the hair as "ribbons" or "clumps," focusing on its form and structure.Add specular highlights to the hair *only* at the very end.Soften (lose) the edge where the hair meets the face to turn the form.Sharpen (find) the edge where the hair meets the background to create a silhouette.Paint the background, working *into* the edges of the figure to create a relationship.Use the background value to adjust the silhouette and "pop" the figure forward (or recede it).Analyze and "lose" edges (soften) to make forms turn away from the viewer.Analyze and "find" edges (sharpen) to bring forms forward.Add the sharpest edges and brightest highlights *only* at the focal point (usually the eyes).Check the painting in a mirror (or flip the digital canvas) to reveal drawing errors.Apply final, thin glazes to adjust color or unify large shadow areas.Add small, sharp texture details (e.g., beard stubble, clothing weave, jewelry).Sign the painting in a location and color that complements the composition.Assess the painting from a distance and ask: "Does it read as a cohesive whole?"
6. Conceptual & Stylistic Prompts
Exaggerate the subject's most dominant feature by 20%.Paint the entire portrait using only a palette knife.Paint a portrait using only complementary colors (e.g., reds and greens).Limit your palette to only four colors (e.g., Zorn palette: White, Black, Red, Yellow).Paint the *absence* of the subject, showing only the chair they just left.Incorporate text or abstract symbols that represent the subject's personality.Paint a "fragmented" or "cubist" portrait, showing multiple views at once.Use an "unnatural" light source (e.g., a phone screen, a fire, a neon sign).Paint a portrait in the style of [an artist, e.g., Lucian Freud, Rembrandt, Alice Neel].Paint a diptych (two panels) of the same subject in two opposing moods.Focus entirely on texture (impasto), ignoring "correct" local color.Paint a portrait where the subject is in motion (alla prima, motion blur).Paint a portrait in pure grisaille (monochrome), focusing only on form.Let the underpainting show through in 50% of the final piece.Paint over an old, failed painting, letting the history of the canvas show through.
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