Pablo Picasso was a master of reinvention — and nowhere is that more vividly captured than in his portraits.
Across a career that spanned more than seventy years, Picasso never stopped pushing the boundaries of how a face could be seen, felt, and understood.
His portraits are not mere representations of appearance; they are emotional landscapes, psychological puzzles, and explosive celebrations of life itself.
From the tender innocence of a young girl cradling a dove to the raw, unfiltered confrontation of his own aging face, Picasso’s portraits chart the evolution of modern art — and the evolution of the man himself.
In this article, we’ll explore some of Picasso’s most famous and fascinating portraits, each one offering a unique window into his shifting styles, personal relationships, and ceaseless artistic experimentation.
Prepare to see the human face — and perhaps even your own reflection — in ways you never imagined.
Picasso Portraits
1. Portrait of Gertrude Stein
This portrait marks a turning point for Picasso as he moved away from the delicate sentimentality of his earlier Rose Period toward a bolder, more structural style.
Gertrude Stein, a major patron and literary figure in Paris, sat for Picasso more than 80 times for this painting — but Picasso was frustrated because he couldn’t capture her essence.
After a trip to Spain, where he studied Iberian stone sculptures, Picasso returned and finished the face in a dramatically different, mask-like style.
Stein famously accepted the change, and when people remarked it didn’t look like her, she replied, “It will.” This work prefigures the stylized, blocky faces that would define early Cubism.
2. Portrait of Ambroise Vollard
Ambroise Vollard was one of the most influential art dealers of the early 20th century, helping promote artists like Cézanne, Gauguin, and later Picasso.
Picasso’s 1910 portrait of him is a dazzling example of Analytical Cubism, where the figure is broken down into a dense, shimmering network of planes and facets.
Vollard’s features are almost unrecognizable, submerged in a kaleidoscope of earthy tones and interlocking shapes. Rather than depicting his sitter’s physical likeness, Picasso aimed to capture the essence and presence of Vollard, presenting multiple viewpoints at once. This painting is often cited as a key moment in Cubism’s development.
3. Portrait of Dora Maar
Dora Maar, a gifted photographer and artist herself, had a turbulent relationship with Picasso, and this intensity often found its way into his portraits of her.
In this 1937 painting, Picasso fuses multiple perspectives into a single, fractured face — sharp angles, clashing colors, and twisted forms combine to create a haunting image. Her eyes often appear in different directions, and her face splits into bright and shadowed halves, symbolizing inner conflict.
Painted during the time Picasso was working on Guernica, this portrait captures not only Dora’s complexity but also the broader anxiety and despair of the era, with Europe on the brink of World War II.
4. Portrait of Olga in an Armchair
Olga Khokhlova, a Ukrainian ballet dancer, became Picasso’s wife after they met during his work on the Parade ballet for the Ballets Russes.
This portrait, painted during the first flush of their marriage, shows her seated elegantly in a plush armchair, rendered with a classical clarity that contrasts sharply with Picasso’s earlier Cubist experiments.
His return to a more realistic, serene style (sometimes called his Neoclassical Period) was influenced by his travels to Italy. The painting conveys a sense of calm sophistication, but future depictions of Olga would grow darker and more fragmented as their relationship deteriorated.
5. Woman with Straw Hat
This vivid, highly stylized portrait likely depicts Dora Maar, although some interpretations suggest Marie-Thérèse Walter as well. In this work, Picasso exaggerates features almost to the point of caricature — wide, staring eyes, a large, mask-like face, and sharp color contrasts.
The straw hat adds a whimsical, almost absurd element. Created during a time of intense personal and political turmoil, Woman with Straw Hat bursts with energy and emotional tension.
The bold, almost violent brushstrokes reflect Picasso’s embrace of Surrealism at the time, blurring the line between beauty and distortion.
6. Weeping Woman
Weeping Woman is one of Picasso’s most powerful and emotional works, painted in the aftermath of the Spanish Civil War and directly influenced by the horrors of the bombing of Guernica.
This portrait of Dora Maar captures raw, anguished emotion — her face fragmented into jagged planes, each teeming with sorrow and pain. The use of bold, acidic colors — greens, yellows, and blues — intensifies the sense of torment.
The overlapping, multi-dimensional eyes reflect the disorienting impact of grief and trauma. The distorted features echo the same fragmentation seen in Guernica, linking the two works thematically.
Dora, who was both Picasso’s lover and a witness to the destruction of the war, symbolizes the suffering of Spain and the devastation of the human spirit.
7. Girl Before a Mirror
This iconic portrait of Marie-Thérèse Walter was painted during a period when Picasso’s relationship with her was at its height, and it showcases his shift into a more surreal and symbolic approach. The girl is reflected in a mirror, but instead of a straightforward reflection, her mirrored self is warped into an alternate version — a distorted, colorful, almost dreamlike image.
Picasso plays with the idea of duality, exploring themes of identity, self-image, and transformation. The softness of Marie-Thérèse’s figure contrasts with the bold, almost geometric patterns in the reflection, making the viewer question the nature of what’s real and what’s imagined.
The swirling colors of the face, along with the juxtaposition of light and shadow, create a sense of internal conflict — the duality of innocence and maturity, as well as the emotional complexity Picasso saw in her.
8. Portrait of Marie-Thérèse Walter
Marie-Thérèse Walter was Picasso’s lover and muse for several years, and many of his most famous works were painted during this time. This portrait, created during a moment of tenderness and intimacy, depicts her in a softer, more serene light.
The painting is full of gentle curves, and Picasso’s characteristic surrealist treatment of her face gives her an almost otherworldly quality. Her lips, eyes, and nose are exaggerated, but not to the same degree as in some of his other works.
The calm and sensuality of the portrait reflects Marie-Thérèse’s status as a central figure in Picasso’s life — she was his muse during a period of great personal joy, even though their relationship was secret, since Picasso was still married to Olga Khokhlova at the time.
9. Harlequin with a Mirror
This piece is painted during Picasso’s Neoclassical period, when he returned to a more representational style after his earlier Cubist and Surrealist experiments.
The Harlequin figure — a traditional commedia dell’arte character — was a recurring motif for Picasso, symbolizing the artist himself, as the harlequin was often seen as an outsider or a person with many faces. The subject here is seated and holding a mirror, suggesting introspection or self-examination.
The geometrization of the body and facial features shows the influence of Cubism, even within the more classical treatment of the figure. The duality between the more traditional forms and Picasso’s lingering Cubist abstraction reflects the tension in Picasso’s own life during this period — balancing his classical training with his evolving personal and artistic exploration.
10. Self-Portrait (Yo – Picasso)
This self-portrait is a bold declaration of Picasso’s identity, painted during his Blue Period. “Yo” means “I” in Spanish, and Picasso here confidently asserts his own artistic persona. The use of the cool blue tones — a hallmark of the Blue Period — conveys the melancholy and alienation that defined much of Picasso’s work during this time.
His expression is introspective, a little weary, but firm, reflecting the emotional turbulence and isolation Picasso was experiencing after moving to Paris and dealing with personal struggles, including the death of a close friend, Carlos Casagemas.
This self-portrait is often seen as a moment of self-reflection, but it also marks Picasso’s emerging confidence as an artist — a key turning point as he moved from the sadness of the Blue Period toward the experimentation of the later years.
11. Portrait of a Young Girl (Little Girl with a Dove)
This touching painting comes from the very beginning of Picasso’s Blue Period. Little Girl with a Dove shows a small child cradling a white dove to her chest — a universal symbol of innocence, hope, and peace.
Painted in soft blues, pinks, and whites, the work is full of tenderness and quiet vulnerability. The background is simple, focusing all attention on the child and the bird, emphasizing their purity. Some have interpreted the dove as a symbol of Picasso’s yearning for emotional security during a time of personal grief (following the suicide of his friend Casagemas).
Unlike the more abstracted or fragmented works of his later career, here Picasso shows a direct emotional sincerity — a glimpse into his compassionate and humanistic side.
12. Portrait of Paul as a Harlequin
In this charming and somewhat nostalgic portrait, Picasso paints his young son Paul dressed as a harlequin — a figure closely associated with the artist’s own self-image in earlier works. Paul is shown seated, wearing a costume with diamond patterns, the traditional attire of the harlequin character from commedia dell’arte.
The painting is gentle, warm, and unusually direct for Picasso, showing a father’s affection for his child. Although the form is somewhat stylized, Picasso keeps it far more representational than his Cubist or Surrealist pieces.
This portrait also reflects his Neoclassical period — when his work temporarily moved back toward traditional forms and themes, full of balance, harmony, and clarity.
13. Woman with Yellow Hair
One of the most iconic depictions of Marie-Thérèse Walter, Woman with Yellow Hair is a glowing, sensual celebration of the young woman who had become Picasso’s secret muse. The curves of her body are exaggerated into soft, almost dreamlike forms. The bright, sunny colors — yellows, soft blues, and pinks — radiate joy and calm.
Picasso captures a sense of blissful abandon; Marie-Thérèse often appeared sleeping or reclining in these portraits, symbolizing eroticism, freedom, and the private world they shared.
This painting marks a period where Picasso’s art moved into a more biomorphic and Surrealist style, with fluid lines and dreamy compositions.
14. Jacqueline with Flowers
Jacqueline Roque became Picasso’s muse, lover, and eventual wife during the final decades of his life. Jacqueline with Flowers is one of the many portraits he painted of her, capturing both her serene beauty and the deep affection he felt for her.
In this painting, Jacqueline is depicted with a bouquet, a symbol of fertility, love, and abundance. Her features are stylized, but not harshly fragmented — Picasso often softened his approach when painting Jacqueline.
The portrait uses bold yet harmonious colors, and the fluid lines create a peaceful, almost regal atmosphere. Jacqueline would go on to be the subject of more portraits than any other woman Picasso painted — over 400!
15. Self-Portrait Facing Death
Painted just a year before his death, this self-portrait is one of the most harrowing works Picasso ever created. Executed in crayon on paper, the image is raw and immediate: Picasso’s face is gaunt, his eyes wide and staring directly at the viewer with a mix of defiance, fear, and acceptance.
The color palette is stripped down, often dominated by stark reds, yellows, and blacks. Every line feels urgent, almost desperate. Self-Portrait Facing Death is a final, fearless confrontation with mortality — Picasso unflinchingly documents the decline of his body but also asserts the enduring power of his spirit and creativity.
It’s one of the most moving testaments to his lifelong obsession with the human condition and his refusal to look away, even at the end.