Outsider Art Portrait Paintings
21st Century and Contemporary Outsider Art Portrait Paintings
Acrylic Polymer
20th Century Outsider Art Portrait Paintings
Gouache
20th Century Outsider Art Portrait Paintings
Gouache
1960s Outsider Art Portrait Paintings
Acrylic
20th Century Outsider Art Portrait Paintings
Gouache
20th Century Outsider Art Portrait Paintings
Gouache
20th Century Outsider Art Portrait Paintings
Gouache
20th Century Outsider Art Portrait Paintings
Gouache
20th Century Outsider Art Portrait Paintings
Gouache
Artist Comments
A fashionable young woman sporting sunglasses, favorite denim pants, and vibrant red boots steps out into a windy early spring day for a brisk walk with her can...
21st Century and Contemporary Outsider Art Portrait Paintings
Acrylic
Artist Comments
In a subway station, commuters engage in various pastimes as they wait for the train to arrive. One reads a newspaper, another talks on a cell phone, while the rest occupy themselves with their thoughts. Amidst the bustle, mumbled conversations, and rumbling railway noises, the red-haired woman sits with her eyes closed, immersed in a contemplative moment.
About the Artist
Words that describe this painting: train, subway, cellphone, newspaper, reading, waiting, Isabel Bishop, Vincent Van Gogh, Pablo Picasso, primitivism, travel, text, urban, people, travel, primitive, oil painting, grey
Anywhere
Connie Millholland...
21st Century and Contemporary Outsider Art Portrait Paintings
Oil
Artist Comments
The painting depicts a typical day of commuting, with passengers lost in thought or absorbed in their phones as they await their stops. The lack of direct interaction between them highlights the solitary yet collective experience of modern urban life. Their different colored attire adds vibrancy to the everyday scene.
About the Artist
Words that describe this painting: bus, cellphone, waiting, sitting, autumn, season, travel, sitting, text, vehicle, people, travel, primitive, oil painting, beige
Bus People
Connie Millholland...
21st Century and Contemporary Outsider Art Portrait Paintings
Oil
Artist Comments
A small group of children huddle around a street fire. The flickering flames cast a modest glow on their pale complexions and provide warmth on a cold winter night. In this piece, artist Connie Millholland...
21st Century and Contemporary Outsider Art Portrait Paintings
Oil
Artist Comments
This painting draws inspiration from an old photograph from 1945, capturing a joyous moment of five ladies holding hands in celebration. Their faces light up with smiles and laughter, radiating an infectious delight. The contrasting colors of red and green bring a simple yet visually harmonious element to the scene.
About the Artist
Words that describe this painting: happy, joy, celebration, women, woman, dancing, dress, friends, friendship, people, fashion, primitive, oil painting, pink
1945
Connie Millholland...
21st Century and Contemporary Outsider Art Portrait Paintings
Oil
Artist Comments
The artwork depicts a snapshot of modern urban life, where people on the streets are glued to their phones. Whether chatting, checking notifications, or scrolling through feeds, the scene shows how busy a city can be in the digital age. Using a harmonious palette mostly with warm orange tones, the painting exudes a vibrant and inviting atmosphere. Loose brushstrokes infuse the composition with liveliness.
About the Artist
Words that describe this painting: street, walking, cellphone, crowd, walking, urban, crowd, pedestrians, shadow, warm, people, primitive, oil painting, orange
Regressive
Connie Millholland...
21st Century and Contemporary Outsider Art Portrait Paintings
Oil
Artist Comments
A young woman wearing a matching gray dress and boots stops in the middle of a city street. Her eyes widen as she looks back on so...
21st Century and Contemporary Outsider Art Portrait Paintings
Oil
1950s Outsider Art Portrait Paintings
Masonite, Oil
Artist Comments
A group of joyful women walks down the street, each holding a glass of wine, a balloon, or a book, celebrating and having a good time. Their laughter fills the air, creating a vibrant and festive scene. Their attire matches the purple and yellow background, adding to the lively atmosphere.
About the Artist
Words that describe this painting: women, woman, friends, friend, fashion, wine, celebration, friendship, people, fashion, primitive, oil painting, purple
1926
Connie Millholland...
21st Century and Contemporary Outsider Art Portrait Paintings
Oil
Artist Comments
In their daily lives, individuals from diverse backgrounds briefly converge in a shared space as they progress toward a mutual destination. The scene portrays a busy subway station where individuals may have brief and disconnected interactions but are all bound by the same journey and humanity. Each person's story weaves together with others, forming a tapestry of diverse experiences and connections.
About the Artist
Words that describe this painting: street, subway, crowd, traveling, shadow, urban, people, primitive, oil painting, grey
Waiting
Connie Millholland...
21st Century and Contemporary Outsider Art Portrait Paintings
Oil
Artist Comments
In a neighborhood building, old friends huddle around a worn table to play mahjong. Their eyes are focused on the tiles, thinking of the best strategy to win th...
21st Century and Contemporary Outsider Art Portrait Paintings
Acrylic
Artist Comments
Artist Johansen Newman depicts a portrait of Timothy from the book "Nothing Here to See" by Kevin Wilson. "This reminds me of my own experiences as an only child, when my room was my headquarters and the things inside were my comrades-in-arms for navigating the world of grownups," shares Johansen. In the painting, the boy finds comfort in his stuffed animals, using them as a shield from the people around him.
About the Artist
Artist Johansen Newman captures various characters through charming scenes that often weave nostalgia. A reflection of her fondness for edge and funk prevails in her dynamic portrayal of humans with animals and objects of their affection. As a toddler, her mother gave her crayons and allowed her to draw on the walls of her room. She pursued a degree in painting and printmaking, then furthered her education by studying with Bil Baird at his puppet theater in New York, ultimately forming her puppet troupe. Years of crafting puppets, designing scenery, writing stories, and performing shows developed her arsenal of skills—going on to be an award-winning fiber artist exhibiting throughout North America. She integrates these learnings into her current art practice. "My paintings capture fragments of a tale in a time and place that was, is, or has the promise to become," says Johansen. She works at her studio and display gallery at Gorse Mill Studios, a 19th Century textile mill building in Needham, MA. Her woodworking shop doubles as her home studio, where she constantly evolves her compositions to satisfy her aesthetic. Johansen's work has been featured on the cover of local publications, in pictorial essays, and toured museums across the United States. She was a professional and published illustrator for more than 35 years, including two dozen children's books, three of which she also wrote. Besides creating art, she finds herself an enthusiast of vintage collectibles, jukeboxes, signages, tin toys, neon lights, cookie jars, carnival chalkware...
21st Century and Contemporary Outsider Art Portrait Paintings
Acrylic
Artist Comments
Artist Johansen Newman presents a portrait of a child in a lavishly decorated room. The girl wears her finest dress while clutching onto her rattiest stuffed animal. With her defiant stance, wild hair, and choice of stuffed animal to hold, Hannah seems to be crying out, “You can dress me up and put me in the parlor, but you can’t make me a girly girl.†The painting reminds Johansen of her childhood when she resisted the effort of adults to define how she should look and act.
About the Artist
Artist Johansen Newman captures various characters through charming scenes that often weave nostalgia. A reflection of her fondness for edge and funk prevails in her dynamic portrayal of humans with animals and objects of their affection. As a toddler, her mother gave her crayons and allowed her to draw on the walls of her room. She pursued a degree in painting and printmaking, then furthered her education by studying with Bil Baird at his puppet theater in New York, ultimately forming her puppet troupe. Years of crafting puppets, designing scenery, writing stories, and performing shows developed her arsenal of skills—going on to be an award-winning fiber artist exhibiting throughout North America. She integrates these learnings into her current art practice. "My paintings capture fragments of a tale in a time and place that was, is, or has the promise to become," says Johansen. She works at her studio and display gallery at Gorse Mill Studios, a 19th Century textile mill building in Needham, MA. Her woodworking shop doubles as her home studio, where she constantly evolves her compositions to satisfy her aesthetic. Johansen's work has been featured on the cover of local publications, in pictorial essays, and toured museums across the United States. She was a professional and published illustrator for more than 35 years, including two dozen children's books, three of which she also wrote. Besides creating art, she finds herself an enthusiast of vintage collectibles, jukeboxes, signages, tin toys, neon lights, cookie jars, carnival chalkware...
21st Century and Contemporary Outsider Art Portrait Paintings
Acrylic
Artist Comments
"She emanates an aura of quiet strength while maintaining a delicate presence at the same time," says artist Sharon Sieben. She captures a woman mid-stride, wit...
21st Century and Contemporary Outsider Art Portrait Paintings
Acrylic
Artist Comments
Artist Libby Ramage shows a father and daughter being swept away by the beauty of the autumn leaves. "They try to grasp that which is beyond their size," says Libby. A horse gallops forward, representing the fading summer days. She chooses highly saturated colors to enrich the intensity of the moment. "Nature looms large in this artwork."
About the Artist
Libby Ramage infuses a playful and whimsical mood into her works. In fact, she credits the children she works with for greatly influencing her aesthetic. She often uses children’s abandoned work in her collages. Libby currently lives in New Jersey and finds inspiration in the work of Rauschenberg. She believes collectors should buy from the heart.
Words that describe this painting: man, daughter, fall, autumn, season, mixed media, small, leaves, people, horse, primitive, primitivism, nature, people, primitive, acrylic painting, orange
21st Century and Contemporary Outsider Art Portrait Paintings
Acrylic
Artist Comments
Artist Libby Ramage presents an autumnal scene marked by large leaves falling from the sky. "As the sun fades, a young boy becomes the man," says Libby. Showing...
21st Century and Contemporary Outsider Art Portrait Paintings
Acrylic
Artist Comments
Artist Jessica JH Roller paints a woman sitting on the ground with her legs crossed. Vibrant wildflowers in pink and red thrive all around her. "Summer is in bl...
21st Century and Contemporary Outsider Art Portrait Paintings
Acrylic
2010s Outsider Art Portrait Paintings
Canvas, Oil
20th Century Outsider Art Portrait Paintings
Oil, Board
21st Century and Contemporary Outsider Art Portrait Paintings
Crayon, Oil
2010s Outsider Art Portrait Paintings
Oil
Late 20th Century Outsider Art Portrait Paintings
Gouache, Ink
Late 20th Century Outsider Art Portrait Paintings
Gouache, Ink
Late 20th Century Outsider Art Portrait Paintings
Gouache, Ink
2010s Outsider Art Portrait Paintings
Canvas, Acrylic
2010s Outsider Art Portrait Paintings
Canvas, Acrylic
1970s Outsider Art Portrait Paintings
Acrylic, Canvas, Wood Panel
2010s Outsider Art Portrait Paintings
Paper, Acrylic
2010s Outsider Art Portrait Paintings
Canvas, Oil
2010s Outsider Art Portrait Paintings
Paper, Acrylic
2010s Outsider Art Portrait Paintings
Paper, Acrylic
2010s Outsider Art Portrait Paintings
Acrylic, Canvas
2010s Outsider Art Portrait Paintings
Canvas, Acrylic
2010s Outsider Art Portrait Paintings
Paper, Acrylic
2010s Outsider Art Portrait Paintings
Acrylic, Canvas
2010s Outsider Art Portrait Paintings
Acrylic, Paper
2010s Outsider Art Portrait Paintings
Acrylic, Paper
2010s Outsider Art Portrait Paintings
Acrylic, Canvas
2010s Outsider Art Portrait Paintings
Acrylic, Paper
2010s Outsider Art Portrait Paintings
Acrylic, Paper
2010s Outsider Art Portrait Paintings
Acrylic, Paper
2010s Outsider Art Portrait Paintings
Acrylic, Canvas
2010s Outsider Art Portrait Paintings
Acrylic, Canvas
2010s Outsider Art Portrait Paintings
Canvas, Acrylic
2010s Outsider Art Portrait Paintings
Paper, Acrylic
2010s Outsider Art Portrait Paintings
Canvas, Acrylic
2010s Outsider Art Portrait Paintings
Acrylic, Paper
2010s Outsider Art Portrait Paintings
Acrylic, Paper
2010s Outsider Art Portrait Paintings
Acrylic, Paper