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Street Art Portrait Drawings and Watercolors

STREET ART STYLE

Street art is a style created for city walls, subway trains and other public spaces. Sometimes it is commissioned, yet most often it is an individual statement of defiant free expression. Although mostly an urban style, street art can be found all over the world, including JR’s pasted portraits on the separation wall in Palestine, Invader’s playful ceramic tile mosaics in Paris and the provocative stencil and spray-paint works by Banksy in London.

The Philadelphia-based Cornbread — aka Darryl McCray — is considered the first modern graffiti artist. He began tagging his name around the city in the 1960s. Graffiti art later flourished in New York City in the 1970s. There, young artists used spray paint and markers to create tags and large-scale graphic works, with Jean-Michel Basquiat and Keith Haring both developing their distinctive styles through the graffiti scene, which would evolve into street art. Artists such as Tracy 168 and Lady Pink pioneered the Wild Style of complex graffiti writing in the 1980s, pushing the movement forward.

Because of its unsanctioned, improvisational and frequently covert nature, street art involves a range of techniques and aesthetics. Some street artists use quick and effective stenciling, whereas others wheat-paste posters, commandeer video projectors or freehand draw elaborate illustrations and murals. Shepard Fairey made his mark with street art stickers before designing the iconic “Hope” poster for Barack Obama’s 2008 presidential campaign.

While the origins of street art are rooted in a strictly noncommercial creative act that confronted political issues, sexuality and more for a general audience of passersby, the art form has moved inside the galleries over the years. Today, just as Basquiat and Haring took their works from Manhattan’s Lower East Side alleyways into Soho galleries, artists including KAWS, Barry McGee and Osgemeos are in demand with collectors of fine art.

Find a collection of street art paintings, sculptures, prints and multiples and more on 1stDibs.

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Style: Street Art
Four Years (The Count) (2020) by street artist City Kitty, graffiti MTA poster
Located in Jersey City, NJ
"Four Years of Frustration, Delays & Missed Appointments (The Count)" (2020) by street artist City Kitty 18.25 x 12.25 x .75" Ink, acrylic and color pencil on MTA poster...
Category

2010s Street Art Portrait Drawings and Watercolors

Materials

Paper, Ink, Acrylic, Color Pencil

Four Years (One Earth) (2020) by street artist City Kitty, graffiti MTA poster
Located in Jersey City, NJ
"Four Years of Frustration, Delays & Missed Appointments (One Earth)" (2022) by street artist City Kitty 18.25 x 12.25 x .75" Ink, acrylic and color pencil on MTA poster...
Category

2010s Street Art Portrait Drawings and Watercolors

Materials

Paper, Ink, Acrylic, Color Pencil

Four Years (Bob Ross) (2019) by street artist City Kitty, graffiti MTA poster
Located in Jersey City, NJ
"Four Years of Frustration, Delays & Missed Appointments (Bob Ross, cat)" (2019) by street artist City Kitty 18.25 x 12.25 x .75" Ink, acrylic and color pencil on MTA poster...
Category

2010s Street Art Portrait Drawings and Watercolors

Materials

Paper, Ink, Acrylic, Color Pencil

Four Years (So Cool Cat) (2022) by street artist City Kitty, graffiti MTA poster
Located in Jersey City, NJ
"Four Years of Frustration, Delays & Missed Appointments (So Cool Cat)" (2022) by street artist City Kitty 18.25 x 12.25 x .75" Ink, acrylic and color pencil on MTA poster, framed. Artist's signature graffiti style of comic relief for subway notice posters, often relating unfortunate news to the public of delays or changes to the regular schedule. Portrait of classic City Kitty character with his third eye and in this case with words written across his open mouth that read in bubble letters, "SO COOL" in pink. Black and white "7" train line Friday night service update poster with purple diamond 7 line train logo. Neon and pastel palette accents include pink and blue. ABOUT THE ARTIST For the past 12 years, NYC-based street artist City Kitty has been pasting elaborate, hand-drawn scenes of an adventurous street cat onto buildings, subway stations and alleyways throughout North America and Europe. Best known for his large-scale drawings of cats...
Category

2010s Street Art Portrait Drawings and Watercolors

Materials

Acrylic, Color Pencil, Paper, Ink

Four Years (Radio) (2020) by street artist City Kitty, graffiti MTA poster
Located in Jersey City, NJ
"Four Years of Frustration, Delays & Missed Appointments (Radio or Streaming)" (2020) by street artist City Kitty 18.25 x 12.25 x .75" Ink, acrylic and color pencil on MTA poster...
Category

2010s Street Art Portrait Drawings and Watercolors

Materials

Paper, Ink, Acrylic, Color Pencil

Four Years (Baby Yoda) (2022) by street artist City Kitty, graffiti MTA poster
Located in Jersey City, NJ
"Four Years of Frustration, Delays & Missed Appointments (Baby Yoda)" (2022) by street artist City Kitty 18.25 x 12.25 x .75" Ink, acrylic and color pencil ...
Category

2010s Street Art Portrait Drawings and Watercolors

Materials

Ink, Acrylic, Color Pencil, Paper

Four Years (Pirate Cat) (2019) by street artist City Kitty, graffiti MTA poster
Located in Jersey City, NJ
"Four Years of Frustration, Delays & Missed Appointments (Pirate Cat)" (2019) by street artist City Kitty 18.25 x 12.25 x .75" Ink, acrylic and color pencil on MTA poster, framed. Artist's signature graffiti style of comic relief for subway notice posters, often relating unfortunate news to the public of delays or changes to the regular schedule. Portrait of classic City Kitty character, in this case a pirate, adorned with pirate hat...
Category

2010s Street Art Portrait Drawings and Watercolors

Materials

Paper, Ink

Four Years (Ecstasy) (2019) by street artist City Kitty, graffiti MTA poster
Located in Jersey City, NJ
"Four Years of Frustration, Delays & Missed Appointments (Ecstasy)" (2019) by street artist City Kitty 18.25 x 12.25 x .75" Ink, acrylic and color pencil on MTA poster...
Category

2010s Street Art Portrait Drawings and Watercolors

Materials

Paper, Ink, Acrylic, Color Pencil

Four Years (Darth Vader) (2022) by street artist City Kitty, graffiti MTA poster
Located in Jersey City, NJ
"Four Years of Frustration, Delays & Missed Appointments (Darth Vader)" (2022) by street artist City Kitty 18.25 x 12.25 x .75" Ink, acrylic and color pencil on MTA poster...
Category

2010s Street Art Portrait Drawings and Watercolors

Materials

Paper, Ink, Acrylic, Color Pencil

Related Items
He who goes hunting... Caroline Veith Contemporary drawing red hunt war ink art
Located in Paris, FR
Acrylic paint and ink on tracing paper Hand-signed and dated lower left
Category

2010s Street Art Portrait Drawings and Watercolors

Materials

Paper, Ink, Acrylic

Life - Original Drawing Portrait Of A Women Ink & Acrylic On Paper by Devie
Located in Carmel, CA
Inspired by the theatre world, Devie had retained her own unique drawing strokes. Her works reflect an approachable other-worldliness. She paints a story to be told and answered. Th...
Category

21st Century and Contemporary Street Art Portrait Drawings and Watercolors

Materials

Ink, Acrylic, Handmade Paper

Original Drawing Young Women Ink & Acrylic on paper by Devie
Located in Carmel, CA
Inspired by the theatre world, Devie had retained her own unique drawing strokes. Her works reflect an approachable other-worldliness. She paints a story to be told and answered. Th...
Category

21st Century and Contemporary Street Art Portrait Drawings and Watercolors

Materials

Ink, Acrylic, Handmade Paper

"Red Lips" Ink & acrylic Original Drawing on handmade Paper, 21" x 17" by Devie
Located in Carmel, CA
Inspired by the theatre world, Devie had retained her own unique drawing strokes. Her works reflect an approachable other-worldliness. She paints a story to be told and answered. Th...
Category

21st Century and Contemporary Street Art Portrait Drawings and Watercolors

Materials

Acrylic, Ink, Handmade Paper

"Wavy Hair" by Devie
Located in Carmel, CA
Inspired by the theatre world, Devie had retained her own unique drawing strokes. Her works reflect an approachable other-worldliness. She paints a story to be told and answered. Th...
Category

21st Century and Contemporary Street Art Portrait Drawings and Watercolors

Materials

Ink, Acrylic, Handmade Paper

"Portrait of a woman" Ink & Acrylic on paper framed by Devie
Located in Carmel, CA
Inspired by the theatre world, Devie had retained her own unique drawing strokes. Her works reflect an approachable other-worldliness. She paints a story to be told and answered. Th...
Category

21st Century and Contemporary Street Art Portrait Drawings and Watercolors

Materials

Ink, Acrylic, Handmade Paper

'Women And Brown Cat' Acrylic And Ink Original Drawing On Paper By Devie
Located in Carmel, CA
Inspired by the theatre world, Devi had retained her own unique drawing strokes. Her works reflect an approachable other-worldliness. She paints a story to be told and answered. The...
Category

21st Century and Contemporary Street Art Portrait Drawings and Watercolors

Materials

Ink, Acrylic, Handmade Paper

'Portrait Of A Woman' Pen & Ink & Acrylic Original Drawing By Devie
Located in Carmel, CA
Inspired by the theatre world, Devie had retained her own unique drawing strokes. Her works reflect an approachable other-worldliness. She paints a story to be told and answered. Th...
Category

21st Century and Contemporary Street Art Portrait Drawings and Watercolors

Materials

Ink, Acrylic, Handmade Paper

Tippie Comic Strip Original Art - Female Cartoonist
Located in Miami, FL
An early example from pioneering Female Cartoonist/ Illustrator Edwina Dumm, who draws a comic strip from her long-running cartoon series Tippie which lasted for almost five decades. Signed and dated Edwina, 9-25, matted but unframed. Frances Edwina Dumm (1893 – April 28, 1990) was a writer-artist who drew the comic strip Cap Stubbs and Tippie for nearly five decades; she is also notable as America's first full-time female editorial cartoonist. She used her middle name for the signature on her comic strip, signed simply Edwina. Biography One of the earliest female syndicated cartoonists, Dumm was born in Upper Sandusky, Ohio, and lived in Marion and Washington Courthouse, Ohio throughout her youth before the family settled down in Columbus.[1] Her mother was Anna Gilmore Dennis, and her father, Frank Edwin Dumm, was an actor-playwright turned newspaperman. Dumm's paternal grandfather, Robert D. Dumm, owned a newspaper in Upper Sandusky which Frank Dumm later inherited. Her brother, Robert Dennis Dumm, was a reporter for the Columbus Dispatch, and art editor for Cole Publishing Company's Farm & Fireside magazine. In 1911, she graduated from Central High School in Columbus, Ohio, and then took the Cleveland-based Landon School of Illustration and Cartooning correspondence course. Her name was later featured in Landon's advertisements. While enrolled in the correspondence course, she also took a business course and worked as a stenographer at the Columbus Board of Education. In 1915, Dumm was hired by the short-lived Republican newspaper, the Columbus Monitor, to be a full-time cartoonist.[2] Her first cartoon was published on August 7, 1915, in the debut issue of the paper. During her years at the Monitor she provided a variety of features including a comic strip called The Meanderings of Minnie about a young tomboy girl and her dog, Lillie Jane, and a full-page editorial cartoon feature, Spot-Light Sketches[3]. She drew editorial cartoons for the Monitor from its first edition (August 7, 1915) until the paper folded (July 1917). In the Monitor, her Spot-Light Sketches was a full-page feature of editorial cartoons, and some of these promoted women's issues. Elisabeth Israels Perry, in the introduction to Alice Sheppard's Cartooning for Suffrage (1994), wrote that artists such as Blanche Ames Ames, Lou Rogers and Edwina Dumm produced: ...a visual rhetoric that helped create a climate more favorable to change in America's gender relations... By the close of the suffrage campaign, women's art reflected the new values of feminism, broadened its targets, and attempted to restate the significance of the movement.[4] After the Monitor folded, Dumm moved to New York City, where she continued her art studies at the Art Students League. She was hired by the George Matthew Adams Service[5] to create Cap Stubbs and Tippie, a family strip following the lives of a boy Cap, his dog Tippie, their family, and neighbors. Cap's grandmother, Sara Bailey, is prominently featured, and may have been based on Dumm's own grandmother, Sarah Jane Henderson, who lived with their family. The strip was strongly influenced by Mark Twain’s Adventures of Huckleberry Finn, as well as Dumm’s favorite comic, Buster Brown by Richard F. Outcault. Dumm worked very fast; according to comics historian Martin Sheridan, she could pencil a daily strip in an hour.[6] Her love of dogs is evident in her strips as well as her illustrations for books and magazines, such as Sinbad, her weekly dog page which ran in both Life and the London Tatler. She illustrated Alexander Woollcott's Two Gentlemen and a Lady. For Sonnets from the Pekinese and Other Doggerel (Macmillan, 1936) by Burges Johnson (1877–1963), she illustrated "Losted" and other poems. From the 1931 through the 1960s, she drew another dog for the newspaper feature Alec the Great, in which she illustrated verses written by her brother, Robert Dennis Dumm. Their collaboration was published as a book in 1946. In the late 1940s, she drew the covers for sheet music by her friend and neighbor, Helen Thomas, who did both music and lyrics. During the 1940s, she also contributed Tippie features to various comic books including All-American Comics and Dell Comics. In 1950, Dumm, Hilda Terry, and Barbara Shermund...
Category

1920s Street Art Portrait Drawings and Watercolors

Materials

Ink, Color Pencil, Graphite

For Nicolai / Head Study No. 88
Located in Burlingame, CA
For Nicolai / Head Study No. 88 , drawing / painting featuring the head portrait of a young woman. in blue. The work is created with mixed media on paper, including stabilo pencil, g...
Category

21st Century and Contemporary Street Art Portrait Drawings and Watercolors

Materials

Color Pencil, Gouache, Charcoal, Ink, Mixed Media, Watercolor

"Looks away" by Devie
Located in Carmel, CA
Inspired by the theatre world, Devie had retained her own unique drawing strokes. Her works reflect an approachable other-worldliness. She paints a story to be told and answered. Th...
Category

21st Century and Contemporary Street Art Portrait Drawings and Watercolors

Materials

Ink, Acrylic, Handmade Paper

Untitled (Sunset Tower Hotel)
Located in New York, NY
Listing includes framing with UV plexi, free shipping and a 14 day return policy. Ed Templeton Untitled (Sunset Tower Hotel), 2019 Image size: 11 ...
Category

2010s Street Art Portrait Drawings and Watercolors

Materials

Acrylic, Ballpoint Pen, Pencil, Color Pencil

Previously Available Items
Four Years (Vacation) (2022) by street artist City Kitty, graffiti MTA poster
Located in Jersey City, NJ
"Four Years of Frustration, Delays & Missed Appointments (Vacation)" (2022) by street artist City Kitty 18.25 x 12.25 x .75" Ink, acrylic and color pencil on MTA poster...
Category

2010s Street Art Portrait Drawings and Watercolors

Materials

Paper, Ink, Acrylic, Color Pencil

House of Slaughter (2021) by Sean9 Lugo, comic book portrait of rapper Crooked I
Located in Jersey City, NJ
"House of Slaughter (Crooked I aka Kxng Crooked)" (2021) by street artist Sean 9 Lugo 13 x 9 x .75" Pen, acrylic and marker on blank comic book variant, framed. Artist's signature s...
Category

2010s Street Art Portrait Drawings and Watercolors

Materials

Paper, Ink, Acrylic, Pen

House of Slaughter (2021) by S9L, comic book portrait of rapper Joell Ortiz
Located in Jersey City, NJ
"House of Slaughter (Joell Ortiz)" (2021) by street artist Sean 9 Lugo 13 x 9 x .75" Pen, acrylic and marker on blank comic book variant, framed. Artist's signature style of teddy b...
Category

2010s Street Art Portrait Drawings and Watercolors

Materials

Acrylic, Pen, Paper, Ink

Garbage Portrait 02
Located in Dallas, TX
Murmure Street is a French street artist duo composed of Paul Ressencourt and Simon Roche. Both graduates of Fine Arts schools, they intervene in the streets since 2010, covering the...
Category

21st Century and Contemporary Street Art Portrait Drawings and Watercolors

Materials

Pencil, Color Pencil

Hindsight by street artist Duel RIS, abstract cubist black & white oil drawing
Located in Jersey City, NJ
Hindsight, 2021, by legendary street artist Duel RIS; Oil marker on 130g Strathmore paper, 17 × 14 in Black and white work on paper featuring layered abstract...
Category

2010s Street Art Portrait Drawings and Watercolors

Materials

Archival Paper

Thousand Yard Stare by street artist Duel RIS, abstract black & white drawing
Located in Jersey City, NJ
Thousand Yard Stare, 2021, by legendary street artist Duel RIS; Oil marker on 130g Strathmore paper, 17 × 14 in Black and white work on paper featuring layere...
Category

2010s Street Art Portrait Drawings and Watercolors

Materials

Archival Paper

Third Eye by street artist Duel RIS, abstract black & white drawing on paper
Located in Jersey City, NJ
Third Eye, 2021, by legendary street artist Duel RIS; Oil marker on 130g Strathmore paper, 17 × 14 in Black and white work on paper featuring layered abstract...
Category

2010s Street Art Portrait Drawings and Watercolors

Materials

Archival Paper

Cyclops Boys
By Megan Henley
Located in Kansas City, MO
Megan Henley Title: Cyclops Boys Year: 2018 Medium: Ink on Paper Size: 11 x 14 inches
Category

2010s Street Art Portrait Drawings and Watercolors

Materials

Paper, Ink

Picasso
Located in New York, NY
Graphite on matchbox Unique in a series framed 7" x 7" 2015
Category

21st Century and Contemporary Street Art Portrait Drawings and Watercolors

Materials

Graphite, Cardboard

Warhol
Located in New York, NY
graphite on matchbox unique in a series 7" x 7" 2015
Category

21st Century and Contemporary Street Art Portrait Drawings and Watercolors

Materials

Cardboard, Graphite

Marilyn
Located in New York, NY
Graphite on matchbox Unique in a series framed 7" x 7" 2015
Category

21st Century and Contemporary Street Art Portrait Drawings and Watercolors

Materials

Cardboard, Graphite

Lennon
Located in New York, NY
Graphite on matchbox Unique in a series framed 7" x 7" 2015
Category

21st Century and Contemporary Street Art Portrait Drawings and Watercolors

Street Art portrait drawings and watercolors for sale on 1stDibs.

Find a wide variety of authentic Street Art portrait drawings and watercolors available for sale on 1stDibs. Works in this style were very popular during the 21st Century and Contemporary, but contemporary artists have continued to produce works inspired by this movement. Many Pop art paintings were created by popular artists on 1stDibs, including and Sean 9 Lugo. Frequently made by artists working with Paper, and Ink and other materials, all of these pieces for sale are unique and have attracted attention over the years. Not every interior allows for large Street Art portrait drawings and watercolors, so small editions measuring 9 inches across are also available. Prices for portrait drawings and watercolors made by famous or emerging artists can differ depending on medium, time period and other attributes. On 1stDibs, the price for these items starts at $250 and tops out at $1,537, while the average work sells for $400.

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