Star Wars Inspired Portraiture by Jenn DePaola

A lifelong Star Wars fan, I create expressive digital portraits that celebrate the emotional depth and mythic power of the saga. Each piece is a tribute to the characters, stories, and moments that have inspired me since childhood.

Illustrated portrait of Princess Leia from A New Hope, featuring her iconic white gown and side buns, depicted in soft lighting and an expression of resolve.

Digital Painting Created with Clip Studio Paint and Photoshop.

Portrait of Padme Amidala in her white battle outfit from Attack of the Clones, showing her fierce determination and readiness for "aggressive negotiations" during the Geonosis arena battle.

Digital Painting Created with Clip Studio Paint and Photoshop.

A playful cartoon illustration of Grogu joyfully juggling three frogs set against a bright blue sky and puffy white clouds. This charming Star Wars fan art captures the whimsy and innocence of The Mandalorian's beloved child.

Digital Painting Created with Clip Studio Paint and Photoshop.

A poignant Star Wars desktop illustration featuring the twin suns of Tatooine and the luminous spirit forms of Luke and Leia as seen at the end of The Rise of Skywalker. With the ethereal quote “No one’s ever really gone” subtly beneath them, this piece honors legacy, loss, and hope in a galaxy far, far away.

Digital Painting Created with Clip Studio Paint and Photoshop.

Live-action Ahsoka Tano portrayed with a calm intensity, inspired by her appearance in The Mandalorian series, with textured brushwork and a muted yet moody palette.

Digital Painting Created with Clip Studio Paint and Photoshop.

Rey meditating as she reaches new heights in her abilities, showing the "world between worlds" as seen in Rebels. She is surrounded by the portraits of the Jedi who reached out to her through The Force at the end of The Rise of Skywalker. This is a spiritually charged and layered composition.

Digital Painting Created with Clip Studio Paint and Photoshop.

Din Djarin in full armor from Season 1 of The Mandalorian, standing against a neutral backdrop with a cinematic, moody atmosphere.

Digital Painting Created with Clip Studio Paint and Photoshop.

A stylized portrait of Ahsoka Tano from The Clone Wars final season, wearing her blue battle outfit with intense focus and animated expression.

Digital Painting Created with Clip Studio Paint and Photoshop.

Dauth Maul in a haunting temple environment of the Nightsisters from The Clone Wars. Bathed in shadows with stylized detail emphasizing his quiet rage and power.

Digital Painting Created with Clip Studio Paint and Photoshop.

Emotional portrait of General Leia from The Force Awakens, dressed in blue at the film's end, with a quiet expression of loss, strength, and hope.

Digital Painting Created with Clip Studio Paint and Photoshop.

A multi-scene portrait of Rey from The Force Awakens, featuring her in a battle stance with her staff and BB-8, surrounded by key moments: Her scavenger days, her speeder, and the Millennium Falcon.

Digital Painting Created with Clip Studio Paint and Photoshop.

Leia in her metal bikini from Return of the Jedi, depicted with strength and dignity, reclaiming a controversial moment as one of resilience and inner power. She is the Hutt Slayer.

Digital Painting Created with Clip Studio Paint and Photoshop.

Padme in her green velvet hooded dress from a deleted scene in Revenge of the Sith, rendered in rich tones with a contemplative and regal air.

Digital Painting Created with Clip Studio Paint and Photoshop.

Animated style portrait of Hera Syndulla in a "Rosie The Riveter" pose, with the slogan "We Can Do It" - celebrating her leadership and strength in Star Wars: Rebels.

Digital Painting Created with Clip Studio Paint and Photoshop.

A quiet tribute to love and memory, this piece features General Leia Organa gazing and reminiscing at an old hologram of Han Solo playing with a young Ben Solo. C-3PO stands by in quiet companionship, honoring the weight of history and hope.

Digital Painting Created with Clip Studio Paint and Photoshop.

Inspired by Star Wars: Bloodline, this portrait captures Leia Organa in a dramatic black gown and cape, framed by a bold archway in tarot-like style. Painted at the moment she reclaims her narrative following the galaxy’s discovery of her lineage, this piece honors her strength, legacy, and unwavering presence in the New Republic.

Digital Painting Created with Clip Studio Paint and Photoshop.

A playful pinup dressed in biker scout armor speeds through the lush forests of Endor, with a mischievous Ewok riding shotgun on the back of her speeder bike. Framed in a circular vintage postcard-style design, the scene bursts beyond its borders with the text “Greetings from the Moon of Endor.” A tribute to Return of the Jedi and classic pinup charm.

Digital Painting Created with Clip Studio Paint and Photoshop.

A bold redheaded Rebel pinup stands against the icy backdrop of Hoth, binoculars in hand as four towering AT-ATs approach from the distance. Styled like a vintage postcard, this circular design features the playful phrase “Greetings from Hoth,” with both the illustration and text breaking the border for added dynamism. Inspired by The Empire Strikes Back and classic pinup aesthetics, this piece combines retro flair with Star Wars action.

Digital Painting Created with Clip Studio Paint and Photoshop.

A stylized pinup of one of Queen Amidala’s handmaidens sits poised on a balcony overlooking the Palace and waterfalls of Naboo. She wears the iconic “flame” gown, with rich gradients of red, orange, and gold flowing to pale yellow at the hem. Inspired by vintage travel postcards, the circular composition is accented with the text “Greetings from Naboo,” subtly breaking the frame along with the figure blending elegance, nostalgia, and prequel-era tribute

Digital Painting Created with Clip Studio Paint and Photoshop.

A First Order trooper pinup stands confidently in front of the stark, snowy landscape of Starkiller Base. With the towering First Order banners behind her, she holds her blaster at the ready, poised for action. The icy surroundings and imposing architecture of the base create a commanding atmosphere, while the vintage postcard-style “Greetings from Starkiller Base” text breaks the circular frame. This piece blends retro pinup style with the cold, precise energy of the First Order era.

Digital Painting Created with Clip Studio Paint and Photoshop.

Darth Maul sketch card created for Topps Star Wars Masterwork series. Based on Maul from The Cone Wars, animated style.

Mixed Media: Markers, Colored Pencils, and Ink.

Obi-Wan Kenobi sketch card from the Topps Star Wars Masterwork series. Based on Star Wars Episode III, Revenge of the Sith.

Mixed Media: Markers, Colored Pencils, and Ink.

Princess Leia Organa from the Topps Star Wars Masterwork series. Based on the scene in the Rebel Hoth base in Star Wars The Empire Strikes Back

Mixed Media: Markers, Colored Pencils, and Ink.

C-3PO sketch card from the Topps Star Wars Masterwork series. Based on the scene in Jabba's Palace in Star Wars Return of the Jedi.

Mixed Media: Markers, Colored Pencils, and Ink.

About the Artist

I'm Jenn DePaola, a digital illustrator who creates cinematic, character-focused portraits using Clip Studio Paint and Photoshop. Star Wars has been a part of my life since I was a little girl. That early spark grew into a lifelong passion for storytelling, myth, and pop culture.

I’ve had the honor of contributing official Star Wars artwork through Topps sketch cards, and I’m continually inspired to explore the iconic storytelling and timeless heroes of our favorite galaxy far, far away.

May the Force be with you... Always.

- Jenn