Everyone's favorite fashion face-off, Project Runway, is currently in its 19th season. The reality show has made household names of numerous cast members, including host and supermodel Heidi Klum and mentor Tim Gunn. Many contestants have used their exposure on the show to springboard into successful careers in the fashion industry.

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Project Runway features a group of contestants who are whittled down with different sewing and design challenges until one is named the winner and the rest are "out." From Jay McCarroll to Dmitry Sholokhov, the winning designer from each of the first 10 seasons went above and beyond "making it work" to make the cut with these iconic and unforgettable looks.

Season 1: Jay McCarroll

Jay McCarroll iconic red dress on the runway in Project Runway

The first season of Project Runway introduced viewers to many memorable characters, including Austin Scarlett (who stepped in as Jay's model in the USPS challenge), Wendy Pepper, and Kara Saun. The very first winner of Runway was Jay McCarroll, who ultimately turned down the inaugural $100,000 prize and went on to have his own spin-off series, Project Jay.

Jay’s best work on the show was hands-down the ruffled red gown from the finale collection. The garment took inspiration from the poorly received cocktail dress that was meant for Nancy O’Dell to wear to the Grammys in episode 9. The dress is an iconic told-you-so moment that proved Jay deserved to be the winner.

Season 2: Chloe Dao

Chloe Dao Project Runway figure skating dress in a collage

Chloe Dao was a consistent top competitor in Season 2 and ultimately beat fellow finalists Santino Rice and Daniel Vosovic with her elegant and wearable evening collection. She consistently presented garments throughout the season that reflected her feminine aesthetic. The most iconic look from Dao during season 2 is the ice skater dress designed for Project Runway guest judge and Olympic figure skater, Sasha Cohen in Episode 7 (“On Thin Ice”).

Though the dress wasn’t chosen as the winner of that challenge, the flirty, flowing blue ruffles were hard to forget. Dao is currently a successful Houston-based designer known for her flattering and wearable garments.

Season 3: Jeffrey Sebelia

Two side by side images of Jeffrey Sebelias plaid yellow dress from Project Runway

Jeffrey Sebelia didn’t hold back his rocker personality and aesthetic in his season 3 looks, and his bad boy persona carried over into the workroom and his interactions with fellow designers. The yellow plaid gown from the “Couture du Jour” challenge was Sebelia’s most iconic look of the season.

Reminiscent of Cher from Clueless’ unforgettable skirt suit, the dress took the traditionally preppy plaid and gave it a sexy rock-n-roll glam-up. Sebelia used his $100,000 prize to support his Cosa Nostra fashion brand and has worked with numerous musicians, including Gwen Stefani and Madonna.

Season 4: Chrisitan Siriano

Chrisitan Siriano's iconic dress from Project Runway

Many Project Runway fans may not know that Christian Siriano is the youngest and arguably the most successful of any of the winners. He is a frequent return guest on the series and his designs have both couture and mass-market appeal.

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Even though the dress in episode 9 (“En Garde”) was a team effort with Chris March, the look is pure Christian Siriano and possibly the most iconic Runway dress of all time. An enormous collar and dramatic ruffles took the avant-garde challenge to new heights. It is a true statement piece.

Season 5: Leanne Marshall

Two side by side images of Leanne Marshall's petal like skirt in Project Runway

Self-described “fashion nerd,” Leanne Marshall used her season 5 prize as a springboard to move to New York City and launch a successful bridal collection. She was quiet and focused throughout the season, leading the way to a well-deserved win. Marshall’s finale collection was breathtaking, featuring ocean-inspired hues and dresses that moved like waves.

The petal-like aqua skirt look is the most memorable from the collection and her most iconic of the season. The look encapsulates Leanne’s romantic and flowing aesthetic.

Season 6: Irina Shabayeva

Two side by side images of Irina Shabayeva's iconic newspaper coat in Project Runway.

Irina Shabayeva came across as a prickly personality in season 6, especially compared to the affable Carol Hannah Witfield. She was a top contender throughout though, and proved her amazing skills as a creative Project Runway designer by consistently producing high-quality looks and winning the last few challenges.

Her most iconic look was a fresh take on a winter coat in episode 5, where the designers were challenged to create a garment out of newspaper. Judge Michael Kors said he saw Coco Chanel in the design, and host Heidi Klum raved about the crinkle effect of the collar and unique textural elements.

Season 7: Seth Aaron Henderson

Two side by side images of Seth Aaron Henderson and his mother daugther design from Project Runway

Seth Aaron Henderson was the first designer to win both Project Runway and Project Runway: All Stars (season 3). He has been focusing on sustainable fashion since his win and has most recently been working as the lead designer for mermaid tail and swimwear company, Fin Fun.

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Henderson's most iconic look of the season was his winning design for the mother-daughter challenge of episode 6. The black and white ensembles were edgy and stylish, while also being practical and wearable. The judges raved about the well thought-out design and integration of Henderson’s own cool style.

Season 8: Gretchen Jones

Side by side image of Gretchen Jones from Project Runway and her jumpsuit

The eighth season of Runway famously featured the judges torn between winner Gretchen Jones’ bohemian looks and runner-up Mondo Guerra, who was a fan favorite with bold and bright designs. Jones consistently produced quality pieces, and her finale win landed her a job at Pendleton.

It’s hard to forget Jones’ incredible iconic jumpsuit for the Marie Claire challenge in episode 2. The winning look was worn by supermodel Coco Rocha on a Times Square billboard and in Marie Claire magazine, giving the designer an incredible amount of public exposure.

Season 9: Anya Ayoung-Chee

Two side by side images of Anya Ayoung-Chee and her chiffon blue and green dress in Project Runway.

Hailing from Trinidad-and-Tobago and a former Miss Universe contestant, Anya Ayoung-Chee was known throughout season 9 for her flowy, beachy looks. Despite having very little sewing experience, she took the top spot after a runway face-off with fellow finalists Kimberly Goldson, Viktor Luna, and Joshua McKinley, making her one of the best Project Runway contestants the show has seen.

Ayoung-Chee’s runway collection was stunning and full of her signature airy chiffon garments perfect for a tropical vacation. Her runway dress in shades of blues and greens with a plunging neckline exquisitely evoked the designer’s aesthetic, with a feminine silhouette and Caribbean vibes.

Season 10: Dmitry Sholokhov

Two side by side images of Dmitry Sholokhov designs from Project Runway

Dmitry Sholokhov consistently proved throughout the tenth season that he was an incredibly skilled craftsman. The designer returned twice more to the runway, winning the fourth season of Project Runway: All Stars and placing second in the seventh season. With a theme that continued into his season 10 runway collection, Sholokhov’s episode 9 (“It’s All About Me”) look featured geometric peekaboo shapes inspired by organic architecture.

This challenge had the contestants create an original print to incorporate into a modern design. The judges lauded the exquisite, expensive-looking tailoring and incredible fit and the iconic look moved the bar even higher for future contestants.

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