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Jenna Lyons' 'Stylish' Evolution, From Sparkle To Streaming TV

A look back at the iconic former J.Crew designer's style, now on full display in her new HBO Max show.
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Three years after Jenna Lyons left her position as creative director and president at J.Crew, she has a new title: reality TV star.

Lyons appears on the just-debuted HBO Max show “Stylish,” in which the designer imparts her decades of fashion industry wisdom to a group of candidates vying for a spot in her new business. It’s part how-to, part competition, and chock-full of good outfits and interior design.

Lyons’ signature style is instantly recognizable, and has been for years. The big glasses, the distaste for buttoning ... while she has undoubtedly elevated her look since she first hit the public stage, there is always that string threaded through.

Below, a look back at some of Lyons’ style over the years.

2007
Patrick McMullan via Getty Images
Jenna Lyons attends a fundraiser in New York City on June 12, 2007.
2008
Patrick McMullan via Getty Images
Jenna Lyons at a Chanel fine jewelry cocktail party in New York City on Nov. 11, 2008.
2008
Patrick McMullan via Getty Images
Jenna Lyons at the 13th annual ACRIA holiday dinner in New York City on Dec. 15, 2008.
2009
Dimitrios Kambouris via Getty Images
Jenna Lyons and Liya Kebede in New York City on April 8, 2009.
2010
Patrick McMullan via Getty Images
Jenna Lyons at a J.Crew event toasting the nine muse-worthy women featured in its catalog on Feb. 25, 2010.
2010
Duffy-Marie Arnoult via Getty Images
Jenna Lyons at the Billy Reid presentation during New York Fashion Week on Sept. 9, 2010.
2010
Andy Kropa via Getty Images
Jenna Lyons at Teen Vogue's Fashion University in New York City on Oct. 23, 2010.
2011
Rabbani and Solimene Photography via Getty Images
Jenna Lyons at the CFDA (Council of Fashion Designers of America) Awards in New York City on June 6, 2011.
2011
D Dipasupil via Getty Images
Jenna Lyons at the CFDA/Vogue Fashion Fund Awards in New York City on Nov. 14, 2011.
2012
Rabbani and Solimene Photography via Getty Images
Jenna Lyons at the Derek Lam fashion show in New York City on Feb. 12, 2012.
2012
Charles Eshelman via Getty Images
Jenna Lyons at the J.Crew spring 2013 fashion week show in New York City on Sept. 11, 2012.
2012
Rob Kim via Getty Images
Jenna Lyons at the CFDA/Vogue Fashion Fund Awards in New York City on Nov. 13, 2012.
2013
Desiree Navarro via Getty Images
Jenna Lyons at the Yigal Azrouel fashion show in New York City on Feb. 8, 2013.
2013
Alberto E. Rodriguez via Getty Images
Courtney Crangi and Jenna Lyons at the Vanity Fair Oscar party in Los Angeles on Feb. 24, 2013.
2013
Jamie McCarthy via Getty Images
Jenna Lyons at the "Great Gatsby" premiere in New York City on May 1, 2013.
2013
Mireya Acierto via Getty Images
Jenna Lyons at the CFDA/Vogue Fashion Fund finalists celebration in New York City on Nov. 11, 2013.
2014
Jamie McCarthy via Getty Images
Jenna Lyons at the Met Gala in New York City on May 5, 2014.
2014
Michael Loccisano via Getty Images
Jenna Lyons at the Elton John AIDS Foundation's 13th annual benefit in New York City on Oct. 28, 2014.
2014
Theo Wargo via Getty Images
Jenna Lyons at the CFDA/Vogue Fashion Fund Awards in New York City on Nov. 3, 2014.
2015
Jamie McCarthy via Getty Images
Jenna Lyons at a screening of Marvel's "Avengers: Age of Ultron" in New York City on April 28, 2015.
2015
Mireya Acierto via Getty Images
Jenna Lyons at the Jonathan Simkhai fashion show in New York City on Sept. 13, 2015.
2016
Larry Busacca via Getty Images
Jenna Lyons at the Time 100 Gala in New York City on April 26, 2016.
2016
Jamie McCarthy via Getty Images
Jenna Lyons, Jenni Konner and Lena Dunham at the Met Gala in New York City on May 2, 2016.
2016
Dimitrios Kambouris via Getty Images
Jenna Lyons at the New York City Ballet fall gala in New York City on Sept. 20, 2016.
2016
Steve Granitz via Getty Images
Jenna Lyons at the Glamour Women of the Year awards in Los Angeles on Nov. 14, 2016.
2017
Theo Wargo via Getty Images
Jenna Lyons and Paul Feig at the Met Gala in New York City on May 1, 2017.
2017
Ilya S. Savenok via Getty Images
Jenna Lyons in New York City on Sept. 13, 2017.
2019
Dimitrios Kambouris via Getty Images
Jenna Lyons at the WarnerMedia Upfronts in New York City on May 15, 2019.
2019
Cindy Ord via Getty Images
Jenna Lyons at the Popsugar Play/Ground in New York City on June 23, 2019.
2020
Gregg DeGuire via Getty Images
Jenna Lyons at the 26th annual Screen Actors Guild Awards in Los Angeles on Jan. 19, 2020.
2020
Craig Barritt via Getty Images
Jenna Lyons at the Self-Portrait fall/winter 2020 fashion show in New York City on Feb. 8, 2020.
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