The 144th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, takes place on Saturday, May 5 this year. From Janet Jackson to Kim Kardashian, Susan Lucci and more, see some of the most unusual hats celebs have worn through the years.
Actor Blair Underwood attends Kentucky Derby 144 on May 5, 2018 in Louisville, Kentucky.
Kid Rock attends Kentucky Derby 144 on May 5, 2018 in Louisville, Kentucky.
Victoria Justice attends Kentucky Derby 144 on May 5, 2018 in Louisville, Kentucky.
Chef Graham Elliot attends Kentucky Derby 144 on May 5, 2018 in Louisville, Kentucky.
Chef Tom Colicchio attends Kentucky Derby 144 on May 5, 2018 in Louisville, Kentucky.
Alicia Etheredge and Bobby Brown attend Kentucky Derby 144 on May 5, 2018 in Louisville, Kentucky.
Actress Aisha Tyler attends Kentucky Derby 144 on May 5, 2018 in Louisville, Kentucky.
American figure skaters Tara Lipinski and Johnny Weir attend Kentucky Derby 144 on May 5, 2018 in Louisville, Kentucky.
Professional boxer Laila Ali attends Kentucky Derby 144 on May 5, 2018 in Louisville, Kentucky. (Photo by Dia Dipasupil/Getty Images for Chruchill Downs)
Actor Anthony Anderson attends Kentucky Derby 144 on May 5, 2018 in Louisville, Kentucky.
Actor Jesse Spencer attend Kentucky Derby 144 on May 5, 2018 in Louisville, Kentucky.
Jill Goodacre
Jill Goodacre and Harry Connick Jr. attend the 143rd Kentucky Derby at Churchill Downs on May 6, 2017 in Louisville, Kentucky.
Dannielynn Birkhead
Dannielynn Birkhead and Larry Birkhead attend the 143rd Kentucky Derby at Churchill Downs on May 6, 2017 in Louisville, Kentucky.
Courtney Sixx
Courtney Sixx attends the 143rd Kentucky Derby at Churchill Downs on May 6, 2017, in Louisville, Kentucky.
Susan Geston
Susan Geston and Jeff Bridges attend the 143rd Kentucky Derby at Churchill Downs on May 6, 2017, in Louisville, Kentucky.
Mira Sorvino
Mira Sorvino attends the 143rd Kentucky Derby at Churchill Downs on May 6, 2017, in Louisville, Kentucky.
Katie Couric
Katie Couric attends the 143rd Kentucky Derby at Churchill Downs on May 6, 2017, in Louisville, Kentucky.
Robin Meade
Robin Meade attends the 143rd Kentucky Derby at Churchill Downs on May 6, 2017, in Louisville, Kentucky.
Laura Bell Bundy
Laura Bell Bundy attends the 143rd Kentucky Derby at Churchill Downs on May 6, 2017 in Louisville, Kentucky.
Giada De Laurentiis
Giada De Laurentiis attends the 143rd Kentucky Derby at Churchill Downs on May 6, 2017, in Louisville, Kentucky.
Mary Wilson
Richie Sambora and Mary Wilson attend the 143rd Kentucky Derby at Churchill Downs on May 6, 2017, in Louisville, Kentucky.
Star Jones
TV personality Star Jones attends the 142nd Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 07, 2016.
The Supremes' Mary Wilson
Mary Wilson of The Supremes attends the 142nd Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 07, 2016.
Brittany Howard
Musician Brittany Howard of the Alabama Shakes attends the Delta Dental Celebrity Green Room during the 142nd Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 7, 2016.
Gayle King
Gayle King attends the Delta Dental Celebrity Green Room during the 142nd Kentucky Derby at Churchill Downs in Louisville, Kentucky on May 7, 2016.
Kate Upton
Kate Upton smiles in the paddock before the 142nd running of the Kentucky Derby horse race at Churchill Downs in Louisville, Kentucky, on Saturday, May 7, 2016.
Hillary Scott
Singer Hillary Scott of Lady Antebellum attends the 142nd Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 07, 2016.
Vanessa Lachey
Vanessa Lachey attends the 141st running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 2, 2015.
Ne-Yo and Crystal Renay
Crystal Renay and Ne-Yo attend the 141st running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 2, 2015.
Kendra Wilkinson-Baskett
Kendra Wilkinson-Baskett attends the 141st running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 2, 2015.
Andi Dorfman
Television personality Andi Dorfman attends the 141st running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 2, 2015.
Luke Bryan and Caroline Boyer
Singer Luke Bryan and wife Caroline Boyer celebrate the 139th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 4, 2013.
Coco Rocha
Coco Rocha attends the 139th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 4, 2013.
Jane Seymour
Actress Jane Seymour attends the 139th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 4, 2013.
Miranda Lambert
Singer Miranda Lambert attends the 139th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 4, 2013.
Kellan Lutz and Sharni Vinson
Kellan Lutz and Sharni Vinson pose with a limited edition 6 liter Moet & Chandon Imperial bottle for the brand's philanthropic initiative "Sign for the Roses" on the red carpet at the 138th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 5, 2012.
Star Jones
Star Jones signs a limited edition 6 liter Moet & Chandon Imperial bottle for the brand's philanthropic initiative "Sign for the Roses" on the red carpet at the 138th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 5, 2012.
Ginnifer Goodwin
Actress Ginnifer Goodwin attends the 138th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 5, 2012.
Kate Flannery
Actress Kate Flannery attends the 138th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 5, 2012.
Mary J. Blige
Mary J. Blige signs a limited edition 6 liter Moet & Chandon Imperial bottle for the brand's philanthropic initiative "Sign for the Roses" on the red carpet at the 138th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 5, 2012.
Miranda Lambert
Miranda Lambert signs a limited edition 6 liter Moet & Chandon Imperial bottle for the brand's philanthropic initiative "Sign for the Roses" on the red carpet at the 138th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 5, 2012.
Cyndi Lauper
Cyndi Lauper with a limited edition 6 liter Moet & Chandon Imperial bottle for the brand's philanthropic initiative "Sign for the Roses" on the red carpet at the 138th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 5, 2012.
Joey Fatone and Shawn Stockman
Joey Fatone and Shawn Stockman sign a limited edition 6 liter Moet & Chandon Imperial bottle for the brand's philanthropic initiative "Sign for the Roses" on the red carpet at the 138th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 5, 2012.
Ice-T and Nicole 'Coco' Austin
Ice-T and Nicole "Coco" Austin pose with a limited edition 6 liter Moet & Chandon Imperial bottle for the brand's philanthropic initiative "Sign for the Roses" on the red carpet at the 138th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 5, 2012.
Vicki Gunvalson
TV personality Vicki Gunvalson attends the 137th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 7, 2011.
Rozonda 'Chilli' Thomas
Singer/TV personality Rozonda "Chilli" Thomas attends the 137th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 7, 2011.
Kate Gosselin
TV personality Kate Gosselin attends the 137th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 7, 2011.
Vanessa Lachey
Vanessa Lachey attends the 137th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 7, 2011.
Jordin Sparks
Singer Jordin Sparks attends the 137th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 7, 2011.
Aubrey O'Day
Singer/TV personality Aubrey O'Day attends the 137th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 7, 2011.
Kate Walsh
Actress Kate Walsh visits the Mott's Garden Blend VIP suite at the 137th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 7, 2011.
Kim Kardashian
Kim Kardashian arrives at the 135th at Churchill Downs in Louisville, Kentucky, on May 2, 2009.
Molly Sims
Actress Molly Sims attends the 134th at Churchill Downs in Louisville, Kentucky, on May 3, 2008.
Heidi Montag
Heidi Montag of MTV's "The Hills" attends the 134th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 3, 2008.
Victoria Gotti
Reality television personality Victoria Gotti arrives at the 131st running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 7, 2005.
Tori Spelling
Actress Tori Spelling arrives at the 131st running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 7, 2005.
Josh Groban and January Jones
Singer Josh Groban and January Jones arrive at the 131st running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 7, 2005.
Jamie-Lynn Sigler
Actress Jamie-Lynn Sigler arrives at the 131st running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 7, 2005 in Louisville, Kentucky.
Jermaine Dupri
Jermaine Dupri attends the 130th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 1, 2004.
Boyz II Men
Wayna Morris, Shawn Stockman and Nathan Morris of Boyz II Men attend the 130th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 1, 2004.
Carson Daly
Television personality Carson Daly attends the 130th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 1, 2004.
LaToya Jackson
LaToya Jackson attends the 130th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 1, 2004.
Kelly Rowland
Kelly Rowland of Destiny's Child attends the 130th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 1, 2004.
Jessica Simpson and Nick Lachey
Jessica Simpson and Nick Lachey attend the 130th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 1, 2004.
Kim Cattrall
Actress Kim Cattrall attends the 130th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 1, 2004.
Nicole Richie
Socialite Nicole Richie attends the 130th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 1, 2004.
Anna Nicole Smith
Actress and model Anna Nicole Smith attends the 130th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 1, 2004.
George Strait and Kid Rock
George Strait and Kid Rock during the 129th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 3, 2003.
Susan Lucci
Actress Susan Lucci is interviewed by the local media as she arrives at the 129th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 3, 2003.
Janet Jackson
Singer Janet Jackson and her family and friends attend the 129th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 3, 2003.
Jessica Simpson
Singer Jessica Simpson sings "My Old Kentucky Home" before the 128th running of the Kentucky Derby at Churchill Downs in Louisville, Kentucky, on May 4, 2002.
Meat Loaf and Deborah Gillespie
Singer Meat Loaf and his fiancee, Deborah Gillespie, pose before the 128th running of the run for the roses Kentucky Derby At Churchill Downs in Louisville, Kentucky, on May 4, 2002.
Source: NewsDay -
By Joann Vaglica
https://www.newsday.com/entertainment/celebrities/celebrities-kentucky-derby-hats-through-the-years-1.11769718
