LAS VEGAS - OCTOBER 28: Actress Leslie Bibb attends the First Annual Radio Music Awards on October 28, 1999 at the Mandalay Bay Resort and Casino in Las Vegas, Nevada. (Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images)
She looks kinda great in this outfit -- which is VERY of its time, and also this photo is a great reminder of the major advances humanity has made in clip-in hair extensions.
2000
CENTURY CITY, CA - APRIL 15: Actress Leslie Bibb attends the 11th Annual GLAAD Media Awards on April 15, 2000 at the Century Plaza Hotel in Century City, California. (Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images)
The year 2000, during which NO ONE left the house without a pashmina.
GLAAD Media Awards 2000
Bryce Johnson, Leslie Bibb, Alley MIlls and the Popular cast (Photo by Jeff Kravitz/FilmMagic, Inc)
This is the cast of Popular, which was Leslie's big break, and this photo is hilarious. I formally apologize to my beloved Leslie Grossman for publishing a photo where her eyes are almost closed; Mary Cherry would murder me for this. I wonder who is giving rabbit ears to my college friend Chris Gorham over there? (We lived on the same dorm floor. I was DELIGHTED to see he's in Sheriff Country now. He is a super nice guy.)
2000
WESTWOOD, CA - MARCH 27: Actress Leslie Bibb attends the "Skulls" Westwood Premiere on March 27, 2000 at the Mann Village Theatre in Westwood, California. (Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images)
Remember when we all dressed like we were going to a rager at The Bronze?
2000
PASADENA, CA - JULY 24: Actress Leslie Bibb attends the WB Summer TCA Press Tour - After Party on July 24, 2000 at the Il Fornaio Restaurant in Pasadena, California. (Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images)
Voila! Here's the look from this part of the slideshow that she could absolutely wear today.
2000
HOLLYWOOD - APRIL 15: Actress Leslie Bibb attends the 13th Annual Nickelodeon's Kids' Choice Awards on April 15, 2000 at the Hollywood Bowl in Hollywood, California. (Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images)
The year 2000 was PEAK halter top. Ask me how I know!
The 2000 Teen Choice Awards
Leslie Bibb during The 2000 Teen Choice Awards at Barker Hanger in Santa Monica, California, United States. (Photo by SGranitz/WireImage)
She looks amazing here and you could also carbon date the year by just looking at her hair.
2000 Teen Choice Awards
Leslie Bibb during 2000 Teen Choice Awards at Barker Hanger in Santa Monica, California, United States. (Photo by Jeff Kravitz/FilmMagic, Inc)
Remember when the Teen Choice Awards were fun and actually meant something?
2001
Leslie Bibb during FHM Salutes the 100 Sexiest Women in the World at La Boheme in West Hollywood, California, United States. (Photo by Ron Galella/Ron Galella Collection via Getty Images)
This was at an event called "FHM Salutes the 100 Sexiest Women in the World," and I salute HER for not wearing something Extremely Sexy.
2002
Leslie Bibb during Movieline Magazine Hosts the 2nd Annual Young Hollywood Awards at Hollywood Galaxy Theatre in Hollywood, California, United States. (Photo by SGranitz/WireImage)
I secretly kinda love this. It's from an event named, "Movieline Magazine Hosts the 2nd Annual Young Hollywood Awards at Hollywood Galaxy Theatre in Hollywood, California." HOLLYWOOD! Like all those things are currently defunct. (Including perhaps actual Hollywood.)
2003
Leslie Bibb during "The Matrix Reloaded" Premiere at Mann Village Theatre in Westwood, California, United States. (Photo by Gregg DeGuire/WireImage)
I suspect she wants this one back.
2006
HOLLYWOOD - NOVEMBER 07: (L-R) Actor Shea Whigham, actress Leslie Bibb, actor Colin Farrell and Director Joel Schumacher arrive at the screening of "Wristcutters: A Love Story" during the AFI FEST 2006 presented by Audi held at The LOFT at Arclight Cinemas on November 7, 2006 in Hollywood, California. (Photo by Michael Buckner/Getty Images)
Here, we've got Shea Whigham, Leslie Bibb, Colin Farrell at the HEIGHT of his mid-aughts hotness but not his sartorial best, and Joel Schumacher at a screening of "Wristcutters: A Love Story," which Colin was NOT in. Leslie looks so lightly annoyed here. I JUST was watching Shea Wigham in that mini-series about James Garfield; he is such a great Hey! It's That Guy.
2006
Leslie Bibb during The Premiere of Columbia Pictures' "Talladega Nights: The Ballad of Ricky Bobby" at Mann's Grauman Chinese Theater in Los Angeles, California, United States. (Photo by E. Charbonneau/WireImage for Sony Pictures-Los Angeles)
This is FINE but I bet she'd re-do this one too; this is from the premiere of Talladega Nights, in which I think she -- hot take -- delivers one of the film's better performances. (I love Amy Adams generally but that movie does not match her vibe.)
58th Annual Primetime Emmy Awards - HBO After Party, 2006
Leslie Bibb and Jeremy Piven during 58th Annual Primetime Emmy Awards - HBO After Party at Pacific Design Center in Los Angeles, California, United States. (Photo by Jeff Kravitz/FilmMagic)
I just thought this photo was funny. They were NOT dating, I think she was just annoyed with him generally in this moment. (She knew him from Entourage.) (She and Sam Rockwell got together shortly after this.)
In Style and Warner Bros. 2007 Golden Globe After Party
Leslie Bibb during In Style and Warner Bros. 2007 Golden Globe After Party - Inside at Beverly Hilton Hotel in Beverly Hills, California, United States. (Photo by KMazur/WireImage for InStyle Magazine)
Reasonable look, maybe slightly regrettable hair.
2008
Stunning Starlet Leslie Bibb Hosts Evening at Prive Nightclub inside Planet Hollywood Resort and Casino on October 11, 2008 in Las Vegas, Nevada. (Photo by Bruce Gifford/FilmMagic)
NO. (Also, this was an "Evening at Prive Nightclub inside Planet Hollywood Resort" that she hosted, and this whole look screams I DON'T WANT TO BE IN VEGAS.")
2009
Leslie Bibb attends the premiere of Confessions of a Shopaholic at the Ziegfeld Theatre on February 5, 2009 in New York City. (Photo by Jim Spellman/WireImage)
Sparkly and slightly like a FOX News anchor at a holiday party.
2010
BEVERLY HILLS, CA - JANUARY 17: Actress Leslie Bibb arrives at the Warner Brothers/InStyle Golden Globes After Party at The Beverly Hilton Hotel on January 17, 2010 in Beverly Hills, California. (Photo by Jon Kopaloff/FilmMagic)
I appreciate the swing taken on the hose and shoes but, ultimately, that was a miss.
2010
HOLLYWOOD - APRIL 26: Actors Leslie Bibb and Sam Rockwell arrives at the "Iron Man 2" World Premiere at El Capitan Theatre on April 26, 2010 in Hollywood, California. (Photo by Jeff Vespa/WireImage)
As noted! Sam Rockwell has entered the chat. She honestly looks great here.
2010 Toronto International Film Festival
TORONTO, ON - SEPTEMBER 11: Actress Leslie Bibb and actor Sam Rockwell arrive to the "Conviction" Premiere held at The Elgin during the 35th Toronto International Film Festival on September 11, 2010 in Toronto, Canada. (Photo by Jason Merritt/Getty Images)
Same color story, a bit less successfully told.
2011
NEW YORK, NY - APRIL 29: Actress Leslie Bibb attends the premiere of "A Good Old Fashioned Orgy" during the 2011 Tribeca Film Festival at SVA Theater on April 29, 2011 in New York City. (Photo by Andrew H. Walker/Getty Images)
This pattern is so fun.
16th Annual Critics' Choice Awards - 2011
LOS ANGELES, CA - JANUARY 14: Actress Leslie Bibb and actor Sam Rockwell arrive at the 16th Annual Critics' Choice Awards at the Hollywood Palladium on January 14, 2011 in Los Angeles, California. (Photo by Jon Kopaloff/FilmMagic)
This is great but it's also the rare instance when I think someone's SKIRT needs a little hoik.
"Schiaparelli And Prada: Impossible Conversations" Costume Institute Gala - 2012
NEW YORK, NY - MAY 07: Leslie Bibb attends the "Schiaparelli And Prada: Impossible Conversations" Costume Institute Gala at the Metropolitan Museum of Art on May 7, 2012 in New York City. (Photo by Rabbani and Solimene Photography/Getty Images)
FABULOUS.
2012
WESTWOOD, CA - OCTOBER 01: Actress Leslie Bibb arrives at the premiere of CBS Films' "Seven Psychopaths" at Mann Bruin Theatre on October 1, 2012 in Westwood, California. (Photo by Kevin Winter/Getty Images)
This is extremely reasonable and basically timeless.
2013 Film Independent Spirit Awards
SANTA MONICA, CA - FEBRUARY 23: Actress Leslie Bibb attends the 2013 Film Independent Spirit Awards at Santa Monica Beach on February 23, 2013 in Santa Monica, California. (Photo by Steve Granitz/WireImage)
This is excellent and her bracelet is perfect.
2015 Sundance Film Festival
PARK CITY, UT - JANUARY 26: Actress Leslie Bibb attends "Digging For Fire" premiere during the 2015 Sundance Film Festival on January 26, 2015 in Park City, Utah. (Photo by George Pimentel/Getty Images for Sundance)
This is SO much like the jacket we just saw, but it's not actually the same jacket. She must love this kind of pattern. The hat gives her Eau de Maria Bello. (Not a bad thing!)
2017
VENICE, ITALY - SEPTEMBER 04: Sam Rockwell and Leslie Bibb walk the red carpet ahead of the 'Three Billboards Outside Ebbing, Missouri' screening during the 74th Venice Film Festival at Sala Grande on September 4, 2017 in Venice, Italy. (Photo by Pascal Le Segretain/Getty Images)
I do love this. (And his tie.) We are entering a three year-ish period where Sam Rockwell was having major professional success and Leslie tagged along and looked SINCERELY BESIDE HERSELF with joy for him. (I don't stan celebrity relationships really but I would be sad if they broke up.)
2018
BEVERLY HILLS, CA - JANUARY 07: Leslie Bibb poses with actor Sam Rockwell holding his award for Best Performance by an Actor in a Supporting Role in any Motion Picture for 'Three Billboards Outside Ebbing, Missouri' in the press room during The 75th Annual Golden Globe Awards at The Beverly Hilton Hotel on January 7, 2018 in Beverly Hills, California. (Photo by Kevin Winter/Getty Images)
This is very charming.
2018
LOS ANGELES, CA - JANUARY 21: Actor Leslie Bibb attends the 24th Annual Screen Actors Guild Awards at The Shrine Auditorium on January 21, 2018 in Los Angeles, California. (Photo by Steve Granitz/WireImage)
Super reasonable.
2018
LONDON, ENGLAND - FEBRUARY 18: Leslie Bibb attends the EE British Academy Film Awards (BAFTA) held at Royal Albert Hall on February 18, 2018 in London, England. (Photo by Jeff Spicer/Jeff Spicer/Getty Images)
I remember this one -- at the BAFTAs. I love it.
2018
SANTA MONICA, CA - MARCH 03: Actor Leslie Bibb attends the 2018 Film Independent Spirit Awards on March 3, 2018 in Santa Monica, California. (Photo by Jon Kopaloff/FilmMagic)
This is fun -- and the Independent Spirit Awards IS where you wear your sparkly green number.
2018
HOLLYWOOD, CA - MARCH 04: Leslie Bibb attends the 90th Annual Academy Awards at Hollywood & Highland Center on March 4, 2018 in Hollywood, California. (Photo by Frazer Harrison/Getty Images)
Beautiful, although I think she needs a stronger lip.
2018
BEVERLY HILLS, CA - MARCH 04: Leslie Bibb (L) and Sam Rockwell attend the 2018 Vanity Fair Oscar Party hosted by Radhika Jones at Wallis Annenberg Center for the Performing Arts on March 4, 2018 in Beverly Hills, California. (Photo by Dia Dipasupil/Getty Images)
I sincerely hope this was their holiday card.
2018
WESTWOOD, CA - JUNE 07: Leslie Bibb attends the premiere of Warner Bros. Pictures And New Line Cinema's "Tag" at Regency Village Theatre on June 7, 2018 in Westwood, California. (Photo by Jon Kopaloff/FilmMagic)
Ooooh, I legitimately love this.
2018
NEW YORK, NY - JUNE 12: Leslie Bibb takes part in SiriusXM's Town Hall with the cast of 'Tag' hosted by SiriusXM's Michelle Collins on June 12, 2018 in New York City. (Photo by Cindy Ord/Getty Images for SiriusXM)
Extremely reasonable and very cute.
2019
BEVERLY HILLS, CA - JANUARY 06: Leslie Bibb and Sam Rockwell attend the 76th Annual Golden Globe Awards at The Beverly Hilton Hotel on January 6, 2019 in Beverly Hills, California. (Photo by Steve Granitz/WireImage)
They're so coordinated here!
2019
BEVERLY HILLS, CALIFORNIA - FEBRUARY 23: Leslie Bibb attends Chanel And Charles Finch Pre-Oscar Awards Dinner at Polo Lounge at The Beverly Hills Hotel on February 23, 2019 in Beverly Hills, California. (Photo by Rochelle Brodin/Patrick McMullan via Getty Images)
I love this and also this makes me think she and contemporary Mandy Moore should play sisters in something.
2019
HOLLYWOOD, CA - FEBRUARY 24: Leslie Bibb attends the 91st Annual Academy Awards at Hollywood and Highland on February 24, 2019 in Hollywood, California. (Photo by Steve Granitz/WireImage)
Maybe a LITTLE washed out?
2019
BEVERLY HILLS, CALIFORNIA - FEBRUARY 24: Leslie Bibb attends 2019 Vanity Fair Oscar Party Hosted By Radhika Jones - Arrivals at Wallis Annenberg Center for the Performing Arts on February 24, 2019 in Beverly Hills, California. (Photo by Daniele Venturelli/WireImage)
This is great, though -- perfect for someone's third wedding.
2019 Emmys
LOS ANGELES, CALIFORNIA - SEPTEMBER 22: Leslie Bibb attends the 71st Emmy Awards at Microsoft Theater on September 22, 2019 in Los Angeles, California. (Photo by Steve Granitz/WireImage)
Brunette!
2020
BEVERLY HILLS, CALIFORNIA - JANUARY 05: Leslie Bibb attends the 77th Annual Golden Globe Awards at The Beverly Hilton Hotel on January 05, 2020 in Beverly Hills, California. (Photo by Steve Granitz/WireImage)
We are approaching her Iconic Bob. (I always liked this dress.)
2020
LOS ANGELES, CALIFORNIA - JANUARY 19: Leslie Bibb attends the 26th Annual Screen Actors Guild Awards at The Shrine Auditorium on January 19, 2020 in Los Angeles, California. (Photo by Jon Kopaloff/Getty Images)
This is excellent and this hair is very good.
2022
NEW YORK, NEW YORK - APRIL 14: Leslie Bibb attends "American Buffalo" Broadway opening night at Circle in the Square Theatre on April 14, 2022 in New York City. (Photo by John Lamparski/Getty Images)
This could be 2022, it could be 2005.
2022
NEW YORK, NEW YORK - JUNE 12: Sam Rockwell and Leslie Bibb attend the 75th Annual Tony Awards at Radio City Music Hall on June 12, 2022 in New York City. (Photo by Dimitrios Kambouris/Getty Images for Tony Awards Productions)
This is fantastic, though. More formal suits at awards shows!
2023
NEW YORK, NEW YORK - MAY 09: Leslie Bibb attends the "About My Father" premiere at SVA Theater on May 09, 2023 in New York City. (Photo by Dia Dipasupil/Getty Images)
This dress is so great and we are inching SO CLOSE to her current (terrific) hair.
2024
Leslie Bibb at the 96th Annual Oscars held at at the Ovation Hollywood on March 10, 2024 in Los Angeles, California. (Photo by Gilbert Flores/Variety via Getty Images)
And here it is! I loved this whole thing.
2024
BEVERLY HILLS, CALIFORNIA - MARCH 14: Leslie Bibb attends the World Premiere of Apple TV+'s "Palm Royale" at Samuel Goldwyn Theater on March 14, 2024 in Beverly Hills, California. (Photo by Phillip Faraone/Getty Images)
I don't HATE it but also could live without it.
2024
NEW YORK, NY - MARCH 21: Leslie Bibb is seen arriving at 'The View' on March 21, 2024 in New York City. (Photo by MediaPunch/Bauer-Griffin/GC Images)
This is EXCELLENT.
2024
NEW YORK, NEW YORK - MARCH 21: Leslie Bibb attends SAG-AFTRA Foundation Conversations - "Palm Royale" at SAG-AFTRA Foundation Robin Williams Center on March 21, 2024 in New York City. (Photo by Dia Dipasupil/Getty Images)
Still excellent.
2024
HOLLYWOOD, CALIFORNIA - MAY 11: Leslie Bibb attends the Apple TV+ "Palm Royale" official Emmy FYC event at Hollywood Athletic Club on May 11, 2024 in Hollywood, California. (Photo by Aliah Anderson/WireImage)
Continuing to be excellent! (Although...are those shoes clear?)
2024
Leslie Bibb at the 76th Primetime Emmy Awards held at Peacock Theater on September 15, 2024 in Los Angeles, California. (Photo by Gilbert Flores/Variety via Getty Images)
And no one will be angry about this.
2024
HOLLYWOOD, CALIFORNIA - OCTOBER 27: Leslie Bibb attends the closing night gala premiere of "Juror #2" during the 2024 AFI Fest at TCL Chinese Theatre on October 27, 2024 in Hollywood, California. (Photo by Monica Schipper/WireImage)
I'm actively in favor of this one, actually.
2025
LOS ANGELES, CALIFORNIA - FEBRUARY 10: Leslie Bibb arrives at the Los Angeles Premiere Of HBO Original Series "The White Lotus" Season 3 at Paramount Theatre on February 10, 2025 in Los Angeles, California. (Photo by Maya Dehlin Spach/WireImage)
As you can see, we have reached the White Lotus portion of the program. She looks fantastic here. I was surprised she didn't get any nominations for this role -- she is excellent in this season.
2025
BEVERLY HILLS, CALIFORNIA - MARCH 02: Leslie Bibb attends the 2025 Vanity Fair Oscar Party hosted by Radhika Jones at the Wallis Annenberg Center for the Performing Arts on March 02, 2025 in Beverly Hills, California. (Photo by Karwai Tang/WireImage)
A tiny bit sheer but whatever: this is 95% perfect.
2025
SYDNEY, AUSTRALIA - APRIL 02: Leslie Bibb attends "The Last Of Us" Season 2 - Australian Premiere at the State Theatre on April 02, 2025 in Sydney, Australia. (Photo by Brendon Thorne/Getty Images)
Perfect!
2025
WESTLAKE VILLAGE, CALIFORNIA - APRIL 06: Leslie Bibb attends HBO's "The White Lotus" Season 3 Finale Event at Four Seasons Hotel Westlake Village, California on April 06, 2025 in Westlake Village, California. (Photo by Jeff Kravitz/FilmMagic for HBO)
And this is so, so good.
2025
NEW YORK, NEW YORK - MAY 14: Leslie Bibb is seen in Midtown on May 14, 2025 in New York City. (Photo by TheStewartofNY/GC Images)
She herself looks great on this but I cannot sign off, for obvious reasons.
2025
NEW YORK, NY - JUNE 03: Leslie Bibb is seen at "LIVE with Kelly and Mark" on June 03, 2025 in New York City. (Photo by Jason Howard/Bauer-Griffin/GC Images)
SO CUTE. I just looked to see if maybe this dress was available anywhere at a super markdown, and apparently everyone agrees with me because it's sold out everywhere.
2025
NEW YORK, NEW YORK - JUNE 02: Actress Leslie Bibb is seen arriving to The Gotham TV Awards at Cipriani Wall Street on June 02, 2025 in New York City. (Photo by Gilbert Carrasquillo/GC Images)
This has a high degree of difficulty, but she wears it well.
2025
HOLLYWOOD, CALIFORNIA - JULY 23: (L-R) Sam Rockwell and Leslie Bibb attend Universal Pictures' "The Bad Guys 2" Premiere at TCL Chinese Theatre on July 23, 2025 in Hollywood, California. (Photo by Unique Nicole/FilmMagic)
Those metallic shoes peeking out at the bottom here are perfect.
2025
Leslie Bibb at the "Frankenstein" Premiere at The 82nd Venice International Film Festival on August 30, 2025 in Venice, Italy. (Photo by Earl Gibson III/Deadline via Getty Images)
