Humble beginnings: Chastain is the ultimate early aughts girl in tattered boot-cut jeans and stripped pastel tee.
Attending a fashion week party in LA, Chastain looked cool and casual in a halter-neck black dress.
Once again, Chastain keeps it simple at classic at the opening of Othello at B-Bar in NYC wearing a little black dress.
Chastain at the Dior Haute Couture Spring 2009 show, this time in a ruffled strapless black gown.
The actress arrived at the InStyle magazine Summer Soiree party, beginning to experiment with color in a printed dress.
At the Somewhere premiere in Los Angeles, Chastain’s sartorial verve appears in this adventurous floral frock.
Arriving at the GQ ‘Men of the Year’ party, Chastain chose a flirty red polka-dot cocktail dress and smoky eye makeup.
Shown here in a structured, ivory frock for the Decades Denim launch party. When in doubt: belt it.
In a flamingo-feathered pink cocktail dress for a Golden Globes party, with an emphasis on the statement pump.
At a W Magazine party for the Golden Globes at a light blue dress and black strappy heel.
For the I Am Number Four premiere in Los Angeles in a gathered, gold dress and matching heel.
Jessica Chastain in Zac Posen at the Tree of Life premiere at the 64th annual Cannes Film Festival in Cannes, France.
A lady-like figure in a shocking pink frock and black pump for a Pre-Oscar party.
At a Vanity Fair launch party in a dramatic Alexander McQueen peplum top and matching skirt.
A gilded McQueen gown for the 84th Academy Awards, as a loose up-do completes the look.
Arriving at the Calvin Klein Fall 2013 show in a chic coat and dress combo.
A vision in glittering Givenchy Haute Couture at the premiere of All is Lost.
Arriving at the 70th Annual Golden Globes in gorgeous celadon gown with plunging neckline.
Chastain wore Armani Privé to the 85th annual Academy Awards in February 2013.
The pockets on Chastain’s black velvet Alexander McQueen dress and the hue of her multi-colored pumps were just fun enough for a daytime photo call.
Statuesque beauty in a custom Prada gown for the Interstellar premiere red carpet.
Recalling Félix Vallotton's 1924 painting Le Retour de la Mer in a beguiling Atelier Versace gown.
Chastain poses on the red carpet for the European premiere of the film Interstellar in London wearing a dusty rose gown by Saint Laurent.
Prim and pretty in an embellished Oscar de la Renta dress and gilded heel at the 40th Deauville American Film Festival.
Chastain arrives at 'China: Through The Looking Glass' in golden Givenchy Couture gown for ultimate movie star glamour.
In an Oscar de la Renta printed dress for the Jameson Empire Awards in London.
Jessica Chastain in Givenchy at the Toronto International Film Festival premiere of The Martian in Toronto, Canada, September 2015.
The lady is a vamp! In a dramatic, plunging gown by Versace at a Golden Globes party.
Jessica Chastain in Elie Saab at the opening of the Metropolitan Opera's 2015-2016 season in New York, New York, September 2015.
Jessica Chastain in Givenchy at the 87th annual Academy Awards in Hollywood, California, February 2015.
Jessica Chastain wore a lace Preen Fall 2015 dress to the Crimson Peak panel for ComicCon.
Jessica Chastain in Elie Saab at the European premiere of The Martian in London, England, September 2015.
In a floral appliqued cocktail dress by Erdem at an event for her film Crimson Peak in New York.
Wearing an embellished hankerchef gown by Altuzarra on the red carpet for the premiere of her film Huntsman: Winters War.
At the opening of Café Society in a canary yellow dress by Armani Prive and shoulder grazing hair.
On the red carpet for 2016’s Met Gala ‘Manus x Machina’ exhibition in a custom royal blue ballgown by Prada.
In a glittering dress of dreams by Alexander McQueen at the premiere of Money Monster with loose, 20’s inspired hair.
Chastain in Giles Deacon at a press conference for The Huntsman: Winter's War in Beijing, China, April 2016.
The actress opted for Givenchy at the MTV Movie Awards in Burbank, California, April 2016.
After sporting a flowing black gown to amFAR's 21st Cinema Against AIDS Gala, Chastain changed into something a little less comfortable. Covered in bronze beads and accessorized with tall strappy platforms, the look was perfect for the formal after party.
Wearing a powder blue bespoke Prada dress with glittering floral embellishments and sleek ponytail at the Golden Globes.
At the Chanel Haute Couture Atelier Fall/Winter show in an ensemble by the house.
At the premiere of Miss Sloane in an ivory Chanel haute couture mermaid gown.
In a chic all-black ensemble with a pop of color via her Louis Vuittion bag in New York City.