Charlize Theron Towers Over Sean Penn in Heels at ‘The Gunman’ Premiere in Gucci and Stuart Weitzman

After her long-term relationship with Stuart Townsend ended, Charlize Theron moved on to another high-profile romance—this time with fellow Oscar winner Sean Penn. Their pairing drew plenty of attention, not just for their strong personalities but also for their striking height difference.

In March 2015, Charlize Theron held hands with her boyfriend Sean Penn on the red carpet at the premiere of his new film The Gunman at Regal Cinemas L.A. Live in Los Angeles. They dated from late 2013 to June 2015.

Sean Penn and Charlize Theron at the premiere of his new film The Gunman held at Regal Cinemas L.A. Live in Los Angeles on March 12, 2015 (Credit: WENN / Apega / FayesVision)

Bohemian Glamour: Gucci Dress & Stuart Weitzman Sandals in L.A.

Charlize Theron, who stands 5ft 9¾ (177.2 cm) tall, was also spotted wearing the same Stuart Weitzman sandals at the film’s London premiere earlier that year.

Standing beside her 5ft 8 (172.7 cm) boyfriend, Sean Penn, the heels added extra height to her already statuesque frame, proving that her go-to footwear can deliver repeat standout fashion moments on the red carpet.

This time, she styled her Stuart Weitzman heels with a blue printed bohemian dress from the Gucci Spring 2015 collection featuring beaded detailing and a deep V neckline. She accessorized with a taupe satin Gucci clutch.

Charlize Theron, towering over Sean Penn in black Stuart Weitzman heels, paraded her long legs in a blue printed bohemian Gucci mini dress at The Gunman premiere (Credit: WENN / Apega / FayesVision)

Halston Heritage Elegance & Nudist Heels in London

In February 2015, Charlize Theron showed off her long legs and towered over her boyfriend at the premiere of The Gunman at BFI Southbank in London, England.

Charlize Theron turned heads with her mesmerizing beauty at the premiere of The Gunman held at BFI Southbank in London on February 16, 2015 (Credit: WENN / Daniel Deme)

The statuesque South African-American actress, producer, and fashion model was there to support her boyfriend, Sean Penn.

Charlize Theron and Sean Penn pose together, with Charlize in a chic black dress and Sean in a sharp suit (Credit: WENN / Daniel Deme)

We love Charlize’s black Halston Heritage halter gown with a modern gold neckline. She carried an Emm Kuo clutch and completed the ensemble with Stuart Weitzman “Nudist” sandals.

Charlize Theron stood visibly taller than Sean Penn in a sleek black Halston Heritage halter gown and strappy Stuart Weitzman Nudist heels at The Gunman London premiere (Credit: WENN / Daniel Deme)

Sean Penn and Charlize Theron began dating in late 2013 and became engaged in 2014. They were seen together on numerous red carpets and public events and co-starred in the 2015 film “The Last Face.”

However, their relationship began to falter in 2015, and they called off their engagement and split up later that year.

Charlize Theron’s Emm Kuo clutch provided a touch of contrast to the all-black ensemble (Credit: WENN / Daniel Deme)

Since Charlize towers over Sean Penn without heels, perhaps he would have preferred if she had worn flats.

Charlize Theron added inches to her height with sleek black Stuart Weitzman Nudist sandals, featuring delicate ankle straps and glossy stilettos—with a slightly worn sole from walking the red carpet (Credit: WENN / Daniel Deme)

Her relationship with Sean Penn received plenty of red carpet attention, especially with the visible height difference when Charlize wore heels. However, it wasn’t her first time dating a fellow actor. Before Penn, she spent nearly a decade with Stuart Townsend, who stands at 5ft 10 (177.8 cm) and may have only appeared slightly taller than her when she was in flats.

Revisiting Charlize Theron’s Past Relationships & Red Carpet Pairings

Her first public relationship was with fellow actor Craig Bierko. Theron dated Bierko from 1995 to 1997. After their breakup, Theron wasted no time entering a new relationship with singer Stephan Jenkins, which lasted from 1998 to 2001.

Theron’s early relationships are overshadowed by those that occurred more recently. Her longest relationship began soon after her breakup with Jenkins in October 2001. A month or two later, Theron entered a relationship with another actor, Stuart Townsend.

Charlize Theron exudes Old Hollywood glamour in a silver embellished gown with retro waves and a metallic clutch, attending the red carpet with Stuart Townsend (Credit: FayesVision / WENN)

They met when they starred in the 2002 crime thriller Trapped, in which she portrayed Karen Jennings and he played Dr. Will Jennings. They parted ways in 2010, but the breakup seemed mutual and the best decision for them.

Charlize Theron shines in a metallic one-shoulder dress with a matching oversized clutch at the Meteor Ireland Music Awards, posing alongside then-boyfriend Stuart Townsend (Credit: Brian McEvoy / WENN)

Before making headlines with her red carpet romances, Charlize Theron continued to prove her fashion versatility on solo appearances, effortlessly balancing edgy and elegant styles. One standout look came during the promotional tour for The Huntsman: Winter’s War, where she embraced a bold, modern aesthetic.

Leather Chic in Reformation & Tabitha Simmons Booties

In March 2016, Charlize Theron proved that age is just a number as she put on a leggy display at a photocall for the 2016 American fantasy action-adventure film The Huntsman: Winter’s War at Park Hyatt Hamburg, located on the famous Mönckebergstrasse in Hamburg’s city center in Germany.

Charlize Theron wears her blonde hair in a wavy bob at the premiere of “The Huntsman: Winter’s War” on March 30, 2016, in Hamburg, Germany (Credit: Schultz-Coulon / WENN)

Director Cedric Nicolas-Troyan, her co-stars Emily Blunt and Chris Hemsworth, and she were joined on the red carpet to help promote the movie.

Cedric Nicolas-Troyan, Charlize Theron, Emily Blunt, and Chris Hemsworth pose on the red carpet (Credit: Schultz-Coulon / WENN)

The then 40-year-old actress stole the spotlight in an edgy monochrome ensemble, flaunting her lean legs.

Charlize Theron flaunted her long legs in a black leather Reformation mini skirt and peep-toe Tabitha Simmons booties at The Huntsman: Winter’s War photocall in Hamburg (Credit: Schultz-Coulon / WENN)

She wore a thigh-skimming A-line black leather mini skirt and a white lace-paneled, collared blouse by English fashion designer Stella McCartney.

Charlize styled the look with a Saint Laurent tuxedo blazer, bracelets, and earrings from Los Angeles-born jewelry designer Anita Ko.

Charlize Theron wears a Stella McCartney top, Saint Laurent blazer, and Reformation skirt on the red carpet (Credit: Schultz-Coulon / WENN)

The “Mad Max: Fury Road” star looked beautiful in her short bob, which was tousled and topped with pink lipstick.

Charlize Theron boosted her 5ft 9¾ frame with edgy black Tabitha Simmons booties, featuring zipper fronts, triple buckle straps, and peep toes that showed off her neutral pedicure (Credit: Schultz-Coulon / WENN)

She drew further attention to her legs with a pair of Tabitha Simmons booties featuring silver-toned zipped fronts, triple buckle-fastening straps, peep-toes, and about four-inch heels.

Stepping Out in Style: Charlize Theron’s Most Iconic Shoe Moments

Charlize Theron, known for her statuesque presence and impeccable fashion sense, has consistently turned heads with her choice of footwear. Here are some of her most memorable shoe moments:

Charlize Theron Embraces Her Height with Sky-High Heels

• Event: Various Red Carpet Appearances
• Footwear: Charlize often opts for luxurious stilettos from brands like Jimmy Choo and Stuart Weitzman, adding several inches to her already commanding presence.
• Read more: Charlize Theron’s Towering Height and Love for Heels

Charlize Theron’s Jaw-Dropping Christian Louboutin Sandals

• Event: ‘Today’ Show Appearance in NYC
• Outfit: She paired Christian Louboutin’s Decoupata sandals with a sleek black Lanvin sheath dress, letting her statement-making heels take center stage.
• See more: Charlize Theron’s Decoupata Christian Louboutin Sandals

Charlize Theron Attends ‘Girlboss’ Premiere in Gianvito Rossi Sandals

• Event: ‘Girlboss’ Premiere in Los Angeles
• Outfit: Charlize stepped out in a black satin slip dress by Nili Lotan, layered under a Givenchy dinner jacket, and completed the look with Gianvito Rossi ‘Portofino’ sandals.
• Discover more: Charlize Theron’s Gianvito Rossi ‘Portofino’ Sandals at ‘Girlboss’ Premiere

Charlize Theron Looks Badass in Christian Louboutin ‘Harler’ Pumps

• Event: Appearance on ‘Jimmy Kimmel Live’
• Outfit: She showcased her lean legs in a black and white silk leopard print dress from Saint Laurent, paired with black suede Christian Louboutin ‘Harler’ pointy-toe pumps.
• See her look: Charlize Theron’s Christian Louboutin ‘Harler’ Pumps

Charlize Theron Dazzles in Shirtless Blazer at CTAOP 2024 Party

• Event: CTAOP 2024 Block Party
• Outfit: Charlize completed her all-black Dior look with the luxury house’s classic J’Adior slingback pumps, which feature an embroidered flat ribbon.
• Explore her style: Charlize Theron’s J’Adior Slingback Pumps at CTAOP 2024

These moments highlight Charlize Theron’s impeccable taste in footwear, showcasing her ability to pair bold and elegant designs with her striking ensembles.