Home Fashion For a generation of fashion-obsessed pop culture lovers who came of age in the aughts, actress Lindsay Lohan was one of the most-watched style stars of her day. Read on for a look at some of her most standout moments during the last two decades.
Fashion

For a generation of fashion-obsessed pop culture lovers who came of age in the aughts, actress Lindsay Lohan was one of the most-watched style stars of her day. Read on for a look at some of her most standout moments during the last two decades.

by admin

She wore cargo pants, so we all wore cargo pants.

For a generation of fashion-obsessed pop culture lovers who came of age in the aughts, New York-born actress Lindsay Lohan was one of the most-watched style stars of her day. Thankfully, the “Lohanaissance” of recent years has been just as epic to witness. 

The globally recognized protagonist of movies so beloved we can still quote them in our sleep—think: The Parent Trap, Mean Girls, and Freaky Friday—found fame as a tot before becoming one of the most well-known teenagers in the industry. And over the decades, her outfits became as relentlessly documented as her personal life. A staple at fashion weeks around the world, a model and muse for brands throughout Y2K, and even the one-time creative director of Emanuel Ungaro, her influence is well documented. At one point, a paparazzi shot of her ankle monitor post-rehab in 2007 was said to have inspired Karl Lagerfeld to design mini Chanel bags to be worn around the leg. (Does it get more iconic than that?)     

Having taken a backseat and a breather from the spotlight once she relocated to Dubai 10 years ago, Lohan has been back to business since 2022, once again appearing in movies and making personal appearances at major entertainment events—even announcing that an update to Freaky Friday will be released in 2025. 

The now mom-of-one, 38, has aced on the red carpet since her return, in scene-stealing Jil Sander, Balenciaga, and Balmain, to name but a few. Thanks to stylist duo Mariel Haenn and Rob Zangardi, we’re hooked all over again—and it’s whetted our appetite for what the Freaky Friday press tour will look like. 

Read on for a look at some of LiLo’s most standout moments during the last two decades.

At the Balenciaga show during Paris Fashion Week in 2024

For a generation of fashion-obsessed pop culture lovers who came of age in the aughts, actress Lindsay Lohan was one of the most-watched style stars of her day. Read on for a look at some of her most standout moments during the last two decades.

She’s back! Lohan made her return to Paris Fashion Week this past season, sitting front row at the Balenciaga show. While her relationship with the brand runs deep—after all, she helped put the City bag on the map in the 2000s—it was the first time the actress ever attended one of the house’s shows. Making this debut even more memorable, her sharp-shouldered, floor-sweeping trench coat and wet-look sequin dress made for a mic-drop entrance. 

At the Kering Caring For Women Dinner in New York in 2024

For a generation of fashion-obsessed pop culture lovers who came of age in the aughts, actress Lindsay Lohan was one of the most-watched style stars of her day. Read on for a look at some of her most standout moments during the last two decades.

At the star-studded philanthropic spectacle that is the Caring For Women dinner at The Pool during NYFW, Lohan caused jaws to drop when she graced the navy carpet in a custom embroidered lace off-the-shoulder gown, crafted specially for her by Demna. Glossy black calfskin Knife pumps and long, tousled mermaid-esque hair completed the look to perfection. 

At the Vanity Fair Oscars Party in 2024

For a generation of fashion-obsessed pop culture lovers who came of age in the aughts, actress Lindsay Lohan was one of the most-watched style stars of her day. Read on for a look at some of her most standout moments during the last two decades.

We can’t say we had LiLo becoming a Balenciaga girlie on our bingo card for 2024, but after all these excellent red carpet moments, it now makes sense. The actress once again stunned in a custom creation from the brand—this time, a silver fringed sparkler of a frock—for her first time attending the famous Vanity Fair post-awards soirée in a decade. 

In vintage John Galliano at the 'Irish Wish' premiere in New York City in 2024

For a generation of fashion-obsessed pop culture lovers who came of age in the aughts, actress Lindsay Lohan was one of the most-watched style stars of her day. Read on for a look at some of her most standout moments during the last two decades.

Now that’s how you compliment your signature auburn tresses! For the premiere of her Netflix flick Irish Wish, Lohan lit up the emerald green carpet in a vintage Old Hollywood-style ruched satin gown by John Galliano, sourced by her stylists Rob Zangardi and Mariel Haenn from The Albright Fashion Library. A cute detail? The delicate nameplate necklace is dedicated to her baby boy, Luai. Irish eyes are smiling!

In Alexandre Vauthier at the Mean Girls premiere in New York City in 2024

For a generation of fashion-obsessed pop culture lovers who came of age in the aughts, actress Lindsay Lohan was one of the most-watched style stars of her day. Read on for a look at some of her most standout moments during the last two decades.

The OG Cady Heron caused headlines when she hit the pink carpet to support the cast of the musical reboot of Mean Girls, showing the new guard how it’s done in a sizzling cut-out and crystal-adorned number by Alexandre Vauthier.  

In Christian Siriano at the Christian Siriano Fall/Winter 2023 show

For a generation of fashion-obsessed pop culture lovers who came of age in the aughts, actress Lindsay Lohan was one of the most-watched style stars of her day. Read on for a look at some of her most standout moments during the last two decades.

We love a Lohan sighting during fashion week. The star looked sublime in copper hues when she stepped out to support designer Christian Siriano for his fall/winter 2023 show at Gotham Hall. 

In Valentino at the 'Falling For Christmas' Premiere in New York in 2022

For a generation of fashion-obsessed pop culture lovers who came of age in the aughts, actress Lindsay Lohan was one of the most-watched style stars of her day. Read on for a look at some of her most standout moments during the last two decades.

Lohan made her return to the spotlight in 2022 after a three-year hiatus, reappearing on screens in the Netflix holiday romance Falling For Christmas. Having just welcomed her son months before, the actress looked resplendent in an embroidered and embellished nude illusion gown by Valentino, styled by Law Roach. 

On Saint Laurent at the MTV EMAs in Spain in 2018

For a generation of fashion-obsessed pop culture lovers who came of age in the aughts, actress Lindsay Lohan was one of the most-watched style stars of her day. Read on for a look at some of her most standout moments during the last two decades.

While on presenting duty at the MTV EMAs, Lohan dazzled with numerous outfit changes, but it was this ‘80s-style ruffled cocktail mini by Saint Laurent that won us over.

At the Women of the Year Awards in London in 2014

For a generation of fashion-obsessed pop culture lovers who came of age in the aughts, actress Lindsay Lohan was one of the most-watched style stars of her day. Read on for a look at some of her most standout moments during the last two decades.

Lohan put a polished and sophisticated foot forward in a simple black shirt dress and belted coat ensemble at the Women of the Year luncheon. 

At the premiere of 'Scary Movie V' in Hollywood in 2013

For a generation of fashion-obsessed pop culture lovers who came of age in the aughts, actress Lindsay Lohan was one of the most-watched style stars of her day. Read on for a look at some of her most standout moments during the last two decades.

Lohan was a poster child for the very-of-the-era bohemian glam that reigned in the aughts. Case in point: her halo braid, leather crochet Louboutin sandals, Hermes bangles, and a gold-trimmed little black dress.

At the G Star New York Fashion Week Show in 2009

For a generation of fashion-obsessed pop culture lovers who came of age in the aughts, actress Lindsay Lohan was one of the most-watched style stars of her day. Read on for a look at some of her most standout moments during the last two decades.

Thigh-high pantyhose aren’t for the faint-hearted, but LiLo helped popularize them with rock n’ roll-ready minis and lace-up heeled brogues, just like this outfit she opted for during NYFW in 2009. 

In Emanuel Ungaro at the Emanuel Ungaro Show in Paris in 2009

For a generation of fashion-obsessed pop culture lovers who came of age in the aughts, actress Lindsay Lohan was one of the most-watched style stars of her day. Read on for a look at some of her most standout moments during the last two decades.

Remember when Lohan was announced as the creative director of Emanuel Ungaro in 2009? The short-lived stint was tanked by critics at the time, but dare we say the whole thing was infamously iconic in its own right! 

At the Calvin Klein After Party During New York Fashion Week in 2007

For a generation of fashion-obsessed pop culture lovers who came of age in the aughts, actress Lindsay Lohan was one of the most-watched style stars of her day. Read on for a look at some of her most standout moments during the last two decades.

To paraphrase a line from her movie Mean Girls, we all saw LiLo wear a silk tank top, bandage skirt, and low-slung waist belt, and we all dutifully ran to Topshop to emulate the look ourselves.

In Versace at the Vanity Fair Oscars Party in 2006

For a generation of fashion-obsessed pop culture lovers who came of age in the aughts, actress Lindsay Lohan was one of the most-watched style stars of her day. Read on for a look at some of her most standout moments during the last two decades.

The brunette star was fresh-faced and ethereal in a silk cap-sleeved gown by Versace for her first-ever Vanity Fair Oscars bash. 

At the Fendi Flagship Opening in New York in 2005

For a generation of fashion-obsessed pop culture lovers who came of age in the aughts, actress Lindsay Lohan was one of the most-watched style stars of her day. Read on for a look at some of her most standout moments during the last two decades.

The young actress showed off her fashion chops at the opening of the Fendi boutique in Manhattan in a mid-length black dress, heeled sandals, hoop earrings, and sultry makeup. 

At the Annual Race to Erase MS gala in New York in 2005

For a generation of fashion-obsessed pop culture lovers who came of age in the aughts, actress Lindsay Lohan was one of the most-watched style stars of her day. Read on for a look at some of her most standout moments during the last two decades.

The style icons of the day! Lohan and her gal pal Nicole Richie were the most-copied A-listers of the moment in the 2000s, with women around the world seeking to emulate their red carpet and off-duty outfits in equal measure.  

At the Hollywood Life 7th Annual Young Hollywood Awards in 2005

For a generation of fashion-obsessed pop culture lovers who came of age in the aughts, actress Lindsay Lohan was one of the most-watched style stars of her day. Read on for a look at some of her most standout moments during the last two decades.

Jeweled gladiator sandals? Check! Metallic accessories? Check! Silk babydoll night dress? Check! Show us a more 2005 cocktail party-ready look, we’ll wait. 

At a Cartier Event in 2005

For a generation of fashion-obsessed pop culture lovers who came of age in the aughts, actress Lindsay Lohan was one of the most-watched style stars of her day. Read on for a look at some of her most standout moments during the last two decades.

A vision in Y2K white! The actress pulled off an-all white moment in 2005, pairing the halter dress with gold sandals.

At a Screening in the Hamptons in 2001

For a generation of fashion-obsessed pop culture lovers who came of age in the aughts, actress Lindsay Lohan was one of the most-watched style stars of her day. Read on for a look at some of her most standout moments during the last two decades.

A star is born! Teenagers everywhere rushed to copy Lohan in cargo pants, tank tops, skinny scarves, and chokers. 

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