Her entree into Hollywood may have been as a naive, comedic tween navigating the social pressures of Millennial women, but Lindsay Lohan's style has always been exciting, even if she has transformed into a totally different person in the intervening years. Transgressions against the law and brushes with addiction aside, Lohan has a penchant for self-transformation not unlike that of Madonna or Miley Cyrus. Most recently, Lohan demonstrated a dichotomous sweet and sultry sartorial inclination for a story with Homme Style Magazine, where the actress donned white T-shirts intermixed with leather corsetry and choker necklaces. It would be an understatement to say that the public never knows quite what to expect from the former Mean Girls star.
Perhaps the most intriguing facet of Lohan's style transformation is that the actress's most drastically different looks make their debut just when audiences think they have Lohan pegged. After years of coupling brightly-hued tops and bootcut jeans, Lohan took an abrupt left turn into decidedly more boudoir-inspired fare. Soon after, the once-reticent Parent Trap star dyed her locks a shocking shade of bleached blond and adopted a Donatella Versace-meets-Los-Angeles-Fashion-Blogger mien that combined short hemlines and a significant amount of ripped clothing. In deference to the actress's latest magazine spread and determinedly unpredictable style, here are 15 times Lindsay Lohan managed to startle even the most cynical fashion critics.
1. The Bedazzled Micro-Mini
Lindsay Lohan's public collectively gasped at the long stretches of leg and bedazzled micro-mini the actress displayed on an outing with then-girlfriend Samantha Ronson.
2. The Modern-Day Corset
Lohan selected an avant-garde and optical design at a Fendi red carpet event that seemed to be a futuristic answer to the traditional corset. Perhaps the look was an experimental precursor to 50 Shades of Grey
3. The Cabaret-Inspired Mini Dress
4. The Micro-Micro-Mini Dress
Lohan sauntered down the runway in a garment that fell somewhere on the spectrum between a terrycloth towel and a micro-mini dress.
5. The Naked Dress 2.0
7. The Dazzling Jumpsuit
Somewhere, Cher is lamenting over the loss of her crystal-encrusted jumpsuit. The unexpected getup made an appearance at the MTV Movie Awards, no less, increasing the befuddlement fans felt when viewing the ensemble.
8. The Bulky Pantsuit
After years of parading her well-toned stems, Lohan abruptly placed them under wraps in a bulky pantsuit, causing press and fans to question the actress's sartorial sanity.
9. The Oversized Vest And Sunglasses
Though the palette of Lohan's ensemble was an unimpeachably classic black and white, the actress appeared little more than a pair of oversized sunglasses, an oversized vest, and lengths of wavy blonde hair. Perhaps the attempted disguise was a deliberate choice.
10. A Prim Button Down And Trousers
Nothing could have shocked Lohan's audience quite so much as viewing the actress dressed down in a demure oxford shirt and black trousers, but then again, the understatement may have been the point of the ensemble.
11. A Monochrome Pantsuit
Following the apparent success of her straight-laced business casual attire, Lohan dove ever further into the realm of workwear, beginning with this monochrome pantsuit. While the shade and cut were admirable choices, Lohan's cleavage-concealing sweater and pearls were rather unexpectedly restrained choices.
12. The Fur-Trimmed Coat
Viewers of Lohan's fur-trimmed topper, unruly locks, and white frock could easily have mistaken Lohan for the Abominable Snow Monster from Rudolph The Red Nosed Reindeer.
13. The Jessica Rabbit Ensemble
Clad in a silken bias cut gown and a fur stole and newly crimson locks, Lindsay Lohan gave Jessica Rabbit a run for her money.
14. The Statement Tee
Clearly, Ms. Lohan had something to say to her fans, and this self-explanatory t-shirt simply says it all. What remained unexplained, however, was where Lohan's pants had gone.
15. The Mermaid Mini Dress
With her cascading strawberry-blonde locks and metallic, teal mini dress, Lohan was the spitting image of The Little Mermaid.
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