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Lindsay Lohan Style Breakdown: What’s Right, What’s Wrong, and How to Fix It

LiLo
Kevin Winter, Getty Images

We know, we know. Lindsay Lohan might be at the point of no return with her mess of a personal life. But when you look at her pictorial history, you’ll see she was once a pretty girl with enviable style — especially from 2005 through roughly 2008, give or take a few months.

Case in point: She’s gorgeous below.

Pretty
Frederick M. Brown, Getty Images

Then she imploded and started to look like she’s on a collision course with Donatella Versace (and that’s not a compliment). No 26-year-old should have such leathery skin. The cream-colored dress is super-flattering, but that hair? Looks bunk.

Donatella
Jemal Countess, Getty Images

Seeing her devolve from cute and fashion-friendly to downright messy is a shame.

The bandage dress below — complete with that infectious smile — reminds us of Linds’ glory days.

BW
Peter Kramer, Getty Images

Sadly, this cute fiery redhead became so haggard right before our eyes. Blame the drugs, the late nights, the partying, or the obsession with her own celebrity, but LiLo broke down for all the world to see. She still tries to be sexy, but it’s not bombshell. It’s desperate. (See her red carpet gown from the ‘Liz & Dick’ premiere for further proof of that.)

Black09
Alexandra Wyman, Getty Images

What’s Right:

She was once super cute and trendy. Between 2005 and 2008, no one, and we mean no to the one, could rock a micro mini like her.

The LBD? She pretty much owned that concept from late 2005 to early 2007. With her constant rotation of flame-hued, chocolatey and bombshell blonde locks, she was a knockout, even if she was always tanorexic and slightly orange.

The photo below, taken in 2006, was Linds at the height of her Lolita sex bomb powers.

Red
Evan Agostini, Getty Images

Look at those gams. She’s a leggy gal, and this purple micro-mini paired with stick-straight blonde locks shows the beginning of the end. This shot was taken in 2008, before she started melting down and looking more plastic. But those stems are enviable.

Purple
Frazer Harrison, Getty Images

Once again, even a knee-length LBD with peep-toe heels looks amazing on her. Whoever styled her during this period was spot-on with their choices.

Young
Getty Images

The white hue of this dangerously short-hemmed dress inspires mixed emotions. While it’s short and sexy, she’s showing luggage-like signs of wear.

Lilo
Michael Buckner, Getty Images

What’s Wrong:

These days, she looks like a trout-pouted Stevie Nicks in some photos …

Steveie
Frederick M. Brown, Getty Images

… and a poorly aging porn star in others. She wears clothes that are ill-fitting, off-trend, and that don’t look thought out. She’s too blonde, too trashy, too showy and too tan.

Porno
Valerie Macon, Getty Images

When she tries to go glam, it’s contrived. This big swath of satiny fabric just hangs on her body. She also looks uncomfortable.

LiLo
Stephen Lovekin, Getty Images

She still has the gams to die for, but in layers, she just looks sloppy. Tired, too.

BlueLayers
Jerrit Clark, Getty Images

How to Fix It:

She needs to hire previous stylists to help bring her 2005-2008 look up to 2013, but in an age-appropriate way. She’s a little older now, and she needs to step it up a notch. She can still rock a mini and show off those legs — in a manner that’s sexy and suggestive, not let-it-all-hang-out.

The photo below is from 2005, but she looks sexy and stylish.

Hot
David Livingston, Getty Images

This layered, Bonnie and Clyde look is so chic and still current. Why not more of this, only updated? It’s polished and suits her age and trendy nature.

LiLo
Donald Bowers, Getty Images

This photo is vintage sexy, stylish, “we want to dress like her” La Lohan. The short hem, the flowing locks and the accessories all work. We also prefer the light reddish-blonde hair. She can rock chocolate and bottle blonde, but this is her best look.

Cute
Michael Buckner, Getty Images

She also needs a serious microdermabrasion to help erase the years of damage done by smoking and the sun. Moisturize, go back to the sunny golden red hair, and get inspired by those 2005-2007 photos. The foundation is still there, it just got cracked along the way. Fill the holes and move on.

Sometimes to leap forward, you need to take a step back. LiLo would do well to adopt that adage with her style.

See the Jessica Alba Style Breakdown

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