The Best and Worst of Celebrity Jailbird Fashion

Sunday, July 16 is a big day.  Its the day Casey Anthony becomes a free woman again.  Well, how free she will actually be is questionable given the fact that no one will talk to her, hire her, befriend her (besides the attempt to get a scoop and first interview) and in all likelihood, she will have to undergo a transplant, both facial and residential, if she has any chance of starting over. However, her release got me to thinking about other high profile releases from jail and how these “celebrities” fared after their releases.  Specifically, I decided to go back to the archives and document the best and worst fashion moments of my favorite jailbirds.  Let’s start with maybe the most notorious:

La La Lohan

Prior to hitting the big house,  Lindsay shut it down in a Bally gown for the CFDA Awards honoring Paul Poiret, the King of Fashion exhibit in 2007.  The bodice fits her perfectly, the hair is simple as to not distract from the drama of the dress and she isn’t oompla loompa orange.  A total win:

Then there is this:

In what I can only imagine is the result of LiLo waking up to her house on fire and throwing on the first thing she found over her lime green negligee, Lindsay showed up to Italy’sVIPRoom launch.  Why oh why she would ever wear this roadkill leopard jacket with heavy platform shoes is beyond me.  Given her bleary, blood shot eyes, she may not have been in her right mind but whatever, its a total fail!


The Original, Paris Hilton

Good as Gold.  As difficult as it is for me to accept, Paris has had a few shining fashion moments and shockingly, the first (and probably my favorite) is what she chose to wear for her release from jail:

Simple hair, no makeup, wearing jeans from her own line and a simple blazer, Paris is fresh, relatable and actually very pretty.  However, if you know Paris, you know she doesn’t do casual very often, especially when hyping one of her many products, as was the case in London for the launch of her Can Can perfume in London.  Wearing a scalloped white Marc by Marc Jacobs dress and a matching fascinator, Paris is the epitome of modern chic:

I have nothing bad to say about this look. And that is rare as Paris striking the right fashion note because normally she is closer to this:

Oy. In 2003, Paris arrived to the MTV Movie Awards with super greasy hair, a bright orange bottle tan and a top that looks like a leftover from Mila Jovovich’s wardrobe for  “Return to the Blue Lagoon”.


Mischa Barton: Fall from Such Great Heights

When Mischa landed on the O.C. back in the early 2000’s,  she quickly became the it girl and together with her costar Rachel Bilson, inspired thousands of fashion trends.  Here is one of my favorite looks:

Mischa is 100% perfect in this floral beaded Matthew Williamson sheath dress at a party honoring the designer.  The colors are gorgeous together and she looks healthy, happy and very sophisticated . (On a side note, Rachel Zoe looked so much better before she started caking on the foundation, red lipstick and eye liner).  Fast forward a few years and Mischa has decidedly lost her previous Ocean County glow:

Oh the lessons we can learn here.  Say no to high-waisted, tapered jeans. Also say no to tying an oxford shirt below the bust when your middle section is less than toned.  Finally, a big no to the brassy blond dye job which most likely came from a bottle.  The whole thing is a disaster and the saddest part is that I thought she was Britney Spears at first glance.


Sidekick turned Fashion Designer, Nicole Richie

After wrestling with, and winning a battle against drugs, Nicole Richie is now a successful fashion designer, having won over celebrities and fashionistas alike with her hobo-chic apparel line, Winter Kate.  She also recently signed a deal to star on Jessica Simpson’s fashion TV show premiering this Fall.  However, even a fashion designer can have bad moments, and Nic’s comes from the same place as her best look, Holt Renfrew.  Visiting the high end Canadian department store to promote her Fall Winter 2010 collection,  Nicole made a rare misstep with this odd ensemble:

The high-waisted, wide leg pants dwarf Nicole who is quite petite at just over 5′ tall.  The silk vest and white tie neck blouse are disjointed and the felt hat is way too heavy.  The next day, Nicole tried her luck with the hat again and this time, wisely paired it with a cute pair of cut off jean shorts, opaque tights, a great bohemian blouse and a fitted vest.  Topped off with the brimmed hat, Nicole is the epitome of what her brands values:

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