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Ashlee Simpson and Evan Ross Win for Most Strangely Dressed Couple

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Aug 01, 2014 7:44 PM
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Ashlee Simpson, Evan Ross, Engagement Ring
1/8
Jason Merritt/Getty Images, FlightRisk/AKM-GSI

Moulin Rouge

It all started with an engagement ring...and a goth fringe gown with coordinating circus master's suit? Ashlee and Evan proved they love drama very early on with these half-vampires, half-French entertainer ensembles.


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2/8
FlightRisk/AKM-GSI

Baggy Matchy Matchy

These aren't exactly the colors we think of when envisioning an engagement-moon to Hawaii, but Evan and Ashlee love their all-black ensembles, and their baggy pants, and their giant t-shirts. Maybe they were shooting a rap video over there?


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3/8
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Pocahontas and a Yeti

...or does Diana Ross' wild-styled son look more like a Game of Thrones character and Jessica Simpson's little sis a super glam flapper? Either way neither of them look like a California-based couple circa 2014.


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4/8
INFphoto.com

Formal Errand Run

Doesn't everyone wear the world's skinniest skinny jeans to go buy their baguettes? Also, is it us or does it look like Evan is wearing Ashlee's lady blazer and Ashlee is wearing Evan's moto jacket?


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5/8
PacificCoastNews

Hat Trick

If only they had a little one to complete the three-pete of the black bowler hats. I'm sure they could also find matching black pants and red shoes for a little girl or black pants and a mini black, velvet jacket for a little guy.


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6/8
Alo Ceballos/GC Images

Johnny Depp +1

We're not sure what pirate ship Evan is off to terrorize or if this is going to be a full-on Bonnie and Clyde job. If so, Ashlee might want to think about better getaway shoes and a skirt that gives a tad more than leather. 


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7/8
CPR/Premiere/FAMEFLYNET PICTURES

Pajamas in the Park

At least the soon-to-be husband and wife finally look comfortable! Though, in exchange for tight jeans and heels we get a frumpy dress and sleep pants.


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8/8
Jean Baptiste Lacroix/WireImage

Just Plain Weird

Evan's patch work Pinocchio shirt worn with yet another pair of pirate pants is strange enough to ruin this entire set even though Ashlee finally looks slightly normal in a black cropped-top combo. Word to the wise Ash, when you're married his image is your image!


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