Both girls have classic styles.  Plaid, headbands, pleated skirts, over-knee-socks, coordinated.  All very naughty-school-girl-with-a-penchant-for-maxing-out-daddy’s-AMEX.  Blair’s style is upper-east side all the way.  Perfect tresses, perfectly styled, never caught in pants.  Its too close a call in this category.  Although, the fact that Cher wore an Alai dress in Clueless is making me believe all you fashionistas know which side of the fence you need to be on.

Cher has it on the attitude.  Both girls have the clever, witty comebacks and good use of pop references.  But Blair will never be quoted as often as Miss Horowitz.  Come on, she’s the girl who taught that  “searching for a boy in high school is as useless as searching for meaning in a Pauly Shore movie”.  Also, it always helps when you are genuinely good-hearted person that isn’t out to sleep with/stab friends in the back/climb to the top.

Oh yes, and the ultimate barometer of cool.  Cher did something before the Olsen twins—she drank Starbucks.

A wool beret is very Parisian, very classic, oh-so-Cher.

This structured blazer cuts in the waist giving you a very sexy, feminine shape.

In the movie Cher can be seen wearing a sheer button-down, like this one, perfect worn over a mini skirt and tiny camisole.

This plaid mini is the more accessible version of Cher’s pleated skirts.

Thank my lucky stars for American Apparel.

Chunky loafers that I think Cher would proudly strut around in.

How to do a party right? Sexy, short designer dress.  And this Alexander Wang is 2009’s answer to Cher’s Calvin Klein.

I just couldn’t resist these. They feel slightly Cher meets Marie Antoinette.