Chelly O The Fashionista: Mrs. Obama’s Best Campaign Trail Looks

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By Keli Goff

One of the many reasons I have never had any interest in running for political office, despite being interested enough in politics to write about it, is because being a politician is one of the only jobs on the planet in which you, your family, your friends, your pastor, and practically anyone you ever ate lunch with, are all scrutinized as part of the job interview. After all, most of us will never be asked in the interview process if our parents or children smoke pot, but any presidential candidate will be asked this and much more.
Not only do the family members of candidates face tremendous scrutiny, but they often face pressure to change who they are or at least who they appear to be to appeal to voters. Rumors first began circulating years ago that Newt Gingrich was going to run for president based solely on one fact: his wife Callista underwent a noticeable makeover, changing her hairstyle and entire wardrobe to appear more First Lady-like. She’s not the only one.
During the 2008 campaign Michelle Obama’s own wardrobe makeover transformed her from the high-powered attorney and executive that she was into the warm Mom-in-Chief she is today, someone that practically every single American, regardless of political party affiliation, has grown to love. (Her approval ratings remain much higher than her husband’s.)
In The GQ Candidate I re-imagine what undergoing such a transformation,  in being coached on what to say, what to wear, and even how to wear your hair, must be like for an independent, career-minded, African-American woman who wants nothing more than to see her husband elected to office, without having to sacrifice who she is in the process.
I don’t know that I could do it. But I am so grateful that women like Michelle Obama are willing to make such sacrifices for all of us. Not to mention manage to look so good while doing it. So here is a slideshow of a few of my favorite Michelle Obama campaign trail looks. I hope that you will suggest your own in the comments section.

Perfect in Maria Pinto

June 3, 2008

Okay, I will admit that I am biased because this is the dress Lady O rocked when she and her husband introduced the fist-bump to mainstream America, and I thought that was one of the coolest and most endearing moments in the history of the American presidency. But fist-bump aside, the future First Lady looks fierce. The color is fabulous and the world got to see her envy-inducing arms. Also this image became so iconic that it practically revived the sheath dress as the ultimate day to evening look. It also introduced the world to a practically unknown designer, Maria Pinto.

Iconic in Isabel Toledo
June 17, 2008

Before Isabel Toledo became an international household name for designing the First Lady’s inaugural suit, she was already a First Lady favorite. The First Lady chose this Toledo design to wear to one of her most intimidating campaign appearances: a fundraising dinner with the most influential people in fashion, hosted by VOGUE editrix Anna Wintour.

Providing a perfect “View” in Donna Ricco
June 18, 2008
Though Michelle Obama’s first ever guest-hosting stint on “The View” was highly anticipated because it was one of the first forums in which she was expected to address some of the criticism she had received on the campaign trail (and some of the criticism her husband’s campaign had received from conservative “View” co-host Elisabeth Hasselbeck), it ended up being best remembered for what she wore, not what she said. Her black and white Donna Ricco summer purchased at the appropriately named White House Black Market sold out within a day of her “View” appearance.

Taking the world by storm in Thakoon
August 28, 2008
It is a night Americans of all political stripes will never forget because history was made. On August 28, 2008 Barack Obama officially accepted the nomination to become the first African-American presidential nominee of a major political party. It’s also a night fashionistas will never forget, because it was the night Michelle Obama let the world know that she was not going to be your run-of-the-mill, pearl clutching, suit-wearing First Lady. She dazzled in a Thakoon cocktail dress.

Terrific in Talbots
October 13, 2010
In her first campaign appearance since her husband’s election Michelle Obama reminded Americans why we love seeing her on the campaign trail. Dazzling in a nearly fuchsia knit dress from Talbots, she also reminded us that you can be fashionable on a budget, particularly in this economy.

Edgy on Ellen
February 2, 2012
Though it’s fun to see the First Lady dressed up, it’s can be even more fun to see her dressed down. If for no other reason than it’s a nice reminder that we have a youthful, fun and cool First Lady. She definitely reminded us all of that with her appearance on “The Ellen Degeneres Show” which ended with a push-up contest between the two. I won’t give away who won the push-up contest, but the First Lady won the fashion contest of the day hands down, sporting a black Reed Krakoff leather blazer and Duro Olowu. She finished the look off with some faboo black jeans and sneakers.  Can you picture Hillary Clinton or Laura Bush pulling off that ensemble?

Rocking Tracy Reese
March 8, 2012
Much has been written about the boost the First Lady has given to up and coming and lesser known designers, but equally important is the boost she has given to designers of color, among them Tracy Reese. One of the few African-American female designers to find long-term mainstream success, Reese has emerged as an Obama favorite. This Tracy Reese dress, first worn at an appearance with the UK First Lady equivalent Samantha Cameron, was most recently worn by the First Lady to a fundraising dinner.

Pretty in Preen
March 19, 2012
In her first ever appearance on “The Late Show with David Letterman” the First Lady did two things: almost cried when speaking of her family and looked fabulous in her fashion forward Preen dress. Not everyone can pull off color blocking patterns but she certainly can.

Timeless in turqoise
May 5, 2012
Back on the official campaign trail for her husband once again it appears Michelle Obama has returned to her roots. Sleeveless, bright, solid dresses made her a hit on the campaign trail in 2008 and it appears she will be sporting them in 2012. But another familiar fashion sighting from 2008 that has made a return? The brooch she wore in her keynote address at the Democratic National Convention. Perhaps it’s her lucky charm. We will see in November.
Keli Goff, who appears regularly on MSNBC, is a Contributing Editor at and the author of The GQ Candidate which has been described as “Boomerang” meets “Entourage” set in the political world, out in paperback this month.

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