Political Fashion Face Off: Condi Rice, Michelle Obama

There can only be one: Killer Bob Condi Versus La Femme Obama

This may surprise some, but while I pretty much believe Condoleezza Rice was an abysmal National Security Adviser and Secy. of State, I don’t dislike the woman. She is smart and seems nice outside of her world-wrecking job. I can also relate to her middle class, classical piano playing upbringing and lifetime of having to compete against white peers, expected to be the best of the best, and dealing with that pressure.

So in that respects, I tip my hat to her accomplishments, but shake my head to uber-allegiance to her BFF-in-chief. She was more an enabler than adviser with Dick Cheney taking on that role and muscling her, as well as then Secy. of State Colin Powell, out.

That said, I’ve enjoyed how Condi Rice’s wardrobe drastically improved after she became Secy. of State. A lot of women struggle to balance power with femininity (see Clinton, Hillary and “pantsuits”), but Condi seemed to find that yin and yang quite gracefully, whether dressing like a chic Darth Vader in knee high black boots to address the troops, or a pastel and tan arrangement of designer and tailored suits.

While I adore Michelle Obama and her often eclectic yet classic fashion sense (which also balances femininity with family and business), the two have very different looks — even when wearing similar duds. And while they’re playing on different sides of the political aisle I’d love to see them go shopping together. If only because I want the answer to this question — who rocks it best?

Let the fashion-off begin!


This is a hard one. I’m a big fan of the Maria Pinto designed pink tweed suit Michelle rocked earlier this year. I love the cut, the pearls, but there is something adorable yet tough about the mint and tan ensemble Condoleezza is wearing. Michelle is at a slight advantage in the way her suit is cut because she is curvy and statuesque while Condi is a tough, shorter skinny mini. I almost want to call this a tie, but I gotta tilt the tweed suit game to Michelle.


Michelle and Condi obviously have different ideas on what a pantsuit should look like. Condi goes for the Hillary Clinton specials, light colored tailored pantsuits whereas Michelle goes for something that’s more casual, yet professional. Michelle’s first brown suit is not a favorite of mine because it’s baggy and makes her look a little slouchy/sloppy, but the second khaki suit is a must have. With a zipper front and that little flare around the bottom of the jacket, Michelle is easily the winner. She found a better alternative to the traditional business suit.


Condi’s tweed: Dark with a wide, flat black lapel. Very flattering. Very dominating. It says, “I’m ready for business, I’m pretty and I can totally destroy you.” Michelle’s tweed is a throwback with two strands of pearls. It’s very vintage, but doesn’t flatter her usually fashion risk-taker spirit. Condi wins the battle of the black and blue tweeds, recovering handsomely of her loss in the pastel colored tweeds.


Houndstooth is a designer staple. It’s been around forever and never goes out of style. If you’re a business woman you should own a jacket or suit that is houndstooth. Condi’s is a bright yellow with frayed edges, buttoned up to the top button. Michelle is more casual — even sexy. How can one make houndstooth hot yet professional? Michelle found a way and it works in the skirt and jacket combo. Game, set, fashion — Michelle.


In the red wars this is a matter of taste. Do you like your daring red conservative? Red is already a powerful color. There’s no need to dress it up. Condi dominates in her red. It says, “Subpoena this, bitches!” Michelle’s red suit with the bunched up sleeves is a flashier, “I’m gonna be fierce for the Lawd this Sunday” suit. Something the pastor’s wife would rock or the leader of the women’s Bible study. Michelle’s suit would be much more popular with certain black women, but may be a little too avant garde for the conservative dresser. I really don’t know how to rule here. Condi’s is more appropriate for work. Michelle’s is more appropriate to show-off. Draw.


I couldn’t find a full picture of Michelle in her gray pinstriped suit, but she looked great it in. I promise you. The cut was adorable while Condi’s, per usual, was more traditional and Hillary Clinton style. It looked like it could be bought at a generic department store near you. Michelle’s had a more flattering cut and shorter jacket. Michelle wins.


I gave an array of color key assortments, mixing black with another solid color. While both Condi and Michelle’s outfits are pretty awesome here I’m going to give Condi the edge based on her adorable yellow jacket and black, A-line skirt mix-n-match. That look is hot. And Condi gets to show a little leg. And isn’t it fascinating that both Condi and Michelle aren’t ashamed of showing off their gams, although Condi is always pantyhose clad and Michelle doesn’t bother with them.


This was also a tough one. Michelle’s look is effortless and casual in her neutrals and browns. And I love the assortment of dark pearls with the long pleated skirt. But Condi is killing in her first outfit from the jacket to the skirt to the shoes. It is a rocking number that is all hotness. I love “Starfleet captain” style jacket with the off-center buttons and jacket flap, the flare of the beige skirt and those shoes, which she breaks out again in a burnt orange tweed suit identical to her mint-tan tweed shown earlier. I like both, but Michelle’s look is really laid back whereas Condi’s is sharper than a knife. Go Condi.


What to wear when meeting with heads of state or when your husband is sworn in at the Senate? Condi goes for power suits, some bright like that stain, blazing blue. Others plain and unassuming. But Michelle is the winner with a different daring look for every serious show down. A boldly striped, boxy suit for a women’s group meeting, a tailored navy, sleeveless dress with a crystal pin for the DNC, sweater dress knit set for kicking it with the kiddies and a gorgeous striped suit with a magenta ruffled blouse underneath at the swearing in. Michelle’s got a different look for every strictly business situation.


Condi is boxy and basic. Michelle is pretty, but the suit is similar to the baggy brown one where she looks a bit sloppy in it. I like Michelle’s look more (as Condi looks a bit like a linebacker in her jacket), but I’m going to call it a draw.


You can always bet on black to be a winner and Condi and Michelle placed their bets well. Condi goes simple, but Michelle, per usual, can’t just wear any black suit. She needs richness, boldness and in a few cases pinstripes. She makes black the new black. Michelle wins. (Although, Condi’s dotted suit with the flared skirt is very stylish.)


Michelle’s jacket dress is hot. Condi’s is not, making her really look like the dark lord of the sith. But this competition is all about the boots and Condi’s dominatrix boots win. I always said that Michelle betrayed her cute coat dress by paring it with some tepid brown suede boots. She needed something black, tough with an exclamation point at the end. Condi’s sexy stiletto boots do just that. Boot Battle goes to the dominatrix!

The overall winner of the fashion challenge is Mrs. O with six wins to Rice’s four, with two draws. How would you score the leading black women of political fashion?

* For more Condi fashion watching (and other political fashion snark) check out the Princess Sparkle Pony’s Photo Blog.

34 thoughts on “Political Fashion Face Off: Condi Rice, Michelle Obama

  1. I wish my Mother was alive to see black power women in 2008. Now we can begin to influence on youth! Boots even make condi seem attractive! But Michelle Obama is no Jackie Onasis. Michelle is much better looking and much better body! Sorry ladies, I am a guy at heart!

  2. In terms of style, Condi does have it over Obama slightly. Both women are sexy to me, despite being diametrically opposed to Rice’s view of the world. She said she doesn’t plan on any more public roles after stepping down as Secretary of State. She probably regrets some of the damage she’s done by being a part of the Bush administration. I can’t wait to see the Oliver Stone movie “W.” I’ve seen the trailer with an actress playing Rice with that dour expression she mostly wears, and it looks like a hoot. With all the other cast of characters like Rove and Powell in it, it resembles a funny SNL skit.

  3. As an Obama supporter, I find her demeanor royal. She is the epitomy of what a true 1st lady is. Condi should have left when Colin Powell did. Her legacy as the 1st Black/Female Secretary of State is forever blemished by who she was Sec. of State for!

  4. I love this post! Excellent. I never really paid that much attention to Condi’s fashion, but I was impressed. I don’t like her politics, but I’ve always liked her. Comparing her and Mickie O was genius.

  5. Here via PSP’s blog, and very impressed! Perhaps it’s my level of hatred for Condi (hotter than the fiery heat of ten trillion suns), but I’m soooo glad Michelle topped her. I think another key is whether each could wear the other’s wardrobe. Michelle would ROCK in Condi’s wardrobe, while Condi would look like she got drunk and hit the wrong closet in Michelle’s outfits. Advantage: Michelle!

  6. This perceptive post does overlook a minor item, understandably so as fashion really has nothing to do with one’s body: Condi has a deficit in hips, whereas Michelle has a surplus. I think both ladies face this reality, clothes-wise, as best they can, and indeed with consirable success, no matter their politics.

  7. Hip, hip, hooray! Love those Obama hips. Condi is no slough either. She’s got that sexy librarian thing going. Both are on my political honeys list.

  8. I love this post. I feel the same way about Condi Rice but I am glad that Michelle O. would win, even though I didn’t doubt that she would.I’ve enjoyed your blog since I discovered it during the Black Weblog Awards. Keep up the good work!

  9. I don’t like her politics, but I’ve always liked her.And THAT, my dears, is the conundrum of Condi’s existence as a public figure. People don’t like her politics, don’t think she’s done a good job, but, gosh darn it, they like her!

  10. I totally agree. IF Sarah Palin can be a trend setter in the US of A for American women, Condi & Michelle not doubt can. Remember Condi was setting trends before Hurricane Obama hit the WORLD. Both women are power-sexy!

  11. Your politics are showing. Condi can dominate me any time. Michelle is always a lttle to casual for my taste. As for getting in front of either one defending her man I amout of here

  12. Great post! For me Michelle hands down kicks Condi’s butt when it comes to fashion. Though as a boot girl, I do love Condi’s boots, they scream “take no prisoners” sadly she works for a moron. I don’t think I have ever seen Michelle in a bad outfit, plus and I am a dreadlocked sista but her hair has so much bounce it almost makes me wish for relaxed hair. Condi, on the other hand needs to see Michelle’s hair stylist, her hair always looks so dated to me.

  13. Just wanted to drop by and tell you that I thought this post was AWESOME, and that I think you’re awesome, Snob. I was laughing and smiling the whole way through this one. Like you and others, I admire both women tremendously for what they have achieved. Despite Ms. Rice’s associations (BFF-in-chief, LMBAO!!!), they both make me proud to be a black woman. Anyway, I’ll stop gushing. Way to go Snob!

  14. Little Malia and Sasha are just adorable!Loving all the looks, but esp. ‘STORMTROPPER CONDI- MICHELLE’S SUEDE SUPERWOMAN’As previously stated, Michelle takes it

  15. This was a GREAT comparison. I think Michelle wins hands down. I love the fact that Michelle has a real woman’s curves and stands and sits with her shoulders back and her head high…Dr. Rice is usually slumped over to me. Reminds me of poor Ceily in “The Color Purple.”Also…I’m REALLY gonna need her to spend some time FOCUSING on her hair. Doesn’t matter what you’re rocking…if your hair looks a mess…YOU look a mess.

  16. This was an excuse to just post more pics of Michelle against her only fashion competitor.Good job tho! LOLAnd just between me and you, wasn’t the competition fixed from the beginning? lol

  17. I can’t diss Condi’s choices. There is only so much “flair” you can have on Capitol Hill. Especially a Black woman in her position. Michelle can push the “flair” envelope a little more, plus she has the height for it. I’m betting when she gets in the White House we’ll see a bit more subdued Michelle.

  18. I am so glad you did this post: As much as I hate Condi, I do think she sometimes gets a short shrift in the Black media, and some of her fashion choices do deserve some note (but not her politics). And I especially love the pics of Obama’s swearing in: That little girl is cheesing big time – I LOVE it!L

  19. I really hope Michelle will bring back the peplum: the skirt like bottom to the jacket, or over a straight skirt. Very flattering to most woman, thin or fat! And maybe she can reintroduce moderate shoulder-pads. Sigh. Good luck Mrs. Obama!

  20. Michelle gets my vote, because she’s not wearing things that are already out of style (i.e. tweed jacket with fringed trim). She has a great sense of style. I’d also point out that they are dressing for very different things- Condi to be authoritative, and Michelle to be soothing and supportive. I’m certain that if Michelle were in Condi’s position, we’d be seeing a stronger fashion statement from her. I’m really looking forward to her wardrobe changes once they’re sworn in. The inaugural ball gowns will be amazing!

  21. Wow ~ you totally rocked this comparison. They DO have different styles, but IMO, bot are FAB. Thanks for this post; I was laughing reading some of your witty remarks.

  22. Michelle all the way. It will always be Michelle vs. any comers. That said, I have this conflicted relationship with Dr. Rice. I respect her intellect; I feel for her, because it’s not easy being Black, Brilliant, Female and not afraid of your own capabilities. In that respect, I do respect her. I know…I know…her politics. I just respect intellect. I honestly believe, when Dr. Rice steps into a room of 100 people, there are maybe 2 that can truly hang with her intellectually. I admire that about her. Plus, always, just as I’m about to give up on her, she gives some sort of interview or another, and lets it slip that she DOES get it. …I think on some level that makes it worse, but I’ve just resolved myself to respect the woman for her intellect. And, I’m rooting for her to find the other half of her Power Coupling. She DOES have cache, and I hope she uses it for her OWN purposes.

  23. One last thing Condi in front of the piano in the black formal dress was not included in the Basic Black category. That ommission cost Condi that category. UNFAIRPS I am still laughing that there were comments about “HAIR”

  24. Michele. No contest at all, Snob! She takes way more risks than Condi, and yet pulls it back enough to work, almost every time.In the bob-off, I think Condi is the victor though. She looks great in the evening gown shot, I’ll give her that. But it’s not enough to defeat La Femme Obama in the overall.

  25. They both dress well but Condi’s been in the national media for longer and has waaaay more discretionary income to spend on clothes. She was at Ferragamo’s when Katrina hit after all. Michelle wins!

  26. Well Condi wins again of course.You didn’t compare photographs of who looks most fashionable "when Barack Obama has his hand on her ass". Oh you didn’t notice, huh?Man I wish Condi would stop taking it up the ass from Obama. I’m looking forward to 2012 when I trust Condi will start beating up on the guy like he deserves.See my Author URL – "What Condi should do to Obama in 2012: beat him in public! (Video)"– Peter DowRice for President Yahoo Group

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