Ever wonder if First Lady Michelle Obama's wardrobe was always as designer clad as it is now? Or if Hillary Clinton has always been buttoned up in pristine political attire? What about Sarah Palin's stints as a beauty queen?

While these ladies are among the District's most influential, politicized and well known, they are also consistently scrutinized by the American public for their bold fashion choices...and occasionally their faux pas! We've compiled some of the best snapshots of these leading ladies throughout the years with everything from gorgeous inaugural gowns to '80s college dorm room attire!

[A young Hillary Clinton studying at Wellesley College via]

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