Wasp Alert

Taylor Swift Dating Conor Kennedy: Style Transformation (PHOTOS)

All it took was a summer in Hyannis Port. Swift has gone from a cowboy-boots-wearing country singer to Jackie O. in training. See our pictures of her style transformation.

Retna; Getty Images; INF

Retna; Getty Images; INF

The name Taylor Swift: it used to bring to mind a head of blonde curls, a twangy guitar; the ultimate girl next door. But this summer, all has changed.

Since the pop star, who is 22, began dating 18-year-old Conor Kennedy, she has undergone what can only be explained as a Kennedy-ifcation. Gone are the trusty cowboy boots, body-hugging minidresses, and trademark curls. Now there are miles of stripes and prim dresses fit for a lunch at the country club in Hyannis Port).

The dynamic between Swift and the Kennedy clan seems like it can be explained, at best, as strained. She reportedly snapped up a $5 million home across the street from Conor as soon as they began dating—and accompanied him to crash his cousin's wedding last week. While her methods of courtship may be heavy-handed, it's her clothes that speak volumes about her strategy: she's just trying to fit in. There's a distinct reference to Conor's grandmother, Ethel, as well as Jackie Onassis. But for now at least, Swift has some big shoes to fill.

—Jeesoo Park

Andrew Orth / Retna Ltd.

Gone Country

Before she was famous, Taylor Swift looked like a sultry country singer with a guitar slung over her shoulder in 2004.

Peter Kramer / Getty Images

Death Becomes Her

In 2006, the year of her first album, Swift ditched her cowboy hat and jeans for a more mature look, channeling Morticia Addams with an overtly grown-up all-black ensemble.

Stephen Shugerman / Getty Images

Down Home 

Nominated for "Favorite Country Female Artist" at the 2007 AMAs, Swift mixed country and formal, donning cowboy boots with a satin pleated dress.

Bryan Bedder / Getty Images

Disney Princess

Swift was the belle of the ball with a gold, poofy gown that looked straight out of Beauty and the Beast at the Country Music Association Awards in 2007.

Marcel Thomas, FilmMagic / Getty Images

Whole Lotta Leg

In an appearance on David Letterman's show in 2008, Swift vamped it up with black lace stockings and a tight black turtleneck top.

Bryan Bedder / Getty Images

Lots of Sparkle 

She showed some skin in a sparkly minidress at the Z100 Jingle Ball in 2009, where she performed with John Mayer.

Jason Merritt / Getty Images

Red Riding Hood 

In a sharp departure from her earlier look, Swift chose a bold color at the Country Music Awards in 2009.

Jeffrey Mayer / Getty Images


Polished and professional at the American Music Awards in 2010, Swift opted for all black.

Jason Merritt / Getty Images

Peachy Keen 

Swift wore a precariously cut, nude backless dress to the Teen Choice Awards in July 2012.


Granny's Coming to Town

Gone are the days of cowboy boots and crimped, curly hair. As Swift began dating Conor Kennedy in the summer of 2012, she went all-out conservative, switching sequins and stilettos for sweet floral-patterns and demure ballet flats.


Channeling Jackie O. 

In a high-waisted polka-dot bikini, Swift appears to be influenced by Wasp style.

All-American Swift

Swift democratically posed with a fan in Cape Cod this summer—wearing, of course, red, white, and blue. Surely the Kennedys would approve.