By Donna Freydkin, USA TODAY

Oh, those Kennedys. The toothy, gleaming smiles. The immaculately tousled hair. The expertly casual ensembles. And joining their hallowed midst? Taylor Swift, who was photographed Friday smooching and holding hands with Robert F. Kennedy Jr.'s 18-year-old son, Conor, near the family enclave in Massachusetts.

Fortunately, Kennedy matriarch Ethel and her daughter Rory, Conor's aunt, already approve of the relationship. At the August Television Critics Association panel about her HBO documentary, Ethel was asked if she could picture Swift, 22, as a Kennedy. "We should be so lucky," she responded. Rory, it turns out, first met Swift at a concert. "And she's a great friend of all of ours. We love her. She's awesome," she said.

Sartorially at least, Swift's transition from her Nashville roots to the nonchalant glitz of America's most famous family has been seamless. Swift's style has swiftly become more casually refined, with her ditching her boho-chic dresses and boots and instead sporting preppy gear, such as a white button-down with a floral printed, calf-length skirt. Or a retro polka-dot bikini top, with equally old-school yet feminine high-waisted shorts. Topping off her recent looks: eye-catching red lipstick.

Shades of Jackie Kennedy Onassis, perhaps?

"It's because Jackie was so up to date and knew how to mix different eras together. Really, the Kennedy look is always classic and never trendy," says celebrity stylist Estee Stanley, who works with Jessica Biel and Lea Michele. "She kept it ladylike and classic and never extreme. You need a great bag. You need great sunglasses and pearls."

When you think of Kennedy allure, says Chanel celebrity makeup artist Angela Levin, you think of Jackie O, who set the standard in first-lady chic. "She had a very specific style about her that at all times remained the same: clean and simple and elegant. It was about accessibility and simplicity. There was an eyebrow. A little bit of liner and mascara, and a vibrant lip color. And nothing was overly done or too worked on. Everything came together," says Levin.

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