Style Guide: What to Wear On Family Christmas Vacay When Your Father is the President


Style Guide: What to Wear On Family Christmas Vacay When Your Father is the President


Packing for a family winter vacation is super stressful, am I right ladies? Thoughts like, “is this bikini too slutty to wear in front of my father” and “but what does this floral sundress say about me” run through our minds while we Google weather patterns to see if we should bring a jean jacket in case it gets a little nippy when the sun goes down.

DRAMA. Now imagine how much more mind-meltingly stressful this experience would be if your father was the president of these United States.

Yes, Barak Obama may be facing the most daunting task of his presidency: surviving a two-week vacation with his wife and teenaged daughters, but for Malia, 16, and Sasha, 13, the stakes are even higher. Typically we see mere glimpses of the president’s daughters, in tightly controlled situations. They’re coiffed and ready for action. They’re in air-conditioned rooms or mild, comfortable climates.

But now they’re in Hawaii, battling 80-degree weather and humidity – oh the humidity!

But the girls were up for the challenge yet again this year, showing off an array of super cute looks that were age and weather appropriate.

So, if you’re planning on being the president’s daughter on vacation in Hawaii anytime soon, take these style cues for every scenario from Malia and Sasha Obama.

Deplaning Air Force One in Honolulu (2014)

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Pro Tip: A president’s teenaged daughter is never seen boarding and disembarking Air Force One wearing the same outfit (obvi). First impressions are important, so go for a look that’s effortlessly chic. Here, Sasha looks fierce (only Sasha Fierce joke, promise) in a pale blue dress, oversized nude tote and really, really cute clogs while Malia opts for a trendier ensemble with her polka dot frock, denim satchel and flats.


Getting from place to place via motorcade (2014)

Barack Obama

It doesn’t matter what you wear – the windows are tinted.

Visiting a Sea Life Park (2011)

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A rare occasion when flip flops are acceptable. Smile big, hold hands with your father (the president) and everyone will be too busy admiring what a normal, loving family you are to notice what you’re wearing.


Hiking the Makapuu Point Lighthouse Trail (2014)



Malia’s hiking outfit is stylish and functional. Her tie-dye T is playful and her sporty short shorts reveal legs that indicate this is not the first daughter’s first experience with physical activity (whatever, big deal).

Attending a college basketball game (2013)

Barack Obama, Malia Obama


Here’s an opportunity to wear something fun and flirty. Here, Malia looks like a major babe in a form-fitting crop top and playful denim skirt. Her father (the president) holds her hand as if to say “take one look at my daughter and I’ll have the CIA make it look as though you never existed.”

Boarding Air Force One to return to Washington (2013)

Obama departs Hawaii to return to Washington

Ever boarded a private jet? Duh, who hasn’t! Tarmacs can get windy. Although Malia looks adorable in this high wasted silver shirt, she runs the risk of a major wardrobe malfunction. Her sister ops for shirt white shorts – a much safer bet. Both wear chic white flats, perfect for ascending and descending stairs.

And there you have it, a guide to looking effortlessly chic on Christmas vacay with your father, the president. For the rest of you mere mortals, wear whatever the hell you want, no one gives a shit.