Vol. 2: No One Has Ever Looked Cooler Than This
Siri, play "Unwritten" by Natasha Bedingfield.
Welcome back to Volume 2 of “No One Has Ever Looked Cooler Than This.” A series where I take a walk down memory lane and highlight the public figures that caught my eye at some point in life and played a formative part in influencing my personal style.
In the first volume, I covered Amanda Byne’s laid-back minimalist style from the late '90s and early 2000s and in this edition, I’m highlighting reality TV’s darling, Whitney Port — specifically her style in “The City.” “The City” was a spinoff to “The Hills” and premiered on MTV in 2008. Despite its short two year run, it really stuck with me. And while Olivia Palermo become a fashion icon for most, I found myself gravitating towards Whitney’s playful looks more.
Her styling felt less buttoned-up and more accessible. It wasn’t designer head-to-toe paired with a glossy blowout — it was edgy, approachable, and something she was clearly still experimenting and having fun with. She didn’t shy away from colors, pastels, edgy leather, and even edgier shoes. And yet, nothing about it seemed manufactured or over-the-top. Maybe it’s her laid-back California roots, but Whitney had me thinking wearing a black-and-white striped blazer with a punchy floral print dress was effortless. I’m particularly in awe of how many of these looks I’d still want to re-create today. Despite leaning into neon, floral patterns of 2008, she somehow managed to style looks that haven’t aged.
So grab your Starbucks frappuccino, turn up “Low" by Flo Rida, and take a walk down memory lane as we explore Whitney Port’s seriously cool 2008 style.
Starting off strong with said black-and-white blazer paired with this frilly floral dress.
Along with florals, Whitney leaned into pastels and neons and this particular outfit screams cool LA girl to me. I love that she added some edge with the black leather bag. Also, the chokehold this sunglass had on me needs to be studied.
Speaking of edge…the Jeffrey Campbell shoes, the leather shorts, and the statement necklace are still my dream going out combo.
The classic Whitney formula. Punchy floral dress + black leather accent pieces. No notes.
Bringing her signature California effortlessness to the streets of NYC with a sundress and flip flops. I’m here for it.
I saved the best for last. The water color pastels! The movement of the silky blazer! The shorts with the caged heels! Couldn’t be more obsessed with this outfit if I tried.
I moved to NY from Florida in 2009 (at age 21) and I am not embarrassed to admit The City was a huge contributing factor to that decision 😂 ah to be young again and make huge life choices because of a reality show 😂😂😂 I even applied to be on several reality shows once I moved .. hilarious! Thank you for this walk down memory lane. “Grab your frappacino” lol!
How much I wanted Whitney's wardrobe during The Hills/The City! And I'd still wear those white sunnies today.