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Preppy & Streetwear Make the Perfect Pair

Once upon a time, I was walking down the street on Melrose in Los Angeles when I saw a skateboarder wearing a rugby shirt paired with chinos and a chain wallet attached. He looked effortlessly cool. It was almost album cover-worthy. His style stood out to me because it’s different than the typical skateboard attire. I found the juxtaposition of preppy and streetwear the perfect combination. I genuinely believe this phase of streetwear is not going to be out of style any time soon. It was unusual to see these two different styles together because they’re from two different worlds. They represent two different cultures. Together, they defy societal norms.


When you think of preppy, Blair Waldorf from Gossip Girl pops into your head. You think of the headbands, the button-down oxford shirts, the pleated skirts, chinos, loafers, and pearl necklaces. We think of a pristine individual who is attending an Ivy League school. The preppy style tends to represent this elitist, upper-class world where you dress to impress at all times. When we think of streetwear, it’s Hypebeast central. We think of T-shirts, hoodies, sneakers, and chain necklaces. Streetwear tends to represent a world of leisure, cool, effortless, and music. Now, I’m seeing these two different worlds morphed into one entity. I’m not even too sure what to call it, but I’m here for it.

The preppy look has never been out of style. I know someone somewhere in the world is rocking a J. Crew fit right now, and I can count on that. There is going to be a variation of preppy being worn throughout time. Since the early 50s, preppy has been in existence, and we saw this from Sandy in Grease. And it thrived over time. Even Princess Diana has sported the iconic style in her time. Since then, we have witnessed the evolution of preppy. For example, In the early 2000s, Avril Lavigne made preppy cool. She revolutionized this idea of clean-cut preppy-ness into a punk, laidback version. Lavigne would wear the tank with a loose tie and low-rise trousers paired with Converse. Her iconic pink hair streaks adding extra flare with her dirty blonde hair. Apart from preppy having a dark edge, it has evolved and become a multi-faceted powerhouse in the fashion world. At Miu Miu’s recent runway for S/S’24, it demonstrated how preppy can be sporty. There were multiple looks that consisted of polo shirts and trench coats paired with sporty-inspired board shorts. The texture of the shorts is what gave the distortion to the original idea of preppy. But now, preppy has become a part of skateboard culture. This transformation almost feels as if an alchemist curated this creation. Growing up I was obsessed with the movie What a Girl Wants. When Amanda Byne’s character, Daphne meets her stepsister, Clarissa, you can see how different those two characters are. Daphne sports a cool, edgy style by wearing her blazer with a tank and jeans. Meanwhile, her stepsister, Clarissa, is the embodiment of preppy. The two never got along. This is the best comparison to describe my feelings about Preppy and Streetwear. They’re different. They’re from two different worlds. Now, these two styles have merged into one unit.

With influential style icons such as Tyler the Creator, Willa Bennett, and A$AP Rocky, who sport this preppy and streetwear combo, it has become a favorite look for many fashion enthusiasts. This could help the resurgence of iconic preppy brands J. Crew and Ralph Lauren. There would be articles saying how J. Crew is struggling to keep up with competition. Recently, an article in Women’s Wear Daily stated how J. Crew's revenue is returning to normal. Could it be because people are shopping for their favorite preppy looks at the place that created preppy? One thing for sure is preppy is never going out of style. Just like Darwin’s Survival of the Fittest, preppy has adapted and evolved in order to stay alive and prevalent in today’s society. It has become streetwear; and streetwear has become preppy. And as we see on the runways and on the streets, it’s a style that is infectious and powerful.

The skater boy who was wearing this new evolution of preppy and streetwear wore a fit that lived in my head rent-free. It got to a point where I’m writing about it. It stood out to me because a skateboarder wearing a preppy outfit in skateboarding culture is unheard of. I have never seen this in real life. He demonstrated that in this world, we don’t have to categorize ourselves as either Daphne or Clarissa. Style doesn’t have to be mutually exclusive. The skater boy proved we are all capable of being both Daphne and Clarissa.

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