How to Dress Like Your Favorite Preppy Villains

How to Dress Like Your Favorite Preppy Villains
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If you’ve been following our blog for a while, you know how we feel about preppy villains. We’ve said time and time again that prep is frequently misunderstood in American films. Our fellow argyle enthusiasts have been repeatedly and unfairly caricatured, stigmatized, and maligned, and we’ve had enough.

 While it was typical for the villain in 80s films to be thrown into the preppy archetype, Hollywood continues to perpetuate this trope today. We want to bring justice to these misunderstood masters of class and society, once and for all.

 …okay, but honestly, we aren’t all that concerned with the arc and development of their characters. The form of justice that felt most fitting for the kings and queens of couture are to revive their timeless, stylish aesthetics. Just daydreaming about the tweed and turtlenecks brings tears to our eyes, if we’re being honest.

 From penny loafers to popped collars, these bad guys look good. So, to show the journey cinematic prep has taken over the last 30(ish) years, we’ve created a short timeline. Using the very best characters that exhibit the crux of best dressed and worst attitude, we’re showing you how to dress like your favorite preppy villain.

 Johnny Lawrence, The Karate Kid (1984)

Even outside of the dojo, William Zabka’s character was a pretty fly guy. With the swoopy blonde hair we all know and love, he even made a black eye look stylish.

If we’re being honest, we aren’t completely convinced Johnny was the bad guy. Sure, he could’ve handled the whole Ali thing better… and maybe laid off Daniel every once and a while… but come on – he’s hardworking, dedicated to his sport, and an impeccable dresser. If anyone was the bad guy, it was Johnny’s sensei!


When he wasn’t clad in his karate gi, Johnny Lawrence kept it simple – khakis, tweed, and a pale blue oxford shirt. That’s practically the holy trifecta of a classic evening look. This gorgeously made, sophisticated Gentleman’s Jacket from Southern Proper is a perfect match. It’s versatile, durable, and has a pocket specifically for your flask and cigars. If you truly want to take inspiration from this dashing dojo dude, pick a solid colored, understated skinny tie and let the tweed do the talking. Sweep the legs at every soiree with a go to look fit for a karate king.

Max Fischer, Rushmore (1998)

“I saved Latin, what did you ever do?” How can you NOT love Max Fischer?? Sure, he’s not necessarily a villain, but as a self-centered, wildly stubborn teen, he’s equally as frustrating as any antagonist. At age fifteen, Max Jason Bateman’s first (and best) role to date is the epitome of style and a good reminder that just because you outgrew your boarding school uniform doesn’t mean it’s gone out of style. 


While you’ll have to find Max’s signature red beret on your own, we can provide the rest. We’ve dressed up the Rushmore uniform a bit with our very own Blue Holiday Check Blazer. It adds texture to the outfit, plus provides the perfect amount of warmth that’ll last through spring semester midterms. Add a sturdy pair of khakis, an oxford, and the perfect crest tie, and you’re golden. Get ready to be swarmed with gorgeous first grade teachers, gents.

Vivian Kensington, Legally Blonde (2001)

There is nothing more intimidating than a well-dressed, wildly intelligent woman.

Vivian Kensington is five feet, three inches of bone chilling comebacks and vicious retaliations, and we love her for it. Her collar always starched and her headband never out of place, Elle Wood’s arch-nemesis knew a little something about dressing for success.

Ms. Kensington’s classic taste is found within the very thread of the Priss Blouse by Gretchen Scott. Aptly named, this unique take on the women’s button down with its ruffled 3/4 sleeves and scooped back tells any classmate that you’re not one to mess with.

If Vivian went searching for her newest string of pearls today, she’d undoubtedly turn to Kiel James Patrick. Breathtaking glass pearls clasped with a silver anchor scream New England prep perfect for any Ivy League law student. The Charlotte Anchor Bracelet was made to be displayed. Tie this look together with the Quinn Penny Loafers by Jack Rogers and you’re sure to dazzle any courtroom.

Chuck Bass, Gossip Girl (2007—2012)

Every 2010 high school girl found a bit of guilty pleasure in loving him, and every 2010 high school boy envied his immaculate sense of style. His name? Chuck Bass.

A character we all loved to hate, Ed Westwick’s portrayal of Upper East Side bad boy billionaire Chuck Bass was somehow equally detestable and enviable.

Chuck is a man unafraid of taking fashion risks because he knows the reward will be worth it. If Mr. Bass is your prep inspiration, turn to exciting accessories like these Pink Gingham Suspenders from High Cotton, or the Sunset Feather Bowtie by Southern Snap Co. Balance bold pieces with an easy-on-the-eyes button down like the Intercoastal Performance Shirt by Southern Tide, or Breaker Pants from Vineyard Vines in a neutral shade like grey or khaki. You’ll make even the most affluent of Chilton grads speechless with a fit like this.

Steve Harrington, Stranger Things (2016—) 

Though he’s the newest character in our timeline, he’s as classic as ever. Rocking layered looks and hair coiffed through the roof, Joe Keery’s troubled 80s teen in the Netflix original series could title his memoir “Not A Villain, Just Misunderstood”.

Nancy Wheeler may be able to keep away from his devilish charm, but we can’t stay away from his charming fashion choices. Steve shows us the beauty of simple prep, sticking to neutrals and earth tones and never underestimating the power of a good sneaker.

Like we said, layers are crucial for our favorite high school basketball star. Start with a plain white tee, then grab the Pisgah Plaid Sport Shirt or the Logan End on End Sport Shirt (or, why not both??), both from Southern Tide. Stay insulated with the Headford Cotton Jacket by Dubarry of Ireland. And finally, because Steve would be disappointed otherwise, we can’t resist a clean white sneaker. We haven’t found an outfit these Swims Knit Sneakers don’t compliment, and we dare you to try.


Whether you see yourself in the school boy charm of Max Fischer, the wit and composure of Vivian Kensington, or the rugged good looks of Steve Harrington, we hope this guide to your favorite cinematic preppy villains’ finest looks was inspiring.


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  • Author image
    Wahoowah81: July 03, 2019

    Anna- thanks for the fun blog post! Billy Zabka was so easy to dislike in any role he had.

  • Author image
    Cullen : July 03, 2019

    This is one of the best blogs I have ever had the pleasure of reading. Thanks to this awesome article full of helpful fashion tips for this summer and beyond, I’ll keep Country Club Prep in mind for my shopping needs. Would love to hear more from this author, she’s very talented!

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