If I were to ever consider my relationship with a particular trend to be a love affair, it would be the preppy school girl look. Few things are finer than a wool houndstooth skirt, a patent leather loafer with a sheer white sock, a sweater-vest, and a collared shirt combo. Iconic.
This nostalgic trend sends me straight into the Hollywood glam era of Audrey Hepburn, Lauren Bacall, and Grace Kelly. And I hope to never leave.
Here’s everything you need to complete the trend for that A+ prepster, Ivy League look.
For starters, no prepster checklist is complete without the legendary argyle sweater vest. It’s sharp. It’s smart. It’s polished. It says, “I know what I’m doing-thanks,” so you don’t have to. Marry this with a crisp white button-down or a short-sleeved polo and you’re basically captain of the debate team. Case closed.
Another thing you will need is a crisp wool blazer. It gives an air of happenings, prosperity, and excitement. It’s not something you’re lounging around at home in. It always contributes a polished look. Say no more. Find this one at Gap:
Let’s be honest — preppy schoolgirl look doesn’t exist without the schoolgirl headband. It’s an essential staple that I simply cannot get enough of. Blair Waldorf was rarely seen without one, and we’ll salute her ‘til the end. I’m dying for this one from J. Crew:
Nothing is more feminine than a plaid or pleated skirt. Truly a Marsha Brady signature. From fabric and pattern to length and accessories, there are so many ways to style them. I’d die for a plaid wool mini paired with black tights and a bold trench. Stunning. I grabbed this one from Banana Republic:
Praise must be paid to ribbons and ponytails. The ribbon is such delicate detail, yet certainly stands strong as a top-tier scholarly accessory. A world without this trend sounds like a joyless existence and I won’t have it. Find these ones at Madewell:
Let’s talk about the power of the patent leather loafer.
It’s quite simple. Important people wear this shoe. And when you do too, others notice. The loafer is comfortable, stylish and can be worn to the office or out with friends. Pair them with tights, a white sheer crew sock, or with no-show flat socks for a sleek, bare look.
Now, I didn’t go to Harvard, but the vintage varsity sweaters with said college’s name scrawled across the front are having a very prominent moment in the fashion world. Not a day goes by that we don’t see our favorite model off duty sporting this one and for good reason. It’s a cozy look with your favorite blue denim, under a wool trench, or with a black watch plaid mini skirt.
When it comes to the matching tweed two-piece set, we think Channel, we think royal lineage, we think abso-fucking-lutely! From Jackie O to Cher Horowitz, this ensemble is woven through history because there’s nothing like it. Honestly, I have PTSD from the time of my life before I knew about them.
We have Aubrey Hepburn, Margot Tenebaum, even Wednesday Addams to thank for the contrast cuff and collar mini dress. This just proves, no matter who you are or what you love about fashion, this dress gives you an err of poise and prowess even after you bottomed-out at Zara. So naturally, I’m all about that.
These pieces always deliver a polished schoolgirl look and have proven to stand the test of time. Whether you simply admire them from afar or adopt them into your own wardrobe, just remember these wise words from fashion legend Giorgio Armani, “Elegance is not standing out, but being remembered.”