The Allure of the Preppy Girl Style

Some styles can get up and go like a fleeting trend, but then there are some others that become legendary. Enter New England preppy girl fashion, the wardrobe equivalent of a cashmere sweater that gets pulled out of the closet three times a week. It’s this blend of looking so polished, yet so playful. It makes you look, effortless, but somehow… so perfect. Think of it as some sort of love child from the classic Ivy league sensibilities and the sophistication of the New England coast. Imagine this, waking up in the morning to feeling salty air coming through your window, it smells like the ocean, and somehow, whatever you put on next makes you look effortlessly perfect.

Time for a history lesson. Preppy style has deep roots in the old-school world of New England’s elite. It’s the ivy-clad colleges, summer houses tucked along the coast, and a rich culture of understated elegance. Preppy was born from the wardrobes of students at Ivy League universities, and what the girls wore in their private school leading up to college applications. This includes those button-down shirts and boat shoes. But, I must say this style in particular has evolved. It’s universal now, a look anyone can embrace, and honestly a look everyone should want to embrace. Who doesn’t want to look like they just got off a yacht?

It’s not so much about trying to look good, but throwing on something that would speak to a legacy of grace and sophistication. The nice look of New England preppy fashion lies in the confidence that goes with it. It’s wearing an outfit that says, “I don’t want to impress anyone other than myself.”

The magic of the preppy girl style is that it lies in the simplicity. Think of it as ironed out white shirts, high-waisted skirts, and the iconic blazer, along with nantucket reds, pastel chasers, and tripes. A lot of stripes. When the outfit is put together, it looks like this beautiful, curated magazine ad from Ralph Lauren.

Since the outfit is supposed to be applauded due to it’s simplicity, you must accessorize. The finishing touches that elevate everything. A good monogrammed tote that lays on your arm, a pair of loafers, and pearl earrings, with a matching pearl necklace, of course. On that tote, find a way to get your initials engraved, or better yet plated in silver. You could even find a plaid scarf to pull it all together. Then, once it’s on, walk around like you’re strolling through Paris, about to walk into that one perfect cafe and read a classic.

Now, that the basics are stated, let’s complicate things and add in some layering. This really what gave the Preppy Girl Style it’s name… There’s something so wonderful about throwing together something chic that is ready for every occasion. You could throw on a cashmere sweater, a plaid skirt, then layer it with a trench coat. Maybe a wool sweater over a shirt. Make it look loose, but not sloppy!

Throughout the winter, it isn’t just about the sweater. You need to wear that sweater with a collared button-down underneath. And don’t worry, skirts are still in, just throw on a pair of tights. They look good, don’t worry. If you get really cold, use that trench coat I mentioned early. Maybe a tailored pea coat. Your call, but don’t think about it too hard because you don’t need to try to be that girl, you are that girl.

Have you heard of boat shoes? Probably, because they are almost as worn as that tote. Whether you’re on a boat or just skipping around, they add this adorable touch of, “I’m about to go to a brunch!” If you can add in a silk scarf, that’s even better. You are now the Preppy Girl.

So, why do we love the style so much? It works because it is never not in. It’s a fashion statement that transcends fleeting trends and becomes part of your wardrobe’s DNA. A preppy girl look isn’t just for the Hamptons or brunch, it’s for the girls who know that style isn’t about the trends, it is about being timeless.

This style is a mix of traditions and modernity, elegant and easy. It’s the kind of fashion that feels as if it was made for you, even if you’ve never been to a place like New England. This style is a lifestyle, an attitude, a way of carrying yourself with sophistication, while maintaining the ability to have some fun with it. New time, you find yourself walking down a sunlit street in a cashmere sweater and some loafers, remember that you’re living the dream. You are that girl, everyone loves that look.