“Is prep the ultimate trend or the denial of all that is trendy?”

I’m sure you’re not surprised to hear that this question from a recent Harper’s Bazaar article certainly got me thinking. We were just recently talking about the Club House trend, the resurgence of preppy style. But if prep is back, I have to wonder…did it ever really go anywhere?

From the serious status symbols of the late 1800s to 1965’s style-defining Take Ivy book to the tongue-firmly-in-cheek Official Preppy Handbook of the 1980s, prep fashion has always been in a state of ebb-and-flow evolution. It originally appealed mostly to wealthy men attending Ivy League preparatory schools (thus the name), extending to well-to-do suburbanites in the 1950s and finally finding mass appeal with the average American in the ‘80s and ‘90s.

Brands like J. Crew and Tommy Hilfiger ushered a modern prep look into the new millennium, and today the style is being reinvented for new generations.

But wait…is it really?

Michael Bastian has been the creative director behind Brooks Brothers, perhaps the most steadfast maker of preppy clothing, since 2020. He seems to think that this is not a reinvention – this is a return to the simple fundamentals. “I don’t need to reinvent the wheel,” Bastian said in an interview with GQ. “Like, that Oxford cloth shirt is perfection. All I need to do is protect it and make sure it’s there in its highest form.”

This is a look that, once seen as the day-to-day symbol of the rich and privileged male, is now being worn by men and women of every status. “It’s coming back in a whole new way,” says Bastian, “which is really amazing because it’s more inclusive, a little cooler, a little less gender specific. It makes it all kind of fresh again.”

So let’s get back to that question: is prep style our most consistent and abiding trend or the anti-trend? To even try to answer this, we need to understand why we keep coming back to the preppy look in our wardrobe.

Prep Is Familiar

Particularly in America, prep is a look we’ve practically grown up on. Brooks Brothers makes it a point of pride that Abraham Lincoln wore their clothing, as have 39 other US Presidents. We’ve seen preppy style on the big screen in movies like Grease and in our living rooms on Gilmore Girls and other shows. Of course we’re drawn to the look — it’s a part of our shared history and the entertainment we love.

The same Casual Oxford shirt Michael Bastian mentioned can be worn by men or women and still looks like it did when Paul Newman or Audrey Hepburn wore it. Even on his days off, President John F. Kennedy favored polos to maintain his “smart-casual” aesthetic and the Brooks Brothers Pima Cotton polo fits right in.

Prep Is Adaptable

Traditionally, prep style was mostly a one-size-fits-all approach, but the difference today is that there’s something there for just about anyone. Preppy outfits can be tailored to the individual, as we saw in our last exploration of modern takes on the look. The fabric itself makes a difference too — unlike the polos of the ‘80s, the Pima cotton that Brooks Brothers polo is made from is luxuriously soft and adds a bit of forgiving stretch to the shirt.

Or look to the Brooks Brothers double knits: you have a 1/4-zip, a 1/2-button and a full-zip hoodie, so there’s already plenty of variety just in the different pieces, all aligned with an overall preppy vibe. Depending on what you wear with them, you can make this casual with a simple t-shirt or pair it with a woven shirt and tie for a professional day in the office.

Prep Is In the Details

If it’s so adaptable, I hear you asking, then what makes it preppy? The difference, as it so often does, lies in the details. Some of these details are hard to miss while others you may not even see at first glance, but they all come together to create something that feels collegiate, contemporary and at least a little bit sporty.

Brooks Brothers is known for its attention to detail, and it shows in the overall finished quality of their pieces. From the beautifully rolled button-down collars on the Pinpoint shirt to the quilted jacket with the Brooks Brothers logo on its faux horn buttons to the tartan plaid inside the pockets of their bomber jacket, the details combine to create an outfit that looks both relaxed and intentional. Nothing says preppy quite like clothes that clearly state “I know my value.”

Now that I think about it, I understand why Bazaar asked the question about prep’s trend status. It’s like our new athleisure — applicable to many different scenarios and representing different things to different people. In an unpredictable world prep styles remain solid and stable, always familiar while regularly offering something new to the conversation.

Best trend ever.

Next month we’ll take our leave of talking about prep style for now and focus on the comfort that’s driving where we’re going, what we’re buying and of course, what we’re wearing. See you then!