Every so often you come across someone who’s clearly put in the reps.
They’ve thought about the fit, the fabric, the reason a look works. Tom Donnelly is one of those people.
Tom built The Classic Preppy into a community of almost 25,000 by making that kind of knowledge feel accessible instead of stuffy, and I wanted to pick his brain on how he thinks about style, building an audience, and what “classic” actually means to him.
Here’s our conversation, over email.
What made you decide to start building something public around your personal style and interests, rather than just keeping it as something you loved privately?
Tom: For most of my life, preppy and classic style was just part of who I was. I grew up wearing button-downs, khakis, loafers, and rugby shirts long before social media existed. I never thought much about sharing it, I was simply wearing what I loved.
That changed when I started noticing how many people were asking the same questions online, in Facebook groups, on Reddit, and across social media: Is this preppy? What makes something preppy? What’s the difference between Ivy and preppy?
Too often, those questions were met with gatekeeping instead of guidance. In one Facebook community, the debates became so relentless that the group eventually shut down. Were there some that were just asking the question for sport? Sure.
However, I realized there was room for guidance. Not to tell people they were doing it wrong, but to explain what a preppy outfit is, maybe the history and traditions along the way. And, if asked, how to build a “preppy” wardrobe.
My wife actually encouraged me to start the page. If I can answer the proverbial question, “is this preppy” and help someone dress with more confidence – or inspire them – then I’ve accomplished what I set out to do.
Additionally, I’ve always believed that classic/preppy style isn’t meant to be exclusive. It’s meant to be shared.
Where does your sense of style actually come from—a person, a place, an era you gravitated toward?
Tom: My sense of style comes from a combination of family, education, and timing.
My father graduated from Princeton in 1961, so Ivy style was always in the background growing up. Navy blazers, oxford cloth button-downs, loafers, and khakis weren’t “fashion” to me, they were simply what we wore.
My mom taught me to appreciate quality and timeless clothing, and I was fortunate to wear school uniforms in both the United States and England, where classic dress was simply part of everyday life.
I also happened to grow up during the original “preppy movement” of the 1970s and 1980s. Looking back, I wasn’t chasing an aesthetic, I was living through a moment in American style.
That’s probably why Ivy/classic/preppy style has never felt like a trend to me. It’s just always been part of who I am.
As I write this, I’m sitting in an airport wearing loafers, an oxford cloth button-down, a crewneck sweater, and white jeans.
How do you define “preppy” for someone who thinks it’s just about boat shoes and popped collars?
Tom: Yes, people often think preppy is about boat shoes, popped collars, or a handful of iconic brands. I’ve even heard unicorns are considered preppy.
Preppy is really about timelessness, buying quality, building a wardrobe instead of chasing trends, and wearing clothes that still look just as good years from now. That doesn’t mean you can’t have fun with it. Experiment with accessories, introduce new colors, or add contemporary pieces that complement the classics. The foundation stays timeless, even as your personal style evolves.
It’s also a style that’s meant to evolve. Every generation adds something to it while respecting its foundations. When I was in high school and college, I never would have worn white jeans— I’m not even sure they existed. they were considered something women wore. Today my white jeans arethey’re one of my favorite pieces because they’ve earned their place in classic menswear. I think clean white sneakers have followed a similar path. What started as something new has become part of the modern preppy wardrobe.
That’s what I try to do with The Classic Preppy: help people understand the traditions, then encourage them to make the style their own. Respect the past, embrace the present, and build a wardrobe you’ll still enjoy wearing ten years from now.
What’s a post or piece of content you made that completely surprised you with how it landed?
Tom: There were actually three moments that really surprised me.
The first was a “What I’m Packing” post for a quick trip to New York City using the 5-4-3-2-1 packing method. I thought it was just a practical way to show how to pack and I wanted to try the method. It ended up becoming one of my best-performing posts, with more than 1,400 likes. It taught me that people weren’t just interested in seeing what I wore, they wanted practical ideas as well.
The second was how well my early “What I Recommend” carousels performed. I started creating simple educational guides around my favorite chinos, oxford cloth button-downs, and polos, thinking they’d appeal to a small group of classic menswear enthusiasts. Instead, they reached a much broader audience. That told me people weren’t just looking for outfit inspiration, they were looking for trusted recommendations.
The last surprise was that my “Follow Friday” posts consistently flopped. I genuinely enjoyed highlighting other creators, but my audience wasn’t coming to my page to discover someone else. That was an important lesson because it pushed me to try to lean into education, helping people build better wardrobes. And, this is one area I want to am growing and expanding.
What’s the hardest part of building a personal brand around a specific aesthetic, versus a broader lifestyle?
Tom: One thing that’s made building this brand easier is that I’m not creating a character for social media. If this account didn’t exist, I’d still be wearing the same clothes.
Most mornings I get dressed for work, for a meeting, or for a weekend with my family, and then I’ll film a quick fit check. The content comes from my life, not the other way around.
I think that’s important because people can tell when someone is wearing something just for the camera. My audience knows that if you see me in a navy blazer, chinos, loafers, or an oxford shirt, it’s actuallythere’s a good chance that’s exactly what I wore that day.
For my flat lays, I design them the night before and schedule the posts for around 5:00 a.m. Then I assemble the outfit/prepand almost always do my best to wear that exact outfit the next day. I might make a small change, but it’s rare. Some days it isn’t a 100% match, especially if I can’t find the same belt or the shirt I planned to wear is in the laundry.
Some days I find it funny that what I would normally wear inspires others or gives them a glimpse of what they can wear from a classic or preppy perspective.
If someone wants to build a following in a niche as specific as yours, what do you wish someone had told you on day one?
Tom: If I could go back and tell myself one thing on day one, it would be this: stop chasing followers and start serving the people who have already found you.
I spent way too much time wondering what it would take to reach my first 1,000 followers. Every day I’d check the numbers and ask myself, “What do I need to do to get there?” Looking back, that pressure was mostly self-inflicted. The moment I stopped obsessing over the numbers and focused on creating useful content, the account started to grow.
The second lesson was mental. It’s easy to compare yourself to creators who seem to be growing faster or landing bigger partnerships. I learned that comparison is exhausting, and it can pull you away from your own voice. The creators I admire inspired me, but the account didn’t really take off until I stopped trying to create like them and started creating like me.
Ironically, it wasn’t the follower count that told me I’d found my niche—it was the direct messages. When people started sending me photos of their outfits and asking for advice, I realized they weren’t looking for another outfit photo. They were looking for someone to teach them how to build a timeless wardrobe.
Those lessons eventually became the foundation for a book I’m writing about building a niche community online. My hope is that it helps other creators spend less time chasing metrics and more time building something that’s authentic, sustainable, and genuinely helpful.
What’s one item in your closet that’s been with you the longest, and what’s its story?
Tom: I’ve lost more than 50 pounds over the past few years, so most of my wardrobe has changed sizes. But one thing has never really changed: the classic navy polo.
I probably own dozens of them, from department store brands to Brooks Brothers, and even a custom Lacoste polo made in Paris. Some are faded, some are newer, but I reach for them over and over again.
I keep coming back to the navy polo because it simply works. It pairs with chinos, shorts, white jeans, Nantucket reds, seersucker, and just about everything else in my closet. It’s one of those rare pieces that’s as appropriate for a casual lunch as it is under a sport coat.
What’s a rule of the preppy aesthetic you’ve quietly broken, and gotten away with?
Tom: I’ve broken a few of the old “rules” over the years.
Growing up, you didn’t wear white after Labor Day, and suede was generally reserved for fall and winter. I follow both of those rules a lot less today. If it’s 75 degrees in October, I’m perfectly happy wearing white jeans. And if a pair of brown suede loafers completes an outfit in July, I’m going to wear them.
To me, those are examples of how classic style evolves. The foundation doesn’t change, but some of the conventions do. I think the trick is knowing the difference between a passing trend and something that’s earned a place in the wardrobe. That’s why I’ve also embraced white sneakers over the past decade. They’ve proven they’re here to stay.
For me, respecting tradition doesn’t mean being bound by every rule. It means understanding where those rules came from while recognizing that every generation adds something to the conversation.
Tom Donnelly is the creator of The Classic Preppy on Instagram, sharing classic menswear, preppy style, and everyday inspiration. Read more at The Classic Preppy on Substack.