Image via Dean/PKP

As a casual reader of Proper Kid Problems, I knew that its author, Dean, was a force to be reckoned with as far as fashion is concerned. So as I slipped into my brown leather loafers and pink gingham shirt, I wondered if I had even scratched the surface of proper, or if Dean would automatically think “get on my level.”

He extended his hand when we met and gave a gracious smile that was more sincere than most in our nation’s capital. While I own the Ralph Lauren Oxford he was sporting during our interview I had never imagined wearing it with the first three buttons casually undone, nor would I be able to so simply pair it with lime green smoking slippers. Yes, the prep was strong with this one.

His popular blog, Proper Kid Problems, started out as an anonymous project in the summer following his 2012 graduation from high school. He wanted “something to do in his spare time” but saw the opportunity as little more than a fun preoccupation before beginning at George Washington University in the fall. However, he didn’t realize the presentation of his beliefs and mindset would resonate with a such a large audience.

In the first year, Dean’s biggest struggle was not planning for such a high level of interest towards PKP. That, coupled with the anonymity of his blog, made for a difficult first few of months. He recalls having to spend time cultivating his blog while not being able to be completely forthcoming with his friends. Making these sorts of sacrifices, Dean points out, isn’t unique to him.

“Making sacrifices and being prepared to make them and knowing that you have to give things up” is just part of any successful student startup. Dean had already “forfeited the typical college experience” and going into his sophomore year he really began to rethink how best to accomplish his goals both in life and work. These considerations led the young entrepreneur to take some time off in order to share his identity with his readers and to really refocus his direction.

The next major chapter in the PKP story came just last summer as Dean announced a merger with J. Bradley (a brilliant 17-year-old designer) whose website and product line, J. Riley, was selling just the sorts of products Dean was talking about in his blog posts. Side-by-side, these two young pros created a brand that benefited them both. J. Riley brought the clean and traditional product line that, while small, really appealed to Proper Kids all over the world. Dean provided the creative writing style that would keep his readers clamoring for more.

While Dean admitted that the merger was tough and involved an over forty-page contract, a new website, and the creation of an LLC, it was certainly worth it in his mind. He now is the co-founder of a website that helps guide the prep-enthused to the best labor day sales and designers ideal to fill a back-to-school closet.

As our interview wound down, I had the opportunity to just shoot the breeze with the Proper Kid himself. He told me his favorite piece was a vintage blazer from his father’s younger days, tailored to fit him to a tee. We also talked about his style background, with Dean casually mentioning that he wore a suit and tie every day of kindergarten, tying his first double windsor at five. Which, in part, made me understand how he manages to be so far ahead of the curve when it comes to style.

It’s clear that Dean knows what he’s talking about when it comes to men’s fashion, but he stresses that style isn’t who you wear or even what you wear, it’s how you wear it. Dean realizes that he sets a high standard and that living up to it would be a difficult job for anyone. Rather than copy him, he urges readers to be themselves. That said, I’m still more than happy to take a page from his book.