Men’s fashion on social media typically celebrates chiseled jawlines, towering heights, and six-packs, often overlooking those who don’t fit this narrow mold. Jon Wiebe, known as “The Road To Dapper”, is challenging and changing this narrative. 

Annoyed by the narrow portrayal of men’s fashion that glorified only fit, tall figures, Jon was determined to prove that being fashionable isn’t size-exclusive. 

Jon embrace the concept that fashion is not confined by height or weight, and started his mission to empower and inspire a community of XL men. He named this “The Road to Dapper.”

Jon’s journey began with sharing his daily outfits and celebrating his finds of inclusive, quality brands. It quickly unfolded into an extraordinary adventure that brought promotional deals, new challenges, a devoted fanbase, and a shift toward a career in personal styling.

Who’s Jon Off Camera?

While followers know Jon for his passion for fashion and classy looks, content creation is only a passion project for him as he juggles a full-time career working at a national Vancouver-based church and is a dad to two teenagers. 

“I don’t share a lot about my family life,” he told Net Influencer in an exclusive. “But I’ve been married for 18 years and have two teenage kids.” 

Despite his online persona, Jon’s family remains a significant part of his life, highlighting the balance he maintains between his personal and professional worlds.

What is “The Road To Dapper”?

“When I hit my 30s, something started to shift in my mind. I started to experiment with different pieces and hunt for the right clothes and styles that worked on my body. “The Road to Dapper” was born to share my journey through building community and shared experiences. A space to show that style has no size.”

Jon explains that this community expands beyond social media, with personal styling tips, coaching, and even a newsletter that keeps XLl men like Hinmsilef up to date on the latest brands, looks, and inspirations. 

Why Invest In An External Community?

Recognizing the risks of relying solely on social media platforms, Jon believes in diversifying his influence beyond these platforms and building a community impervious to technological shifts or trends. 

“I revamped my website and relaunched my newsletter,” he says, ensuring that his followers can stay connected regardless of changes in the digital landscape.

The Journey To Now

Jon began creating content over eight years ago, motivated by a wish to refine his own style. He drew inspiration from others on Instagram, where the trend at the time was to post simple, straightforward photos of outfits. 

He started a separate account dedicated to his fashion journey to actively participate in the menswear community without overwhelming his personal feed “I started by following other guys online who posted their outfits. Back then, Instagram was all about carousel aesthetic photos back then,” he said.”

He quickly recognized that his personal outfit posts might not appeal to his friends and family. 

“I realized that posting on a minor scale might only annoy friends and family while going all in and cultivating a community of similar interests would be more rewarding,” he explained.

Jon’s following grew as his content began resonating with a broader audience, leading him to a supportive community that valued his insights.

Inspiration and Growth

One of Jon’s early inspirations was Chris Mehan, a menswear influencer whom Jon followed even though Meehan had fewer than 10,000 followers. 

“Seeing him post regularly inspired me to do the same,” he stated.

Significant milestones have marked Jon’s content creation journey. “Hitting 10,000 followers was huge because it unlocked features like swipe-up links in Instagram stories,” he recalls.

 Another memorable moment was when a brand first reached out, offering to send him a tie in exchange for a post. 

“It was crazy to think someone wanted to send me a product,” he laughs.

The Business Aspect Of Fashion Content

Jon’s creative and informative fashion pursuits were never backed by financial motivations, as brand deals shocked him. 

“I didn’t even know making money from this was possible,” he told us. “One of the first brands I worked with was offering me free products and a $200 financial incentive to post.”

Despite learning to navigate the business aspect, Jon remains true to his goal of documenting his journey with fashion and inspiring people in a similar space. 

Now, he balances incoming offers with proactive pitches to brands he wants to work with. He’s selective about partnerships, ensuring they align with his values and the interests of his audience. 

In addition to many promotional opportunities, Jon recently signed with a modeling agency, which has led to more professional recognition and brand deals.

Advice for Aspiring Creators

Jon’s advice for new creators is: “Be yourself. Don’t try to copy someone else.”

He stresses the importance of authenticity and valuing one’s time. “Brands will try to take advantage of you, wanting free work. Know your worth.”

What Would You Do Differently If You Were To Do It All Over Again? 

Reflecting on his early days in content creation, Jon Wiebe had expressed a desire to approach things differently if given another chance. “If I could do it all over again, I would spend more time initially figuring out exactly who I’m speaking to and what value I’m providing,” he shared.

Jon had identified this as a pivotal moment, realizing 18 to 24 months ago that having a clear understanding of his audience and content’s purpose could have sped up the growth of his online presence. 

He noted the inherent tension between striving for perfection and the need to just start, stating, “If I had known that niching down and focusing on the engaged minority rather than the broader potential, I’d be further in my career by now.”

From his eagerness to represent an overlooked demographic to cultivating an engaged community and forging a profitable career, Jon continues to reshape perceptions around men’s fashion.

His initiative, “The Road to Dapper,” has transformed his path and challenged the broader conversation around fashion. As Jon’s influence grows, his journey promises to inspire and empower even more individuals, proving that fashion knows no bounds.