Dapper Dan’s name is synonymous with Hip Hop and fashion. Born Daniel R. Day in East Harlem, his life journey from hustler to self-taught designer and business owner is the type of story they make movies about. As one of the most revered and pioneering names in fashion to date, Dan ushered in an era of ready-to-wear before luxury houses even thought of the idea in the early ’80s — and faced his share of triumphs and failures because of it. Despite the many setbacks, Dan always reinvented himself, relying on his creativity, the lessons he learned and his keen knowledge of culture to continually guide his way. Now well into his eighth decade, the visionary continues to inspire individuals to use fashion and style as a tool for self-expression and empowerment.

Below are 13 lessons the fashion mogul taught us about style.

1. Be authentic

The fashion icon embodies the importance of being true to oneself. His unique style, which merges African culture with high fashion and street culture, reflects his identity, upbringing and worldwide travels. The way he boldly conducts himself and his business teaches us to incorporate our stories into our style.

2. Be confident

Dapper Dan is a huge believer in the idea that clothing can significantly boost one’s confidence. He often speaks about how the right outfit can make a person feel powerful and self-assured. Dressing well can change how you perceive yourself and how others perceive you.

3. Think outside the box

The king of knock-offs is responsible for ready-to-wear fashion as we know it. Before luxury houses started making clothes, he saw the potential for logo-filled clothes and created his own signature designs. By thinking outside the realm of what was deemed possible at the time, the talent was able to corner the market and introduce a new era of style.

4. Tailor your clothes

Tailoring your clothes is an important element in personal style, according to Dapper Dan. He places significant importance on the skill, since tailoring ensures that garments perfectly fit your body. A well-tailored outfit can make a huge difference in how you look and feel.

5. Pay attention to detail

One of the cornerstones of Dan’s design philosophy is paying attention to detail. The fashion designer even built a business focusing on it. Whether it’s a pocket square, stitching or a hemmed length, focusing on each element contributes to the overall development and quality of one’s style.

6. Always cater to your clients

When the New York native opened his first boutique on 125th Street in Harlem in the early ’80s, he kept it open 24 hours a day to cater to his clients. The customers included drug dealers, gangsters, professional boxers and rappers who didn’t shop solely within the traditional 9-to-5 hours and wanted accessibility at all times. To this day, he is still the only designer that ever offered a 24/7 clothing store.

7. Reinvent yourself

The legend’s life and career are great examples of the power of reinvention. He emphasizes the necessity of embracing change as it is inevitable, crucial for personal growth, and can guide one’s outfit choices.

8. Be bold and experiment

Always known for his bold approach to fashion, the legend blends high-end luxury with streetwear in innovative ways and has always been experimenting with new technology or silhouettes since the 1980s. He’s a living example of never being afraid to take risks and try new combinations.

9. Be a student of culture

Understanding culture has always been of great importance. One of Dapper Dan’s main mantras is: “I don’t dictate fashion, I translate culture.” Understanding culture and style indicators contributes to social discourse and identity expression.

10. Adapt trends to your style

The godfather of Hip Hop fashion believes that trends are rooted in history. By understanding past fashion movements and styles, one can learn how trends evolve and re-emerge in popularity over time. With knowledge of circular trends, one can choose what trends resonate as inspiration to create new perspectives and experiences.

11. Use fashion to empower

Dapper Dan sees fashion as a means of empowerment, and advocates for using fashion to assert one's presence, command respect, and help navigate different social and professional environments. He also sees it as a way to break away from conventional and stereotypical norms.

12. Blend high and low fashion

One of the mogul’s signature approaches is blending high fashion with streetwear and everyday clothing. He teaches that style is not defined by a price tag but by the craftsmanship and the creativity of thought behind the outfit.

13. Create a legacy

Style is intertwined with the legacy you create and ultimately leave behind. Dapper Dan personifies this idea. He emphasizes the importance of leaving a lasting impression on the next generation through one’s creativity and contributions to the culture and society. He has demonstrated this through mentoring emerging talents and fostering innovation in Harlem.