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5 Things You Need To Lead a Successful Fashion Brand Today

Michael Hollingsworth Of Hollingsworth Sole On 5 Things You Need To Lead a Successful Fashion Brand Today - An Interview With Ben Ari

"You’ve got to have positive, peaceful influences feeding your ideation process. Prayer helps me tremendously." - Michael Hollingsworth

As a part of this interview series, I had the pleasure of interviewing Michael Hollingsworth. Michael Hollingsworth is the founder & CEO of Hollingsworth Sole, American footwear designer and serial entrepreneur. Mr. Michael Hollingsworth aspires to see Black culture well-represented in the luxury brand space. Uninspired and tired of wearing clothing and accessories by designers he didn’t know, Mr. Hollingsworth sought to create a meaningful culture-representative brand experience. Hollingsworth paired his proven business acumen and a nostalgia for the classic era of dressing to impress in Harlem, New York. The epicenter for entrepreneurial Black creatives, Hollingsworth’s soulful Harlem home provided the greatest inspiration for his launch of Hollingsworth Sole luxury brand experience.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your childhood “backstory”?

I grew up in Harlem. It was a bustling village of people wanting to see and be seen, wanting to be acknowledged. As a young boy I remember “wanting what “the Man” had” economically and in status. I was child with small feet, not able to wear the “big boy” shoes, My mother purchased shoes, which weren’t impressive to the children in the community, this particular style of shoe would be ones that I was teased for and this feeling and experience had a major impact on my desire to make my own money.

I was entrepreneurial child, my first experiences where my first “job” working a fruit stand, I began to learn the ways of business & finance at young age and go on to own and s arcade business at the age of 14. Guided by my mentors, I rented retail space and outfitted my shops with digital video games. My role models were businessmen in the Harlem community and my Papi.

Can you tell us the story about what led you to this career path?

I was inspired to bring back “a real, authentic style” I’m born and raised in the mecca of Harlem, so style and dressing well is in my DNA. Harlem is considered the fashion capital of Black culture, it’s the epicenter of dressing to impress, styling creatively, leveraging color to make bold statements. People would visit from all parts of the world to see, and learn about Harlem Style, they also came to seek a stamp of approval.

Can you share the most interesting story that happened to you since you began your career?

The constant doubting and challenging of my business concept by close friends and people from my community. There are many that told me that I would not be able to win in this game of fashion. Close friends have told me: “Who do you think you are?” “You’re not a luxury brand, your price point’s too high” “You’re not an Italian designer” Five years later, I’m here just having launched new categories and collections for spring and summer.

You are a successful business leader. Which three-character traits do you think were most instrumental to your success? Can you please share a story or example for each?

The all-important three P’s, Patience, Perseverance, Prayer

Patience: There’s the saying “tomorrow isn’t promised” in spite of that you still have to work as if tomorrow is coming your way, move and believe as if better tomorrow is coming your way.

Perseverance: It took time to establish the Hollingsworth Sole signature style. It took me 15 tries to get it right. On my 16th try I designed my signature shoe that resonated with customers, which is a classic leather lace up and leather slip on.

Prayer: I am grounded by my spiritual beliefs, daily prayer guides me, it gives me hope, keeps me faithful.

What do you think makes your company stand out? Can you share a story?

Hollingsworth Sole is 100% Harlem Heritage luxury. The quality and attention to detail is exceptional. We are the first and only multi-category Harlem based brand. I’m not speaking about licensing the Hollingsworth Sole brand name to licensees to grow my product portfolio, I’ve personally funded and invested in manufacturing and production in the categories of shoes, sneakers, fragrances, clothing, time pieces and eyewear. I’ve designed as well as written the strategy and plan for all these products.

Additionally, I create for a size 2 to a size 16. I don’t make clothes for the runway; I create for real men and women. This past August I presented my new fall collections at a Harlem Week show. I heard over and over that out of all the presenting brands on the stage that day, Hollingsworth Sole was the only brand that resonated with guests.

Do you have a favorite “Life Lesson Quote”? Can you share a story of how that was relevant to you in your life?

I have several, I share many of them in my first and second books “Mike’s Stinking Thinking One and Two” But one of my favs is “Stay where you look good at” Don’t allow what someone else has or appears to have alter your direction in life. People mimic what others are doing, when they see something that appears to be successful, for example the juice bar trend, which is the shiny new penny in business, you’ll have many that rushed to open this kind of business because of the perceived success. But you must do what works for you. You also must do the work. Fashion and lifestyle

brand building is my lane, it’s my “good look”. I didn’t follow a trend, I stay true to my beliefs and what inspired me when I founded Hollingsworth Sole.

Ok, thank you for that. Let’s now jump to the primary focus of our interview.

Do you see any fascinating developments emerging over the next few years in the fashion industry that you are excited about? Can you tell us about that?

The industries approach to “unisex” is evolving. Brands and Designers are celebrating diversity by an inclusive approach in who and how their garments are worn. I design my lines with the broadest appeal to a diverse consumer base. Most of my items are unisex, and I’ve altered some of the items to appeal to feminine styling.

Can you share how your brand is helping to bring goodness to the world?

It’s said that we make decisions about people in the first 3 seconds of meeting them. and then spend the next 90 seconds trying to confirm the first impressions. Before you’ve uttered one word you’ve been sized up and profiled.

A Hollingsworth Sole wardrobe is a confidence builder, you can dress from head to toe in Hollingsworth Sole. it’s amazing to see how people respond to a finely dressed person, it’s euphoric feeling, it’s the ultimate high.

It’s been my intention that Hollingsworth Sole’s style is used to shape personal influence. Being well dressed makes you feel like you’re on top the world, you can conquer what’s in your path. Hollingsworth Sole is building on the incredible legacy of Harlem culture. I’m a proud ambassador of my neighborhood, Luxury Brands can be borne here in Harlem, I’m proving it.

Can you share with our readers about the ethical standards you use when you choose where to source materials?

Responsible sourcing is incredibly important to me, I make sure I’m working with artisans and makers who manage excellent standards in manufacturing and creating. Most importantly I’m working with people in communities in Brazil and around the globe who are passionate about their craft. They take pride in the work they do, and that quality and excellence is evident in Hollingsworth Sole’s final products.

Fast fashion has an advantage, that it is affordable for most people, but it also has the drawback that it does not last very long and is therefore not very sustainable. What are your thoughts about this? How does your company address this question?

Fast fashion works because it’s cheap and steals design intellectual property from creatives who doing the work to innovate. Within hours of a new collection being sent down the runway, factories all over the globe are copying styles and throwing up knockoffs that ship to retail, in weeks.

I don’t compete in that market. I’m a designer who respects creativity and originality. The Hollingsworth Sole Man and Woman are looking for quality, materials, and items that will last. They’re investing in themselves, and they are seeking reliable, sustainable wardrobe solutions. I am from an era where your parents invested in a good pair of shoes, those shoes were re-heeled and tapped and lasted for a lifetime.

Fast fashion can’t do that.

Thank you for all that. Here is the main question of our interview. What are your “5 Things You Need To Lead a Successful Fashion Brand”. Please share a story or example for each.

1. Open Mind — be flexible in your decision making. Don’t be set in one direction, there are always different paths, and other options to take.

2.Peace of Mind

It’s impossible to create beautiful garments if you’re sitting in the middle of chaos.

You’ve got to have positive, peaceful influences feeding your ideation process. Prayer helps me tremendously.

3. Creativity

I believe it’s a gift from God, it can’t be learned, it’s been a gift for me as a Designer.

Because of it I’m thinking of a thousand possibilities at any one time. I’m always asked about my collections and vast variety; because of creativity I’m able to act on inspirations and offer my customers a breath of options.

4. Stay ahead of Trend. I keep my ear to the pavement to stay ahead of the curve. I’m a Gen x’er and I make it my job to understand Gen Z’ers and Millennials. They’re incredible inspiration. They’re smart, they’re quick, and they demand brands like Hollingsworth Sole to deliver on style, quality, sustainability, and social purpose, they keep me sharp.

5. Believing in Yourself. I’m a visionary, an entrepreneur. Visionaries see their ideas to completion with an almost tunnel vision, we can almost feel and taste what it is that we want to happen. Entrepreneurs don’t give up, we’re relentless and we don’t wait for opportunity. I’m believing in myself, my ideas, my vision. If you can’t do that you won’t have a chance. Facts.

Every industry constantly evolves and seeks improvement. How do you think the fashion industry can improve itself? Can you give an example?

The industry should be more intentional in creating spaces for creative expression, expanding the what’s and not only rubber stamping “industry approved fashion”. The gate keepers filter-out authentic voices and points of view.

Brands like LVMH partnering with Harlem Fashion Row to support Black Designers is a good start, but we need more. Historically we’ve been pushed onto the sidelines, the margins.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

The movement I’d lead with no hesitation is eradicating homelessness, making that initiative a priority, driving a meaningful effort to solving the problem. I’d like to see an industry sponsored effort to support the homeless.

I was homeless for two years, during that period, my eyes were opened, we don’t pay attention to the homeless, you never pay attention until it happens to you. I vowed to never let it happen again. The homeless are judged by their appearances, they aren’t considered people who are capable, they are the “unseen”. Therefore I’m so passionate about the work I do at Hollingsworth Sole, enabling people to make amazing first impressions.

I’ve been in the position to be judged for my appearances during that difficult time. My success is what’s possible when given an opportunity to emerge from being homeless. Building a company like Hollingsworth Sole is what’s possible when we are given the tools we need.

How can our readers further follow your work online?

Help Hollingsworth Sole reset the algorithm on social media we appreciate your likes, shares, and comments! We appreciate the support! Visit our website find, follow, like and share us on Linked In, Instagram, Facebook at and Twitter @HWBlueSole

This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!

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