To become successful in this business requires long hours and overcoming even longer odds, taking your lumps, learning from mistakes, adapting on the fly, and, above all, refusing to quit. It can take years. Many don’t have what it takes.
Sierra (Cee Cee) Massey does. What she endured just to complete a cobbler program at the Jewish Community Center (JCC) in New York shows the ultimate determination, not to mention the makings of a Hollywood movie. For six months, Massey commuted to the once-a-week class by bus—from Detroit. She’d arrived at the bus station in Detroit two hours early to get a seat for the Monday redeye to New York, roam around Manhattan for hours until her four-hour class began at 5 p.m., then race downtown to catch the return redeye. As soon as she got off the bus, she’d change clothes in a bathroom and head straight to her job as a CVS pharmacy tech or to classes at Wayne State University.
There was a program offered by a school in nearby Ohio, but it was only a one-week course and the same price as the JCC’s. The main reason Massey chose the JCC was her determination to learn as much as she could about shoemaking. “I needed the longer program to truly teach me the craft,” she says, noting that she learned how to create patterns and make shoes by hand. “I learned how to create quality product, as well as how to communicate effectively with manufacturers overseas, because I didn’t want them to think I was this young, dumb girl trying to play in the big leagues.” Massey adds, “I couldn’t afford to travel to China or India, and I couldn’t draw, so I needed to learn how to make prototypes and speak the footwear lingo to get exactly what I wanted.”
What Massey, a size 15, wants is to fulfill her lifelong dream of launching a women’s extended sizes (10 to 16) footwear fashion brand. “Growing up, I dreamed of being on Rip the Runway to showcase my brand mission, which was before body positivity was a thing,” she says. “I wanted to promote that we’re here, we’re vibrant and beautiful, and we aren’t going anywhere. Acknowledge and accept that we ‘Big Steppas’ exist.”
Massey believes she has a leg up on the competition because she’s also a customer. “I’ve lived the trauma where it was next to impossible to find styles in my size, and shoes were often forced to fit by not creating the proper tooling for larger sizes,” she says. She is far from alone. Massey’s research reveals that upwards of 13 percent of the women’s footwear market is extended sizes. That’s millions of potential customers. “It’s very difficult to find stylish, quality footwear in sizes 10 and up, and any that are out there sell out fast,” she says. Growing up, she usually wore men’s sneakers. “At age of 15, I wore size 13 women’s, and dreaded shopping, so much so that I’d have tears in my eyes on most trips. If I did find my size, they were usually matronly looking and in basics colors like black, navy blue, and white.”
Massey is determined to change that narrative. She first sourced a tight collection out of India but has since moved to China (with a few styles made in Detroit) for her official debut collection launched this season. The Cee Cee Massey aesthetic is bold colors, classic hardware embellishments, and design details that flatter and aid in comfort. “Wherever it makes sense, I also love a little glam,” she says. “My life is all about passion, joy, confidence, and feeling great, and my shoes will always reflect that. For too long, women with larger sizes couldn’t express themselves through fashion.”
What is your first shoe-related memory? It’s the reason I got started on this journey. It was middle school (2004/05). I was at a Valentine’s Day dance, where all the girls were wearing holiday-themed pink or red Nike shoes with a heart on the heels. I wanted a pair so bad, but of course they didn’t come in my size. I remember calling my mom to pick me up early from the dance. I ran to her crying. She held me so tight, asking what was wrong. That’s when I told her I wanted to start my own brand one day, so no other girl felt how I did. She made me promise that if I didn’t give her trouble in high school—no babies, no boy drama, and maintained my straight A status—she’d help start my brand. I did just that! I graduated with a 3.9 GPA/National Honor Society member. She held to her promise, too. She used to give me money for my bus trips to New York so I could buy food. She was always there to listen and help where she could. She means the world to me!
How would you describe Cee Cee Massey? I want our shoes to empower our customers throughout their day. Our overall aesthetic is what I like to call City Vibes. That’s where my ladies need me, which is a spectrum of styles for their entire wardrobe. Pumps, slingbacks, and loafers speak to businesswomen. Ballerinas, loafers, and slip-ons speak to minimalists.
Who is your target customer? Extended-size women looking for a brand that truly understands them—one that is dedicated to offering feminine style, fit, comfort, and fun. That includes women of any age. Cee Cee Massey is all about inclusivity, self-expression, and body positivity.
How might your Detroit background influence your designs? Detroit is home to great art and creator talent—murals everywhere, bright lights, fancy cars, and music. It all influences me, and you’ll see more of this in my upcoming collections.
Was there a muse behind your debut collection? God and my family have always been my foundation! I named the styles after my mom, sister, and two nieces. They’ve been my No. 1 cheerleaders.
Do you have a favorite? That’s a hard question; I love them all! Maybe the Nia diamond slides. They shine so much that they’re mesmerizing.
Where do you envision Cee Cee Massey in three years? As the go-to brand for extended sizes available on our site and in brick-and-mortar stores. Also, an expanded line, including apparel, handbags, accessories, and outerwear.
What’s the best business advice you’ve ever received? Do my own research and follow my heart to be sure my brand message doesn’t get distorted. Also, know how to maintain my books so I always know what’s going on in my business. Finally, know how to complete a S.W.O.T. analysis quickly so you I pivot at any given moment when challenges arise.
Any designers you admire? Steve Madden. He has lots of grit, and I’ve always admired his shoes. I watched his documentary and realized we had so much in common. It’s very inspiring that he never gave up and, if it didn’t exist, he created it, defying the odds and making a big impact.
What do you love most about designing shoes? That feeling of imagining how my customers will feel finally being able to buy a stylish pair that fits them. That’s priceless. I see myself in each of my customers, and I want them to be as excited as I am.
