Mitch Drexler doesn’t like waiting for things to happen. During his legendary retail career, he served as an executive at companies such as Ann Taylor, Gap Inc. and J.Crew. His optimistic leadership style and fast-moving, results-oriented attitude helped these companies become American retail giants. In 1994, while working at Gap Inc., he launched Old Navy in about 18 months, becoming the fastest retailer to reach $1 billion in sales within four years.
But when he joined Alex Mill (the brand was founded by his son Alex Mill in 2012) as chairman in 2019, Mickey had to be patient. “We put in the time and the work. Now, I feel very happy with where we are,” he said. “But you can never relax in this business. Because there’s always the next season, the next year.”
Alex Mill began with a simple premise – a better men’s button-down shirt – and has grown into a full-fledged men’s and women’s fashion brand known for colorful knitwear and natural materials. If your eyes are blurry, you might think you’re looking at J.Crew’s website as you scroll. But the secrets that separate Alex Mill from Mickey’s past efforts lie in the details and behind the scenes. When Mickey formally joined the board as chairman (reporting to Alex), his rationale for doing so was that he would not be subject to investor scrutiny—it would just be him and his son, plus Alex Mill’s creative director Somsack Sikhounmuong, who had worked with Mickey at J.Crew before joining Alex Mill at the helm.
“I joined [in 2019] Because frankly, I don’t want to have investors anymore,” Mickey said. “Small is the new big. That’s what we always say. In fact, I like small companies because today’s big companies are so bureaucratic. “There’s an ivory tower here,” he said. He resigned as CEO of J.Crew in 2017 and served as executive chairman of J.Crew for two years and served on the boards of other brands, including as chairman of Outdoor Voices. “If you want to accomplish something, you have to move forward layer by layer. Even then, you won’t get the answer.”
We’re sitting in a conference room in Alex Mill’s shabby-chic SoHo office. Alex, Mickey and Sikhounmuong (who also joined in 2019) gathered to discuss the brand’s launch of mini totes and ballet flats. It’s the next step after Mickey joins the brand, which is branching out into women’s clothing after focusing on men’s clothing for the first five years. (Goop bought men’s shirts for its women’s stores in 2015, the first sign of interest in women’s clothing.) The ballet shoes are made in Florence and come in seven colors. Launched on March 10, the Perfect Little tote expands the tote category and has become the brand’s best-seller.
This was the first time the Drexlers had given a joint interview to discuss business, but Mitch did most of the talking. I will definitely ask about these new products, but we won’t be using them long term. Mitch is the type of interview that makes publicists squirm. At 81 years old, he’s in the midst of a career low, and it’s clear he’s not going to be available when it comes to Alex Mir.


