Holly Cohen didn’t just build a career – she built brands, teams, and opportunities across the world’s biggest retail giants, including Gap, Banana Republic, Claire’s, J.Crew, Madewell, and Nike. From leading J.Crew’s real estate expansion during its game-changing turnaround to shaping Nike’s global footprint, Holly has never been one to shy away from the unknown.
Now, as the founder of Holly Cohen Retail Advisory Services, she’s leveraging her decades of experience to help brands scale smart, transform retail spaces, and mentor the next generation of women in commercial real estate.
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“Say yes to the scary stuff. The doors that intimidate you the most? Walk through them. That’s where growth happens.”
Holly Cohen appears on my screen from her Miami home, a burst of energy against a backdrop of dogs wagging their tails and late-afternoon light.
She’s a veteran of retail real estate, a woman who has shaped the global expansion of brands like Nike, J.Crew, Gap, Banana Republic and Claire’s, only to step away from the corporate ladder and build her own perch with Holly Cohen Retail Advisory Services. Her career is a map of ambition and reinvention, dotted with late-night calls to Asia, a triumphant IPO, and a puzzle-piece philosophy that binds teams and communities alike. In this conversation, Holly reflects on a life spent navigating change – with a candor that feels as bracing as it is illuminating.
You’ve led real estate strategy for some of the world’s most iconic brands before founding your own firm. What was the pivotal moment that drove you to chart your own course?
Holly settles into her chair, her voice a blend of resolve and reminiscence. “It wasn’t one big bang – it was a slow build. I’d moved to Portland for Nike, running global real estate – Converse, Hurley, the whole portfolio. Three years of gray skies tugging at my East Coast soul. I knew going in it’d be my last big corporate stint – signed up for that. I’m a born and raised New Yorker, and after 16 years in Miami, I’d thrived on the grind – 2 a.m. calls with Tokyo, the overall global hustle because the sun is always rising somewhere, so you’ve got to be ready for the action. But when we landed back in Miami, late 2017, early 2018, I was done giving everything to someone else’s clock. I launched my firm to take the reins; I had 3 goals: consulting clients, taking on a board seat or two, and paying it forward by mentoring. My husband saw it before I did: ‘Holly, you’ve earned this.’ It wasn’t escape; it was ownership.”
You’ve had a front-row seat to the evolution of retail and real estate – from Nike’s global reach to J.Crew’s revival. What’s one trend you see reshaping the landscape ahead?
Her eyes brighten, tracing an unseen horizon. “Retail is a snake – it sheds its skin and comes back sharper. I’ve watched brands vanish, malls overbuilt over the past 30+ years, yet we keep evolving. What’s gripping me now is technology’s dance with experience. AI’s rewriting the store – cash registers are history; now it’s pickup zones, returns that hook you into buying more. Supply chain and tech are the crucible – legacy players like Gap and J.Crew have to sprint to match Warby Parker’s agility. Bed Bath & Beyond’s gone, movie theaters fading – we’re reallocating space for new stories. I’m hooked on how AI will weave connections into those places, and turn them into something we haven’t named yet. But I think the ‘net, net’ is we will always evolve in retail. Concepts will go, and new concepts will emerge, and reallocation of space will create new opportunities”.
You were a critical part of J.Crew’s iconic turnaround and expansion. What’s the biggest lesson you learned about navigating change and reinvention, and how do you apply that wisdom today?
“Absolutely! I’ve had some incredible career opportunities, and one of the biggest lessons I’ve learned is the power of saying ‘yes’ – even when it feels daunting.”
Holly reflects on how women, in particular, tend to hesitate before stepping into big opportunities. “We’ve all heard the stats – men will confidently say they can do a job with 60-70% of the experience, while women with 100% of the qualifications will second-guess themselves. The biggest lesson? Walk through the door anyway and take on the challenge!”
At J.Crew, she had to do exactly that. She was recruited by the legendary Mickey Drexler – widely regarded as the ‘Merchant Prince’ – to help turn the company around.. “He had transformed Gap, Inc. into an iconic brand, and when he was fired, took $10 million of his own money and invested it into J.Crew. That’s when he recruited a team of us to take on the challenge.”
It was a huge leap for Holly. “At Gap, I had been part of a larger real estate team with a defined role. At J.Crew, I was in charge of everything – some areas I had experience in, and others I had to learn on the fly. The day I started, 90% of my team was gone – either fired or too intimidated to stay. One of the remaining two quit on my first day. So, I had to rebuild everything from scratch.”
Instead of letting imposter syndrome take over, Holly leaned into strategy. “I knew what I was good at – strategy and leasing – so I outsourced those functions that allowed me to focus on hiring the right leaders: a VP of Construction, a VP of Legal, a VP of Operations, and heads of purchasing and facilities.”
Her approach paid off. Under the leadership of the new team, J.Crew underwent a complete transformation, ultimately leading to its public offering. “Standing on the floor of the New York Stock Exchange the morning of our IPO was one of the highlights of my career. We had put in the work, we had rebuilt the brand, and now, here we were. The IPO happened. We did it. And I’m very proud of that and grateful for a once in a lifetime experience.”
You also played a role in launching Madewell – tell us about that.
“Madewell was a completely new concept for J.Crew, but it started with something unexpected: a name.”
Mickey Drexler had purchased the Madewell trademark – a legacy workwear brand – and saw potential in bringing it back to life. “We had to figure out what it would be, where it should live, and how to position it in the retail landscape.”
For Holly, launching a new concept meant more than just finding storefronts. “Every time you launch a brand, you have to rethink everything: Who’s the customer? Where do they shop? What kind of retail environment makes sense for them? And do you even have the right relationships with the right landlords who own those properties?”
She had done this before. When she worked at Gap during the launch of Old Navy, she had to transition from dealing with mall landlords – Gap’s traditional retail partners – to navigating big-box shopping centers, a completely different real estate landscape. “It’s always about adapting, learning the players, and making the right decisions for the brand.”
You’ve spent years paving the way for the next generation of women in commercial real estate. What’s one piece of advice you wish you had received when starting your career?
Holly laughs. “Do I get to give more than one answer? Because I can’t keep it to just one.”
She pauses for a moment before continuing. “I mentioned earlier that I have, a wonderful partner – someone who has been by my side my entire adult life, pushing me when I didn’t think I was good enough. When I would’ve been the one saying, ‘I’m about 90% qualified, maybe not 100%,’ and thinking I’d just have to learn and listen my way through the last 10%. My husband Jon always says I lead with my charisma and vision, he was the one saying, ‘Go for it. You’ve got this.’”
She smiles. “So my first piece of advice? Say ‘yes’ to the opportunities, even when they scare you. I’m a big believer in Eleanor Roosevelt’s ‘Do one thing every day that scares you.’ Because that’s how you grow. I spent almost 15 years at Gap – 10 in operations, 5 in real estate. I could have left much sooner, should have, honestly. But I was comfortable. I had a great title. Gap was hot. Everything was great – except I kept asking myself, ‘What’s next?’ And that’s what got the best of me.
“So when doors open, walk through them. Even when they seem insurmountable.”
She leans in, her voice steady. “The second thing? Imposter syndrome. Everybody knows the label now, but that wasn’t a thing when I was coming up. And if it was, you certainly didn’t talk about it. Women had a tough enough time making it in this industry, and God forbid we show too much passion or emotions, or that we don’t know everything, right? So I lived with a great deal of, ‘Oh my God, what if they figure me out? What if I don’t really know what I’m doing?’ But here’s the thing: everyone feels that way. Men feel it, too. We just weren’t talking about it. So my advice? Don’t let it hold you back. Talk about it. It’s not a weakness – it’s a sign of strength.”
She grins. “And my third? Better done than perfect. We get so wrapped up in perfection, especially as women. We tweak, we refine, we hesitate. Meanwhile, what’s falling behind? What’s not moving forward? Because sometimes, good enough for now is exactly what’s needed. Most times things are fluid and you can usually tweak as you go.”
She gestures toward a puzzle piece on her desk. “That’s why I’m big on succession planning. Some people lead with, ‘This is how it is, follow me.’ And then there are leaders who build, train, and empower others – that’s me. Because leadership isn’t about holding on to power – it’s about recognizing people along with you.”
Holly leans back, thinking. “Here’s an example. Back in 2010, I was asked to join the Board of Trustees for ICSC – a global organization of 35,000 people. And at the time? Only three women sat on that 52-person board. That was a huge deal. To even be invited, you had to be a CEO or head of real estate. And how many women were running global real estate back then? Very few. I hesitated. I was at J.Crew, traveling every week, and I thought, ‘I can’t take this on.’ But my husband (a commercial real estate attorney) said, ‘You’ll make it work. You’ll figure it out.’ And I did. And you know what? The amount of relationships I built from that experience – CEOs, decision-makers, industry leaders – was invaluable. That’s the power of saying ‘yes.’”
She laughs. “Did I answer the question? I feel like I go in circles because I have so much I want to share.”
A pause.
“Well, let me sum it up because I think we remember things in 3’s:
✔ Say yes to the scary things. Have the courage to walk through the door.
✔ Don’t let imposter syndrome hold you back. Talk about it. It’s not weakness, it’s strength.
✔ Better done than perfect. Get it out there. Move forward.
And if you remember those three things? You’ll be just fine.”
Speaking of leadership, you served as the 2024 president of CREW Miami, championing women in commercial real estate. What’s been your biggest takeaway from that experience?
“CREW has been an incredible platform, and one of my biggest goals was to shine a light on retail real estate – an often-overlooked sector in South Florida’s CRE community. While many brands have a presence here, few are based in South Florida.”
Even though Miami wasn’t as big a market as some of the other global cities she worked in, Holly always made it work. “For most of my career, Miami was my vacation and playtime place because I traveled every week – not my work market. But as my career evolved, and I launched my firm, Miami became home, and the retail growth has been incredible. I realized how much opportunity there is to grow retail here.”
She also emphasizes the power of networking and referrals. “A great example – one of our CREW members recommended me for a project where the developer needed help merchandising a shopping center. That’s exactly what CREW is about – connecting women to opportunities.”
Beyond Rent: The Bigger Picture in Retail Strategy
For many developers, the focus is straightforward: What’s my rent? What’s my return? It’s a numbers game, and understandably so. But what often gets overlooked is the overall caliber and merchandising of the shopping center.
“We all know the shopping centers we like to go to, the ones we enjoy spending time in. Why? Because there’s a good mix – great coffee shop, a place to get a blowout, a selection of stores that make it an experience rather than just a transaction.”
Holly helps developers and brands step back and look at the full picture, not just the lease agreements.
“When I work with brands, I ask: where are you on your journey? If you think about a butterfly’s metamorphosis, some of the questions become, are you still in your ‘larva’ stage? Maybe you’re an online brand that hasn’t yet figured out how to step into brick-and-mortar. I can help with that.”
“Or maybe you’ve got your first few stores open, and now you’re trying to scale. Everyone has an opinion on real estate, your mom tells you one thing, your business partner another, but how do you actually make informed decisions that drive long-term success? That’s where I step in, helping not just with real estate but with operations and strategy.”
“Then there are the legacy brands, the fully developed butterflies, ones that have expanded perhaps too much. Maybe they have too many stores. How do we reassess the portfolio? What do we close, where do we expand, where do we relocate? That’s what I do now, helping brands of all sizes make smart decisions about their growth and increasing value to their portfolio.”
And while Holly’s expertise started in fashion retail, her work spans across industries.
“Whether it’s a coffee shop, a restaurant, or a boutique brand, I thrive in helping consumer-facing businesses scale smart. That’s really my sweet spot. I’m not your industrial or office-space person. Could I be? Sure. But that’s not what excites me.”
What excites her? Retail.
“I grew up loving fashion. I went to the Fashion Institute of Technology in New York. I studied buying and merchandising not because I wanted to be a designer, but because I loved the business side of it. I don’t have a creative bone in my body when it comes to art, but I have a creative brain for problem-solving and leadership.”
And it’s that mix of strategic vision and industry experience that makes her a sought-after trusted advisor, helping brands not just open stores but thrive in them.
Your career spans Gap, Claire’s, Old Navy, J. Crew’s international expansion and the launch of Madewell – what’s one unexpected skill you picked up launching new concepts that you still lean on today?
She smiles, a spark of mischief surfacing. “Launching concepts – like Old Navy at Gap or Madewell – taught me to pivot fast. At Gap, we went from being mall tenants to big-box strip centers for Old Navy – 15,000 to 25,000 square feet, a whole new landlord community to build relationships with. I didn’t know those players, but I learned to map the terrain quickly: who’s the consumer, where do they shop, what’s the vibe? Same with Madewell – Mickey bought the name, and we carved a niche. Today, I use that with clients – a coffee brand breaking into the U.S., a developer re- merchandising a tired shopping center. It’s about sniffing out the landscape, building relationships, and scaling smart. I started in operations at Gap – working with store management teams and getting my hands dirty. Something my boss at the time still reminds me of and we laugh at, I wore a professional white winter suit to my interview for a job where you’ve got to jump in. That experience proved that I can still roll up my sleeves and scale anything.”
As the Immediate Past President of CREW Miami, an ICSC Past Trustee and a longtime advocate for women in commercial real estate, what’s one piece of advice you wish someone had offered you at the start?
Holly laughs, warm and unfiltered. “Beyond the 3 tenets I mentioned earlier, I’d add my tagline that was our 2024 theme for CREW Miami, #setforsuccess. Is what you’re doing setting you up for success? What about others? Your team? CREW is a volunteer organization, as President, you have to ask yourself, how do I set others up for success and inspire them to hopefully repeat the behavior. You develop an additional set of ways you can’t predict. Lululemon may use it in their marketing it, but Eleanor Roosevelt said it first – ‘Do one thing every day that scares you’. That’s how you grow.”
Second, don’t bury the imposter syndrome – it’s not weakness, it’s grit. I hid mine back then; I own it now.
Third, better done than perfect. I was Type A, tweaking every detail – I stayed at Gap 15 years, too comfy with the title. I’d tell young Holly: ‘You’re enough, take the plunge.’ I lived that later – moving to Miami in ’04, not knowing what’s next, just trusting the path.”
Commercial real estate, especially at the executive level, has historically been male-dominated. How did you navigate those spaces with authority, and what can women do to secure their place?
Her voice steadies, a quiet force emerging. “I was never shy, but authority? That’s earned. I poured myself into brands – J.Crew’s evangelist, Gap’s lifeblood – sometimes too much. At Gap, I built a network that has lasted with my colleagues and every job I’ve had since Gap? J. Crew, Claire’s, Nike – came as a result of a former colleague recruiting me. My Gap crew? We’ve stayed friends for 25+ years, and we just got together for our 18th annual dinner at ICSC New York – these relationships have carried me. I’d walk into rooms – ICSC trustees, Nike board meetings – and fully show up, I’m known for being tough but fair. Women need that: show up fully, no apologies. I was an all-in – brand ambassador to the bone – and it paid off. Build a network that’s real, not just a stack of cards – it’s your anchor.”
Many women hesitate to self promote or negotiate boldly in their careers. You’ve successfully led teams across multiple continents and industries. What’s your strategy for owning your value and advocating for yourself in high stake negotiations?
Holly laughs, shaking her head. “You know, my husband always tells me I push the envelope too far when I negotiate for myself. ‘Holly, you need to stop – you’re going to push too hard.’ But I don’t. I’ve learned my value. I didn’t always stand up for it, but when I did, it changed everything.”
She leans in, reflective. “J.Crew is where I really found my voice. I started in ’04, commuting from Miami to New York – at a time when that wasn’t common. I didn’t even know what my future in Miami would look like. But when they wanted me to take on more responsibility, I walked straight into the CFO’s office and said, ‘Look, I can take on X, Y, and Z, but this situation has to change.’ I was already making great money, but I was worth more. I wanted it to be better. And I got it. That was a pivotal moment for me – realizing that advocating for yourself isn’t asking for too much; it’s asking for what you deserve.”
She pauses, then adds, “But negotiation isn’t just about getting what you want – it’s about building relationships and understanding mutual goals. I learned early on that the best deal is one where both sides feel like they’ve won something but each has left a little on the table. If one side gets 100% and the other side walks away resentful, that’s a bad deal. Maybe you got the win today, but in the long run, you’ve burned a bridge. I’ve always been known as tough but fair – I negotiate hard, but I back it up with facts, I’m reasonable, and I listen.”
Then, she smiles and pulls up a puzzle from her desk. “That’s why I love this analogy – negotiation, leadership, teams, everything in life, really – it’s all a puzzle. Some pieces are big, some are small, but without each one, the puzzle isn’t complete, nor is full picture. Whether it’s the CEO or the janitor, everyone has a role to play and a great leader can pull that talent together for the greater good of the brand or team. That’s how I approach leadership, and it’s why succession planning is so critical. A great leader doesn’t just make deals – they build the next generation to carry the mission forward.
“That’s why I led with #setforsuccess last year. It’s not about one person getting ahead; it’s about making sure we’re setting up our teams, our companies, and our future leaders for long-term success. You don’t do that by hoarding knowledge or making every decision yourself. You do that by empowering others, bringing people along, and recognizing that we’re all pieces of a larger puzzle.”
“I mean, listen, it’s not about me. But what I love about CREW and organizations like it is that we’re constantly planting seeds. Whether it’s through scholarships, mentorship, or just having conversations that open doors, we’re setting people up for success before they even know it’s possible.”
She smiles. “Take Mia and Maddie, for example. They both won our CREW Miami scholarships last year. I met them at different UCREW events, where they followed up, asked insightful questions, and demonstrated a strong desire to learn more. And somewhere in those conversations, I said, ‘Hey, do you know we have this scholarship? Why don’t you apply?’ And guess what? They applied – along with others – and they were the best of the bunch.”
Holly shakes her head, laughing. “And we scrutinized. I mean, we were sitting there going, ‘Okay, this one has like 0.5 more on this metric…’ It wasn’t handed to them, they earned it. But that’s what excites me – watching people step up, take the initiative, and then seeing where it takes them.”
Her expression turns thoughtful. “You know, real estate wasn’t something you could study in school when I was coming up. You were either born into it – like David Simon of Simon Property Group – or you fell into it, like I did. Now? Thanks to organizations like ICSC and CREW and universities that are offering actual real estate programs, we’re seeing more young people – more women – enter the industry with intention.”
She pauses. “So yeah, it’s good work we do. We plant the seeds.”
Retail’s faced seismic shifts – e-commerce, experiential demands, even health and wellness tie-ins. Where do you see it heading in the next five years?
Holly leans in, her foresight crystalline. “Five years is a tech sprint, but here’s the trajectory: as a traditional retailer, you can sink or swim on supply chain and tech lag. Newcomers, those ‘caterpillars’, will bloom or flop. We’ll always crave the communal experiences – high streets, malls, live-work-play zones. Experiential is the heartbeat, AI its rhythm. Right before Covid, I advised a housing developer launching a wellness concept – sleep, vitamins, lifestyle, beyond the gym. Wellness is everywhere now – athleisure like Alo, spas, blow-dry bars. I’m unpacking this with Evie Gross at CREW Palm Beach, April 8th – join us. Retail’s not fading; it’s shedding for a bolder skin.”
Mentorship is a cornerstone of your work – through CREW, ICSC, and beyond. What distinguishes a good mentor from a transformative one?
Her tone softens, intimate and sure. “It’s listening – truly hearing their pulse. I’ve mentored with CREW, ICSC Women of Tomorrow, University of Miami – structure is my backbone: ‘Monthly calls, three topics emailed a day ahead.’ It’s accountability with heart. A transformative mentor tunes in, adapts, lifts. I’d ask: ‘What do you need?’ – then deliver. With ICSC’s retail entrepreneur award, I’ve guided winners since it started – $10,000 grants, but the real prize is watching them soar. I’m all in, because their rise is mine too.”
You’ve built a career in fashion and retail – your sweet spot, as you’ve said. What drew you to this world, and how does it shape your advising today?
Holly’s voice lifts, a thread of joy weaving through. “Fashion’s my first love – I went to FIT, a buying and merchandising major, no creative bone for design, but a brain for problem-solving. I started in the Manhattan garment district, then transitioned to Gap in operations – yes, in that infamous white interview suit. Specialty retail, restaurants, developers – but that fashion lens shapes me. I help clients scale, merchandise, find their consumer, because I’ve lived it. Product is key and you have to have a pulse on “meeting the consumer, because I’ve lived it. Product is key and you have to have a pulse on “meeting the consumer where they want to be met”, in store, at a sidewalk for pick up, online, etc.”
What’s one resource you’d recommend to every ambitious woman in business?
Her enthusiasm spills, measured but vivid. “I’m a Sagittarius – I roam, I can’t pick one. Mel Robbins’ ‘Let Them’ theory – balance, not spite. Guy Raz’s ‘How I Built This’ – founders’ stories that light a fire. Richard Branson’s ‘Ask the Leader’ on LinkedIn, he inspires me because he takes risks, isn’t afraid to fail, and he aims to improve people’s lives whether it’s in a hotel, cruise or other sectors. I’m not looking to return to the corporate world, BUT if there was one company I’d work for if given the chance, it would be Virgin. Who knows? Maybe putting it out to The Universe will prove fruitful! I also read lots of trade journals, fashion magazines like Vanity Fair, and classic management books like the ‘One Minute Manager.’
You’ve spoken about overcoming self-doubt and fear of failure – what’s a mantra or mindset that’s carried you through the toughest moments?
Holly leans in, thoughtful. “I always go back to Eleanor Roosevelt: ‘Do one thing every day that scares you.’ I constantly check myself – am I stepping outside my comfort zone? Because it’s easy to let a month go by without pushing yourself. I try to keep that in mind.”
She pauses. “And then, control what you can control. You can’t control everything, so instead of getting mad or stuck on what’s out of your hands, focus on what you can do. What’s the reaction going to be? How do we handle this situation? That’s where I put my energy.”
She smiles. “I like solving problems. If I hadn’t gone into real estate, I probably would’ve gone into HR. Back when I was at Gap, the same week I was offered a job in real estate, I was also offered one in HR. I always wanted to go into real estate first, but it was only men, so I never thought I’d break through. HR felt more open – more women, more people-focused – but ultimately, I love working with people no matter what. And not in that ‘I just graduated from college and love people’ kind of way.” She laughs. “I love helping people succeed. That’s what drives me.”
Her expression turns serious. “That’s why succession planning matters so much to me. Leadership isn’t about holding onto power – it’s about bringing people along, mentoring, and setting them up for success. If we’re not lifting others up, then what’s the point?”
If you could turn back time and speak to Holly stepping into her first major leadership role, what would you tell her?
Her words soften, urgent yet tender. “Nike’s ‘Just Do It’ – I’ve learned this is how you move forward and grow. Also, be mindful of building your own personal brand while you’re helping companies succeed. Steve Tanger, Chair of the Board at Tanger, Inc. once told me, ‘ You only have one reputation to lose, build it, protect it.’ I hold that advice close and aim to build, expand and protect my reputation. I’d urge her: ‘You’re not a cog – build Holly Cohen, the name that endures, now.’ I was loyal to brands, but learned late: promote yourself too. Get out there.”
For women dreaming of a career like yours, what’s one step they should take today?
Holly’s voice rises, firm and clear. “Make your list – five companies you’d kill to work for. As I mentioned, Virgin would still be one of mine. Break it down: what’s the mission, product, culture, leadership that’s attracting you? Maybe you don’t land there, but distill what pulls you – soft skills, hard skills, whatever. Be curious in your current role – why’d you sign up? I fell into real estate at Gap – it’s the only official interview I did, after that, opportunities were presented to me. How can you get involved to understand these companies and yourself better? Build real ties – students I’ve met at UM or FIU students I’ve met that follow up, ask to meet for coffee, and asked great questions about CRE as a career. Plant seeds, remember a name, a story. You never know who’ll say years later: ‘You changed my path.’ That’s the spark – start now.”
Holly’s legacy isn’t just brick-and-mortar – it’s the puzzle she gave her 2024 CREW Miami board, each piece a soul, a testament that brilliance is collective. Her legacy isn’t just about stores, leases, or square footage – it’s about transformation. It’s in the brands she’s shaped, the leaders she’s mentored, and the teams she’s built. It’s in the way she walks into a room – whether at Nike, J.Crew, or the ICSC board – and makes space for herself and others.
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