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#WeAreGapInc: Meet Ilana

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More than the clothes we create, Gap Inc. is defined by its people. Our dedicated, eclectic, passionate culture is driven by pros, with personality. Say hello, get to know us, and take a closer look at what (and who) we’re made of. Meet some of the many people who make Gap Inc. great. #WeAreGapInc


There’s nothing like a first impression. (They’re lasting, after all). And when you first meet Ilana Stern, and she meets your gaze squarely and shakes your hand firmly with a smile, you are just that: impressed. There’s an energy and electricity she emits that lets you know she means business, but there’s a warmth and familiarity she exudes that feels like a friendship you’ve known before.

Funnily enough, all of the same can also be said of Weddington Way, the company Ilana founded in 2011 and Gap Inc. acquired at the end of 2016. The digital-first wedding party boutique is all about bringing you in, and making the experience of shopping for bridal dresses easier, faster, more connected — really with the end goal of bringing joy back into process. And that’s clear right from the get-go, whether you’re walking into the beautiful downtown SF showroom, or browsing online. (She really has that first impression thing nailed.)

But beyond making great first impressions and bringing joy and ease back into a historically painful shopping experience, Ilana is all about following her passion — a theme that runs in her family — and that’s exactly what she’s doing with Weddington Way. “My dad’s dad worked in meatpacking after he fled Germany and came to the U.S., and eventually started his own business. And my dad started his own business, too! There’s definitely a pattern in my family of work ethic pushing you to follow your passion instead of doing what society expects of you.”

Hear more about Ilana’s passions (some of which include her grandmother’s vintage Chanel handbags), the song that soundtracks her breakfast every morning, and the “epiphany moment” she had involving Google Docs. Meet Ilana.

Ilana Stern Gap Inc. Weddington Way founder

What do you do for Gap Inc.?

I run Weddington Way, Gap Inc.’s newest brand. At Weddington Way we’re building a new way to shop for weddings, starting with bridesmaid and special occasion dresses. We launched online with a community based shopping experience that enables friends to shop together no matter where they live in a shared virtual showroom.

We have evolved our offering from third party dress brands to an exclusive dress assortment we design and manufacture in-house and are expanding our digitally-native brand offline through shop-in-shops, which is really exciting for our customer (and us!). As the founder, I have led the company through all of these stages of evolution and joke (but it’s true) that I’ve done everything from being the janitor to customer service to shaping the vision for our business (all with the help of the most amazing team in the world).

What inspires you?

More than anything, I’m inspired by the incredible team I get to work with every day. As we work relentlessly to delight our customer through the evolution of our experience, offering and ultimately brand, there is nothing more inspiring than seeing Weddington Way become more than anything I could have imagined or created on my own. This evolution extends to the incredible culture we have built that is so full of heart. All of this is powered by this most inspirational team.

Style personality

I guess my style is sort of boho meets classic with subtle, special details (I grew up in L.A. and spent my formative adult years in N.Y.C., which resulted in a sort of confused style personality).

Go-to outfit

Rag & Bone jeans, a cotton tee or flowy silk blouse. I’m currently loving my grey and taupe double faced coat by Cuyana (I love supporting local brands based here in S.F.) and my grey wool Supergas.

All-time favorite piece of clothing

My favorites are actually a few pieces of timeless accessories passed down to me by my Nani (dad’s mom) – a few vintage Chanel bags, necklaces and a belt, all of which I love equally. My Nani was a Holocaust survivor from Germany and lived until the age of 98 – she was incredible – and I think of her every time I wear one of her pieces.

Last purchase

Happy hour drinks last night for the Weddington Way team and everyone celebrating a going-away party for our beloved team member Olivia (she’s off to Kellogg for her MBA and is going to rock it!).

What you’ve learned from customers

EVERYTHING. We start with our customer in everything we do and work backwards from what she’s telling us. What our customer is looking for and not finding is what informs our merchandise direction. The reasons she doesn’t purchase or is frustrated informs our user experience direction, site feature development and the direction of our store experience. It literally always starts with her.

Favorite Gap Inc. moment

Seeing my team and the BR store team light up with excitement on opening day of Weddington Way’s first shop-in-shop at BR Flagship store on Grant Ave. here in San Francisco – the energy across teams was incredible after so much hard work getting the shop launched (we launched the shop only 6.5 weeks after our first meeting with the BR team – an amazing feat!). I also love every time someone says to me, “What can I help you break?” (Tanya gets the award from most mentions) – as an entrepreneur, it’s music to my ears.

First job

Sales associate at Everything But Water when I was 16.

Epiphany moment

When Weddington Way’s first two bridal parties purchased from me after going through a scrappy paper prototype experience I had built using Google docs, Survey Monkey, etc. (pre-website) – they had to send me checks in the mail because we hadn’t incorporated yet, so I didn’t have a bank account for payments to go to. Despite all the friction, the shopping experience I had built for them in paper prototypes was better than the alternatives…and that’s when I knew we were really onto something.

Always puts you in a good mood

A smile from my 18 month old son, Theodore.

Theme song

Lately it’s been “You Are My Sunshine” – Theodore asks Alexa to play it every morning while we’re eating breakfast.

Something people don’t know about you

I have dual citizenship – U.S. and German. I was born and raised in the U.S. and my brother, dad and I became German citizens as adults (my dad’s parents were stripped of their citizenship when they escaped Germany during WWII so it was a big deal for us as a family to reclaim our citizenship).

What’s your favorite thing about Gap Inc.?

The people – everyone has been so warm and welcoming with the Weddington Way team – we’ve been really grateful for that.

What makes your job unique?

My job description changes every few months – the job evolves as quickly as the company does, which is quite fast. It keeps me on my toes!

What’s your favorite thing about your job?

It’s an honor to lead my team – they’re the smartest, most passionate, highest caliber group of people, and I’m humbled daily by the opportunity I get to work with them and lead our small crew to build something big and impactful.

Why Gap Inc.?

As we were going through the acquisition talks we just loved everyone we met – smart, thoughtful, humble, kind. Once that piece clicked, it was the strategic synergies that got us so excited about being a part of Gap Inc. We’ve been plugging away to build an experience of the future – one consistent and personal brand journey for our customer with Weddington Way, no matter the touch point (online/offline). We know our millennial female customer really well and how to leverage data to build an experience suited to her (from the merch we assort to the features we build on our site). Gap Inc. has the expertise and scale in real estate and retail operations, brand awareness, supply chain and more that can take all of the hard work we’ve done even further. There was a real yin and yang between the two companies that got us excited about how we could help each other, and the scale of impact that would be possible for us as an entrepreneurial team.


Learn more about Weddington Way joining the Gap Inc. family.

Discover more #WeAreGapInc profiles.