The Founder Files with Kara Cummins: Why Your Next Outfit Is Already Hanging In Your Wardrobe
Welcome to The Founder Files, an inside look at the women building the next generation of category-defining companies. These conversations capture founders in moments of becoming. No polished retrospective or glossy highlights reel. This is where we catch ambitious women in motion: when the decisions are still hard, the outcomes still uncertain, and the lessons are still fresh enough to actually be useful.
Kara Cummins is no stranger to staring into her wardrobe, paralysed by feeling like she has nothing to wear. A problem-solver at heart, she knew there had to be a better fix to the daily outfit meltdown, one that didn't involve buying more stuff.
That fix is exactly what she's building. Kara is the co-founder of Wear Next, the platform that outsources outfit decisions for everyday people. After a career spanning product, tech and sustainability, building what many have described as "Pinterest for your own wardrobe" feels like the role she was always working towards.
In this conversation, Kara gets into the mechanics of building a fashion tech startup from scratch: the trademark dispute that forced an unexpected rebrand, what the co-founder search actually entails, and why she's betting that the 80% of people who feel excluded by the fashion industry are the ones most worth building for.
Q. Tell us about Wear Next in your own words. What are you building, and why does it need to exist?
“We all need to get dressed every single day (public nudity is illegal). But some of us are still having meltdowns deciding what to wear to the pub.” — Kara Cummins
“Wear Next helps people outsource their ‘What to wear?’ decisions.
We remove the meltdowns in two ways:
A fun and free quiz that (in under 3 minutes) learns enough about your style and what’s in your wardrobe to give you outfit suggestions using clothes you already have, and
By connecting you with affordable stylists for more personal advice & recommendations.
Wear Next needs to exist because what you wear impacts how you show up in the world. If we can help people remove the decision fatigue, dress more confidently & shop more intentionally, the flow on effect is massive.”
Q. What does building this business actually look like right now? What's consuming most of your energy this week?
“Welcome to my calendar of chaos!
Tech design and build for our launch:Tackling problems like scaling the amount of outfits in our database while still maintaining stylist-quality, and deciding what to automate via agents vs what needs clever humans.
Coming up with a new name! The trademark for “Wear Next” was disputed by the multi-billion-dollar retailer NEXT, so now we (with the help of our Instagram community) are doing an unexpected brand refresh.”
Building out a community of stylists that our users can book sessions with.
Building an advisory board of rockstars which means lots of coffees and calls with clever people.
Making content (thankfully, my co-founder runs the show here, but every day is an opportunity for content).”
Q. What do you know about fashion tech that most people, and most of the industry, are still sleeping on?
“100% of people need to get dressed every day, but only 20% of people subscribe to the aspirational language which the industry uses.
The other 80% feel excluded from ‘fashion’, but they still want to show up as their best selves for work and play. We need to meet people where they’re at.
If you’re speaking to a mum with young kids who lives in black tights, let them! Suggest one small improvement that will help them feel more put-together when they need to face the world. Maybe it’s adding a pair with sport sidelines or a cool trench coat to layer over the top.
And obviously don’t tell them to wear white clothes that will get baby vomit on them.”
Q. Wear Next's origin story is so relatable: that feeling of a full wardrobe and nothing to wear. What was the moment you realised this was a problem worth actually solving, and not just venting about?
“After my own styling experience rocked my world and changed how I got dressed, I started talking about it. And I quickly learned that most people were desperate for styling advice but felt like it was only for the rich and famous. Meanwhile, stylists were struggling to find those exact people, and needed to charge big $$$ to compensate for the manual customer acquisition. There was a gap begging for a bridge.
I’d spent my career building complex tech platforms and saw an opportunity to bridge that gap via tech and AI.
I also care deeply about sustainability, and the scale of fashion waste is incomprehensible. I figured that if people knew how to style the clothes they already have, then they’ll buy less, and buy more intentionally.”
Q. What's the hardest call you've had to make so far, and would you make the same decision again?
“Deciding to build for women first, rather than for everybody, or only men.
While that might sound surprising, men are generally less confident in putting together outfits and more likely to accept style advice than women. They’re an underserved market who again, still need to decide what to wear every day (and still spend big $$$ on clothes they don’t know how to style).
However, I’d make the same decision again because we’re building such a brilliant community of women who are generally more interested in style. And our feedback from men has been to build for the women first, and then they’ll trust it more.
So men, stay tuned! We’re coming.”
Q. You've recently brought on a co-founder. How did you know this was the right person, and what did the process of finding and deciding on a co-founder actually look like?
“Finding a co-founder was like dating.
I knew I wanted to build this with someone else. Not only are things more fun with a friend, but I was realistic that for Wear Next to be successful, it needed a co-founder who had style authority, influence and who complemented my strengths. So while I was obsessed with building Wear Next, I knew I needed to prioritise this critical missing piece before I invested too much time, energy, or capital into the business.
Just like dating, I made a wish list of what I'd want my dream co-founder to be, and then I started putting myself out there! Talking to people, attending every single event, lots of coffee dates and accepting every intro that I was given.
When I was introduced to Tina, it was a serendipitous, perfect fit. She had built a brilliant online community where she helps everyday people dress more confidently and buy more intentionally. And we shared a mission for sustainability. She was also at a point in her life and career that she was ready to jump in headfirst and build a business. Plus, she's just like the nicest person I've ever met. A dream!”
Q. What's the one thing you wish someone had handed you at the start (a framework, a rule, a piece of advice) that you've had to figure out the hard way?
“‘Increase your surface area for luck.’
I've always found it SO difficult to tell the world what I'm building. I'd much rather let the work speak for itself. But as a founder, you are the megaphone for your company. No one else is going to do that for you.
“You literally cannot afford to pay for all the expertise a startup needs to succeed, so you need some luck. And to invite luck in, you need to put yourself out there. Coffees, events, awkward LinkedIn posts, telling the person next to you at a barbecue what you're working on. All of it.” — Kara Cummins
What looks like ‘luck’ for Wear Next (brilliant advisors, incredible interns, opportunities to pitch, rockstar connections) is actually the result of inviting people in before we were ready. Building in public on Instagram has especially helped invite this ‘luck’ in. It’ll amaze you how nice, generous and helpful people are, if you give them the chance!”
Want to follow Wear Next’s journey?
Wear Next is launching to the public in July 2026, and trust us, you'll want to be first in line. Join the waitlist at wearnext.com.au to get early access and be the first to know when the quiz goes live.
In the meantime, follow Wear Next's build-in-public journey on Instagram at @wearnext__ and keep up with Kara directly on LinkedIn to see exactly what it takes to build a startup from the ground up.