Startup Stories: Designing Jeans that Adapt to Daily Life

Founder: Karina Gupta ’26

Venture: KarinaJ Denim creates slip-on denim jeans that adapt to daily weight fluctuations, so that wearers don’t have to choose between comfort and fashion. 

What’s the problem you’re trying to solve or the gap you’re trying to fill?

Women’s bodies change constantly. Our weight can fluctuate by up to five pounds in a single day due to hormones, stress, travel, water retention, or simply life. Traditional jeans, however, are built around buttons and zippers—structures that are inherently rigid. No matter how much stretch is added to the fabric, jeans are still designed to fit a single moment in time, not an entire day.

Even custom-made jeans don’t solve this. If you measure yourself while bloated or on your period, they’ll feel loose the rest of the month. If you measure first thing in the morning, they may feel tight by lunchtime. The result is a product that looks great briefly but rarely feels good for long. On the other end of the spectrum are jeggings or pull-on jeans, which are often cheaply made, poorly designed, and treated as disposable. They tend to use low-quality fabric, itchy or rigid waistbands, and silhouettes that don’t feel modern or elevated. Ironically, they often end up being just as uncomfortable as the jeans they’re trying to replace.

KarinaJ Denim exists in the space between these two extremes. We make slip-on, premium jeans that are genuinely comfortable and designed to adapt to real women’s bodies and real lives. Over the past three years, we’ve obsessively prototyped to get the fit right, and we source our denim from the same mill as many of your favorite premium brands to ensure durability and longevity.

The brand is built for women with demanding jobs and full lives outside of work—women who want jeans that look polished enough for meetings or dinners, feel good all day, and accommodate changes in their bodies. In short: jeans that let women have their cake and wear their jeans too.

What was the moment when you had the idea for this startup?

The idea came from a repeated, deeply personal frustration. Despite having the income to buy “good” jeans, nothing consistently worked. When I first realized I wanted to redesign jeans, I sat on the idea for a couple of years. I had no idea where to start. Eventually, I began reaching out to people with apparel experience on LinkedIn and was lucky enough to have an incredibly generous conversation with consumer brand consultant Amy Kapolnek. That conversation gave me just enough confidence to take a leap.

Shortly after, I impulsively booked a flight to New York to attend Kingpins, the world’s largest denim trade show. I had never navigated a trade show before, so I did the only thing I knew how to do—I talked to everyone. I asked questions, listened closely, and tried to absorb as much as possible. People were surprisingly generous with their time. In particular, Katie Ague of the denim company Artistic Milliners spent hours walking me through the basics of denim, and those early conversations still shape how I think about the product today.

What’s the biggest milestone your startup has hit so far?

Over the past three years, I’ve built a vetted supply chain, secured a U.S. manufacturer, and finalized prototypes for four styles. But emotionally, the biggest milestone has been launching the brand publicly.

For a long time, this venture lived quietly in the background. I only told close friends about it for the first couple of years. The idea felt so big—and at times so far-fetched—that I didn’t want to share it until I was sure it was real.

That changed when I came to Yale with refined prototypes and began seriously pushing the brand forward. I launched the website and social channels, led two photoshoots—one in New York and one with Yale’s undergrad fashion club—and finally put KarinaJ into the world.

The response completely surprised me. Friends, acquaintances, and even friends-of-friends reached out saying they couldn’t wait to buy a pair or offering to host try-on parties because they genuinely believed in the product. Being able to point to something tangible and say, “This is my brand,” made everything feel real in a way I hadn’t anticipated.

What was the most important resource Yale SOM contributed to your startup?

The most impactful resource Yale SOM has provided is the Startup Founders Practicum, led by Professor Jennifer McFadden. The course has connected me with thoughtful speakers, provided invaluable feedback, and given me consistent, weekly touchpoints to refine both my thinking and execution.

Just as importantly, the practicum introduced me to an incredible group of fellow student entrepreneurs. Building a company while being a student is a constant juggle. While many second-years are preparing for full-time roles post-graduation, our year has been defined by long days, late nights, and a lot of mutual encouragement. Being surrounded by people like Bailey Ehrens, who is also building an apparel company, and Jaya Dadwal, who is building a device to measure and analyze female hormones, has made the process feel far less isolating.

Yale’s startup accelerator Tsai CITY has also been an invaluable resource, connecting me with mentors like venture advisor Margaret Cartiera, who has helped me think more clearly about scaling, storytelling, and staying grounded as the company grows. Having access to people who genuinely want to help you think better—not just move faster—has made a meaningful difference.

With help from all these people, KarinaJ is launching on Kickstarter this February. We’ll be debuting four styles: a bootcut and a straight leg, each available in both light and dark washes. Follow our journey on Instagram and learn more about the brand.