Mind Vacation № 20: Goal = keeping the heart intact
This month's Mind Vacation let’s you in behind the scenes. Why our "small but mighty" clothing production runs are so challenging, and how the biggest battle right now is figuring out how to keep Jenny Pennywood’s heart intact while making production more sustainable.
Okay! You launched t-shirts, and this was big for you! What were some of the challenges to producing the shirts? Or clothing in general?
First off, I’ve always wanted to move in the direction of what I call "patterned basics"—pieces that are effortless, simple but bold, and something you feel you can wear all the time … like just throw it on and feel good in it. I’ve made T-shirts and loungewear before, but the price always felt too high … and that’s because producing in small batches in San Francisco is just expensive. So the biggest challenge has been figuring out how to keep production local while also keeping prices as approachable as possible. It’s a tricky balance, but one that feels worth it.
You’ve had a few wearables produced over the years, why was making a T-shirt so much harder?
Honestly, it all comes down to keeping production costs manageable while staying true to my values. I’m deeply committed to producing as much as possible in San Francisco. It’s been a core value of my brand from the start—supporting small, local businesses, working with people I trust, and keeping production slow, thoughtful, and intentional. But the reality is, making things in SF, in small quantities, is expensive, and as much as I want to keep it all here, I know it may not be sustainable long-term.
That said, I’m holding on as long as I can. Partnering with Gravel & Gold has been a huge help—we’ve been able to team up on fabric sourcing and production, which makes local manufacturing more feasible. But I also know that shifting some production to Los Angeles is on the horizon, and honestly, that still feels local to me. I grew up in LA, and in many ways, it makes sense for me to have more of my work rooted there.
Straight up, what’s the biggest challenge right now?
Quantities. The only way this truly works financially is if I can print in 500-yard minimums in Los Angeles—that’s when I see real price breaks. Printing in SF is more than three times as expensive as printing in LA, and that’s just not something I can sustain at scale. The problem is, 500 yards means 500+ T-shirts in a single color and a single print … and that’s never been the way I’ve wanted to run my business. I love variety, and printing in small batches here in SF has allowed me to offer that. But now, printing in SF is financially out of reach for me to do consistently, which leaves me at a crossroads.
And beyond just quantity, I’m in between production scales. Printing 500 shirts at once wouldn’t be a problem if I had the working capital upfront to pay for it and knew I could sell them all. But I don’t quite have the cash flow to produce at that level just yet. I’m always trying to get to that place where I can do the 500-shirt thing, but I’m not sure how to make that leap without the upfront cash to invest in it. It’s such a huge bridge to cross for a business like mine – how to stretch the gap between where I am and where I need to be to make my production truly sustainable.
How does it feel to produce more wearables compared to focusing on home goods?
HARDER! Squares and rectangles feel easy—not just for the folks cutting and sewing them, but in my mind too. Clothing? A whole different beast. It’s more complicated, especially since I have zero training in sewing, clothing fabrication, or even the language people use to talk about it. But, imposter syndrome be damned, I still do it. It’s also harder to sell, but expanding into wearables has felt like the right direction for Jenny Pennywood, bringing in new customers and new creative challenges. And through it all, we’re always working to keep the price point as approachable as possible while staying true to our values.
What are some of the values you stick to when producing wearables (and really, any of your Jenny Pennywood goods)?
I try to keep it local—always. Supporting small, mostly women-owned businesses is at the heart of Jenny Pennywood, and I feel it’s important to hold onto that for as long as possible, keeping this creative ecosystem thriving. Whether it’s wearables or home goods, staying true to slow, thoughtful production and working with people I believe in is what matters most.
Aesthetically, I value texture, softness, durability, and longevity. I love pieces—whether for the home or the body—that are meant to be used, washed, worn, and lived with, not treated as too precious. The more love they get, the softer they become, and over time, these items hold memories, making them even more special.
