Shopping for
clothing isn’t much fun these days, and Stitch Fix thinks it’s so bad people may need group therapy to recover. That’s the
set-up for the personal styling service’s comical new ads, which highlight all the ways retail gets it wrong these days. One member has to order clothes in three sizes to find one that fits.
Another is having a denim identity crisis: “Am I relaxed? Boot cut?” CMO Debbie Woloshin tells Retail Insider how the ads aim to build confidence, win laughs, and win back
customers.
This interview has been edited for length and clarity.
Retail Insider: What problem were you trying to solve with this campaign?
Debbie
Woloshin: Traditional apparel shopping is broken, and it really doesn’t work for our clients. You walk into a mall, can’t find help, dressing-room lighting is victimizing, or
you’re endlessly scrolling online. People feel stress and self-consciousness when they’re trying to find clothes that fit. We wanted to explain how Stitch Fix can be the solution,
combining trusted stylists with data to deliver personalization no retailer can match.
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Retail Insider: How did that lead to this creative execution, with a nurse who wears scrubs even
on vacation, and a guy stuck in a giveaway T-shirt rut?
Woloshin: Listening to clients and stylists, we kept hearing the same pain points. So the spots start with “shopping is
hard, let’s talk about it.” The goal is empathy and levity, paired with solutions.
Retail Insider: Who are you trying to reach?
Woloshin: Beyond
demographics, we target clients at a moment of need, like a wedding, back-to-school, or a lifestyle change. Our message is that when you need style help, Stitch Fix is there.
Retail
Insider: Stitch Fix started in 2011 and has changed a lot since the early days. Are you talking to new customers or reintroducing the brand to those who may have tried it in the past?
Woloshin: Both. These new spots are the latest in a campaign we introduced last August, and since then, we’ve seen stronger brand awareness, new prospects, and returning clients whose
needs have shifted. People come back after body transformations, postpartum changes, or even divorce. We’ve evolved alongside them.
Retail Insider: Who handled the
creative?
Woloshin: It’s all in-house. We started with support-group spots tied to our rebrand, then one-on-one therapy sessions. We also invited stylists and clients to share
unscripted stories. One man credited his stylist with pushing him out of his comfort zone. One longtime client said her stylist helped her through breast cancer and learning to dress a new body. Those
stories were powerful.
Retail Insider: Where are the ads running?
Woloshin: We’re on broadcast, digital, streaming, YouTube, Reddit, and dating apps. Influencers
amplify it too, like Shawn Johnson and Andrew East, who share how busy parents use Stitch Fix, or creators who’ve documented weight loss and pregnancy journeys.
Retail Insider:
People aren’t just stressed about what to wear. They’re also worried about money, with many cutting back on apparel spending. How does that impact you?
Woloshin: People
are doing mental math, sitting down with spreadsheets, deciding what they can buy for kids versus themselves. Adding Stitch Fix takes stress out of those choices. Clients tell us we help them stretch
budgets while still feeling confident.
Retail Insider: How do stylists build that confidence?
Woloshin: The relationship between a client and stylist is
deeply personal. Sometimes we know about a new job or pregnancy before the family does. That trust is authentic and real — stylists even get invited to weddings. Data and AI help,
but relationships drive the confidence. We're so lucky to have clients who share their information and trust with us, and we're really here to deliver and help. This is such a generous brand. Our
mission isn’t just to deliver clothes. It’s to help people discover a style they love, look and feel their best, and reduce the stress of shopping. The retail therapy campaign brings that
mission to life.