Profitability through Personalization: How DAILYLOOK Elevated the Personal Styling Model

Retail Fashion has Fallen Behind

The retail fashion experience has remained largely unchanged for decades. Even granting the rise of fast fashion, consumers in stores as distinct as H&M and Neiman Marcus are still faced with many of the same challenges — most acutely, an overwhelming selection of styles and sizes, the majority of which are ill-suited to their personal tastes or body. Rather than solving this problem, most ecommerce offerings actually make it worse, offering the anti-benefit of near-infinite selection coupled with the inability to ensure quality or fit through the screen.

This is the antithesis of what modern, digitally savvy consumers have come to expect elsewhere in their lives. From Netflix to Amazon, consumers expect frictionless personalized experiences, smart curation that eliminates complexity, and social feedback loops that makes them feel great about their purchase and their broader relationship to the brand that facilitates it.

This holy grail has been stubbornly illusive in the area of fashion. But I believe that when executed thoughtfully, the personalized styling subscription model can deliver each of these benefits. In fact, I’ve seen it first hand.

Enter DAILYLOOK

In the three years since launching its premium personal styling service, DAILYLOOK has grown exponentially, while achieving higher levels of customer satisfaction and stronger loyalty than nearly any fashion ecommerce business I’ve seen — a fact that I can only attribute to delivering the kind of personalized, convenient shopping experience not available anywhere else in the market.

All credit goes to founders Brian Ree and Eric Marston, who identified a large and previously ignored market opportunity in premium contemporary women’s style — think Saks, Nordstrom, & Zara customers. They’ve spent the last few years refining the model, leaning on the wealth of technology and knowhow they developed during years of operating a (since abandoned) transactional styling business to build something truly exciting.

On the strength of its proprietary, data-driven merchandising and styling platform and premium brand and manufacturer relationships, DAILYLOOK now generates tens-of-millions in revenue and serves tens of thousands of customers; figures that are more than doubling annually. The margins and LTV:CAC ratio are closer to SaaS benchmarks than what you’d typically find in retail. And, perhaps most impressive given all of the carnage in the broader commerce category, DAILYLOOK has been profitable for two years running. It’s really quite a remarkable story.

So how’d they do it?

Premium Service + Data = Magic

DAILYLOOK offers its customers a service that delivers a personalized collection of premium fashion items directly to their home. Every shipment includes roughly 10–12 items from premium, advanced contemporary brands like ALC, Kate Spade, J Brand, Vanessa Bruno, Velvet, Canada Goose, Equipment, 360 Cashmere, and Parker (among many others), alongside private label brands of equivalent quality, but designed exclusively by our in-house team based on the years of style and fit data we’ve collected across millions of customer interactions.

Consumers keep what they like and return the rest at no charge. This sounds simple (and familiar) enough, but that no-hassle customer experience belies the complexity and magic of the operating infrastructure and technology to support it which company has built behind the scenes.

Like other styling services, every interaction with DAILYLOOK begins with a personal style consultation. In our case, however, each customer is matched with a real human stylist, who although supercharged through technology, builds a personal, trusted, and ongoing advisory relationship with that customer over time. Rather than a rotating cast of part-time stylists who are beholden to a styling algorithm, DAILYLOOK hires full-time fashion professionals and offers everyday consumers celebrity-like access to their expertise and service.

On the back-end, DAILYLOOK uses data science and machine learning to plan and merchandise its inventory and also to provide leverage to the human stylists in selecting the perfect pieces for each collection based on a customer’s personal style and fit data. The result is that DAILYLOOK customers purchase more items per transaction and stick with the service longer than any ecommerce business I’ve encountered (blowing away traditional retail metrics in the process). In fact, 80% percent of boxes sent result in a purchase of at least one item, a figure that has nearly doubled in the last two years through refinements in the styling model.

The Holy Grail of Fashion Ecommerce Business Models?

It’s worth pausing here to reflect on why the personal styling model engenders such loyalty and allows for such strong unit economics, and what specifically DAILYLOOK has done to build what we believe may be the best instance of this model in the market.

There’s a unique feeling that is created when someone who knows and cares about you spends time to select an item (or items) specifically for you. Think about the last time you received a thoughtful gift, how cared for and appreciated you felt. A personalized styling service creates a similar kind of feeling; and it does so every month (for the majority of customers).

Rather than a consumer browsing hundreds or thousands of generic, impersonal items at retail or online, each DAILYLOOK client is presented curated collection of items chosen for them by someone they trust. When done effectively, these items fit well, match her personal style preferences, and complement what she already has in her closet (or fill in gaps she’s specifically identified). And unlike online shopping, the items are physically in her home, available to be tried on and mixed with other existing wardrobe items.

In many ways it’s “push” rather than “pull” commerce. And in DAILYLOOK’s experience, this results not only in far higher conversion, but even more importantly in greater customer satisfaction and loyalty than traditional retail or ecommerce models. The results speak for themselves.

Leaning in and Scaling Up

I’m thrilled to announce that DAILYLOOK has closed an $8 million in Series A round co-led by Forever21 and Upfront. As important as the capital will be to further scaling the business, I’m equally excited to have the strategic support and endorsement of Forever21, which at $4B in revenue is one of the largest fashion retailers in America (and still family-owned, no less). F21’s long-time President Alex Ok has joined the board, adding a wealth of experience in scaling a global retail operation and supply chain — something I’m confident DAILYLOOK on its way to achieving.

I consider it such a privilege to work closely with a pair of founders who are not only gifted operators, but relentlessly committed to building something massive. Brian and Eric are two of the most focused and high-conviction individuals you’ll find in any company — so focused in fact that they’d rather just keep their heads down and continue building than tell anyone what they’ve achieved. They had to be to get this far. Most people wrote them off as dead years ago; thankfully, an outcome they refused to accept.

This is all a lengthy way of saying DAILYLOOK has emerged from the proverbial forest, wiser and healthier for the journey. The business is growing rapidly and the underlying unit economics give me confidence that this is a model that can really scale. With a team of 100 employees and growing, the team has never been stronger. With the addition of F21 as a world class partner the time has come to lean into what’s working.

I’m especially excited to see Brian, Eric, and the entire DAILYLOOK team being rewarded for their hard work and vision. Few entrepreneurs have the fortitude — and luck, admittedly — to get this far in the journey. I can say without reservation that they’ve earned every bit of their success.