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Image Credit: Stitch Fix

Does the Algorithm Know that Black Socks Don’t Go With Those Pants?

Personalization, Trunk Club, Stitch Fix, and Amazon’s Prime Wardrobe.

Shopping in a physical space can be a painful experience that takes time and energy. And now that I normally have 3 young kids in tow, my chances of losing one child under a table or mysteriously finding an item in the bottom of the stroller can sap the joy from the experience.

Shopping online isn’t always better.  I can find almost anything on Amazon – if I know exactly what I am looking for.  When I don’t know, then millions of choices can be overwhelming.  And shopping with a trusted retailer or brand might narrow the assortment, but I still worry about fit, feel, and whether the colors work together.

Many digital companies have set-out to erase the pain of shopping.  Answer a few questions for a personal stylist and then let them choose for you.  Trunk Club was an early personal stylist entrant.  The space – now crowded on the women’s and men’s side of the business – has a category leader in Stitch Fix – at a reported $730 million in revenue in 2016.

The business model for the online personal stylist is challenging.  First there are the high customer acquisition costs.  Then there are the shipping and returns costs – even when they are defrayed by service fees. Each mistake made by the retailer’s stylist threatens to a) result in lost money on the transaction and b) a lost customer.

The key to success is the ability of the stylist to identify the customer’s needs and taste quickly.

Stitch Fix and Trunk Club use different approaches to getting it right.  Trunk Club wants their customers to establish a relationship with a real person.  You meet your stylist digitally or on the phone (or in-person at their clubhouse locations, but that isn’t the focus of this article.)  With Stitch Fix, the customer establishes a relationship with a stylist – aided by a team of data scientists.

I was curious if either approach to becoming my stylist would succeed.

In total, I spent an hour letting Trunk Club and Stitch Fix get to know me.  I answered lots of multiple choice questions (Stitch Fix asked me 50!) and then added comments.  I described my own style – I wanted to look classically cool.  Not fashionable – I don’t want to feel silly at my kid’s soccer games.  No graphic tees.  Nothing loose and baggy.  Nothing that says I work in Silicon Valley or spend my summers on the Cape. I identified brands I liked, indicated what categories I needed to update, and selected images of outfits that fit my style. I actually enjoyed it.  Believe it or not, but I felt like the stylist cared –  even though I hadn’t met them.

And how did the stylists do?

Image Credit: Stitch Fix

The initial process was much smoother with Stitch Fix.  After I answered my questions, the order was officially placed and I waited patiently for the box.  With Trunk Club, I met my stylist on Thursday – via the app.  Because of my delays answering questions, and her delays getting back to me, I didn’t complete the order until Monday.  That was very frustrating.

But the Stitch Fix box did not hit the mark.  I was sent black socks to go with light blue 5-pocket pants. Not only did I lost confidence in my stylist, but they also picked a brand that I associated with Saturday nights in Vegas.  I should have added in my description that Vegas burned me years ago and that I avoid Vegas looks at all costs.  For any retailer, there is an inherent risk in choosing brands for someone without knowing that customer well.

The quality of the Trunk Club items was high, and the selection was much better, albeit expensive.  I was slightly offended when offered $500 sneakers, but I rejected those via the Trunk Club app before they shipped them to me.

What I realized:

Neither order succeeded.  Admittedly – I am not the best customer for this kind of test.  I worked in apparel retail for nearly twenty years.  I know my likes & dislikes pretty well.

Trunk Club seems a step ahead for only one reason; they provide an option to reject recommended items before they ship. I didn’t wait for that box that would disappoint me with ridiculously over-priced sneakers.  They didn’t waste money shipping something that I wouldn’t like.  And if I have a good stylist, my rejected items would teach them more about me for my next trunk.

Stitch Fix didn’t provide that option.  For a company intent on gathering data, providing the opportunity to get instantaneous feedback on the selected assortment seems a no-brainer.  And despite the company’s offer to discount my order 20% if I kept all five items in the box, that wasn’t going to deter me from returning an item I didn’t like.

And here’s where Amazon casts its shadow.  Their Prime Wardrobe service is now in beta testing.  Presumably, styling tips will come through their feature – “outfit compare” – launched in March.  Although they are trumpeting “try before you buy,” their free shipping and free returns remain the same as normal Prime services.  The real difference from the past is that Prime Wardrobe offers a 20% discount on multiple item orders – no matter what.

Why should Stitch Fix care about that?

Because Amazon is encouraging their customer to order as much as possible.  Their order size isn’t limited to five items, and they are competing on price. Amazon will learn from both what their customer keeps and what they return.  They will gather data more quickly than Stitch Fix – and Wardrobe will outpace Outfit Compare in its contribution to making accurate recommendations.  This is a powerful tool for making Amazon a style recommendation leader.

Partner David Weiss has three children and still loves shopping – most of the time.


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