How Personal Shopping Services Are Messing Up — And 5 Ways They Can Improve

Personal shoppers, whether they’re entirely human or a human/algorithm combination, typically have a major advantage over a salesperson or a web site welcoming an unknown visitor: Time to plan. When meeting a store-based personal shopper (at a department or specialty store), it’s often a scheduled appointment. And when working with an online personal shopper (such as Keaton Row or PS Dept, or a box like Stitchfix or Trunk Club), the customer has signed up for a service.

When there’s time plan, the customer almost always provides information - by phone, e-mail, or questionnaire - in advance. In these cases, a customer expects what’s suggested to her will closely resemble what she said she wanted. But my recent shopping experiences with a number of online and offline services have fallen far short of that expectation. Simply put, there was plenty of time to plan and it wasn’t used well. Some examples:

  • I warned I had more than enough X and wasn’t looking to buy any more, yet was sent or shown a lot of X
  • I asked for “polished casual” (if you work in fashion, that’s a term you know) weekend looks, yet was sent, separately, a wear-to-work top and ripped jeans
  • I said I had plenty of wear-to-work dresses but could use casual ones that would be flattering worn with with flats, yet was presented with one structured crepe dress and one more casual dress that’s length required heels to look decent
  • I shared I was shopping for a very specific purpose yet, when I arrived, it was clear before they stylist even showed me anything that she hadn’t understood from my e-mail what the purpose was
  • I explained I don’t like to wear boxy, billowy, or overly baggy tops (yes, I used 3 adjectives to describe exactly what I didn’t want), yet that’s exactly what I was sent
  • I acknowledged I was willing to spend a certain amount per item, yet I was sent items that cost a fraction of that amount (which wasn’t a bonus, because there brands were unknown and the quality didn’t match what I’d expect at a higher price point)
  • I stated my height, yet was given pants to try on that hadn’t been pinned to remotely show what they could’ve looked like if not 5 inches too long
  • I tried on a pair of jeans that were very obviously unflattering, yet the stylist took much too long to agree they were the wrong style for me 


  1. Listen. It sounds obvious, but there are ways to convey you’re doing it. If I told you I’m all set on accessories and you really want to include a necklace in the box, jot a note explaining you know I’m not looking for jewelry but this is a favorite of yours and you think it would be perfect with another item you’re sending.
  2. Be realistic. You might be 26 and work in fashion but if you know I’m 37 heard me used the term “polished”, I probably don’t want torn, distressed denim. If you’re not sure, at least ask when I arrive rather than showing it to me as though you’ve found me a perfect piece.
  3. Customize. If I told you I’m 5’5”, you may not know exactly how long my legs are, but it’s safe to assume full-length pants I told you I want to wear with flats will need to be hemmed. So pin them up a little before having me try them on, or at least be ready with pins so I can better visualize the look.
  4. Be honest. When it’s obvious I put something on and I hate how it looks on me, acknowledge it’s not a purchase I should make.
  5. Don’t take a customer you can’t serve. If you don’t have the items or price range I said I want, save us both the time and tell me you’ll follow up if or when your selection changes.

Obviously, these suggestions assume the stylist has advance information. In the case of a pre-planned appointment, not making every effort to gather information ahead of time is a missed opportunity. In one case, I made an appointment and asked the stylist whether I should tell her what I was looking for. She said it was up to me and that she could just “pull looks” (not really a customer-facing term) once I arrived. I still wrote back with a ton of information, but it turned out I was overly optimistic she’d apply it.