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Aneta was a petite blonde with architectural glasses and artistically shredded jeans. Robyn was a demure brunette in a taupe sweater, well-tailored skirt, and pointy heels. They shared the same mission: to make me less of a slob.

And they shared the same "agent:" Airbnb’s new Experiences subsection, which, among many other options that are tailored to many destinations, hooks up hopeless shoppers with experts. Over the course of a week in Paris, I plunged into the maelstrom of the City of Light’s boutique streets with both guides at my side, an afternoon each, and learned that just as there are 2,000 ways to tie a scarf, there are likely thousands of styles of stylists. The key is to suss out who will be best for you—not an easy task on Airbnb, where the user reviews tend to be raves for every vendor, and the descriptions of the tours can be vague.

With Aneta, the experience was all about the buy. We met on a rainy street corner and after a brief hello, we headed right into the first shop, a resale store where fashion editors drop off clothing recently used in shoots and fashionable Parisians consign their gently used designer duds. The racks were crammed and Aneta got quickly and silently to work, pulling pieces for me to try, which I did behind a makeshift screen in the rear of the store.

At the next stop, a Parisian designers’ boutique, the drill was the same: She’d pull, I’d try, and then we’d stand before a mirror with her gently draping scarves, blousing shirts, adding accessories, and explaining, when I asked, why she was making tweaks.

With Robyn, my second guide, coffee and a chat preceded the shopping foray. As we sat in a cafe, toddlers hovering nearby (they were obsessed with her color wheels), she gave me a quick lesson on what types of clothes I should be seeking. Because of my (now) salt-and-pepper hair, my optimal color palette is no longer "winter" but "intense summer," though those colors only matter on the clothing that frames the face.

She taught me I could wear any colors below my waist, but because I apparently have an "H" shaped body—shoulders and hips the same width, undefined middle—I was instructed to restrict the bolder colors and choices to the hips down to draw attention away from my stomach. Big patterns are a no-go, since I’m short. And to be on-trend this season, I should look at plastic clothing, '80s throwbacks, and pieces accented with sparkle—maybe. It turns out that being on-trend is less important than finding your own style, though having a knowledge of trends is key to not looking like a fuddy-duddy.

After this quick tour through my bodily flaws and opportunities, Robyn and I hit the shops—in this case a number of French chains and a few small boutiques. Just as Aneta did, Robyn pulled pieces, and as she did, she explained how they reflected what I’d just learned. I tried them on as-is, with little tweaking from Robyn.

So which tour was better? Looking at the numbers, Aneta wins. With Robyn, I ended up buying one shirt and one bracelet. My haul with Aneta was far larger: two jackets, a sweater, one scarf, three shirts, and three pairs of trousers. Aneta seemed to know instinctively that I’d want to get pieces that I’d only find in Paris, though I paid dearly to buy them. For those seeking to shop on a budget, Robyn was the better pick.

As for which tour was more educational, I’d say that’s a draw. I have a notebook filled with specific rules from Robyn that should be helpful. But observing Aneta, as she pulled and tucked my clothing and chose certain types of pieces over others, was highly instructive. From her I developed a feel for fit and an eye for the striking detail. Or it may have been that Aneta’s aesthetic better matched my own, something I wouldn’t have guessed, as Robyn’s outfit was more in line with what I’d normally wear.

If you decide to try a stylist tour—and I highly recommend them both for the fun of it and the education—here are some suggestions:
  1. Pepper your guide with questions before you go, particularly regarding budget. Doing so will give you a better idea of the types of shops you’ll be visiting, and how much money you should allot.
  2. Be sure to set an upper limit to your budget so you can tally up costs as you go along. It sours the experience if you discover you overspent at the end.
  3. Be open to trying on whatever the stylist pulls. You’re here to learn from these experts—and both truly were experts in my case (Aneta works as a stylist on fashion shoots and makes money from her fashion blog; Robyn is designer). Those who refuse to try on clothes, a common occurrence according to both stylists, are squandering the opportunity to learn what actually flatters their figure.
  4. That being said, if you know you’ll never wear a teal tutu to the office—or anywhere else—ask to move on. This is your time. Though tours average 3.5 hours, that goes fast.