The Yes Shopping App Made It So Easy to Find a Pair of Denim Shorts That Actually Fit

Here’s an embarrassing admission: The last time I bought a pair of denim shorts was in college. To be more specific, I was still a teenager when I acquired two pairs of vintage Levi’s and chopped them into teeny tiny shorts. And I’ve been wearing them for the past decade without a second thought. So, yeah, it was about time I invested in a new pair of cutoffs.

I knew exactly what I was looking for and what I wanted to pay but I didn’t want to scour the ends of the internet to find a pair of high-rise shorts that actually covered my butt and would flatter my larger hips. Further, I didn’t want to spend a dime over $200 for my new acquisition. So, I figured I’d take my quest to The Yes, a new shopping app that can currently only be used on iPhones (sorry to Android users and anyone reading this on their desktop computer). The app was created by Julie Bornstein, whose resume boasts stints at Stitch Fix, Nordstrom and Sephora, and is intended to provide a personalized shopping hub, tailored to everyone’s specific needs. Whatever they may be.

Once I signed up for The Yes, I was greeted with the best quiz of all time: a slew of trends and basics with one simple prompt, "Would you wear this?" As I tapped through saying, “Yes,” I love cropped denim but, “No,” I’m not such a huge fan of one-shoulder tanks, I felt like I was playing a well-designed fashion video game. Or swiping through a dating app. I also entered my measurements, including height and size, as well as what I usually wear in my go-to brands so The Yes could accurately suggest what sizes to buy in the future.

Finally ready to shop, I navigated right to the denim shorts section and felt like I had hit the jackpot. It was what my denim dreams were made of: all high-waists, button-fly closures, raw edges and only a few booty shorts. The latter I easily weeded out by clicking the “No” button underneath their pictures and *poof* they were gone. Among the mix of well-priced Madewell, Mango and Zara options, there were fancier picks from Anine Bing, Citizens of Humanity, Rag & Bone, Alexander Wang and Acne Studios, most of which were on sale and only shown to me if it was available in the size that The Yes predicted I would wear.

After days of deliberation—during which I regrettably lost some shorts that swiftly sold out—I settled on three pairs and clicked buy. Since The Yes lets brands send out items on their own, my purchases trickled in one by one.

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The Yes

First up: the Re/Done cut-offs that sat slightly lower on the hips than I’m used to. But the wash was so good and they flattered my thighs just so, meaning they went directly into the keep pile.

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The Yes

A pair from Agolde followed shortly after, and they were like the Cinderella pair: They slid over my wide hips but hugged my waist without creating any bumps or lumps. And they were long enough to keep my bum securely tucked away.

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The Yes

My purchase from Madewell arrived last. And apparently the ones I selected had sold out, but The Yes emailed me that they located the exact same pair from Zappos and would be sending them my way, ASAP. With no additional work on my end. Unfortunately for my wallet (but fortunately for my closet), this pair zipped up flatteringly. I had to keep them.

So, I now have three new pairs of denim shorts in my arsenal. Sure, I went over budget but shopping on The Yes turned out to be such a fun experience—which isn’t usually how online shopping feels. In fact, when friends reach out to me asking where they should get a new floral dress or how to find a comfy pair of flats, I’ve been sending them over to The Yes, since I’m confident the app will be able to size up their taste as well as it did mine.

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Fashion Editor

From 2019-2021 Dena Silver held the role of Fashion Editor covering product recommendations, trends, and what you should be shopping this season.