Welcome to our podcast, Who What Wear With Hillary Kerr. Think of it as your direct line to the designers, stylists, beauty experts, editors, and tastemakers who are shaping the fashion-and-beauty world. Subscribe to Who What Wear With Hillary Kerr on Apple Podcasts and Spotify.

Los Angeles–based stylist and designer Alejandra Hernandez knows how to make a smash hit.

Recently, Hernandez’s work was in the headlines when she styled SZA in a Princess Diana–inspired photo on the cover of her latest album, SOS. Surprisingly, Hernandez didn’t know which look would make the final cut in the cover artwork until a few minutes before the public did.

In addition to her work with SZA, Hernandez has worked with the likes of Iggy Azalea, Eve, and Britney Spears. She is also the designer for Year of Ours, the female-led activewear and lifestyle brand.

In the latest episode of Who What Wear With Hillary Kerr, Hernandez shares how all of the looks came together for SOS, the differences between preparing for editorials and music videos, and more.

For some excerpts of their interview, scroll below.

Can you tell me a little bit about how you started out and eventually found your way into both parts of your fashion career?

I grew up in L.A., and I always knew I wanted to be a fashion designer. When I was a kid, I didn’t know what being a stylist was. We had a family friend who was a costumer, and she was my childhood hero. Because that was the closest thing I knew to what I wanted to be.

I always wanted to be a fashion designer, and my goal was to go to FIT in New York City right after high school, but September 11 happened, but that derailed my moving to New York City.

I did a semester at SMC [Santa Monica City College], and then I went to FIDM. I went for fashion design. I had a teacher—I even remember her name; it was Mrs. Owens—and she was a designer. She actually had just gotten a job as head designer of Apple Bottom jeans.

She was portfolio teacher, and I remember she told me that I would be a good stylist. She had previously worked at MTV as a stylist, and she introduced me to what that was because I didn’t really know what it was. I interned for her at Apple Bottom after I graduated. Then I interned at a few different denim companies. I eventually got a job with a small L.A. brand as women’s designer, and I was there for four years.

There, I met stylists, and I started assisting. I did freelance design after I left, but I focused more on styling.

I read that your folks were both hugely influential in your career for a number of reasons. Your mom is from Peru and is a jeweler and that your dad is from Argentina and used to sell 501s and other American-made denim brands at his store before immigrating to the U.S., but that they did not fully understand your career and what you were doing for a number of years. Can you tell me a little bit about that?

I think they both were influential, and they both really inspired me because they’re both very entrepreneurial. Neither of them had a formal education in business, yet they both did well for themselves. That kind of showed me that I didn’t have to have a formal education in business even if the business is myself. You know what I mean? I consider myself a business. They helped me in that way, for sure. They always supported everything I wanted to do.

Culturally, it’s something that I think a lot of first-generation Americans experience when we work in creative fields or we work in American mainstream media. Our parents are not in tune with American pop culture. They don’t care. My parents are really Latino. They are still listening to Latin music. I could be doing the coolest video that got a million views in 10 seconds or something, and I’d show my dad, and [he’d] be like, “Oh, yeah, that’s nice.”

My sisters have master’s degrees and are working on their PhDs. They’re just such accomplished scholars. I know they’re proud of me, but it took a while I think for them to fully understand that what I was doing is cool, too.

You’ve worked with all kinds of interesting folks, from Iggy Azalea and Eve to Britney Spears. Most recently, you have been ushering in a new fashion era for the one and only SZA. I’m curious about how the two of you first connected and started this collaboration.

The first time I worked with her was actually on her “Drew Barrymore” music video. Then I started working with her again at the end of 2018, so that was the beginning of our working. I think we became friendly after the “Drew Barrymore” video but really working together was at the end of 2018.

I’d love to talk about the album artwork with that cover graphic that was inspired by that iconic shot of Princess Diana. That photo of Diana on the diving board looking into the sea and then the interpretation of that and elevation of that for the cover has generated a lot of conversation and love online. Did you have that whole vision in your mind? How did the jersey come about? Were there other options?

There were other options, including one custom jersey that we made on set that we pieced together different jerseys, and we made this reconstructive jersey.

There were different options and with different combinations with different shoes. There was also swimwear that we pulled just in case. She didn’t even try it on, because I think, like I was saying earlier, she’s always right. In the end, it wouldn’t have been so amazing if she would have worn anything that would be expected.

You see that photo, and you know it’s a Princess Diana reference, but she’s herself on it, which is also symbolic. If it would have been anything else, it wouldn’t have been as amazing.

I didn’t know which one was going to end up as the cover artwork until probably like 30 minutes before the public did, when we saw the picture!

This interview has been edited and condensed for clarity. Next up, check out our previous episode featuring Madelyn Cline.