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The word “iconic” might be thrown around a lot these days, but what really makes someone worthy of the descriptor is less about their fame or accomplishments and more about their attitudes, their drive, and very often their style (arguably the easiest of the three to elevate). When it comes to updating our looks and getting dressed each day with this main-character attitude in mind, Who What Wear’s co-founder Hillary Kerr suggests beginning with jewelry. “Fashion trends may come and go, but jewelry is forever,” she tells me.
Having worked in the fashion industry for nearly two decades now, Kerr is the expert on iconic style, fashion rules to live by, and, of course, all things jewelry. She even gave me a lesson in styling her favorite pieces from Cartier’s most iconic collections. Read the full interview with Kerr below.
How has your personal style evolved over the years?
I grew up in La Jolla, California, and so much of what I wore as a teenager was informed by surf culture and the beach. I had more variations of flip-flops than anyone should own! By the time I ended up in New York for grad school and my first job at Elle, I was starting to figure out what actually worked for me and my taste instead of just what was trending. I found myself gravitating toward some of the 1950s-adjacent silhouettes that I still rely on today. I still have a soft spot for tailored pieces, but lately, I’ve embraced pieces that are a little more relaxed while still paying homage to the feminine silhouettes I prefer.
What are some of the style rules you follow?
You can make anything look expensive if you get the fit right. Gray goes with nothing, so therefore, it goes with everything. Some of the chicest women in the world have a personal uniform, so don’t feel like you constantly need to update your style. Fashion trends may come and go, but jewelry is forever.
Tell me about some of the fashion pieces in your wardrobe that you would describe as iconic.
So many! I will always adore a pointy black pump, my beloved trench coat, my classic tuxedo blazer, a sculptural cocktail dress, a romantic little white sundress (pictured here), perfectly broken-in gray T-shirts, a black leather pencil skirt, and my beloved motorcycle boots that I’ve had for over a decade.
I know you’re a firm believer in investing in jewelry. Why is that?
It’s truly my favorite aspect of fashion and one that is unquestionably worth investing in. I would rather invest in a piece of jewelry or a watch than almost anything else. In addition to being a sentimental purchase, these items can truly elevate anything you wear and make your outfit look purposeful and thoughtful. Plus, they hold their value!
Tell me about this daytime look you put together.
I think of this look as equal parts Laurel Canyon and 1950s Italian summer dressing. Because the dress is more casual, I wanted to elevate it with gold jewelry and a stronger men’s watch. To me, there’s something inherently intriguing about contrasts, whether that’s a woman wearing a man’s watch or styling a more substantial piece, like this Santos watch, with a dreamy daytime fabric. It’s just a little unexpected, and that always feels fresh to me. Jewelry can sometimes feel a little formal, but wearing it in a more whimsical way—mixing metals or wearing similar styles in varying shapes—makes it feel much more approachable. After all, there’s no wrong way to wear a Trinity ring, right? Style it on whatever finger you want! Wear two of them in different sizes like I am here! It’s honestly just about whatever mood you’re in.
How long have you been wearing Cartier jewelry? What was the first piece you owned?
My first Cartier piece was a Tank Française watch, which my parents gave me as a birthday and college-graduation gift. I had always loved the watch but never even dreamed of asking for such an incredible present, so when they surprised me with it, I burst into tears. It was the first truly sophisticated thing I owned. I felt so confident and protected when I wore it; it felt like a symbol of my parents’ love and their belief in me and my future. It’s still in my rotation to this very day, and I still feel so proud to wear it.
How has your approach to wearing jewelry changed over the years?
When I first started investing in jewelry, I tended to save it for important or formal occasions. Now I wear it all the time, no matter what I’m doing. If a piece of jewelry puts a smile on your face or makes you feel joyful, why wouldn’t you want to wear it as much as possible?
What are some ways to style classic pieces to feel modern?
I think it’s all about the mix! Mixing styles, mixing metals, mixing materials—rather than being precious about what “works” together, think about having fun with it. I also think wearing classic jewelry with more casual clothing always looks extremely modern.
Let’s talk about this watch because I love that you styled it with an evening look.
I adore watches and wear one at all times. I’m a Virgo; they’re essential to me! An accessory that elevates your outfit and keeps you prompt? What could be better? At night, I love how a more elegant watch looks styled with slim bracelets. There’s something slightly serious about a watch, so I think it’s lovely to juxtapose that gravitas with pieces that bring more glamour and effervescence to your wrist. (That’s code for diamonds.)
What else did you consider when styling this look?
I would describe this look as a sculptural statement moment: The dress is simple, but the silhouette and vibrant color are unexpected, while the jewelry is both subtle and strong. Just because something is an evening look doesn’t mean you can’t have fun with the jewelry. I loved pairing the sharpness of a diamond Juste un Clou with the elegance of the Panthère de Cartier watch and styling two Love rings together, in white and yellow gold, on my pinky. The Love necklace is so simple and elegant, but the lines are powerful, and the overall result is very impactful. I thought it was such a lovely sculptural moment that paired nicely with the neckline of the dress.