Take a Break From Scrolling The RealReal to Read Its New Book, ‘Real Style’

Sometimes the vast expanse of The RealReal feels like a savior and sometimes it feels like a void. The resale platform has given so many of us—more than 40 million current members—a place to turn to when we’re sick of all our clothes, or nothing fits, or we have a wedding whose dress code is “think Studio 54 in a barn.” Or maybe an influencer has enticed you to set an alert for Prada lipstick-print skirts, or you’re sick of influencers and just want to scroll vintage Armani at 2 a.m., dreaming of a wardrobe for a different, more cohesive version of your life.

But the question for a lot of us, once the box arrives, becomes more existential. Even if the floral Tory Burch dress fits, is this who you are now? With what shoes do you wear it? Why do all your barrel-leg jeans feel outdated? Do not ask an AI agent this kind of thing, for many reasons, but chiefly because it takes the pleasure out of finding your style and answering the question of how you want people to see you. The RealReal attempts to answer these deep concerns with its own book, Real Style: Dressing With Intention & Expressing Yourself Through Style.

How long has it been since you’ve read a style book? They’re usually filled with illustrations of so-called essentials like crisp white shirts, a great-fitting suit, a strand of pearls, or your grandfather’s passed-down cufflinks. They speak of an imagined and vague lifestyle and a person who doesn’t really exist. It does seem a little odd that a shopping site would put out a style book, but it makes an entertaining case, with pages on “anatomy of a really good outfit” (wear things that shouldn’t look good together but do), aphorisms like “tax brackets don’t determine taste,” and advice on taking a “no-shopping shopping trip.” It asks question prompts such as “what would your inner child want to wear?” Vanity Fair talks to chief brand officer and coauthor Kristen Naiman about how a website becomes a book, the changing zeitgeist of style, and what she buys.

This interview has been edited and condensed for clarity.

Vanity Fair: How do you turn something that’s so online into an actual book?

Kristen Naiman: It came out of a conversation we were having internally about the way that we saw people’s relationship with their style changing and how that was showing up in the way we saw them behaving with us. In my mind, it was a return to a sense of singularity and individuality about style that was bigger than a capsule wardrobe. [A member of our team] was like, “We should do a book about it.” It’s really a cultural conversation and one that we’re really interested in igniting.

Can you define that conversation?

It’s that style is a practice, and it’s a practice that’s a personal relationship with yourself. And the better you know yourself, the more true you can be with the way you articulate yourself through style, and the more fun that relationship becomes, and the more it serves your life.

You mentioned those outdated style guides, and I sometimes love buying them. I have Marisa Berenson’s; it’s from the 1980s. There is, like, a whole section on styling turbans.

Which, actually, I think would be very valuable.

True. I own a turban. Give me some of your style-book inspirations.

We were feeling like a book that says to you that, in order to have style, you need a trench coat, a Rolex, a white shirt, a ballet flat—we were like, That’s a no. But that is the baseline for many style books of recent memory. But to your point, I actually collect them, love them. Cheap Chic by Caterine Milinaire and Carol Troy—I found it in a thrift store in my 20s, and that kicked the whole thing off. I absolutely love Women in Clothes from Sheila Heti, Heidi Julavits, and Leanne Shapton. How to Have Style by Isaac Mizrahi!

You mentioned that outdated idea of the capsule wardrobe of the white shirt, the trousers, the suit. But is there anything core that you think people need now?

If it’s core to you. And there are so many factors that contribute to that. Like, I love a white button-down shirt. I just do. I also love a colored trench coat. But you never will catch me dead in a moto jacket. I look ridiculous in a moto jacket. But for somebody else, I recognize that that’s completely core to them. When you see someone who has really good style, usually what’s really good about their style is not the specific thing, but how aligned they are with the thing that they’re wearing, how much it feels like a part of them or true to them.

Is that what some of the exercises in the book are meant to do?

It’s hard to know yourself because you’re always changing, and you have to be quiet enough with all of the cacophony of noise around you to hear the thing you like and why.

I would love to hear some real RealReal stories because it is such an obsession for many people.

I will start with me. I routinely discover new brands that I wouldn’t have potentially found on my own. I had to have my picture taken, and they called in this Attersee dress that was white and had this fringe on the bottom. By the time I went back to find it, it was gone.

Do you have white whales? There is a Phoebe Philo loafer that I love, but I refuse to pay full price, and I know that one day my alert will come in.

Well, that Attersee dress—last April or something, the alert popped up. I grabbed the dress, and I’ve worn it 10 times. I also really love vintage Kenzo, like original vintage Kenzo. And last year I found a piece at the end of spring, which is my other hack.

Shopping off-season? What else?

One of my favorite concepts in the book is “always be browsing.” You’re always looking, and your light is always on, and your eyes are always open, and you’re always paying attention to the things around you. You buy the dress not because of the event you go to, but because the dress will find a place.