Jenny Walton’s World: Her New Book, Miuccia Prada, and a Fixer-Upper in Tuscany
Step into the universe of the coolest creatives in the fashion industry with our series My World, where readers will discover how the top stylists, designers, and tastemakers built their careers; their favorite restaurants, beloved albums, and fashion finds; etiquette rules they stand by; and so much more.
If you work in fashion, you might already know of Jenny Walton, or chances are you’ve seen a street style photo of her without even realizing it. Take one scroll through her Instagram, and you’ll immediately feel her sunshiny personality—a genuine candor (that’s never cloying) that comes through on our call.
Since growing up in rural New Jersey and getting a BFA in fashion design from Parsons School of Design, Walton has been designing, illustrating, and writing and become known for her distinctive personal style—meticulously curating a dream wardrobe through hours on Vinted and The RealReal, sifting through vintage stores around the world, and dressing herself for fashion shows. This led to her becoming Vogue’s vintage shopping columnist.
Now, she has a book coming out on April 29, Jenny Sais Quoi: Adventures in Vintage & Personal Style, named after her Substack newsletter, which is currently available for preorder. Ahead of its release, we talk about everything from her closet and makeup bag to style icons like Georgia O’Keeffe, Diana Vreeland, Edith Sitwell, and Virginia Woolf; New York, Milan, and what’s next (California); and an assortment of her other all-time favorite things: Miuccia Prada, The Red Shoes (1948), caffè macchiatos, and her best vintage find yet, a fixer-upper in northern Tuscany.
Below, take a look into the world of the illustrator, designer, and writer.
How would you describe growing up in South Jersey?
Cornfields—randomly rural. I think most people in New York City think of Jersey and picture North Jersey, like Newark. The only thing we really enjoyed doing was going to this 24-hour diner nearby called Colonial, and that was the fun place to go late at night. But there really wasn’t too much else, and my mom was too afraid to drive into Philly, so we mostly stayed in New Jersey. But it was also really fun because there were a lot of vintage markets and yard sales. It was very suburban—going to Goodwill and the mall. So it was kind of simplistically nice in a way.
Can you talk me through your career trajectory?
I basically moved to New York when I was 18 to study fashion design at Parsons, and I ended up living there for about 15 years. I thought I’d be a designer or creative director—that was the plan. But then I was an assistant designer at Calypso St Barth for two years. It was a lot of it was emailing with factories and following up on samples, which I wasn’t that good at. I was always more obsessed with going to the flea market on the weekend to find a cool vintage sweater and bringing it in and saying, Can we remake this? I used to take this long subway ride—from the length of the G to the 7 train—because I lived in Park Slope and the office was in Queens, and I would just sketch for the whole hour to work and the hour home.
This was around 2014, when Instagram was really first taking off. So I would post a sketch at the end of the subway ride, and it was the early days where, if you were posting, you could actually gain traction pretty quickly. I got featured on a Discover page, and pretty soon editors and people were reaching out to me to illustrate. That’s when I went off on my own after two years, and I started traveling more. I began getting invited to shows. Over time, I started just by posting my illustrations, and then every once in a while I’d post wearing something vintage. People would say, Oh my God, I love that—where’d you get it? I realized I could document my life—whether it was traveling, vintage finds, or artwork I was working on—and people enjoyed following along.
There are so many people who are creative but might be in a job that doesn’t feel aligned, and they want to figure out a way to get out of it. What advice would you give them?
I think even though online it’s a lot more crowded now, if you have a distinct voice, you can still cut through. It happens all the time—there’s a new voice and you’re like, Oh, who is this person? But they’re so confident, and you really believe them. I guess my main advice is that you really just have to kind of jump, even though it’s horrifying.
My first illustration job—I remember they asked me how much I wanted to be paid. It was to live illustrate in a store in SoHo, and I said $700, because that was my rent. I quit my job based off that. My dad was like, What are you doing? What are you going to eat? You can’t just make your rent. And I was like, I’ll be fine. That’s something that’s kind of nice about being younger—you’re a little bit naïve, so you’ll take those big jumps. Even when I was older—30 or 31—I moved to Italy after COVID, and that was also a big jump. I didn’t speak Italian. I moved there with an ex, and then we broke up, so it was like, Okay, I’m on my own—I have to sink or swim. And I ended up figuring out how to get a visa and staying. There were a lot of really hard moments, but it was always worth it to take that jump. You really start to believe in yourself when you fully commit to it.
Do you feel like there was anyone who instilled that sense of self-belief in you?
My friend recently told me, You know, you’re kind of delusional. I think my mother’s a very strong kind of woman. There’s no convincing her. And I have two sisters. It was very important that we were incredibly independent and we went after what we wanted, and she never pushed us to study a certain thing, or that we needed to rely on a man or anything like that. So she really helped me be very independent.
Do you remember any formative memories of deciding to pursue fashion design?
My mother’s an amazing quilter, and I learned how to sew from her, so I was already making my own clothes in middle school. As dorky as this is, that’s when Project Runway was in its heyday. My dad’s not a fashion person at all. He would work late nights, but he would come home, and whatever night it came out, it was our bond. We loved that show, and we would watch it together. And I think that’s also where my obsession with Parsons came from. I already had these sewing skills, so I was like, Oh, I think I could actually do it. I think those early reality TV shows opened up this world to us.
Is there a piece of advice that stuck with you from your time at Parsons?
I had great teachers at Parsons, and they instilled in me the importance of hard work, and you can’t really get around putting in the hours. I have an essay about this in the book called “10,000 Hours of Style.” I argue that you have to spend a lot of time doing it. Even an aesthetic choice tunes your eye, and I’ve spent hundreds of thousands of hours in vintage stores, looking through racks of things. Now I’m at the point where I can hold something up and I know exactly know how it will look on me—what I like and what I don’t like.
All of our main classes were six hours long at Parsons. I had a lot of great fashion illustration teachers. They really taught us this commitment to taking a lot of time, and there’s no kind of way around it. We were the only building in Parsons that was open until 2 a.m. because we would all stay so late.
I would love to talk about your book and how it came about.
An editor from Phaidon reached out to me two years ago and was like, I’d love to do a Jenny book. I’ve been following you for a long time. What could that be? And I was like, Oh my god, I don’t know. So it took a year of these two-hour-long Zooms we would do every week just talking about what would be fun, what would be cool. I felt like I was up against this thing of… there aren’t really that many good books about fashion or style. It’s really hard to apply rules to everyone, or say You should dress this way or This is the silhouette that looks good. And I say in the book, everybody is different. I grew up with another show, What Not to Wear, where it was really like, Oh, this is your style? It’s ugly. We’re throwing it in a trash can. I really didn’t want anything that felt like a guide, so I wanted to talk more from the perspective of how I found my style or things I’ve found helpful and hopefully inspire people through what I’ve learned but not necessarily tell them what to do.
Can you give a preview of more of the advice or ideas in the book?
I have another essay called “Off the Algorithm,” about how you have to get off this thing that’s being fed to you because it’s being fed to a million people, and it’s too easy, too passive. You really need to go into a vintage store—it could be an old bookstore or record store—or watch an old movie. It takes time. I have another one called “Flow State Fashion,” all about how you should make a mess—pull out all your stuff and start putting together weird combos, put on music, have fun with it. The beginning is awkward, and you’ll make combinations you’ve done a million times or feel boring, but as you go, you get into a flow state, and then exciting things happen. Another main takeaway, and why I named it Jenny Sais Quoi, is that I use vintage as a special little touch. Whether it’s a new Toteme blouse or a pair of jeans, then you have a cute little vintage belt or a vintage silk scarf, even your grandmother’s ring—it can be that simple, but those little things take your style to a whole new stratosphere and make it unique to you; something nobody can copy.
You have an incredible vintage collection. I know it probably changes, but what is your most prized piece in your collection right now?
I’m obsessed with a very, very bright blue, and there is this 1950s cardigan that I found on Etsy years ago. It’s just in this acrylic kind of wool, not too scratchy, but you just don’t see sweaters this bright. It’s the same kind of blue that I hand-painted the [book] cover. So many minimalist brands now rarely go for color, which is frustrating because with Toteme or The Row, I want to see their color choices. The Row just showed a beautiful blue and white long dress at its last show, which was nice. I want to see people take more chances. Even last year, a pop of red was the It color, and it’s like, Okay, for everybody?
People always talk about style words. Do you have ones you identify with?
I hate the defining your style—although it’s a very lovely idea, and I see why it’s very tempting—but it feels so reductive. People often ask, What is your style? And, of course, I could say vintage-inspired or classic with a twist or colorful. There are all these adjectives. Thinking in a world where it’s already so reductive, everyone’s style is becoming more and more similar, then also being like, Okay, how can I define it in a few words? feels to me limiting, but I’m slightly a rebel so…
Do you have style icons?
Honestly, I realized as I was writing the book, so many of them are artists, which is really interesting. There’s a great book by Charlie Porter called What Artists Wear. Diana Vreeland, incredible dresser. Edith Sitwell, really interesting. Virginia Woolf, also Georgia O’Keeffe. There are a lot of artists who had incredible style and designers too. Miuccia Prada has probably our current-day best style. Although, I’m obviously very biased.
Why do you think you gravitate toward Miuccia Prada?
She helms one of the most fascinating brands everyone’s dying to see every season. And yet, even the most anticipated moment of that show is when she takes the bow at the end. For me, it’s like, What is she going to be wearing? I think this is what makes personal style so interesting. It’s why everyone’s obsessed with Carolyn Bessette Kennedy—trying to replicate someone whose personal life is elusive. What you wear gives a glimpse of what might be going on behind the scenes, and so it’s much more fascinating than a model who’s been styled. Personal style actually embodies something that’s going on behind the scenes.
All of her references—whether it’s an old film from the ’60s or these five different books she’s reading about women’s role in society—she’s questioning that as much as she can while still running her global fashion brand, and it’s really fascinating. She just has a great eye as well. She has incredible antique jewelry. She has a really modern way of wearing really luxe items, like a beautiful pointed silk heel and then a gorgeous vintage diamond brooch, but she’ll put it on a very simple sweater, obviously Prada, but you could also find something aesthetically similar at J.Crew or Uniqlo. But she’s got these little touches. I think accessories are very, very helpful as well.
Obviously, there are a lot of people who have a minimalist style, with The Row being so popular and especially with Carolyn Bessette Kennedy. Do you have any advice for people who gravitate toward that kind of style?
Even just a cute little knee-length skirt and a kitten heel. When you go online, so many people’s style looks so similar that it’s hard to tell them apart. They’re all getting the same resources, looking at the same things, shopping at the same places. So it could be going and looking through a family member’s wardrobe, and being like, Oh my god, I love that, and maybe they let you borrow something. That’s what’s really unique. It’s so clear when people are trusting their instincts and going searching in other places.
What’s something that you never wear and doesn’t really have a place in your wardrobe?
I never really wore sneakers outside of the gym. However, I love the soft sneaker trend of the past few years. The Loewe Ballet Runner. When that first came out five years ago, I was like, Oh my god, this is the softest—there’s just no structure to it. I still have those The Row mesh flats. I essentially love a shoe that’s basically not there, as much as possible. I don’t like big chunky, bulky sneakers or footwear in general, unless it’s very much a fashion thing, like Wedge Balloon heels—it has to be completely absurd. I did give in to a puffer jacket—a short black one for going to the dog park. It’s a Uniqlo one that I’ve had for like five or six years.
What’s your process for vintage shopping?
It’s an addiction. This is why I have an old stone house in northern Tuscany that I’m restoring now. Because when fashion wasn’t enough, when late-night scrolling on Vinted and The RealReal wasn’t enough, I started going to local, small real estate websites in rural villages in Italy because I was like, Oh, I’m never gonna be able to buy a house in America. I’m a millennial—this is a dream that has tragically passed my generation—but in rural Italy, maybe. So I’m working on that now. That’s my best vintage find.
(Image credit: Sephora; Fara Homidi; Glossier; Gucci; K18)
Are you loyal to a specific nail polish color?
It’s exactly the same as getting my hair done, which is just complete and sheer terror—color paralysis and cut paralysis. I can only really do my hair on a completely random walk, in Milan, at a place that’s 25 euros. I can’t plan it. When it comes to nails, I didn’t paint them at all for the last year or two—really never did anything. But I am so in love with Diana Vreeland and her style that all it takes is seeing one photo of her in her completely red living room on the Upper East Side with her long red nails. Then I go into the nail salon, but I’m horrified because they give you so many options. I basically try to go somewhere in that kind of Chinese red, a lacquered shade you sometimes see on furniture from the ’60s. Sometimes I call it “spaghetti red,” something with a little bit of orange in it, like a nice pomodoro sauce. I don’t like too dark; I don’t like too bright.
What are your most repurchased beauty products?
I’m obsessed with Fara Homidi—have you ever tried the lip compact? The color is perfect, and so is the liner. It’s so chic. Then there’s the lip liner that goes with it, the Smudge and Contour Lip Pencil. My favorite lip product of all time is the Glossier Generation G in Zip. It’s a little coral. I’ve had it since it came out, and nobody’s ever been able to touch this color.
For eyebrow pencil, I love Gucci Beauty. They have a waterproof pencil in Brown 04, and sometimes I also use Boy Brow. I also use a Gucci foundation in 210N, which is good for 24-hour wear. Recently, I became obsessed with these K18 hair treatments because I dyed my hair blonde, and my hairstylist in New York said my hair needed it. Any black eyeliner works for a cat eye, but right now I’m using the Glossier one. I also keep a Kiko pencil on hand—it’s a cheap makeup brand in Milan, but I always have one. Hermès makeup is amazing too, and everything’s refillable.
Is there anything that you learned that has forever impacted the way that you do makeup?
I mean, I have always done a cat eye, and I really like doing that. I remember asking a makeup artist how to know where the line should go, and they told me you should basically just extend the curve of your bottom eyelid and follow that line up. That’s how you get a cat eye because it’s so hard to know whether to go down or up. Sometimes I’m doing it, and I think, Am I living in the 1960s? Should I be doing this? But I paint a lot, so I really like painting things. It feels like a modern version of painting, in a way. It’s kind of fun, but stressful.
Fara Homidi
Essential Lip Refillable Compact
Fara Homidi
Smudge & Contour Lip Pencil
Glossier
Generation G Lipstick
Glossier
Boy Brow Eyebrow Gel
Gucci
Natural Finish Foundation
Where are you living now?
Actually, I just moved out of Milan. I’ve been renting in Milan the past few years, but my fiancé is from California, so we’re looking to find a place there. I moved my stuff from Milan to Tuscany, and the plan is for it to hopefully be at least livable in the next few months so I can spend the summer there because it’s two hours below Milan but only a half-hour from the sea.
What’s one thing you like to do whenever you’re in Pennsylvania where your parents live?
My number one thing is finding a vintage store—it could be clothing, it could be a bookstore. There’s an amazing free library in the basement of this little library nearby parents in Pennsylvania, and I found the most incredible book there. It’s called Plant Dreaming Deep by May Sarton. She’s an amazing poet, but it’s just a little book about how she bought this old farmhouse and restored it. I found it just at the time that I had just bought in Tuscany. There’s this little vintage store called Pink Flamingos Vintage, and that’s in Brookville, Pennsylvania, also near my parents. Those are the places I’m always wanting to go to, in addition to the cutest coffee shop I can find, especially in Europe. I have to find the cute café, and then I just sit there and bring my dogs.
What kind of dogs do you have?
I have two. I have a beagle, but she’s the world’s smallest beagle. She’s eight kilograms, which is the limit for flying with them by some miracle, and then a wire haired dachshund.
Is there anything you always try to do when you’re in New York City?
I always go to The Strand because I just love used books and finding old, strange books. There’s also a great bookstore in the East Village called Bonnie’s Cookbooks. She’s just this New Yorker who tells it like it is. It’s this walk-down-basement kind of store with all these old used cookbooks.
What about in California?
I’ve been spending some time in San Francisco because my fiancé’s family is from the Bay Area. It’s a fascinating city, and they have a lot of great vintage there. I’m really excited to explore California vintage more because there’s so much amazing mid-century stuff. It’s like in the later seasons of Mad Men, when they go to California and the wardrobe just pops off.
There’s a great vintage store called Relic Vintage there that I’ve completely fallen in love with—with a lot of things from the ’50s and ’60s. To live, I’m thinking more around Santa Barbara County or Ojai. My fiancé went to school there, and I never really spent much time in Santa Barbara, so we’ve been visiting more so I can get a better idea.
Is there an item that wherever you live, your home isn’t complete without?
I have a collection of the little coffee cups—the little espresso and macchiato cups. I’ll go to a random little store or café, and if they have a cute cup, I’ll even go to the person and be like, Can I buy this? Please? I’ll give you 20 euros. Usually, the barista just slips it to me. When I’m in the U.S., if I have some of those with me, it makes me feel like my little Italian spirit is still with me.
What is a song that you currently have on repeat?
I love the new Harry Styles album. It’s so good. Track five is called “Taste Back,” and it mentions Paris, so immediately you’re like, yes—croissants, Paris, the whole mood. I’m very tied to him because his last album came out four years ago, right when I moved to Milan. I was breaking up and had to stand on my own two feet, and my girlfriend was with me. Then, four years later, when Harry’s new album came out, she was helping me move out of Milan again. We always have this kind of tied feeling. We were checking on the house in Tuscany, picking out flooring, and then drove back along the coast the morning the album came out.
What are some of your favorite movies?
I watch a lot of old movies, especially when I’m painting—beautiful ones that inspire me and have incredible cinematography. One of my favorite movies to rewatch is The Red Shoes. It’s about a ballet dancer who loves her art so much it kind of drives her to insanity. It’s stunning—the set decoration, the costumes, and the Technicolor are just gorgeous. All the reds and blues are extra saturated; it’s very cinematic and so fun.
I also love the old Barbara Stanwyck, Joan Crawford, and Bette Davis movies with really strong women. Recently, I saw Hamnet. Here’s a beauty tip: Don’t wear mascara to see Hamnet. I wore mascara and cried nonstop for two hours because Jessie Buckley is the most incredible thing I’ve ever seen. I was jaw-on-the-floor amazed. The last film I saw that hit me that way was Perfect Days from Japan. I kept going back to watch it.
Are there any books that you would recommend?
I always go back to certain ones from high school that I just always reread, like The Great Gatsby. I have my old copy of it that I keep together with a ribbon because I was reading it on the beach in Portugal, and the pages were literally falling apart. I love Salinger as well because I’m just eternally an angsty teen inside my head. I like Catcher in the Rye and Franny and Zooey.
Do you have a hot take?
Cold foam is just whipped cream. I’m not saying it’s bad—there’s no shade. It’s just that cold foam is basically a rebranding of whipped cream. I started going with my dad when he would go to Dunkin’ Donuts last year, and I was writing the book in Pennsylvania. He’d be like, Do you want cold foam? And I was like, What is that? It was whipped cream basically.
For me, the perfect drink is a café macchiato, taken at the bar. I put in a little dolcificante, which is like a tiny sugar pill that comes out of a dispenser in my house. It’s not the kind of fake sugar that causes cancer—or so Google tells me. I have it at the bar like four times a day. It’s quick, easy, fun, and a great way to learn Italian and see how people actually speak because you’re just hanging out at the bar. Italians have been drinking coffee like that for ages.
What’s something that living in Italy has imposed on you?
The best thing about living in Europe in general is the work culture. And this is coming from somebody who works for herself, by herself, walks her dogs, does whatever she wants. The fact that they take a long, nice lunch together—and they eat lunch together as an office—is amazing. They know how to be normal people, have fun conversations, be silly, and even have a glass of wine at lunch. When you do that, you can be more productive because you’re not going crazy, pulling your hair out, and super stressed.
The salad-at-your-desk culture—that’s nobody’s fault, but it’s just the culture we created—is psychotic. Italians have a really good work/life balance. People make fun of it, but it’s so much healthier. They take off the entire month of August. If you go to Milan in August, it’s legitimately scary—it’s a ghost town. Everyone goes to the sea, the mountains, Thailand—they travel. A lot of them are out of office by the end of July, and then they come back refreshed. The whole culture appreciates that. They’re much healthier this way. I really love that—I’ve learned a lot from it.
Is there a piece of advice you’re living by right now? Or, alternatively, the classic question of what advice would you give your younger self?
When you’re trusting your instincts and being true to yourself, you know when you’re kind of faking it to make somebody else happy or going into people-pleaser mode. I’ve done that, whether it’s been in relationships or working a job that didn’t feel right for me. And there was always that voice in the back of my head that was like, Is this… Jenny? That’s what I really wanted to show in the book as well—knowing yourself. I have another essay called “Mistakes Make Style” about how I hold my pen in a really weird way. In third grade, the teacher tried to rubber-band my hand to the pen to make me write “the right way.” But all of these little quirks make you who you are, and they’re reflected in your style as well.
I have another essay called “Perfect as a Prison.” I started off talking about how my dog, Aurora, the dachshund, is my favorite knitwear designer. I’ll go to bed wearing a sweater, get hot in the night, and take it off. Aurora went through a phase for months where she would chew holes in everything. It was so funny—like, you go into a Yohji or Comme des Garçons store and see a 1000-euro sweater with holes everywhere. There’s also an Italian idea that means “a little messed up.” Style should be a little bit messed up—it shouldn’t be perfect—and that’s what makes it unique. Even Prada last season, all the cuffs were really stained, and people were like, Ah…! But those things make style unique. Leaning into what makes you unique is always the right way to go. That’s the advice I would give my younger self: Trust yourself, and know it will all work out, even if it’s scary.
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