That’s me on the right (chatting with Sally Albemarle and Francisco Costa), wearing a Tuleh gown at a Guggenheim benefit honoring Azzedine Alaïa, 2004.
Every single day I was at Tuleh was an invitation to act out some fantasy about myself. Josh and Bryan loved seeing me arrive in the studio wearing the clothes that they had designed but that I had styled to create my own look. One dress was made of red silk printed with black and white stars. I showed up at Aerin Lauder’s son’s birthday party wearing it with black point d’esprit stockings and black leather Manolo Blahnik pumps with a white grosgrain ribbon on the toe, and red lipstick to match the dress. To Anh Duong’s art opening, I wore a pair of purple floral-print cotton men’s tailored trousers with a feminine puff-sleeve blouse that had sequined lilacs all over it. As if that weren’t enough of an outfit, I put on my vintage purple silk YSL pumps with a giant bow on the toe. Karma must have wanted to bring me down a notch, though, because my pants split right down the middle of my butt halfway through the evening.
Tuleh was both an ideal job and style inspiration for three thrilling years, but I grew tired of expending so much of my creative energy with no salary in return. The company had grown a lot while I was there, but there was always a reason why they couldn’t afford to pay me even half the salary I’d been earning at Hogan. So, after a period of heartbreak and coming to terms with my disappointment, we eventually parted ways.
• • •
At this point I was turning thirty, and as I reflected back on my twenties, I was anxious to make sense of where I had started and where I was then, both in terms of my style and my career. I was dedicated to fashion and I was making headway. I had learned an awful lot, but had had a string of one- and two-year jobs that all seemed to lead to something else or arrive at a dead end. I was tired of being someone new all the time, and with the birth of my second child, I didn’t have the energy to invent new looks or dedicate my workday to a project I wasn’t passionate about. What I felt confident in, however, was how much I had come to know about myself through the clothes I had worn, and how valuable the cumulative experiences and relationships I had created for myself in fashion, photography, and the art world were to my future career plans, whatever they might be.
No one makes simple, classic clothes look so chic!
STYLE INFLUENCE
SOFIA COPPOLA
IF I COULD pick one person to swap wardrobes with, it would be Sofia. Her style is a balanced combination of evolved good taste, refined simplicity, classic chic, with just a tiny bit of trend thrown in. I can’t imagine she ever looks back at outfits she has worn in the past and asks herself, What was I thinking? Often when I need a quick break from my work, I Google Sofia so I can save and file her latest outfits. (Yes, I am a bit of a cyberstalker when it comes to her.) Or sometimes I look through my saved Sofia files—black dresses, NYC apartment, flowers, hotel in Italy, Louis Vuitton bag, nineties style, L.A. house—just to give myself a high sartorial bar to aspire to. She may just be my favorite of all style setters.
Amy in chic fashion-editor mode.
STYLE INFLUENCE
AMY ASTLEY
AMY IS the editor in chief of Teen Vogue and has held that position as long as we have been friends, which is now more than a decade. Before I knew Amy well, I always admired her glamorous and well-defined personal style, but I didn’t get to really know her until we became summer neighbors. When I first visited Amy at her beach house in Long Island, I was so impressed and relieved that the house wasn’t all “editor-in-chief-ified.” Don’t get me wrong—her house was awesome, charming and super-stylish, but it was relatable, too. Her outside furniture was a bit rusty (as is mine), she had her toddler’s crib in the living room, and she herself was casually dressed in a batik Gap sundress. Amy’s casual and laid-back lifestyle outside of fashion gave me confidence in embracing the reality of my own.
When we go to a picnic at the beach, which we often do, we make our sandwiches, schlep our beach chairs, and read the Sunday paper while our kids play in the sand and chase one another into the ocean. I’ve got on my $50 Rainbow flip-flops and my J.Crew shorts, and Amy is wearing her daughter’s tie-dye shirt from American Eagle with the same Gap sundress, now worn as a skirt. Once Amy brought a Prada beach bag that she’d gotten at a sample sale—it had the most gorgeous orange crocodile trim on it—and we came back from a walk to see that the tide had soaked all our belongings. “That is the last time I try to be chic at the beach!” she declared. That’s what I love about Amy’s style—it inspires me to know when it’s time to be chic and when it’s time to be real.
I have asked Amy about her fashion philosophy and I always keep in mind what she said. She explained to me that, as a person, she feels open and approachable and she wants her clothes to reflect that whether she’s at the beach or in the front row of a fashion show.
“The last thing I want my style to say is ‘Fashion person: Stand back!’” says Amy.
Amy and her daughter Ingrid visiting me in the Adirondacks. I love Amy’s Stephen Sprouse for Louis Vuitton scarf worn with a nineties L.L. Bean anorak!
My son, Zach, and I modeling for Tod’s in a photo by one of my heroes, Elliott Erwitt. I organized the shoot as one of my consulting projects for the Della Valles and was thrilled to be featured in it as well.
MISTAKES ARE OKAY, AS LONG AS YOU LEARN FROM THEM
MY FIRST BIG career failure happened while I was creative director of Hogan. Creative director is a big title for a twenty-five-year-old. I’m still not sure how I got it. It may simply have been because I had the nerve to ask for it. What happened was, I was at Fekkai, and when the first collection of bags I had worked on came out, they received a good deal of press from fashion magazines, and Emanuele Della Valle took notice. Emanuele is the son of Diego Della Valle, owner of Tod’s and Hogan, and he was managing the U.S. side of the Hogan business. After following what I did for another season, he called me in for an interview. We chatted and he consequently proposed that I work with the design team on expanding the collection to better suit the American market, and also, with my photography background, work on putting together the team (photographer, stylist, set designer, art director, hair, makeup) for the ad campaigns. At twenty-four, Emanuele had just about as much experience as I had (meaning an impressive amount for our age, but still not much), and together we confidently moved in the direction of our ambition.
On average I spent a week each month in Italy at the leather factory, working with the design team on new products and future collections, sometimes seeing evidence of my ideas in the collection, and other times not. Sometimes I would leave Italy thinking I had finally made some headway, and then I would return again weeks later to see that many of the changes I had requested had been ignored and progress I had made had been changed according to the design team’s liking. Other times, I would return to the factory to see an idea I had that had come to life just as I had imagined it. I would wonder aloud how the bag might look with a different color stitching or with shorter handles, and the bag would be whisked off to the factory and returned just moments later with the changes I had requested completed. That aspect of the design process was immensely satisfying.
On the advertising front, however, I had vastly more weight and influence. Diego had entrusted Emanuele and me to conceptualize, produce, and execute the Hogan ad campaign from New York, something he rarely allowed. Diego was so personally and professionally invested in the ads (I would be, too, if all that money was coming from me!) that he usually never let the ad campaign be shot too far away from his command central in Milan. But Emanuele was his son, and so I think he was trying to give him some independence.
Everything had come together so well. We hired a fashion dream team, including photographer Nathaniel Goldberg and stylist Emmanuelle Alt (now the editor in chief of French Vogue) and models Karolina Kurkova and Raquel Zimmermann (then at the very start of their careers), and
we chose an inspired location—the world-famous but out-of-commission Eero Saarinen–designed terminal at JFK. Because the Hogan collection was based around sneakers and an active lifestyle, we thought the idea of travel fit perfectly into the concept of the brand.
The day before the shoot, Emanuele and I were feeling excited and confident. We had a great idea in place, and after careful planning and research had hired an excellent team to execute it. Clothes were packed, models were hired, access permissions were granted. All that was left to do that afternoon was to walk through the actual terminal with the photographer and the production company to figure out where each shot would take place. Susan, the production head, had arrived before us and came to greet us with a grim expression on her face. “The place isn’t in great condition.” It was in that precise moment that the entire shoot fell apart. Enthusiastic as we all were that it would be fine, the truth was that the whole terminal was made from white tiles that were dirty and cracked. If you shot from a distance, it would have been okay, but we were shooting shoes—up close!—and the place just wasn’t up to par for a close-up. I tried so hard to convince everyone that surely we could just retouch the flaws, but in the end the producer and the photographer put their collective foot down. It wasn’t gonna work.
At this point, everyone was on a plane or in some sort of transit, day rates were guaranteed, and the shoot was confirmed. We were having the shoot whether we wanted to or not. So we settled for a much newer but far less stylish terminal at JFK. I was both crushed and scared, and Emanuele was rightfully pissed off the whole day of the shoot. We both knew right away that it wasn’t what we’d envisioned. It wasn’t a strong or graphic enough background for the concept we had imagined, and no amount of styling or clever camera angles was going to fix it. The mood on the set was gloomy—everyone was acutely aware of things not going as we all had hoped and apprehensive about the part each of us had played in that. I was sure I would be fired immediately once word got back to Milan. I kept reassuring myself with thoughts of all the people I had known who had been dismissed from their jobs and went on to be successful in other capacities.
In the end, the ad campaign was thrown in the trash, wasting hundreds of thousands of dollars. But by some miracle, I was spared. The production manager was blamed for not discovering the sad state of the terminal sooner, the art director was dismissed for not thinking up a miraculous solution, and the ad campaign duties were handed back to Italy. I felt so much better when I learned that this wasn’t the first or last time Diego had chucked out an ad campaign regardless of the talent he had entrusted it to. But still—the pictures weren’t good and it had happened on my watch. While I finished out the year of my contract contributing ideas for design and advertising, I never felt very effective in my job at Hogan. I did feel like I had a lot to offer, but it was clear to everyone involved that the way my job was set up wasn’t working.
After a year, we agreed that I would be a consultant to the company, and this arrangement worked infinitely better. In fact, working with the Della Valles in subsequent years—at Hogan, Tod’s, and Roger Vivier—would be one of the most satisfying experiences I had in my time as a consultant. Among the highlights was getting to work with my old friend Bruno Frisoni, who had since become creative director of Roger Vivier, and doing a projet and then a whole ad campaign for Tod’s with one of my photography heroes, Elliot Erwitt.
Diego is an incredibly focused and creative businessman, and his story as the son of an Italian cobbler who became the eventual owner of an entire empire is one of fashion’s greatest success stories. I have also been inspired by Emanuele’s cultural curiosity and appreciation of Americana. As an Italian he sees American life and style with completely fresh eyes and gives me a new way of seeing things I may have dismissed as being too familiar. In his own career path, he has gone on to revolutionize how we interact with fashion in digital media. I continued consulting for Emanuele and Diego on and off for many years, successfully and happily, and I consider it a real achievement that we were able to eventually find a formula for working together that made sense for all of us.
Emanuele and I can now laugh about our disastrous time together at Hogan. It’s so easy to see now that we were handed too much responsibility too quickly. But God, it felt so terrible at the time. I felt powerless and pathetic. And I was scared all the time—scared of failure, scared of being fired, scared of being blamed.
The experience of my Hogan disaster made me understand the importance of communication, working relationships, and company structure in a way that I hadn’t before. In future working arrangements I would spend hours with my lawyer before agreeing to anything, making sure that my potential employer and I both understood each other’s expectations, requirements, and working style. This habit of up-front understanding has never failed me since.
My T. Anthony luggage, Céline bag, and Chanel jacket at the airport in Milan.
FASHION LESSON NO. 4
PACKING FASHION
THE FIRST time I went to Milan for fashion week was when I was working at Hogan, age twenty-five. I had to pack ten days’ and evenings’ worth of great outfits. As I worked for a designer, I wouldn’t be going to other designers’ shows, but I would attend all the presentations and events hosted by Hogan and their parent company, Tod’s, and I would have endless breakfasts, lunches, and dinners with fashion editors from both American and foreign magazines and newspapers. Because Hogan is an accessories company, the outfits I chose were based around the various shoes I wanted to make sure editors saw me wearing. It being Hogan, I had a variety of “fashion sneakers” packed, as well as a pair of fur-covered boots, a wedge-heel “secretary” loafer, and purple snakeskin pumps from Tod’s. I also packed a half dozen handbags—some sporty totes from Hogan and some more refined shoulder bags and clutches from Tod’s. Then, of course, there were all the trousers, sweaters, dresses, skirts, and coats that went with the all-important accessories. I didn’t plan—I just selected from my closet everything I thought I might need that week and threw it in two oversize wheelie bags.
I knew I was in trouble as soon as I was leaving my apartment. If you can’t even get from your front door to a taxi unassisted, then you know your traveling experience is going to be a nightmare. Collecting my bags and going through customs in Milan was the worst. The bags were too big to fit on one trolley and so I dragged them both behind me on their wheels, one in each hand, and did my best to steer them both in the same direction at once. It took hours to unpack at the hotel, and most of my beautiful handbags had been crushed by the journey. Of course I didn’t even end up wearing half of what I’d packed during the trip. I can look back now and see that I was nervous, wanting so much to look and feel good, and wanting to be prepared. I can also see that packing like that is not the way to feel prepared, secure, or more relaxed.
After that trip, I made some rules that I have lived by ever since. These rules have gotten me through vacations, weekend stays, work trips, and, most notably, seventeen days of business travel through Milan and Paris, going to nonstop fashion shows, cocktail parties, and meetings feeling well dressed, organized, and at ease in the airport (well, as much as you can be). Here they are:
1. Lay out a few things you are most excited to take with you. Your favorite new dress, your chicest coat, your go-everywhere blouse, the shoes you bought last week . . .
2. Come up with a color story around these pieces. Does everything go with black shoes? Are you packing mostly neutrals? Or is it a colorblocking moment?
If I am going on a short trip, I will limit myself to two pairs of shoes in the same color—flats and heels. Then I choose a bag that coordinates with the shoes, and maybe a clutch for the evening.
On longer trips, I will pack two or three accessory “color stories” (and usually neutral, like brown or black), but no more than that. Limiting accessories by sticking to this principle makes a huge difference in packing. Accessories ar
e heavy, take up space, and often get scuffed or misshapen in your bag.
3. Layer in the more useful items—camisoles, tights, sweaters, cardigans—based on what you will need to wear with the favorite pieces you have chosen in step 1. I usually lay all this out on my bed so I can see how everything is coming together.
4. Then put everything in the suitcase you intend to travel with. Pack your toiletries, your computer chargers, your socks and undies, your exercise gear, and then when all of that is in, if you have more space, pack one or two things that weren’t priorities but still work within your color story. I might pack an extra coat I didn’t think I had room for, or a few more skirts.
5. Never take more than one main suitcase with you when you travel, unless you are going away for more than three weeks. And if you are away for only a week, just take a carry-on (easier in summer than in winter). Your mental health will thank you for it.
Some people make all their outfits in advance and take Polaroids of them when traveling. This takes the fun and spontaneity out of getting dressed for me. Even when traveling I still like to feel that nervous energy of not knowing what I am going to wear in the morning. I find that if I think some outfits through in my head, plan my general color stories, and include the crucial things I need and/or want to take, mixed in with some practical and versatile basics, then I am set to travel stress free and in style.
Always Pack a Party Dress: And Other Lessons Learned From a (Half) Life in Fashion Page 9
