Jessica Simpson's Stylist Told Us the Secrets Behind Her Book Tour Looks

Longtime fans of the vocal powerhouse, fashion mogul, mother of three, and author know that Jessica Simpson has always been an open book. Therefore, it comes as no surprise that Open Book, Simpson’s recently released memoir, has struck a chord with anyone who came of age in the early oughts. For years, Simpson was everywhere—on the radio, on the MTV reality show Newlyweds, and, with the Jessica Simpson Collection, in department stores across the country—then suddenly she wasn’t. Simpson took a step back from the spotlight for a few years during which time she not only grew her fashion empire, but also nurtured her family and made time for serious reflection on her past, which she candidly chronicles in her memoir. 

To celebrate, Simpson has embarked on a five-city tour in celebration of Open Book, which also signals the start of a new chapter—consider it the second, third, or even fourth act for the multi-talented 39-year-old. In addition to lessons learned, she has also accumulated quite an impressive wardrobe, and she is taking pieces of it on the road, offering fans not only a peek inside her life but also into her well-curated closet. 

Thanks to close collaboration with her friend and longtime stylist Nicole Chavez, Simpson’s Open Book tour outfits (or #OpenBookLooks as they’ve been tagged) have been earning accolades on social media, with fans championing her on-point outfits and A+ execution of timeless staples and of-the-moment trends. We caught up with Chavez ahead of Simpson’s most recent stop in Dallas to get the scoop on the inspiration behind this slew of on-point outfits. Read on below for our Q&A, then shop a few of the pieces Simpson has worn recently.

You’ve been working with Jessica for a long time! When did you first meet? Do you remember the first event you styled her for?

We met in the mid-2000s through her sister, Ashlee, and then found out we had a lot of mutual friends. We were friends first, so I can’t remember what our first event together was, but she would call me sometimes for little jobs here and there in the beginning. There was a lot of stuff we would do on the side and some personal shopping, too. 

I remember doing the show Fashion Star with her and styling all of those looks. Plus, I styled her whole entire wedding! I think there were 13 bridesmaids, plus all the groomsmen, all the kids and grandparents—I styled over 40 people for the wedding. It was such a fun experience because Jess and I got to do it together. 

Now, press tours are a natural progression because we’ve been doing this kind of work together for ages. I like working on a lot of looks for one specific thing, like the wedding. I came from television and film, so it’s a lot like getting into character for a special project.

As Jessica’s career has evolved from pop singing sensation to fashion empress, mother of three, and now celebrated book author, what have been the biggest changes to her style? Is there anything in particular that has stayed the same since day one? 

Jessica’s style is truly her own, and that’s why she has such a successful empire. She’s always been really good about knowing what she loves to wear, what looks good on her, and what she’s comfortable in. She has her iconic looks like her oversize sunnies, bags, and high, high heels—those pieces have always been a thread throughout our process working together.

As a stylist, it’s really fun to work with someone who is so open, loves fashion, and is always up for everything. As a friend, I am so proud of her and this book, so I wanted this tour to be chic and strong and feel powerful but also feminine and true to who she is as an artist, mother, and all of those things. Jessica definitely had a vision for the tour in the sense of knowing that she wanted it to be more elevated, sophisticated, and strong, with very tailored suiting.

Jessica is pulling off so many great trends right now like animal print, matching sets, and jumpsuits. Are there any specific trends that you think work particularly well for her petite stature? Are there any trends that you’re avoiding because they aren’t a fit for either her personal style or her 5’3” frame?

Jessica has an hourglass figure and is also quite petite so I try to really create and elongate her silhouette as much as possible. She feels the most comfortable in really high platforms, which help add height. For the tour, I found the flare trousers and flare jeans which are her go-to—they work well because they elongate her legs and are super flattering. We also do a lot of strong shoulders, paired with a cinched waist for a look that is super tailored. I especially love the monochromatic looks she's worn lately because they're super elongating. And I always love head-to-toe black on a blonde as well. 

On a personal note, I’m 5’2.” Are there any specific brands you think are tailored to suit shorter women? Any styling tips for making someone look taller? Or do you recommend getting to know a good local tailor?

As a stylist working with anyone who is petite, tailoring is so essential to making everything fit the way that it should. Everyone should invest in a good tailor—find a nice local place where you can take your stuff—even the smallest little nips and tucks make a big difference.

What’s really cool about this specific tour is that when we started the process at the beginning of the New Year, we went through her closet first. She has an incredible archival closet full of amazing gems that she has collected over the years. We pulled out some amazing pieces and built the looks around those. A lot of what you’re seeing are special pieces to her that were gifts or carry a personal meaning, which is a nice tie into her memoir.

I love that so many of these outfits mix new and old pieces, so it’s championing the movement towards more sustainable fashion practices. We didn’t have to go buy 40+ new looks for the tour, but instead, we consciously decided to use what Jessica already had in her closet and update it. We used quite a few Alexander Vauthier pieces from her closet, which have a super strong shoulder, are fitted, very feminine, very strong.

I think people should be shopping their closets all the time! Choose pieces that you love, like statement pieces and accessories, and you can always build basics around them. For example, the Giambattista Valli jacket has been in her closet for a long time, and we easily repurposed it with a turtleneck and styled it with an updated flare instead of as it was shown with wide-leg pants. Changing silhouettes around basics updates everything. That's a great example of a classic but very Jessica look, so it was fun to go through some really great piece she had and reimagine them. That's also a great example of what I love about statement pieces: when you are investing in your wardrobe there are pieces like that which will never go out of style.

I really love the sustainability of this press tour. It’s really cool to re-wear and re-purpose your clothes, especially when you have a great eye, fantastic closet, and the clothes fit you perfectly. 

You and Jessica seem to be having a ton of fun creating outfits for the tour that not only look great but are also very social-media friendly with cheeky nods to Jessica’s early oughts roots. What made you decide to pay tribute to the iconic Elle Woods look from 2001 today, almost 20 years later? Were you more inspired by the character and her evolution, or that incredible Saks Potts coat? 

That outfit happened completely organically—we didn’t have a vision for a Legally Blonde tribute, but it’s fun that it worked out that way. The coat is her personal coat and we jumped off of that, again playing into the monochromatic story. Jessica can pull off anything—that look is so fun and has so much personality, it is so true to who Jessica's spirit is and her love for fashion. I embrace that she was open to something so bold. 

The Matrix-like trench is newer, but we styled it with some really solid basics so that it feels both timeless and really fresh and modern. That coat will probably live in her closet for a very long time—it’s super wearable.

Who are some other recognizable characters that might be on your vision board for Jessica’s book tour style? How do you take inspiration from something from a previous era and update it and translate it so it feels right and fresh for 2020?

As a friend I knew the book was coming, so I intuitively knew that this was the next phase in her life. She’s an author now, which is a different role that Jessica is playing. With this in mind, I envisioned her in this really elevated fashion editor role, with a very structured and powerful wardrobe. It was my own idea of how I was seeing her, so when I was pulling clothes from her closet and also shopping, those are the kinds of pieces that I kept gravitating towards.

In my mind, Jessica has always been a jeans kind of gal. From the low-rise flares of the ’00s to Daisy Dukes to today’s high-waisted and relaxed-fit jeans, she always looks good in denim. Do you and she have any go-to denim brands? What are your thoughts on bringing back the low-rise styles from 20 years ago? What is a great everyday pair of jeans that you think are timeless?

We recently found the most fantastic pair of Mother Denim flares that Jessica just wore with the Gucci blazer. They’re fantastic, really dark, dark black so they almost read as a pair of trousers. They flare and are a bit oversize, which we love to pair with a big platform shoe. Plus, they have a black button, which is something so simple but makes such a big difference. As a stylist, finding black jeans with black buttons is like discovering a unicorn.

We're also big fans of vintage Levi's. They take a little bit of time to find the perfect pair, but when you do, it’s so good and they are timeless and worth the investment. I also love the Khaite line right now and how its denim feels—it’s thick and strong and has a great fabrication.

As for bringing back the low-rise style, that's a tough trend for most body types. Like me, a lot of my clients are moms that are over 40, so we're not feeling "contained" by the low rise style. I'm still a fan of the mid- to high-rise denim style. Plus, a higher rise elongates curvy and petite figures. 

When it comes to style, obviously Jessica has her own point of view as a fashion entrepreneur. Is there ever a moment when she’s really into something but you’re not, or vise versa? Are there brands or designers you both agree on 100%?

I’ve been really really blessed in my career that all of the women I’ve worked with are very trusting and open to my guidance. When I say that I love a piece, Jessica will always try it on. It usually comes down to if the fit is not right or takes too many alterations, then it gets edited out. But she'll always try it on for me and we’ll either have a good laugh or find something else that's amazing.

It’s so worth taking the time to try pieces on because that's how you bring the look to life. I can also tell by the client's body language if they feel good in it. If they aren’t sure, I say take it off because to me it’s not worth it. I’m all about how their clients feel in their clothes because confidence shows.

Jessica is very down to earth but loves to get dressed up, which is a fun combo and allows me to pull a wide range of different things. She loves Gucci, so that's a big brand we always look at, but I never get locked into the same designers because from season to season, things change a lot. I always go in with a vision—I’ll see it, shop it, and pull it. I don’t really care about labels when I'm shopping, because I'm looking for specific silhouettes and things that I know will be flattering for a particular client. One brand we discovered for this tour is Safiyaa. We found it on Net-a-Porter, and it is seriously fantastic. That line has amazing fabrication and strong silhouettes, which were in line with our vision. Plus, everything we put on Jessica fit like a glove—that was a fun surprise—so we got those pants in every color.

Let’s talk accessories: so long micro-bags, hello giant sunglasses? It seems like Jessica has always been into oversized sunglasses and never got on board with the retro ‘90s trend. Are you picking out specific glasses to go with each outfit? Does Jessica have her own collection of shades that you have in rotation? What is it about the oversized Gucci glasses that just seem to work with everything?

Oversized accessories are two very iconic things for Jess, she just loves big sunglasses and a big bag—anything over the top feels little more glam. 

The micro-styles are not always flattering—same with a mini bag—what are you going to put in there? We did do some smaller bags on this tour, like the vintage Louis Vuitton on The View that she’s had for over 10 years. She is also going to carry the first Fendi bag she was ever given when the tour stops in Nashville. 

We didn’t buy any new glasses for this tour—even the pink ones were hers! The archive of fashion that this woman owns is insane—she really truly loves and appreciates fashion. 

What about shoes? I know Jessica can rock a high heel — do you and Jessica have any favorites from her eponymous shoe line currently in the mix? 

She’s definitely wearing a lot of Jessica Simpson collection platforms on this tour—she loves them and they’re really comfortable. She’s on her feet during every event, so comfort is key for her. At the Macy's event in New York City, Jessica these really beautiful silver and gold platforms that had a fun disco vibe.

Finally, Jessica’s latest looks just ooze confidence, femininity, and power. Given that she’s been behind-the-scenes for a minute, and a lot of what she shares in her memoir is super personal and revealing, what are some conscious style choices you’re making that speak to this latest chapter in her life?

It really comes down to working with a very tailored silhouette, cinching in the waist, elongating the legs, and monochromatic outfits. I feel like Jessica is such a fan of the animal print, leopard, tiger, snake. I know they’re on-trend but to me, they are neutral but also very powerful, feminine and sexy. They all play into what we’re doing right now. 

More of Jessica Simpson's Open Book Tour Looks

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