When Stephanie Seymour first entered the world of fashion, she had no idea that she wasn’t just going to be any old model. As Seymour electrified the photoshoots she attended and stomped her way down the runway, it became apparent to everyone that she was something special. How did Seymour go from everyday American girl to worldwide supermodel? Read on to find out!
1. She Started As A Normal Kid
Seymour’s childhood years stand in stark contrast to the turmoil of her later life. We know Stephanie Seymour for her sophisticated beauty, business smarts, and sense of humor, but you never would’ve known if you met her as a child! Born on July 23, 1968, in San Diego, California, Seymour was pretty much your average, everyday kid. As a middle child, Seymour didn’t particularly stand out from her siblings either.
However, when she grew older, it quickly became clear that Seymour was a special child indeed.
2. She Grew Into Her Looks
As Seymour grew into her teen years, it soon became that this awkward duckling was becoming a beautiful swan. To say Seymour grew into her features is an understatement; by the time she hit her teens, she was tall, slim, and had a smile that would make anyone swoon. Seymour wasn’t just a pretty face though; she knew that she could use her beauty to her advantage. And so, Seymour quickly turned her beauty into a precision weapon.
3. She Joined A Life-Changing Contest
In 1983, Elite Model Management held their first-ever Look of the Year modeling contest. Seymour immediately ceased her chance to use her natural beauty to her advantage; not only was it her chance to take the modeling world by storm, but the top prizes were enticing ones: the top three winners won modeling contracts ranging from $100,000 to $200,000.
She just needed to scrounge up a measly $15 entry fee, which turned into an unexpected challenge.
4. She Got A Bit Of Help
Like most teens, Seymour was flat broke, and like most teens, she went to her parents for help. Her dad, a real estate contractor, wasn’t exactly thrilled with the idea of his little girl entering a modeling contest, but her mother dearest secretly slipped Seymour the entry fee and encouraged her to join. The 14-year-old handed in her entry (she was just one out of 23,000 other entrants competing for a spot in the competition!), crossed her fingers, and waited…
5. She Became A Contender
With one fateful call, Stephanie Seymour’s entire life changed. Soon, she was informed that she made it into regionals. On September 16, the now 15-year-old Seymour, accompanied by her mother, joined the other throngs of hopeful models at the Grossmont Center in San Diego. Before they even got a chance to start the competition though, Seymour’s mother noticed a very particular-looking man in the crowd.
6. She Met Someone That Changed Her Life
This man’s name was John Casablancas, the head of Elite Model Management and the individual responsible for creating the contest. At first, Casablancas only had eyes for Seymour’s mother, but Seymour’s “long legs and cute little face” eventually caught his eye. His interest worked to Seymour’s advantage; Casablancas eventually chose Seymour as the regional winner.
Unfortunately, the rest of the contest didn’t go as Seymour hoped.
7. She Faced Stiff Competition
The next, and final phase of the contest took Seymour to Acapulco, and winning wouldn’t be easy. On top of looking good, Seymour needed to be photogenic, be able to rock current fashion trends, and have a winning personality. After competing with many other young girls (including Cindy Crawford), Seymour fell short of the win.
It must’ve been gut-wrenching for the young teen, but it wasn’t a total loss for her.
8. She Never Gave Up
After losing the contest, Seymour returned to San Diego, but the intrepid young teen refused to let the fashion world forget her. She began regularly writing letters to Casablancas, full of silly drawings and riddles. In response, Casablancas hand-wrote letters back to her, urging Seymour to join Elite as soon as possible. Seymour didn’t take him up on the offer right away, however.
In many ways, Seymour’s career as a model was already beginning in San Diego.
9. Her Career Officially Began
Although Seymour didn’t come out on top, the contest got her noticed. Local newspapers and department stores rushed to offer Seymour various jobs, giving the young teen her start in modeling. It wasn’t quite as glamorous as being on the cover of Vogue, but it wasn’t too shabby for a beginner either! However, Seymour wasn’t content with these small-time jobs.
Seymour wanted more, and soon, she got her chance.
10. She Got The Chance Of A Lifetime
In June 1984, Casablancas suggested that Seymour fly over to Paris for a summer of fashion and modeling. Of course, Seymour’s answer was a resounding “Yes!” After convincing her dad that this was a great idea (with a little help from her mom, who once aspired to be a model), Seymour packed her bags and hopped on a plane to the City of Love.
It was everything that Seymour thought it would be, and more.
11. She Got A Taste Of Luxury
In Paris, fashion insiders pampered, fussed over, and wined and dined Seymour—in short, it was everything that Seymour could dream of, but there was more to come. Casablancas managed to convince an Italian fashion editor to fly Seymour over to Rome for the fashion collections. All too soon, Seymour needed to leave the lights and sights of Europe behind.
She returned to San Diego, and she wasn’t exactly happy about it.
12. She Couldn’t Go Back To “Normal”
How did Seymour adjust to being thrust back into her quiet life in San Diego after experiencing the highs of the fashion world in Paris and Rome? Long story short: Not well. Seymour was constantly restless and yearned to get back into modeling. Seymour just couldn’t stand being trapped in a classroom anymore, so when Casablancas reached out to her again later that fall, she left San Diego, and she never turned back.
13. His Had A Hidden Agenda
Casablancas wanted Seymour to attend that year’s Look of the Year contest as a spectator, but it soon became apparent that his reasons for inviting her were much more sinister. According to someone who attended the contest, Casablancas spent the contest “…fawning over [Seymour] and flirting with her mother.” Something forbidden was blooming between Seymour and Casablancas, and it soon turned Seymour’s world on its head.
14. He Completely Won Her Over
Eventually, Seymour persuaded her mother and father that modeling was her dream career, and they gave her permission to study and work in New York. She moved into an apartment on the East Side, where other young models also lived. Who else happened to live nearby? None other than Casablancas. He began inviting her out for dinners, but it wasn’t long before the dinners turned into something more.
15. Their Relationship Was Problematic
According to Seymour, the relationship between herself and Casablancas “just kind of happened.” She found him attractive and completely charming, but that wasn’t the issue with the relationship. At the time, Casablancas was 42, and Seymour was only 16; the age gap was huge! This was bad enough on its own, and more than enough to raise a couple of eyebrows—but wait; it gets so much worse.
16. Her Love Came With Baggage
While Casablancas was publicly wooing the teenager, he was hiding an even darker secret. You know how we mentioned that Casablancas lived near Seymour? Well, guess who else lived near Seymour? Casablancas’s wife, Jeanette Christiansen, and his kid. Yep, Casablancas was already married (since 1979 in fact!). All in all, this was not a good look for Seymour or Casablancas, and plenty of people made their concerns about the relationship clear to young Stephanie Seymour.
17. She Worried Her Family
In the fall of 1985, Seymour knew she couldn’t hide her relationship with Casablancas any longer. She broke the news about her relationship to her mom and dad, and her dad’s reaction was an unexpected and chilling one. He didn’t get angry or even yell at her; instead, he quietly suggested that she might just be making a mistake.
Unconvinced, Seymour insisted Casablancas was worth the risk—and she would do anything to prove her dad wrong.
18. He Charmed Her Family
On Thanksgiving, Seymour’s new beau flew over to meet her dad and did everything he could to prove himself. He cooked meals for the family for three days, and played basketball and tennis with Seymour’s brother and father. He completely won Seymour’s dad over—but what Seymour had to say about that time was chilling. She claimed that, in hindsight, Casablancas “brainwashed” them.
Not knowing any better, Seymour went full-steam ahead with her new relationship, which, to be fair, had its fair share of perks.
19. She Achieved Her Dream
To the surprise of no one, Seymour began working as a model for Elite. Thanks to her new boyfriend, Seymour received a plethora of tips, tricks, and insider knowledge on how to navigate the industry, smoothing her path to stardom. They eventually moved in together in an apartment on 57th Street, and mostly lived a normal life (for a model). Under the surface, however, things between them were not quite what they seemed.
20. Their Love Had A Dark Side
Seymour’s new beau didn’t exactly describe Seymour in the most flattering light. During an interview in New York magazine, Casablancas described Seymour as a “woman-child… her voice is a child’s, her attitudes, the way she holds her feet and her hands are those of a child, at the same time with an incredible sensuality to it.” It’s enough to leave anyone with a sinking feeling, and when the public found out about their relationship, they were less than kind.
21. The Press Attacked Her
When the press discovered the relationship between Seymour and Casablancas, the gossip columnists kicked into high gear. The New York Post ran an article about Seymour and Casablancas (which Seymour thought was “tacky”). Disturbingly, most were relatively unfazed by Casablanca’s “lifestyle choice,” but many commented on Seymour’s young age.
Still, Seymour wasn’t going to let that stop her—she was going to prove those articles wrong.
22. She Did It All For Love
Poor Seymour endured the gossip that came at her from all corners. During public business meetings, Seymour made a point of joining Casablancas, despite her discomfort with the stares and whispers. However, as the months passed, Seymour (now 17 years old), began needing Casablancas less and less. All too soon, the truth became clear.
23. She Stopped Needing Him
After two years of staying with Casablancas, Seymour’s love started to fizzle. She began spending more time with friends around her age, and eventually felt like she had (ironically) outgrown her relationship with Casablancas. Seymour broke off their relationship, moved out, and began living with another model in the East Village. It was time to start anew, but that’s not to say that her time spent with Casablancas was completely wasted.
24. She Got Noticed
Thanks to Casablancas’s guidance, Seymour had a pretty good handle on the industry. This, combined with her good looks and skill in front of the camera, rocketed the young lady to fame. In the late 1980s, Seymour appeared on the cover of Sports Illustrated Swimsuit Issue for the first time, accelerating her journey into becoming a fashion icon. After this, her next career move cemented Seymour as a bonafide supermodel.
25. She Became A Star
In 1988, Seymour got the chance to grace the cover of American Vogue. That was already spectacular on its own, but it was the photographer shooting her photos that really got Seymour excited. Seymour’s photographer was Richard Avedon, whose skill behind the camera rocketed several models to fame. The attention Seymour got after her photoshoot was unreal—and it had an unexpected side effect.
It caught the attention of her next love.
26. She Met A New Love
In 1989, Seymour married a guitarist named Tommy Andrews. Sadly, “happily ever after” eluded the model; just one year later, the two divorced, quickly ending the relationship. It wasn’t all bad news though: Seymour’s relationship resulted in her first child, a son named Dylan Thomas Andrews. Having a child may slow some people down, but Seymour barely skipped a beat; she kept on going, and someone became even more famous.
27. She Became A Household Name
By now, Seymour had appeared on the cover of Vogue in addition to Sports Illustrated Swimsuit Issue, and she even walked the runway for the likes of Karl Lagerfeld and Gianni Versace. Those achievements were just the tip of the iceberg; starting in the late 1980s, Seymour posed for Victoria’s Secret, advertising for their hosiery and lingerie lines. Seymour was riding high, and she was about to soar even higher.
28. She Bared It All
In March 1991, Seymour posed for the infamous Playboy magazine. For Seymour, posing for Playboy helped her to realize the power she had as a supermodel, role model, and icon. According to fellow supermodel Christy Turlington, being in Playboy helped the two see how they were “… making tons and tons of money for these companies.”
With so much power at her fingertips, it’s no wonder that Seymour’s relationships became increasingly high-profile.
29. Her Relationships Were Complicated
A few months after her debut in Playboy, Seymour met and began a relationship with famed singer Axl Rose. Unlike her previous two relationships, Seymour’s relationship with Rose was very public, very high-profile—and very, very tumultuous. The fact that Seymour’s new boyfriend had a bit of a troubled history certainly didn’t help, but at first, all seemed well between Seymour and Rose.
30. He Loved Her Son
As their relationship progressed, Rose became deeply fond of Seymour’s son, Dylan. Having never had a good father figure in his life, Rose became determined to be a good role model for Seymour’s son, which probably delighted Seymour to no end. Rose’s love for Seymour and her son, along with the perfect melding of their professional lives, only made the end of their relationship all the more devastating.
31. She Dabbled In Acting
There’s no doubt that Seymour and Rose didn’t feel the need to hide their relationship—in fact, their relationship seeped into their professional lives. Seymour appeared in two of Rose’s music videos for Guns N’ Roses, “Don’t Cry” and “November Rain,” where she acted as Rose’s significant other. The music videos were elaborate too: the “November Rain” music video is one of the most expensive music videos ever shot!
It’s not surprising that Seymour quickly took their relationship further.
32. Their Relationship Took An Awful Turn
In February of 1993, Stephanie Seymour and Axl Rose became engaged. For many, this was a time for celebration—but it quickly spiraled into a nightmare. Three weeks later, Seymour and Rose broke off the engagement, effectively ending the relationship. The reason for the split isn’t exactly clear (although Rolling Stones noted that the split was an “ugly” one), but the aftermath of the separation made it obvious that the two didn’t end things on good terms.
33. He Went After Her
In August 1993, Seymour received some shocking news. Rose, her now ex-finacé, wanted to sue her. Rose accused Seymour of not only physically attacking him, but he also accused her of trying to walk away with $100,000 worth of jewelry. Shocked, Seymour denied his allegations—but that wasn’t all she did. She wasn’t about to let Rose walk all over her, so she did what she thought she had to do: she swung back with accusations of her own.
34. She Fought Back
According to Seymour, Rose physically lashed out at her during their relationship—and she had proof. Seymour subpoenaed Rose’s ex-wife, Erin Everly, to testify that Rose had attacked her during their relationship. The court situation probably turned nasty pretty quickly; at the very least, it got ugly enough that Seymour and Rose eventually settled things out-of-court.
Seymour found a new love shortly after, but this relationship wasn’t any less dramatic.
35. The Runway Terrified Her
Being a supermodel meant captivating your audience both in photos and on the runway. While Seymour was a natural in front of the camera, being on the runway was a whole other story. According to Seymour, “I used to be booked for every show in New York and cancel the day before, because I’d have panic attacks.” It just goes to show that everyone starts somewhere, and it helped that Seymour’s supporters gave her a ton of incentive to overcome her fear.
36. They Convinced Her To Face Her Fears
How exactly did Seymour finally conquer her fears? It came down to experience… and a fat paycheck. As Seymour put it, “Gianni [Versace] would offer you so much money that you couldn’t say no.” After getting over her initial fears, Seymour began to rock the runway in no time flat, making her one of the most sought-after runway models of her day. While she no longer takes on quite as many jobs as she once did, she still managed to leave her mark.
37. She Had A Father Figure
One of the first people who really saw Seymour’s potential was the famed Paris couturier, Azzedine Alaïa. In an interview with Vanity Fair, Seymour revealed that “I had this kind of bubbly rear end, and for [Alaïa’s] clothes, it worked.” From there, Alaïa introduced her to various photographers, clothed her, and became something of a father figure to her.
Thanks to people like Alaïa, Seymour came to be a household name.
38. He Swept Her Off Her Feet
Barely any time passed since the end of Seymour’s relationship with Rose before she publicly began dating a man named Peter Brant, a real estate developer, publisher, and art collector. But there was one big, awkward problem. Brant happened to be married and was already the father of five children. Needless to say, Seymour’s relationship with Brant was just a tiny bit complicated, and what happened next only made it more so.
39. She Had A Son
On December 30, 1993, just before New Year’s Eve, Seymour gave birth to their son, Peter Brant II. While this was a happy occasion, the fact that Seymour’s husband was still married to someone else probably threw a wrench into things. Still, Brant was the calming presence she needed, and the family—Seymour, Brant, Dylan, and baby Peter—grew close.
To Seymour, it was clear that she and Brant needed to take things to the next level.
40. She Finally Got Hitched
In 1995, Brant filed for divorce, allowing Seymour to finally marry him. On July 14, 1995, Seymour tied the knot with Brant just outside of Paris and even gave birth to another son named Harry Joseph just one year later. They settled into a 300-acre estate, where Seymour and her new family maintained a polo field, collected fine art, and housed 50 ponies.
Seymour’s life was definitely glamorous, and it only made her more alluring on the runway.
41. She Received Her Wings
The same year Seymour married Brant, the supermodel finally got the chance to rep Victoria’s Secret on the runway. Two years later, Seymour finally got one of the most coveted titles in the fashion world: Victoria’s Secret named Seymour a Victoria’s Secret Angel. The title put her in the same league as the likes of Kate Moss, Naomi Campbell, and Cindy Crawford, but that wasn’t all. Seymour didn’t confine her success to just the fashion world.
42. She Hit The Silver Screen
In 2000, Seymour got the chance to try something a little different than what she usually dabbled in: acting. She appeared in the movie Pollock, a biographical film about the life of painter Jackson Pollock. For an art enthusiast like Seymour, this was a dream come true, and it even gave her a chance to act in a Law and Order episode two years later. Soon, even the rest of her family got in on the fun.
43. Fashion Ran In Her Family
After giving birth to a daughter named Lily Margaret in 2004, Seymour collaborated with Gap for a very special session in 2006. Seymour, along with her four kids, participated in an ad campaign for Gap, which sparked Peter and Harry’s love for modeling. For Seymour, being able to share her passion for fashion was a joy, but her life wasn’t without its problems. In 2009, Seymour’s marriage hit a major road bump.
44. Her Relationship Took A Turn For the Worst
After nearly 14 years of marriage, Seymour filed for divorce in March 2009. This divorce wouldn’t be a simple one, however. Both Seymour and Brant brought home millions in revenue, owned several homes, and, of course, needed to sort out custody of their four children. Unsurprisingly, the divorce proceedings got ugly fast, with Seymour and Brant doing everything they could to sling mud at each other’s reputations.
45. They Came Out Swinging
Seymour’s high-profile divorce with Brant resulted in thousands of heart-wrenching and horrific court documents. In May 2009, Brant demanded that Seymour undergo treatments for substance addiction, while Seymour claimed that Brant tracked her by placing a GPS unit underneath her car. Seymour demanded that the court throw Brant out of the house for engaging in “intimidating behavior” towards her. One month later, the proceedings got nastier.
46. She Ran Into Trouble
In June 2009, a security guard hired by Brant shoved Seymour into a door during an altercation. According to the guard, he was showing up for his first day of work when Seymour suddenly grabbed his resume out of his hand. The authorities charged the hired guard, and the court threw out the case he attempted to open against Seymour. All in all, the divorce case was becoming a complete mess, but Seymour’s next move surprised them all.
47. She Ended Things Once And For All
In 2010, Seymour shocked gossip columnists and newspaper reporters alike with an unexpected revelation. She released a joint statement with Brant, announcing their reconciliation. The two appeared hand-in-hand when they announced their decision, ending the year-long feud and turmoil that ruled over Seymour’s life for the past year.
Their reconciliation came at just the right time, because they needed each other when tragedy struck Seymour and her family.
48. Her Family Was In Trouble
In public, Seymour’s youngest son, Harry, led a life that was just as glamorous as her own, but it came with a dark side. Just like Seymour, Harry became a model and socialite, and led the perfect life in public; in private though, Seymour’s son was struggling with addiction. Seymour’s son soon realized that he needed help, but that realization came too little, too late.
The consequences for both him and Seymour were devastating.
49. She Lost Her Son
On January 17, 2021, Seymour lost her 24-year-old son to an overdose. Seymour and the rest of her family were absolutely heartbroken at his passing, especially at such a young age. According to Seymour and her family, “He achieved a lot in his 24 years, but we will never get the chance to see how much more Harry could have become.” Since then, Seymour keeps a relatively low profile, but her legacy still resonates throughout the fashion world.
50. He Sang A Sinister Song For Her
What do Stephanie Seymour, Axl Rose, and the infamous Charles Manson have in common? It’s Manson’s song, “Look At Your Game, Girl.” The song, which a critic once said was “an eerily accurate picture of the methods [Mason] used to manipulate the members of his cult,” was covered by Rose, who intended it to be a personal message to Seymour after they broke up. Major yikes!
Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17