It was 2007. Oscar De La Hoya was the undisputed "Golden Boy" of boxing. He had the Olympic gold, the movie-star looks, and a reputation as a clean-cut hero in a sport that usually smells like sweat and cigar smoke. Then, the internet exploded.
A few blurry photos surfaced showing Oscar—the guy who fought Floyd Mayweather and Manny Pacquiao—wearing fishnet stockings, high heels, and a frilly skirt.
The Oscar De La Hoya dress photos didn't just trend; they fundamentally shifted how the world viewed one of the most powerful men in sports. For years, the narrative was that they were faked. Photoshopped. A malicious hit job. But as we’ve learned through Oscar’s own admissions in recent years, the truth is a lot messier, darker, and more human than a tabloid headline.
The Night Everything Changed
The photos were taken in a Ritz-Carlton hotel room in New York. At the time, Oscar was deep in a spiral of cocaine and alcohol addiction. He’s been very open lately about how he was "loaded" and barely remembers the night.
Basically, he was with a woman named Milana Dravnel, a former dancer. According to Oscar, he was in a state where he didn't even know who he was anymore. He was escaping the "Golden Boy" persona that he felt trapped by.
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Dravnel eventually sold those photos to a tabloid. When they hit the public, the denial machine kicked into high gear. Oscar’s team didn't just deny them; they went to war. They hired "forensic experts" to testify that the images were digitally altered. They claimed the proportions were off, that Oscar’s head had been pasted onto a woman’s body. Honestly, for a long time, people actually believed it.
The $20 Million Cover-Up
You’ve gotta realize how much was at stake. Oscar wasn't just a fighter; he was a brand. He had Golden Boy Promotions. He had massive sponsorships.
To keep the lid on the scandal, Oscar reportedly paid Milana Dravnel a staggering $20 million settlement. There were even wild stories involving the Russian mob and lawyers jumping into rooftop pools to check for wires. It sounds like something out of a Scorsese movie, but for Oscar, it was just another Tuesday trying to keep his image from crumbling.
He spent years lying. To his wife, to his fans, and mostly to himself.
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Coming Clean: The 2011 Admission
The facade finally cracked in 2011. During a sit-down with Univision, Oscar dropped the act. He admitted the photos were 100% real.
"I'm tired of lying," he said. He explained that the Oscar De La Hoya dress incident happened during the peak of his substance abuse. He wasn't doing it as a fashion statement or a publicity stunt. He was a man who had lost his identity and was looking for any way to act out.
- The Substance Factor: Oscar admitted to using cocaine and alcohol heavily during that period.
- The Identity Crisis: He felt he was "living someone else's dream" and the pressure to be perfect was suffocating.
- The Aftermath: Even after the admission, another scandal popped up in 2011 involving similar allegations from a model named Angelica Marie Cecora, though that case was eventually dismissed.
Why the "Dress" Still Follows Him
In 2026, we look at these things a bit differently. Today, a celebrity in a dress might be seen as "subverting gender norms" or "being brave." But in the mid-2000s boxing world? It was seen as the ultimate weakness.
The tragedy isn't that he wore women’s clothes; it’s the misery he was in when it happened. In his HBO documentary The Golden Boy, he revisits this era with a lot of regret. He talks about how he felt like a "robot" conditioned to fight since he was five years old.
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The photos weren't about the clothes. They were a cry for help from a guy who had everything on the outside and nothing on the inside.
What We Can Learn From the Scandal
Looking back, the way Oscar handled the Oscar De La Hoya dress controversy is a masterclass in how not to handle a PR crisis, but also a lesson in the power of eventual honesty.
- The Cover-Up is Always Worse: Spending $20 million to hide the truth didn't work. The photos stayed on the internet. They always do.
- Addiction Distorts Everything: You can’t judge someone’s "kinky" behavior without looking at the mental health crisis happening behind the scenes.
- Redemption is Possible: Despite the photos, Oscar remains one of the most successful promoters in history. He proved that a "scandal" doesn't have to be a death sentence if you eventually own it.
If you’re following Oscar today, you see a guy who is much more comfortable in his own skin—even if that skin is covered in tattoos and he's talking trash on Twitter. He stopped trying to be the perfect Golden Boy.
The best way to move past a situation like this isn't to buy someone's silence. It's to stop being afraid of what people think. Oscar eventually reached that point, but it took him a decade and a lot of money to get there. If you're facing your own "leaked photo" moment—metaphorically or literally—the fastest way out is usually through the truth, not a $20 million check.
Moving Forward
If you want to understand the full scope of Oscar's journey, watch the HBO documentary The Golden Boy. It provides the most raw, unfiltered look at his childhood trauma and how it led to the hotel room in New York. Understanding the "why" behind the photos changes how you see the man in the ring.
Focus on building an identity that doesn't rely on being "perfect." Perfection is a trap, and as Oscar De La Hoya proved, it's a very expensive one to maintain.