One of These Winona Ryder’s Oscars Dresses Is $10: She Wears Clothes until They Fall Apart & Was Caught Shoplifting Once

• Hollywood icon Winona Ryder grew up in a family that did not have a lot of money, and as a kid, she was bullied over her appearance.
• She became a star and got arrested in her early 30s for shoplifting.
• Today, despite achieving wealth from her illustrious career, Ryder re-wears inexpensive clothes until they fall apart, including a 32-year-old Tom Waits T-shirt and dresses worth $10 she wore at the Oscars.

Before becoming a big star in Hollywood, Winona Ryder, 51, was born in a small town that shares her namesake, Winona, Minnesota, in 1971. She grew up in a commune located just outside of San Francisco with her writer parents.

Ryder's family did not have much money, although the star reveals that her parents compensated where they lacked financially with love. During a past interview, she recalled how her father would do his best to turn what little they had into something exciting.

Far from being ashamed or wishing for a different childhood, Ryder asserts that she would not trade her parents for the world. She emphatically stated that her parents are her best friends and said she would choose them all over again had she not been born to them.

As an adolescent, Ryder experienced being bullied by her peers at school. She detailed how girls in her eighth-grade class would call her weird and throw Cheetos at her because she wore her hair in a crew-cut style and liked the rock band, Sex Pistols.

By the time she reached her 20s, Ryder's mental health took a turn for the worse when she started experiencing paralyzing anxiety attacks and had a brief stay in a psychiatric ward. A decade later, she admitted to still struggling:

"My early thirties were rough. I went through stuff that I would have gone through, and probably should have gone through much younger, but I had spent my twenties working."

Winona Ryder Was Caught Shoplifting in Her Early 30s after Becoming a Successful Actress

When Ryder refers to the tough times she went through in the past, one incident which saw her having a run-in with the law was when the "Girl, Interrupted" star shoplifted from a clothing store.

One day, Ryder, who was in her early 30s at the time, was at an expensive store in Beverly Hills when she got busted for shoplifting $5,000 worth of clothes, hair accessories, and a purse.

Police also charged her with the illegal possession of anti-depressants, as she had no prescription for the medication. Ryder sat in custody for approximately four hours before being released on bail set at $20,000.

When police apprehended the actress charged with a grand felony, they described Ryder as cooperative, kind, friendly, and ladylike. Surveillance footage from the cameras set up at the shop caught Ryder red-handed, stuffing items of clothing into a large bag she had brought with her.

Ryder proceeded to steal as she attempted to cut the security tags off the items with scissors, despite her already being an accomplished actress living in a Beverly Hills mansion worth $3 million. Although she had to appear in court following the incident, her lawyer, Mark Geragos, labeled the event as a misunderstanding and asserted that all charges would most likely be cleared.

Additionally, in a previous 2014 interview, Ryder disclosed that among her vintage wardrobe of re-worn clothing items, she has dresses that she has worn to the Oscars that cost as little as $10.

Nowadays, Winona Ryder Re-Wears Cheap Clothes, Even When Attending Formal Events Like the Oscars

Apart from her assorted and colorful past as an adolescent and young woman, Ryder also became known for her inimitable edgy and vintage style over the years. When it comes to how she decides on what to wear and how to go about crafting an outfit, the "Beetlejuice" talent has a special formula she follows and describes her process as somewhat of a mathematical equation:

"If I have three pairs of similar black pants and four black slinky viscose shirts, I have more than 12 potential mix-and-match options to wear throughout the five-day work week and...two instances in which I will wear the same thing again."

When it comes to wearing the same clothing items more than once, Ryder is a pro. In fact, she expressed being obsessed with rocking the same outfit multiple times because she says it makes her feel good and confident. She still wears the iconic Tom Waits T-shirt she has been known to wear since the 90s.

According to the Hollywood icon, she basically only needs five items of clothing in her wardrobe. These are inclusive of underwear, socks, a reliable and comfortable set of jeans, a favorite shirt, and a plush sweater.

Ryder also unashamedly re-wears clothes until they end up quite literally falling apart from overuse. In another past interview, she spoke about how she inherited her dad's knack for archiving things. That, she says, is the reason she loves repeating outfits until they get worn out:

"I just had to retire an old Clash T-shirt from the first time I saw them in 1980 because it was so incredibly thin and just disintegrating. But I ended up framing it."

Although Ryder loves a good rinse-and-repeat when it comes to clothes, the "Edward Scissorhands" star revealed that sometimes she gets self-conscious when repeating an outfit as a result of living and working in one of the biggest fashion capitals in the world — New York City. Ryder stated:

"In the fashion industry, the bar is set so high that I feel like I should be drowning in rare vintage or off-the-runway pieces, all different, every single day. But what's the big deal about wearing the same thing again? Is it that taboo?"

Additionally, in a previous 2014 interview, Ryder disclosed that among her vintage wardrobe of re-worn clothing items, she has dresses that she has worn to the Oscars that cost as little as $10.

She also detailed how she has worn the same $10 dresses to star-studded events, like Sean Penn's Haiti gala, where she wore an inexpensive vintage dress she had already worn at a 2005 film premiere.

Ryder explained that she knows that re-wearing outfits is usually frowned upon in the fashion world. However, she maintains her stance of seeing nothing wrong with wearing the same thing repeatedly, especially when it's an item she loves.

Many may wonder why someone of Ryder's fame, stature, wealth, and success indulges herself when repeating inexpensive outfits. However, the talented actress pays them no mind and continues to be secure in how she approaches fashion as a star.

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