Anna Kournikova was the blueprint for the modern tennis celebrity. She wasn’t just an athlete — she was a fashion icon, media darling, and marketing powerhouse rolled into one. Her magnetic presence on and off the court made her a pop culture phenomenon long before Instagram influencers and TikTok trends. From glossy magazine covers to red carpets, she was everywhere. But with that level of visibility came a fashion spotlight — and it didn’t always flatter her.
Let’s be real: Anna Kournikova served us plenty of lewks during her rise to stardom in the late ’90s and early 2000s. But even the brightest stars have their style missteps. Whether it was a questionable color choice, an outfit that didn’t suit her frame, or just something that screamed “Y2K chaos,” not every look was a winner.
So buckle up for a nostalgic (and fashionably honest) ride through Anna Kournikova outfits that just didn’t work — and why we secretly loved the drama anyway.
1. The Metallic Mayhem: 2000s VMAs
Who could forget the 2000 MTV Video Music Awards? The era of frosted lip gloss, tiny sunglasses, and metallic everything. Kournikova hit the red carpet in what can only be described as a silver explosion — a two-piece set with a shiny bandeau top and matching pants that looked like they were made from recycled spaceship parts.
What went wrong?
While the idea was bold (and very in tune with the Y2K aesthetic), the fit and fabric did her no favors. The pants bunched awkwardly at the knees, and the bandeau top offered minimal support, drawing attention away from her athletic frame and toward unfortunate angles. A little tailoring could’ve made this a space-age moment — but alas, it was more moonwalk fail than fashion fantasy.
2. Tennis Couture Turned Costume
Kournikova had partnerships with Adidas and other brands that often blurred the lines between performance and high fashion. One such attempt — a neon green tennis dress with asymmetrical mesh cutouts — was meant to turn heads. And it did… but not in the best way.
Why it didn’t work:
The dress was caught between being athletic wear and runway-ready, and it landed in a weird in-between. The neon shade clashed with her skin tone, and the mesh detailing looked more “craft project” than couture. Add in some clunky sneakers that screamed ‘promotional prototype’ and you had a full-blown fashion double fault.
3. The Mesh Disaster at a Miami Club Appearance
Anna was known to frequent high-profile parties and appearances, especially in hot spots like Miami. But one particular outfit — a sheer black mesh top over a lacy bra paired with ultra-low-rise jeans — was peak early-2000s chaos.
Why this missed the mark:
The look was trying to be edgy and sexy, but it ended up feeling more like a time capsule of questionable club fashion. The low-rise jeans cut her frame in a way that wasn’t flattering, and the sheer top looked unfinished. While this outfit might’ve been trendy in its time, it didn’t age well — and neither did the visible belly chain.
4. Over-accessorized and Underdone
At the 2001 ESPY Awards, Kournikova showed up in a white halter top and mid-length denim skirt combo that could’ve been passable — if it weren’t for the accessory overload. Oversized silver hoops, a thick chain necklace, stacked bangles, and a sequined belt all fought for attention.
Style lesson missed:
Sometimes less is more. With each piece screaming for attention, the look ended up chaotic rather than cohesive. Anna’s natural beauty and effortless vibe got lost in the clutter. The denim skirt was also a little too stiff and boxy, adding to the unflattering silhouette.
5. The Faux-Leather Fiasco
There was a time when faux leather pants were the statement piece. And Kournikova tried to ride that wave during a red carpet appearance for a sports award show. She paired the pants with a tight black turtleneck and heeled boots.
The problem?
The pants were too tight — visibly uncomfortable — and the sheen of the material picked up flash in the worst way. Plus, the whole look felt too heavy and harsh for someone known for her youthful, energetic presence. It was more “motorcycle club” than “tennis royalty.”
6. Too-Sporty Off the Court
While Anna made athleisure cool before it was even a word, some of her off-duty sporty looks didn’t quite hit. A memorable miss was an oversized Adidas track jacket, long basketball shorts, and sneakers ensemble at a charity event.
What didn’t click:
It wasn’t that the outfit was casual — it just didn’t feel her. The masculine cut and bulky fabrics swallowed her frame. She looked less like a tennis star and more like a high school coach caught mid-practice. A better fit or a splash of color could’ve transformed the look, but this one just felt uninspired.
7. Red Carpet Romance Gone Wrong
At a 2003 movie premiere, Kournikova wore a long lavender gown with heavy ruching and a side slit. On paper, it was elegant. In execution? Not so much.
Why it didn’t work:
The fabric clung in awkward places, and the ruching bunched unflatteringly around the waist. The color washed her out under the camera flashes. Combined with a dated updo and minimal makeup, the look didn’t match her usual glam standard. It was one of those rare moments where Anna looked like she was trying too hard — and it showed.
8. Denim on Denim (and Then Some)
Ah yes, the iconic early 2000s trend we all tried to block out: double denim. Anna went full throttle with it during a promotional event, donning a denim crop top, flared jeans, a denim bag, and even — wait for it — denim heels.
Where do we start?
This look was the Canadian tuxedo’s rebellious cousin. Too many textures, mismatched denim shades, and an unfortunate cropped jacket made this one a fashion nightmare. It was denim overload in the worst way. And not even her mega-watt smile could save it.
9. Overly Girlish Gala Gown
In a charity gala appearance, Kournikova opted for a pastel pink strapless ball gown with a bubble skirt. It was sweet, sure — but also very “high school prom” adjacent.
Why it flopped:
The silhouette was too youthful and princess-like for someone who had already established a strong, mature style presence. The gown didn’t reflect her confident persona or her athletic sophistication. It made her look like she was playing dress-up rather than owning the red carpet.
10. Too Much of a Good Thing
Kournikova was undeniably stylish, but sometimes her looks suffered from doing too much. One infamous outfit included cargo pants, a crop top, a bandana, and tinted shades — all at once. While each piece on its own could’ve worked, the combination screamed “style overdose.”
Final takeaway?
Kournikova’s worst looks often came from trying to fit too many trends into one outfit. When she kept things clean and modern, she shined. When she went overboard, it all got lost in translation.
So, What Can We Learn from These Misses?
Fashion is a form of expression — and when you’re a global icon like Anna Kournikova, it becomes a language everyone wants to decode. Even when her outfits missed the mark, they still told a story. A story of a young woman navigating fame, fashion, and femininity in an era defined by its own chaotic trends.
If anything, her fashion misfires make us appreciate the hits even more. They remind us that style evolves, and even the most glamorous stars have “What was I thinking?” moments. Anna’s risks, even when they didn’t work, showed she was never afraid to stand out — and that’s what made her unforgettable.
Final Serve: Why We Still Love Her Style Anyway
Anna Kournikova may have missed the fashion mark a few times, but she was always serving something — confidence, charisma, and an undeniable “it” factor. Her missteps weren’t failures; they were moments. Moments that we remember, talk about, and secretly admire for their boldness.
Because let’s face it — the best fashion icons aren’t perfect. They’re daring.
