Olympic Figure Skater Tara Lipinski's Worst Fashion Mistakes Are More Chilling Than The Ice Rink

After taking home the gold at the 1998 Nagano Winter Olympics at just 15 years old, figure skater Tara Lipinski had nothing left to prove. She made history as the youngest figure skater to win gold, and she has bragging rights for the rest of her life. But while the athlete has our full admiration, we can't help but notice that she's fallen victim to a few notorious styling mistakes over the years. Clearly, it happens to the best of us!

Since leaving behind Olympic figure skating, Lipinski moved into the broadcasting side of sports, covering the 2014 Sochi Winter Olympics, as well as appearing on several talk shows. In early 2026, she appeared on the hit reality show "The Traitors," solidifying her transition to entertainment proper and solidifying to a wider audience that she's one of the former Olympic skaters who looks completely different today. With these career changes, she left behind her sequin-clad bodysuits for red-carpet-ready 'fits, often showing a trend-forward approach to styling. But in order to cultivate a true sense of style, you have to take risks and experiment, which invariably leads to fashion mistakes. 

Like many of us, Lipinski's sartorial errors have come about in many areas, but a repeat offender seems to be her confusion about how to accentuate her petite frame. She has constantly opted for hemline and boot combos that cut off her legs and make her look even shorter than her 4'10" stature, but at least these blunders remind us that she's only human. Rather than holding them against her, maybe we can learn something about the laws of style from reflecting on Lipinski's looks that definitely failed to win the gold. 

The year was 2003, and pleated A-line miniskirts were in, so we don't blame Tara Lipinski for that. But pairing it with under-the-knee boots was absolutely the wrong choice for the Olympian. At less than 5 feet tall, Lipinski should always consider proportions in her styling, but at Mercedes-Benz Fashion Week in Los Angeles, California, her legs looked even tinier thanks to the combination of the hemline and the boot height, which swallowed her on one side and left only a patch of skin on the other.

At the Young Hollywood Awards in 2013, Tara Lipinski went with an earthy animal-print shirt dress, which she dressed up with a belt cinching in her waist. While she did win style points for adding accessories that kept the look from being boring, her belt did more harm than good. Specifically, it just didn't work with the short sleeves, crew neckline, and baggy fit of the garment, leading to a boxy silhouette. With sheath-dress shoulders and a tighter fit, the belt would've saved the day, even while making her look shorter.

A red strapless dress with a sweetheart neckline will always be a classic at formal events. Unfortunately, Tara Lipinski's take on the iconic look didn't quite land at the 2018 Elton John AIDS Foundation Oscar Party in West Hollywood. The biggest issue was the gown's tailoring, which left excess material at the front. Undoubtedly, this made it difficult for the Olympian to walk. There's a delicate line when it comes to dresses with trains, but good tailoring ensures that the fabric doesn't gather in the wrong place and threaten to trip the wearer.

We don't hate the essence of the red dress that Tara Lipinski wore to the Miss America competition in 2018. The embellished sheer material would've made for a bold and sexy moment in a parallel universe, but here, a few seemingly inconsequential features brought the whole look down. Namely, the creases descending from the waist band of the skirt teamed with the bright hue evoked crepe paper. The tiny bit of lining being visible at the top of the thigh slit was the nail in the coffin, unfortunately.

Tara Lipinski has attended the Kentucky Derby several times, and we love to watch her get into the spirit with her glamorous outfits. But in 2016, a look that attempted to be avant-garde came out looking like she nabbed it from the costume department of a slasher film. This was so close to working, but the particular pattern of the red embellishment, and the way it faded toward the outer edges in smears and splodges, imitated a blood splash, not flowers. Thankfully, no figure skaters were harmed in the wearing of this dress.

Petite frames can look square with the wrong clothes, and Tara Lipinski has suffered from this affliction more than once. At a 2016 NBC Sports event in Austin, Texas, Lipinski wore a flowy strapless top that she tucked into a white lace-trimmed skirt, and the result was sadly "box." With her toned décolletage and shoulders on full display, a cinching belt would've helped even out the proportions since the color-blocking already cut her in half. Some fashion rules are made to be broken, but failing to balance isn't one of them.

Tara Lipinski is the queen of minidresses; they suit her frame, and she usually pulls them off like a pro. But at the Olympic Committee's Best of U.S. Awards in Washington, D.C. in 2014, she made a few blunders that made her look shorter instead of taller. First, her belt created a line that effectively cut her in half. This undermined the black sides of the dress that would've otherwise created the illusion of height. The ankle straps did the same thing, cutting her at an angle that did her no favors.

In 2015, Tara Lipinski attended the Kentucky Derby in a dress that was trying to be whimsical but ended up looking more ghost than fairy. The light-pink tones left the figure skater washed out, though we're grateful for the swipe of pink lipstick. The beige closed-toe platform pumps were completely uncalled for, as they created a clash of color (or lack thereof). Meanwhile, the knee-line hem was just a few inches too long, which was then worsened by the flowing material on either side drawing attention to it.

Oversized cardigans come and go from the hot list, so we understand Tara Lipinski's desire to wear one at Mercedes-Benz Fashion Week in 2006. But styles that leave you swimming in them generally aren't recommended for petite folks, who can get lost in all the material. At least the look was redeemed slightly by the skinny jeans, which balanced out the oversized proportions of the cardigan, but the below-the-knee boots once more left the figure skater's legs looking almost cartoonishly stunted. You can't win them all!

A white midi with lace overlay is perfect for summer, and dress-code-wise, it was a style-forward choice for the Annual Garden Brunch in Washington, D.C. in 2015. But Tara Lipinski should've had the dress hemmed to suit her height, as the hemline cut off too much of her legs and left her looking shorter than she is. It's a shame because with the slim fit of the top of the dress, the thin camouflaged belt worked well to create a snatched silhouette that balanced out the flowy skirt.

Ultimately, we love Lipinski, but she should take a look at our best fashion tips for making yourself look taller.