Melbourne, 31 August 2012 | Amy Price

Since Gertrude Moran rocked the tennis world in 1949 with lace-trimmed panties beneath her white tennis dress, the fashion sense of the more daring has become one of the beloved pastimes of the world game. But fortune doesn’t necessarily favour the brave. As the players take centre stage in New York this week, the city at the heart of the fashion-forward, we decided to delve through the back of the closet to count down the US Open’s less-triumphant fashion moments.

10. Martina Hingis, 1996 – Age appropriate

Martina Hingis. GETTY IMAGES Just making the cut at number 10 is the Swiss Miss—although in this outfit she could easily be mistaken for the Swiss Madam. While the look isn’t a complete fashion disaster, the matching dots, black-and-white colour scheme, and waisted skirt feels a little more ladies luncheon than 15-year-old tennis star.

9. Andy Roddick, 2004 – Mapping success

Just in case he got lost, defending champion Andy Roddick looked as though he’d embedded a train route on his shirt in 2004. Unfortunately, the map looked more like America’s west coast than New York, and the American couldn’t find his way to a consecutive title, going down to Joachim Johansson in the quarterfinals. Andy Roddick. GETTY IMAGES

8. Katarina Srebotnik, 2006 – Shades of grey

Katarina Srebotnik. GETTY IMAGES While most memorable fashion disasters in this countdown come from the more eccentric statements, it doesn’t always pay off to play it safe. At number eight is Slovenia’s Katarina Srebotnik, who in 2006 topped off this muddy grey and pale yellow combination with white detailing and a black shoe. She might be missing some primary colours, but props to Katarina for wearing an outfit comfortable on the tennis court, unlike some of the higher candidates in our countdown.

7. Mary Pierce, 2006 – Running rings    

French darling Mary Pierce was always well-liked for her attire, but her combination of black, blue and yellow circles in 2006 sees her sitting in number seven on our countdown. Perhaps it belongs more as an abstract art piece than on a tennis court, but playing just her second tournament in over six months we think it could be an artistic reflection of Pierce’s frustration at the time. Nevertheless, the two-time Grand Slam champion can be excused for this slight fashion blunder.  Mary Pierce. GETTY IMAGES

6. Andre Agassi, 1991 – Let’s get physical

Andre Agassi. GETTY IMAGES While we can look back at a lot of past decades with hand over mouth, it’s hard to excuse the legendary Andre Agassi for this one in 1991. From head to toe it’s hard to know where to look—the trademark hair kept by a pink headband, oversized shirt, denim-style short shorts and all topped off by pink bike pants.

5. James Blake, 2006 – Nineties nostalgia

At least Andre’s look was on trend at the time. James Blake seemed to be suffering a bit of idol-imitation with this Agassi throwback in 2006. The pink and black geometric pattern and bandana was one thing, but we’re not sure the new generation could handle the pink bike pants. They even look a slightly different shade of pink than his shirt. This nineties no-no sees Blake jump a spot ahead of his American style icon. James Blake. GETTY IMAGES

4. Bethanie Mattek-Sands, 2007 – Animal instincts

Bethanie Mattek-Sands. GETTY IMAGES No fashion countdown would be complete without American statement-maker Bethanie Mattek-Sands. In fact, she seems to make a point of sewing herself onto lists like these, rocking the tennis world for the past decade with eccentric patterns, knee-high socks and even American-inspired war paint. There are almost too many options when it comes to Mattek-Sands, but this leopard-print halter and matching visor was a definite head-turner in 2007 and clawed her all the way to number four.  But we have to give credit to Mattek-Sands for owning her own style on the tennis tour—even if it’s not always so well-received.

3. Dominik Hrbaty, 2005 – Cut it out

It’s hard to imagine a man could pip Mattek-Sands in the fashion stakes, but Slovakia’s Dominik Hrbaty takes the cake for this number in 2005. We’re not sure what function the cut-outs serve, whether it was a revolutionary cooling feature or he just lost a bet, but it ultimately didn’t work out as well as he might have hoped. He eventually lost in the fourth round to Australia’s Lleyton Hewitt, who said post-match “I just couldn’t lose to a bloke wearing a shirt like that.” Nevertheless, “the shirt” certainly made its mark. We’re sure there were a few topless training sessions for Hrbaty after the tournament to get rid of those tan lines. Dominik Hrbaty. GETTY IMAGES

2. Venus Williams, 2010 – Careful not to blink

Venus Williams. GETTY IMAGESVenus Williams. GETTY IMAGES The Williams sisters love to push the boundaries when it comes to their tennis apparel, certainly becoming the most celebrity of our tennis stars, and it’s no surprise to see them once again fighting for number one on our countdown. Venus, designing her own clothes under her label “Eleven”, seemed to turn the 2010 US Open into her very own fashion show, turning up in a new outfit every match, each as individual as the last. With fringing, diamantes, patterns and cut-outs all in one tournament, Venus has earned her place at number two.

1. Serena Williams, 2004 – The midriff mishap

Careful not to be outdone by her sister, Serena claims the trophy for biggest US Open fashion disaster with this midriff mishap in 2004. While her infamous 2002 catsuit may be more memorable, this blue-jean skirt complete with studded midriff top and hoop earrings takes the prize. Straying far from the traditional modest tennis attire, Serena strode out in black knee-high boots, which she amazingly unzipped before she started play.  A far cry from Hingis’s mature number in tenth, Serena’s James Dean-inspired outfit—along with the sight of her belly-button piercing—surely sent shockwaves through tea cups around the world. But, the 14-time Grand Slam champion has never been one to shy away from a statement and nobody makes a statement quite like Serena. Serena Williams. GETTY IMAGESSerena Williams. GETTY IMAGES