From Gaudy to Glam

Talk about a flashback: The brash black dress Heidi Klum wore to a New York benefit in April (left) could have come straight off the set of Dallas. At an L.A. premiere in June, the Victoria's Secret model went further back in time but to far better results, recalling Marilyn Monroe in a sexy, stylish halter dress (right).

At the Young Hollywood Awards in Los Angeles in May, Aisha Tyler came up short in this flimsy flapper number (left). The former host of E!'s Talk Soup got her groove back in vibrant shades of orange, purple and pink at the New York premiere of Sex and the City in June (right).

In New York City in June, Eva LaRue Callahan's tacky tweed dress and train (left) turned classic tailoring on its head. Later that month, the All My Children star slipped into something a lot more elegant (right) for the Gracie Allen Awards.

We can live with the dress, but it seems Rosario Dawson's sloppy shrug and boffo boots (left, at an April benefit in New York) were made for walking – right off the red carpet. When she turned up at an L.A. premiere later that month in a sweet sundress and strappy shoes (right), she was all smiles – and so were we.

At the Goya Cinema Awards in Madrid in February, the usually elegant Penelope Cruz (left) looked less-than-stellar in this figure-flattening dress and over-the-top hat. By May, Cruz, who appears in this month's Masked and Anonymous, was back to her normal state of stylishness in Ralph Lauren (right) for one of the designer's events in New York.

Connie Nielsen, who has played everything from an astronaut to a Roman emperor, certainly has range as an actress. The same could be said of her red carpet appearances: In New York in May (left), Nielsen's neckwear was more Mardi Gras than marvelous, but in New York a month later (right), she was positively pretty in pink.

It's admirable that Eve is willing to take style out on a limb – but unfortunately, her getup at the MTV Movie Awards in May (left) looks more rag doll than baby doll. In New York in June (right), the rapper, who is set to launch her own clothing line, donned a more elegant, empire-waist floral dress.

In this skimpy sequined take on her Wimbledon whites (left, at a sports awards show in Monte Carlo in May), tennis pro Serena Williams lost the style game in straight sets. However, while in Paris for the French Open in June, the top-ranked player left her tennis skirt at home and donned a Roberto Cavalli gown (right) with a plunging neckline for a fashion win.

One might expect crossover chart-topper Shania Twain to be a little bit country and a little bit rock and roll, but her Goth look (left, at May's Academy of Country Music Awards in Las Vegas) took things to the extreme. For her induction ceremony to Canada's Walk of Fame in June (right), the singer-songwriter struck a lighter chord in a pink, beaded sheath.

Is Chloe Sevigny on the red carpet or at home, getting ready for bed? It's hard to tell at this March Oscars party, where the actress looks like she's tangled up in her dressing gown (left). But in June, the Boys Don't Cry star ups the ante by paring down to sexy basic black and strappy stilettos (right).

The Grammys have never been known for inspiring understated attire, but Foxy Brown's show-and-tell Dior at February's ceremony (left) took things a bit too far. The tailored white suit she sported at the BET Awards in Los Angeles in June (right) still revealed plenty of lace, but managed to live up to the singer's name.

At February's MusiCares tribute to Bono in New York, model Naomi Campbell took the word "catwalk" a bit too seriously by turning up in this furry number (left). In June, she traded in her saucy stole for a sleek beaded gown (right, at Sir Elton John's White Tie amp Tiara Ball in Windsor, England) and looked purr-fectly regal.

Kylie Minogue's cotton-candy confection (left) would have been more appropriate for a performance of Swan Lake than the charity ball she attended in June in the U.K. Thankfully, the saucy Aussie channeled her inner chic in the black ensemble she wore to Chanel's fall fashion show in August in Paris (right).

It's not easy to make Garcelle Beauvais-Nilon look less than gorgeous, but the knit dress she wore to a Beverly Hills party in May (left) did just that. In June, however, the NYPD Blue star was back to her elegant, sexy self in this strapless little number (right, at the BET Awards in L.A.). Case closed.