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Spotted: Leighton Meester on the set of Gossip Girl looking every bit the all-American collegiate in a navy military-inspired coat, red Anya Hindmarch tote and grey patterned tights! While the Queen B is still struggling to rule NYU, she certainly knows how to dress for the cool. Take a cue from Blair Waldorf and invest in a classic double-breasted navy coat and statement-making red bag this fall—and keep your gams warm in striped, dotted or checkered tights!

• Mulberry Coat, $998; visit theoutnet.com.
• Anya Hindmarch bag, $650; visit net-a-porter.com.
• See more Gossip Girl style.

Last week, Kim Cattrall was spotted on the set of Sex and The City 2 wearing a head-to-toe purple ensemble—shades included! Her Jee Vice sunglasses retail for $250, but InStyle.com readers can enter now for a chance to win one of 15 pairs. Additionally, Jee Vice is offering an exclusive discount of 25 percent off all the styles on their website. Just enter discount code “Instyle09″ during checkout when you shop at jeevice.com (offer valid through October 23rd).

If anyone has the power to step into a TV series—it’s Oprah Winfrey. The talk-show titan is taking a trip back in time—and into Mad Men—on a special ’60s-themed episode of her show. She enlisted series costume designer Janie Bryant to design a custom curve-clinging dress a la Joan Holloway (as played by Christina Hendricks, right). The result, a red satin number with a brooch closure, is worthy of a night out on the town with Don and Betty Draper. Let’s hope Winfrey invited January Jones and Jon Hamm (left) out for a cocktail after their visit to her retro set—even the Queen of Talk shouldn’t let such a wonderful beehive ‘do go to waste.

“The Oprah Winfrey Show: Oprah Goes Back in Time—The ’60s” airs on September 21st. Check your local listings for times.

Usually our first question for leading ladies on the red carpet at TIFF is “Who are you wearing?” But we’ve seen such great hair on the actresses this year, we find ourselves asking, “Who did your hair?” At the premiere of Whip It, Drew Barrymore showed off her dip-dyed tips. “It was her idea and I was like, ‘How am I going to do this?’” says hairstylist Tracey Cunningham, who gave Drew her rock and roll mane. “I used clear foils and a stencil that I made out of paper to get everything to line up. This is the craziest look I’ve ever given her!” Meanwhile, Mariah Carey showed off soft waves when she stopped by our photo lounge with the rest of the cast of Precious. We love the natural look, which reminded us of her early ’90s style.

See more hair from the Toronto Film Festival!

—Bronwyn Barnes

On the set of the Sex and The City sequel yesterday, Sarah Jessica Parker’s third costume change had her channeling Jennifer Beals in the ’80s classic Flashdance in an off-the-shoulder sweatshirt and permed hairstyle. Is this a look at a younger Carrie’s move to the Big Apple? If the vintage luggage and vehicles spotted on-scene are any indication, it looks like we might be on to a plot line.

Stay tuned for more on-set updates! Until then, get your style fix with our coverage of the first Sex and The City film.

While Betty is rumored to get a makeover on the new season of Ugly Betty, it sounds like Wilhelmina Slater may be getting a makeunder. The super stylish editrix’s wardrobe has been hit by the recession, leaving the show’s wardrobe team to search sale racks and vintage bins for designer steals. In an interview for WWD Vanessa Williams said, “With the economic situation, we scaled down in terms of the type of clothing … we are being mindful of the budget and waiting for markdowns.”

Watch Ugly Betty‘s season premiere on October 9 on ABC.

Spotted: The entire Gossip Girl cast clad in ensembles better fit for a 1920s saloon than present day Manhattan (think Chuck Bass in head-to-toe pinstripes). We love Taylor Momsen‘s gangster-style jumpsuit and Hillary Duff‘s jeweled headband, but it’s Leighton Meester in black pearl necklaces and a netted cloche that gets our style vote.

• See more Gossip Girl style.