Danielle Anderson
December 15, 2010 12:00 PM

As she was being lavished with compliments on the bright yellow cocktail dress she’d donned for a dinner at the governor’s mansion in Nashville on Aug. 24, Naomi Judd was having a “What? This old thing?” moment. But with Naomi, you can believe it. For her evening with Tennessee Gov. Phil Bredesen, Judd had stepped into her glamorous 410-sq.-ft. closet and stepped out in a 25-year-old dress by Isabel Toledo. “I just hadn’t gotten around to wearing it yet,” says Judd. “They said I looked like something out of Mad Men and I thought, ‘How fun!’ ”

And fitting for a country diva with more than three decades in the business and the closet to match. “This has always been my ultimate fantasy,” she says of her closet, where every dress has a name (including one she calls “What Was I Thinking?”) “My mom had only one church dress. She didn’t even own a hat, but I’ve always had this fantasy about clothes. I just always loved beautiful things.”

Judd, 64, will soon pack up some of those beautiful things and head out with daughter Wynonna, kicking off their 18-date The Last Encore tour in Green Bay, Wis., Nov. 26. Her style for the tour? “Fantasy fairy tale,” says Judd proudly.

But she admits her stage style hasn’t always been on target. Case in point: the satin dresses she and Wy designed themselves for the 1984 CMA Awards. “I didn’t know that everyone was making fun of us cause Wynonna and I were just busting with pride about those dresses,” she says. “Then someone said we looked like saloon girls on peyote. I look back and think, ‘Taste takes a holiday!’ ”

Now Naomi credits her daughters with helping her avoid fashion faux pas, like her penchant for matching everything from her earrings to her shoes. “Wynonna and Ashley wanted to know if Betty Ford had a wing for my addiction to matching,” says Judd. “That’s been my big learning curve. I see women my age and they’re totally matchy and I don’t know what to say.”

Her other big style rule: “Know what’s passe,” says Judd. “I dream about shoulder pads, but I can’t do them anymore.” She’s also sworn off sky-high heels. “Don’t fall for those ankle-breaking, you’ll-need-a-chiropractor shoes,” she says. “If your shoes hurt, it’s distracting.” These days Judd’s favorite fashion finds are long cashmere cardigans. “I probably have them in every color,” she says. “They travel well and they are so snuggly for planes.”

And for Judd, comfort really is as important as couture. “This is the kind of thing I dreamed of as a child. I only had three dresses and now PEOPLE magazine is in my closet!” she says. “But the minute you leave I’ll be in a pair of pajamas with socks, slippers and my hair in a ponytail.”

NAOMI’S DRESS COLLECTION!

2000

“My Fairy Godmother dress. I had pixie dust in the basket.”

1987

For a Christmas show at the London Palladium.

1986

“I call this ‘The Flower Garden,’ ” says Judd. “You can imagine why.”

2000

A Badgley Mischka design for her Power to Change tour.

1993

From the ’93 TV film Rio Diablo. “I played a saucy wench called Pepper.”

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