This year, to solve the holiday what-to-wear dilemma, we decided to look for inspiration in the past, hoping to spice up our wardrobe with some vintage finds. Joy Bianchi, with her Helpers of the Mentally Retarded boutique in Ghirardelli Square, seems the perfect person to help women rediscover old-school elegance. A San Francisco native, Bianchi has couture in her blood: her mother wore all the latest fashions from Chanel, Bill Blass, and Dior, and her father was an Italian shoemaker who worked for Salvatore Ferragamo. Never one to disappear into a crowd, Bianchi knows how to dress for any occasion—you might find her in an exquisitely tailored Ralph Rucci dress, vintage Balenciaga hat, and Roger Vivier heels. “When I’m 90 I’ll still be wearing high heels,” she says. She also knows it’s the details that make the best vintage pieces timeless. “Sometimes I want to wear a Rucci dress inside out, because the masterfulness of it is within the garment,” she says. With her knack for chic, Bianchi demystifies vintage shopping and guides us through this holiday season’s must-have accessories (she says a hat). Helpers Boutique, 900 North Point (Ghirardelli Square), S.F., 415-441-0779.

Can someone wear vintage head to toe and still look current?
That’s not a look I agree with. Most people should buy one vintage piece and accessorize it with modern. It shouldn’t scream “I’m wearing vintage!” Lots of clothing spans the 20th and 21st centuries—Yves Saint Laurent and a black Geoffrey Beene sheath dress from the 1980s is completely now—but most vintage shoes are going to date your outfit, unless they are Roger Vivier or an over-the-top-fabulous pair of Halstons. I usually send my clients to Manolo Blahnik or Christian Louboutin to buy shoes to wear with a vintage dress.

So YSL, Beene—these are the designers to look for?
Don’t ever buy a vintage piece just because of its label. Look for great fabrics and turn it inside out to see how it is made. See how you look in it and how you carry it, and ultimately always buy the piece because it is beautiful for you, it reflects what you’re all about in one instant. I remember when I bought my first pair of alligator shoes. I was so proud—they were by Lucille de Paris. But the first thing my father did was look at the sole. He only cared about the quality.

But quality vintage can be quite expensive.
Invest in one fabulous piece each season. Instead of constantly buying T-shirts and jeans, save those dollars for one amazing dress or vintage bag. Those are the pieces that will be timeless.

Are there particular styles that I should look for?
Always try the simple pieces. Most people look at a plain dress on the hanger and don’t realize that the genius is in the cut. And a simple vintage dress can be played up with current accessories. For a cocktail party, you could modernize a great black velvet dress with a big belt—or the accessory could be the crucifixion of the piece. You’ll never know

If I find the perfect party dress, how many times can I wear it?
If you wear that dress to three parties in a row, so what? If it’s fabulous, it’s fabulous every night.

What do you love for the holidays?
Red, of course! There is a red satin Bill Blass dress in the boutique right now—you will be impossible to miss in it. I say if you choose a black dress, do something, dammit, with the accessories. Just run with it. I love the idea of putting a stunning red velvet shoe with a simple black dress, or adding a clutch in a metallic or brocade fabric.

Can I wear vintage jewelry with a vintage dress?
As long as it’s current. Big faux jewelry pieces are in style today and make a strong statement. I have a faux piece in the store that is just divinity, a Kenneth J. Lane four-strand pearl choker with a diamond clasp that would be perfect for a simple dress.

You are almost never seen without your signature frames. What’s their story?
I had bought a pair from Robert Clergerie in Paris, but then the sides broke and couldn’t be replaced because they had stopped making the style. But then I also had some vintage Gucci glasses from the ’60s, and someone was able to put the two designs together. I’m probably the only person with half-Gucci, half-Clergerie frames.

It’s the top
Vintage hats are fabulous, but they can be intimidating. The fearless Bianchi gave us her take on topping off a look.

How do you convince women to try wearing a hat?
I have such a passion for them! Ninety-nine percent of the women who come in think their head is too big for a hat. But the problem is most people just put it down—bam—right on their head, which is wrong. The designer made that hat like a dress, to fit the head a certain way, with grace and charm. You have to play with it, bring it down, tilt it.

Which eras should I look for?
A little fringed cloche from the 1940s is now. And I love veils and feathers on little cocktail hats. But for day, the bigger the better.

But where do I wear it, and are there rules I should follow?
I was brought up with the thought that every day of life is something to celebrate, and you did that through clothes. With the party season, even with going out to dinner or to a museum, we create the occasions to wear special pieces. But that said, smaller hats are best after 6 p.m. From Easter to Labor Day, wear straw, and from Labor Day to Easter, felt and fur.