So, Andy, what’s it like being on a reality TV show?

“Everyone hated me; I was villainized,” says Andy Paige. She was the one viewers loved to hate in season 1 of the Daytime Emmy Award-winning Starting Over. The show, which ran from 2003 to 2006, brought together a group of six women who moved into a house in Chicago, some of them for months, to work with life coaches and psychologists to sort out their lives and transform their careers.

I hated her, too. She’s beautiful, talented, funny, outspoken, and blunt – the perfect recipe for the one you love to hate. Walking New York City streets while the show was running, dealing with the glares became so difficult that she bleached her gorgeous dark hair blond. “I had to disguise myself.”

By the end of the season, she’d become one of the most loved cast members. I loved her, too. She’s still best friends with the coaches that helped change her career – and her life. 

Before landing on the show, Andy was a fit model, a well-proportioned, middle-size 12 that 170 designers relied on to fit their new lines. “They could scale down to a size zero and up to a 24,” she says. “It was my bread and butter from age 18 to 30.” It was also a graduate-level education in patterns, construction, and materials. But she wanted to break into media.

Starting Over was a springboard to several other reality TV and talk shows, a book Style on a Shoestring, speaking appearances on style and fashion, wardrobe consulting, and styling for a host of celebrities, including Lisa Lampanelli, Lisa Rina, Jeanie Mai, Debbie Gibson, Dr. Robi, and all of the big names on Celebrity Apprentice. 

She and her husband divide their time between an apartment in Manhattan and a farm in Massachusetts, so she’s equally familiar with Manolos and Wellies. We were delighted that she joined us for a discussion about creating a powerful style at any age, particularly as we drift beyond 50.

What’s Your Style Philosophy?

“You don’t have to spend a fortune to look like a million; it doesn’t take money, just courage. Style is courage and guts and curating amazing pieces.

“There is this idea called Old Money Dressing. It’s all about investment pieces. Invest in clothing that is not disposable, that you’ll wear for twenty years, and add in the trendy and transitional with handbags, shoes, and jewelry. That’s powerful, luxe. Every day, when you get dressed, you’re messaging – how you dress tells the world where you’re going, how you feel, and how you should be treated.

“Start with ten to twelve key pieces and build from there. Trousers that fit like a glove, a great pair of jeans, and a basic black dress. Anchor your look with beautifully fitted classics, then build your style with statement pieces and accessories.

“Think of yourself as a Christmas tree – if the tree is great, you can decorate it any way you want.

“But you don’t want to dress in a costume. You can enjoy trends and stay current, but be selective. I love street style, but I would never do street style head-to-toe. I would add a fabulous hoodie to a pencil skirt or jogger pants with a blazer and heels. I would take one piece and add it to the classic.”

I immediately think of a woman I know who’s over 80 and looks fantastic. Her clothes are simple: slim pants, a beautifully fitted blouse, and spectacular suede over-the-knee boots – one dazzling thing that vaults her into now. She’s also rail thin, so of course, everything looks great. So, of course, we asked Andy how to pull off a power when you’re not built like a coat hanger.

Forget super skinny.

“Your figure should be an hourglass – no matter your size. We’re naturally attracted to the hourglass shape; it’s in our blood. It highlights our femininity, and when we show it off, we have more confidence and power.

“The geishas, antebellum women, women throughout time – the greater the ratio between waist and hips, the better.”

Ah, Scarlett O’Hara and that 17” waist, right?

Want a waist? Get a bra, she says. “A good bra is the most important thing to have.  Get your boobies up and off your waist,” At some point, for many of us, breasts begin to sag, obscuring the waistline. “A good bra hoists them up, so you’re showcasing the smallest part of you.”

“Choose things that visually help you to create a waist. Wear seamed, darted blouses and items that pull into the belly button and then release to the hip. A t-shirt with an open or “V” neck makes the body appear smaller.”

It also distracts from the jowls, I’ve found.

“Clothes that don’t fit well are doing you a disservice. Wearing larger clothes and drowning in fabric is a big mistake that people of size make. Create an hourglass, no matter how large the hourglass.

Cost Per Wear

When you figure out how often you’ll wear a garment, you’re calculating whether you’re getting the most value for your investment. If it has great style, expresses who you are, and you’re able to wear it multiple times and feel great, buy it, she says.

“Say you’re looking at a $100 garment. Visualize it with three things already in your wardrobe and three ways to dress it up for Saturday night and down for Sunday morning brunch. Does it look great with jeans? Run through the scenarios in your mind. When you buy something you love but have nothing to wear it with, you’ve created a new chore.

“Those investment pieces should also not be size specific. The truth is, statistically, we’re getting bigger. I always buy coats up one or two sizes to go over a sweater or a suit — or if I gain weight. The best statement pieces aren’t going to lock you into a button or a zipper.

“Invest in things that don’t care if you had waffles for breakfast.”

I feel like the older I get, the higher the cost per wear – there are only so many years and occasions for a splurge. About four years ago, I bought a little black shrug for $150 at a craft/design show. It’s a beautiful thing, laced with black ribbon and a flattering stand-up collar. I’ve worn it once.  That makes it $150 per wear, not the best value – but I would have hated to pass on something so gorgeous because I’ll never wear it enough.

“I wanted pink leather pants, thinking I’ll wear them forever,” Andy replied, “But they stretch so much that I passed. However, I have my grandmother’s Burberry trench coat and my mom’s Fry boots. My Aunt Mildred left me two Hermès scarves that she enjoyed in the 70s, and I’m wearing them now and will give them to my girls someday.”

So, my daughter will get the shrug, and if she wears it once, that will bring the cost down to $75 per wearing. If she passes it along, it’s beginning to sound like a reasonable investment. Maybe.

Bargain hunting

What if you want to look like a million, but your bank account hovers at zip?

“You can wait for things to go on sale, but a great bargain involves time. It’s a hunt. If you don’t have the money, you need to invest time.”

“There’s a huge movement revolving around no longer spending money on disposable pieces. One of my three daughters has not bought a thing for a year. She’s dedicated to thrifting – she can find classics almost anywhere. They never go out of style – you just have to dig for them. You can find amazing deals.”

Is there a point in buying a T-shirt for over, say, $50? Mine are always from Target and under ten bucks. And Wolford stockings for $50? That sounds totally nuts.

“I have t-shirts from Target, too. With a $50 t-shirt, you get quality textiles; they wear longer and last longer. Wolford uses silk, nylon, and lycra spandex. They are like surgery – they’ll take a size or two off you, and they’re beautiful.”

Oof. Sold.

Shaping Up Your Closet

“Most of us only wear 20% of our closets,” she says. “When I work with someone, I start in the closet, looking for chronic mistakes. There was a period [in our lives] when we felt best, and…we’ve filled our closets with attempts at replicating those outfits.”

Pull everything out and make four piles: recreate, contemplate, fit me great, and donate.

Recreate: these are things that could probably be tailored so you can get more value out of them and lessen the cost per wear – nip the waist, hem the skirt. A thirty-dollar investment would bring it back to life.

Contemplate: You haven’t worn it in a year, but it was an investment piece – put it at one end of the closet. See how often you reach for it.

The Fit Me Greats: that’s a shockingly small number of clothes for most, but they’re the clothes that help you present yourself as powerful — and that’s what you want to build on.

One final power tip:

“As we get older, the first thing women give up is lipstick, which creates a colored ring around your information box. We now have more to say, more knowledge to share, and a different view on life that needs to be heard. Lipstick is the one thing that brings vibrance to your face. Get back to lipstick – gloss doesn’t cut it. Pick a color and just do it.”

Where to Shop?

“I’m a Zara, TJMaxx.com, and Poshmark girl for sure. 

“I sort my TJMaxx search from high to low to discover the incredible high-end brands that secretly liquidate on TJMaxx.com. You won’t believe it. 

“I trust Poshmark with gently loved items over $500 because they verify, and I’ve never been burned. Burberry trenches, Chanel flats, Gucci loafers, Hermès scarves, and high-end designer bags are all investment pieces you can find hugely reduced on Poshmark. 

“Zara is unquestionably the best fashion bang for the buck. They have a wide variety of sizes, fabulous chic styles, and traditionally classic items that will look luxe for years. You can build an entire old money wardrobe at a Zara flagship store for a couple hundred bucks!”

That sounds like a challenge, Andy. Let’s go shopping at Zara!

For a dress that can take you anywhere, try this strapless midi from Zara. A just-below-the-bust zipper adds a little quirk, and the whole thing can be dressed up with a jacket or scarf and dressed down with a motorcycle jacket and high boots. You could even pull a sweater over it and call it a skirt. $50

Happily, they’ve got just the cover-up with this cropped jacket that stops at your smallest part. Wear it partly unzipped to better frame your face and lengthen your lines. $30

Or go with this faux leather jacket with zips and self-belt, a cool, trendy topper for anything from jeans to that strapless midi. It’s just $69.90

Stride about like Condoleezza Rice, talk about power dressing. These gorgeous knee-high leather boots, with not too killer a 2.5” heel, come in beige, black, or silver metallic. $169.

Is there a more essential basic than a good pair of jeans? These beautifully tailored mid-rise straight-leg jeans are not too baggy, not too tight. Just right. $60.

If your waist goes from a size 8 to a size 10 after dinner, you’ll bless the drawstring on these slinky, spun wool pants.  $90.

They show it pulled down below the belly button, but it’s not called a high-waisted knit midi skirt for nothin’. $50.

Sexy, flowy, fabulous with those jeans, a pencil skirt, or menswear trousers, this semi-sheer blouse has a bit of rhinestone dazzle and comes in black or white. Wear it with a cami or without – if you dare. $46.

Classic, classy, and oh! is this a rich bargain! The minimalist wool-blend Chesterfield coat tops everything in your wardrobe. Swagger about for $199.

Read Next:

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