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Dress Your Age? No Way, Says Fashion Expert

This is the time to let your chic flag fly

Many years ago, somebody or other — some annoying self-appointed style guru — came up with the concept of age-appropriate dressing. The basic idea is as follows: The older you get, the more conservatively you should dress. Color and flamboyance are for young people. Restraint, propriety and formality are for elders. For some reason it was decided that once women hit 50, they should ditch that metallic snakeskin disco purse and start dressing like depressed librarians, circa 1940. Yawn!

I've been in the fashion industry for decades, and this oppressive concept of age-appropriate dressing has never made any sense to me. In fact, I propose the exact opposite: I believe that the older you get, the more bold and playful you should become in your dress. Do not allow yourself to be inhibited by someone else's notions of good taste and bad taste. You have paid your dues. You have earned the right to sassy it up!

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I am not suggesting that we all start dressing like circus performers, burlesque queens or pole-dancing hoochies. Au contraire! I am talking about injecting your style with fun and creativity, and — this is the really important part — I am talking about expressing yourself. We are living in a fashion-obsessed universe. Between H&M's trendy togs, Target's designer collaborations and those online flash sales, stylish clothing has never been more widely available, and it has never been cheaper. You can basically buy any item at any price, in any size, at any time of the day or night. (I just typed the words "leopard pants" into my search engine and got 29 million hits. The size ranges and price ranges will blow your gaskets!)

You may well find the array of options a little bewildering. Don't freak out. Reinvigorating your personal style is not as complicated as it may seem. There is an easy formula, whether you're a man or a woman.

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Michelle Obama stuns with sophisticated style for every glamorous occasion. Sophisticates bring to mind the polished outfits of Jackie Kennedy, Kate Middleton and Audrey Hepburn.
Getty Images

We'll start with the gals. Chances are that you, madam, fall into one of the following three categories: You are a Sophisticate, a Gypsy or an Eccentric.

Sophisticates first

Encompassing everyone from Katie Couric to Oprah, from Anne Hathaway to Carrie Underwood, this is by far the biggest category. Think Jackie Kennedy. Think Michelle Obama. Sophisticate style is about looking turned out and glamorous. It's feminine, it's appealing, and depending on the cut of your frock, it can be quite alluring. (I avoid the word "sexy." Call me prudish, but I think it reads "tacky" when it's set down in print.)

For the Sophisticate gal, fit and simplicity are the keys. Sophisticates love a tailored jacket over a well-cut shift. And then they accessorize. Big-time. Nobody loves a designer handbag more than a Sophisticate. She is unapologetically addicted to shoes. Sophisticates like to appear happy, prosperous and optimistic. Sophisticates get manicures. Sophisticates get their hair done. (Tip: This season every Sophisticate is going to be carrying a duffel-style purse. Whether it's Coach or YSL, the key thing is having that nifty duffel in the crook of your arm.)

But maybe this sounds like too much work. Maybe you would rather spend time making art or growing organic veggies instead of schlepping to makeup counters and nail salons. Maybe you are in the next category.

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Goldie Hawn's fashion is boho chic with flowy locks to match her flowy dress. Gypsies favor a relaxed, floaty style — sort of an updated hippie chic.
Riccardo Cesari/Splash News/Corbis

Gypsy gals

Fewer in number than the Sophisticates, yet no less important, are the Gypsies. Think Ali MacGraw kicking back. Think Goldie Hawn having a Malibu moment. With their flowing locks, artfully distressed jeans, chunky knits, turquoise jewelry, embroidered caftans, flounced satin skirts, crafty espadrilles and tooled leather bags — sharp intake of breath — Gypsy gals are the epitome of boho chic. This look is easy-breezy and hippie-happy, but not to the point of being dippy.

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Gypsy style is great for people over 50. More forgiving than Sophisticate style, the Gypsy attitude is groovy, comfortable and loose. It's about a hand-stitched tote. It's about a poncho instead of a structured coat. It's about making your own jewelry. It's about wearing a fragrance with a bottom note of patchouli. Just don't get too literal. You do not want to be mistaken for someone who went out on Halloween in 1974 dressed as "a hippie" and never came back. (Tip: This season Urban Outfitters has some great neo-hippie fringed vests and bags.)

Before we move on to the last group, let me emphasize that these categories are not watertight. Many gals play the Sophisticate card for special occasions, then retreat to their Gypsy caravan for everyday wear. Or vice versa: Sophisticate by day, Gypsy by night. Think tambourines and blazing campfires!

Influential Eccentrics

Now, last but not least, we have the Eccentrics. Though small, this group is very diverse and includes everyone from Whoopi Goldberg to Lady Gaga. Think Auntie Mame! Think Cher! These gals are noteworthy because they have created their own unique, uncategorizable style. Some Eccentrics, like Tilda Swinton, have close ties to the fashion world. Others are just creative gals from hither and thither who enjoy the act of adornment … and the act of showing off!

And this is a wonderfully age-inclusive group. Examples of eccentricity can be enjoyed on one of my favorite websites: Advanced Style. Ari Seth Cohen, the visionary founder of this site, celebrates the fashion daring of ladies over a certain age.

Despite their small numbers, Eccentrics are influential. What Cyndi Lauper, Pink or Gwen Stefani wears today, you may wear tomorrow, or in three years. Or maybe never. Who cares! The primary role of Eccentrics is to make the world a more interesting place, to entertain us and to inspire us to step outside our comfort zones. (Tip: This year snag a wacky sculptural hat just like the vintage chapeau that Pharrell Williams wore at the Oscars. This style was originally created by Vivienne Westwood for gals back in the early '80s.)

Now that we have analyzed the female style landscape, let's switch gears.

A little ink to the fellows

In my experience, men are less flexible than women when it comes to clothing. While there are a few who will embark on a style odyssey, most men are looking for a uniform, a simple system. But even a uniform can be freeing, if it's the right one.

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Simon Doonan's No. 1 style icon: Mick Jagger, Fashion Role Model.
Matt Cardy/Getty Images

I find that most guys have a secret fashion role model: a butch vintage style icon lodged in their brain somewhere. It's just a question of finding it. I am talking about Steve McQueen or James Dean. I myself always wear a button-down floral shirt. Why? Because Mick Jagger used to wear them back in 1966, and, call me crazy, old Mick is still my No. 1 style icon.

To help discover the icon that speaks to you, ask yourself what man you admire for his sense of presence. Maybe it's Marlon Brando in On the Waterfront: T-shirts, turtlenecks and a short plaid jacket. Or maybe it's Cary Grant looking very Monte Carlo and suave but casual in To Catch a Thief.

Once you have a mental picture of your style role model, keep it simple: Select a few key items and buy multiples. You want to be Clint Eastwood in Play Misty for Me? With the aid of a bunch of stripy shirts, you can get your Clint on. While you may not have as much hair as Clint did back then, you can still grow those Eastwood sideburns. Don't let anyone tell you you cannot! If the missus puts her foot down, then refer her to me.

A word of advice for both men and women: Take baby steps. It's not possible to revolutionize your closet overnight. Why not start by adopting a signature flourish? Johnny Cash had his black shirts and his bolo ties. Willie Nelson has his braids. Meryl Streep has her subtle cat-eye glasses. All you need is a little something to help people remember how fabulous you are. It could be a vibrant new Nars lipstick or maybe matching oversize bracelets — or, for the dudes, a nifty paisley pocket square.

So, bon voyage! Enjoy your fashion journey! Happy trails!

Simon Doonan is creative ambassador for Barneys New York and a regular columnist for Slate. He is the author of six books on style, including The Asylum.

This article originally appeared in the June/July 2014 issue of AARP The Magazine.


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