I don’t believe in the concept of “dressing your age.” It rankles when I see posts with headlines like, “10 Things You Should Never Wear After 50,” largely because the advice seems so arbitrary.
What clothes look and feel best on you has more to do with your body, lifestyle, preferences, and confidence than the year you were born—an essential truth I’ve learned in more than 25 years as the fashion director of major magazines such as InStyle and Glamour.
That said, my personal style has certainly evolved over time, as my body and lifestyle have changed.
Here are some secrets I’ve picked up from my years in the fashion world that have helped me with my style evolution and may help you too.
Secret No. 1: Repeat this mantra: “quality over quantity”
When I began my career as an assistant at Vogue in the ‘80s, the sheer bounty of insider perks (ordering clothes wholesale! invitations to designer sample sales!) went to my head. I bought into every trend, and often found myself eating Ramen noodles for dinner as a result.
In retrospect, I realize that when I was in my 20s, I could wear almost anything—and since I didn’t really know who I was yet, I wasn’t sure what I wanted my clothes to say about me. I was trying on identities.
My closet was a mess.
By the time you are 50 or older, you probably have a closet bursting with clothes from the various identities that have defined you over the years too. Some items you wear constantly, some still have the tags attached, some fit, some don’t, some you’ve forgotten you even owned.
Standing in front of that chaos can be completely overwhelming.
Having fewer choices, but ones you really love, can make your everyday life feel lighter and happier.
Secret No. 2: Focus on what you want your clothes to communicate.
Weed out anything that doesn’t speak to your current lifestyle.
If you are employed, perhaps you have been promoted in recent years and need to convey more authority. Or maybe you have retired and no longer need so many work-appropriate items.
Maybe you find yourself dating again after the end of a relationship and want to add some more playful pieces that express a sense of adventure. Or maybe you have moved and need to reevaluate the way you dress in light of your new environs.
Whatever your circumstances, be ruthless in narrowing your options to items that truly suit your lifestyle now.
Secret No. 3: Dress for the body you have—and be grateful. It’s your only one.
By the time, I was in my 30s and was the fashion director at Glamour, I had discerned which shapes flattered my long-waisted, not-so-long-legged, flat-chested figure. I always put the focus on my slim upper body and tried to elongate my lower half.
It helps to take a long, honest look at yourself in front of a full-length mirror. Squint and see where you are long vs. short, wide vs. narrow.
Then put the clothing spotlight on your favorite part.
If, for example, you have wide hips and narrow shoulders, favor dark-colored pants and light tops to visually balance your proportions.
You can also use texture and pattern strategically. Keep fabrics and solid and matte on the part of your body you want to minimize and use shiny materials (such as satin), textural details (say, pleats or ruching), or bold prints on your slimmest area.
Curvy all over? The biggest mistake is to try to cover everything up.
Show some skin somewhere—maybe at your neckline or hemline.
Life is too short to keep waiting for the body of your dreams. Make the most of what you have.
Secret No. 4: Choose a few neutral colors as your foundation.
I learned this trick in my 40s when I was the fashion director at InStyle and had to pack for weeks-long business trips to the fashion shows in Europe. I needed clothes for all kinds of occasions, and everything had to fit into two pieces of luggage.
The solution, I found, was to stick to a neutral palette.
Here’s why: Everyone will remember if you wear a red blazer twice in one week but a black or ivory one, not so much.
Also, neutrals mix easily with each other.
I gradually realized I was better dressed on my business trips than in my daily life. So I did a major overhaul of my wardrobe using the same technique.
I chose black, ivory, khaki, and gray as my base colors. Anything that didn’t work with at least two of these shades, I evaluated piece by piece.
If I hadn’t worn something in a year or two, I got rid of it. Any new purchases had to complement my new focused color scheme.
I learned to use splashes of color as as an accent to the “main course.”
Bonus: having fewer colors makes accessorizing a breeze.
Secret No. 5: Go for little, unexpected flourishes.
The “secret sauce” to evolving your style is to accessorize with abandon. Spice up your classics with of-the-moment accents.
I will admit the four-inch stiletto heels I wore a decade ago are long gone. These days I want to be comfortable and fast on my feet.
But a strappy, mid-heel sandal makes me feel sexy. Long, dangling, tasseled earrings often replace my discreet diamond studs.
Wearing a leopard-print dress gives me pause, but a leonine bag does the trick.
It makes financial sense to splurge now and then on beautiful accessories. Since you can wear them with a variety of outfits, you can amortize the cost per wear.
Secret No. 6: Keep evolving your style.
Post-menopause, my proportions changed. I began shopping for minimizing bras and loose tunic dresses—and I’m okay with that.
I simply tried on everything in my closet and let go of anything that no longer flattered me.
Structure is my new best friend.
Flowing, fluttering shapes made me look older, I found. The softer my jawline or my midriff, the more I gravitated to sharp collars and shoulders, tailored coats and blazers, and avoided anything droopy or pouffy.
Comfort is also important, so most of my clothes these days have a little stretch.
That said, it’s important to keep trying new things.
Next time you’re clothes shopping, you might try a technique that a good friend who co-owned a trendy store in New York City used to help customers expand their style horizons.
First, try on a few items you’re comfortable with. Then try a couple of things you’d normally shy away from but would work with what you already own.
Last, try some wildcards, just for fun.
My friend said her customers would be so delighted when they realized they could pull off some dramatic, new styles, such as an off-the-shoulder blouse or leather pants. It made them feel rejuvenated!
Secret No. 7: In the end, wear whatever you want!
Now, I am 61, run my own fashion consulting business and mostly work from home. My wardrobe is a tightly-edited mix of basics and unique, beloved items.
These days you’re more likely to find me in jeans and an Oxford shirt than a designer outfit. But when I have the occasion to dress up, I really go for it.
What hasn’t changed: I still believe that looking your best matters. How you dress helps tell the world who you are and what you value.
Only the person you should most want to dress your best for is you.
So, if you have fabulous legs and want to show them off? Do it!
Prefer to dress quietly and discreetly? That’s fine too.
Here, in the end, is the only rule that really matters: First and foremost, your clothes should make you feel good.
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