The New Rules of Dressing Your Age (They’re Not What You Think)

By Andrea Linett

My first job in fashion was at Sassy Magazine in 1987, right after I graduated college. I was a kid at an irreverent teen magazine, so I got to wear whatever I wanted (bubble skirts and over-the-knee socks were my choices for work). But my boss was well into her late thirties and basically wore the same things as I did, including overalls and clogs, and she never once looked like – ahem – “mutton dressed as lamb". She had her own rules, one being if you wore it the first time, don’t wear it when it comes around again (for her, bell-bottoms).  

Through the years, I realized the rules of "dressing your age" should be about the subtleties of what you choose to wear, instead of some crazy cut-off point for jeans, leather jackets or fill in the blank. I first got the idea to write my book The Cool Factor after I attended a Maria Cornejo trunk show in Brooklyn. The minute I walked into the room, I was taken with all of the guests – women ranging in age from thirties, sixties and beyond. What struck me was each and every one of them looked chic as hell and did it in her own special way. None of them subscribed to an old-fashioned “older lady” way of dressing, and I immediately wanted to smash all the old notions and break down some of the new ones.

Dressing your age is such an old idea, right up there with not wearing white after Labor Day. Which isn’t to say I don’t often see women who aren’t dressed appropriately given their age. The rules aren’t so fast and hard – it’s not necessarily about what you should and shouldn’t wear, but what versions of said clothes you should go for, and how you actually wear them. And I think most of us have that internal “age alarm” that goes off ever so quietly when we try something on that just doesn’t feel right. So here, I’ve broken it down into five “rules” (and I use that word loosely!)

Rule Number 1: If It’s a Classic, You Can Wear it Forever

The other day, my mother-in-law Irene, who is absolutely stunning and in her late 60s, went shopping at Madewell for a denim jacket. “I know I shouldn’t be wearing one, because I am too old, but…” her words trailed off. “BUT WHAT? I asked – the right denim jacket is a classic and you can wear it forever! Think about women like Patti Hansen or Lauren Hutton who would wear a piece like this without even blinking. But the trick is in the details – look for regular-sized chest pockets (small ones look “junior” and, well, cheap), a regular nice blue wash (no rips or acid treatments, please) and just plain regular styling. Some more forever pieces include a good army jacket, a great pair of jeans, and comfortable-yet-chic ankle boots. And, if you’re happy in your own body and you love a good bikini, don’t force yourself into a maillot just because you think you have to (just be sure to go for a classic style and forgo any ruffles and cutsie details).

Rule Number 2: Fit and Detail are Everything

Back to the denim jacket. Irene was worried about the way it fit and ended up with one a bit larger that she would have liked because the sleeves were better. Turns out larger was the winner because one that was too small would just feel a bit teenager-y. Also, she picked out a completely evergreen style with brass rivet buttons and no tricky rips, patches or extra embellishments. In other words, perfect. P.S.– She also rocks Converse Chuck Taylors like nobody and looks great for it.

Rule Number 3: Feel Free to Shop in the Millennial Stores, Just Be Careful What You Choose

You can shop pretty much anywhere at any age, and this is something I’ve always noticed while shopping around Paris. You see mothers and daughters strolling around the shops almost dressed identically, but with a few minor (or major) differences: Let’s say they’re both in jeans, blazers and sneakers. The mom’s sneakers and jeans will be completely classic with no added zsuzh, and maybe she’ll have some important watch on or a cool gold chunky chain, while her daughter gets to play just a little bit more, with fun beachy bracelets and bright colors on her kicks. So they’re both rocking jeans, just in a slightly different way.

Rule Number 4: Rethinking the Classics is Always a Good Idea (See Rule Number 1) 

I’m not suggesting every over-50 run out and buy a leather mini, but a good pair of classic leather pants, a blazer or simple biker jacket can last a lifetime and make you feel fabulous the second you put it on.

Rule number 5: When It comes to Hair and Makeup, Less is More.

If you love your long hair, don’t cut it! And with makeup, less really is more (and it's easier if you take great care of your skin.) I am a proponent of natural beauty – using products to enhance – never cover – what you’ve got! To quote my book, too much makeup is never a good idea, and overdone hair and makeup just feel, well, overdone. So if your hair is long and wild and you love it, keep it healthy and trimmed and un-frizzy and you’re good to go – think natural beauties like Georgia O’Keeffe and Mary Ellen Mark, who kept their locks long way late in life.

And remember, no matter what, if you feel good in it, it’s working for you.

Andrea Linett is the author of The Cool Factor, A Guide to Achieving Effortless Style with Secrets from the Women Who Have It. Follow her @ShopIWTBH on Instagram for more great style tips. 
Photo by Michael Waring

1 comment


  • Margie

    I’m 57 and love to Wear blue jeans and T-shirt is that wrong


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