You’ve finally gotten into a style groove. You know what looks good and even have some killer go-to looks — but then, your life changes. You’ve nabbed the big job, had the first (or second) baby, entered a new decade — and suddenly, the clothes you once rocked just don’t just don’t seem to rock quite as much anymore. That flared skirt silhouette looks too young. Ditto on the girly prints and too-low skinny jeans that just aren’t channeling that glamour vibe you’re craving. Suddenly, after a milestone (or many) you have to suss out a wardrobe that works for the playground, the big meeting, or your 40th birthday party.So, how exactly do you navigate these big life transitions, with really great style on your side? We’ve asked three sartorial gurus — Glamour’s fashion market director, Sarah Meikle, Barneys New York’s Creative Ambassador at Large, Simon Doonan, and super stylist, Annabel Tollman — for advice on how to stay current through life’s iconic moments.
Annabel Tollman, Stylist
“You should look at the way French women dress. They don’t consider aging to be a negative thing. They sit there with their face in the sun and don’t really care about wrinkles because they think it adds character. You don’t see a bunch of plastic surgery strolling around Paris, do you? They like to be very svelte and are immaculately dressed, but French women are not scared of aging. They can still be sexy, but are being sexy for how old they are — in a knowing, more mature way. They’re happy to be themselves and looking good for the age they are, rather than expecting to look 25 forever. I think, the really big sin is trying to look younger. That’s what makes people start to look foolish. When you try and look younger, mistakes start to happen. It’s good just to feel comfortable in your skin.”
Do you think there is a big change between your early 30s and your late 30s?
“I think the main change that occurs is that you start to know yourself better and understand how certain things are not for you. Perhaps you develop more of a uniform, but you no longer buy novelties that don’t suit you. I became much less rock ‘n’ roll and much less concerned with things being cool once I hit 33-ish.”
What changes should a woman make to her wardrobe from her 30s into her 40s?
“From your 30s to your 40s, I think that clothes should be less overtly sexy. If your legs are slamming, then by all means wear a miniskirt, but then cover your décolleté.”
At age 40, do you think a woman has to think about stepping it back or stepping it up in terms of fashion? What advice do you give your clients?
“There are two ways of looking at it. One is: Wouldn’t you rather look amazing and fabulous? When you are dressed up, it gives you that air of authority and power and makes you hold yourself differently. We always look better when we are in a high heel. But, the other is: I actually think it makes you look younger to dress down in jeans and less makeup. There is something to be said for being a bit more casual.”
What designers love women as they age?
“Alber Elbaz, L’Wren Scott, Céline, Derek Lam, Michael Kors, and Donna Karan.”
Do you think there is an age when you should pack up the bikinis?
“I think you can wear a bikini as long as your body is good enough. Look at Elle Macpherson at almost 50 — she looks amazing. But if your stomach is stretched to shreds after having a baby, then consider a one-piece. You have to look at your body.”
When should women update their look?
“Birthdays, holidays, the New Year, or even for us in the fashion business, September — all are a chance to reflect. You always want to be your more fabulous you. What better excuse to take stock and decide how to move forward?”
Simon Doonan, Creative Ambassador At Large, Barneys New York
You want women to age fabulously, so how can they use fashion to do that?
“The most important thing as you get older is to maintain a physicality — it doesn’t matter if it’s through Zumba, tap dancing, hula hooping, or playing darts. I think you would be miserable if you just became inert and think that buying clothes is going to make you feel good.”
At what points in life do you think a woman needs to amp up her style?
“I think you should amp up your style from the get-go. There is a big conformity dynamic, particularly among teenagers and people in their early 20s that is very peer driven. By the time you are careening toward 30, you should be extricating yourself from this and finding out who you really are. And, by the time you reach 40, 50, or 60, you should be at the ‘don’t give a shit’ age. You should be feeling more empowered, less inhibited, and that you don’t need to please other people.”
What is your advice for a woman who wants to stay current at 40?
“I think every time she finds herself worrying about what other people think, just discard that thought. Develop a very independent way of thinking. This is very hard for women because they are constantly cross- referencing other women’s opinions.”
After 40, there’s a fine line between being current and dressing too young; how do we avoid the dressing-too-young trap?
“You don’t see any adults anymore. If you look at old movies from the ’30s, ’40s, and ’50s, there were grown-ups, and there were children. Now, everybody is trying to dress like a 16-year-old hippie girl, counter-culture chick. Nobody wants to be a grown-up. If you want to look different and stand out, then try dressing more like an adult. Think Dita Von Teese. She is a standout because she is not dressing like a 14-year-old. She looks like a (grown-up) ’50’s movie star.”
How do we look grown-up, without looking too granny?
“Granny only works when you are very young, like those Japanese girls that dress like Victorian dolls. By the time you are a granny, it is good to go architectural and be quite severe. An older woman with gray hair wearing some amazing Comme des Garçons or architectural Issey Miyake — that is a good look. You no longer need to worry about being seductive, you can look strange and interesting.”
Do you think the fashion industry is youth obsessed?
“I think the media and the beauty industry have a hard time with aging. I think fashion has always been intrigued by women like Anna Piaggi and Diana Vreeland. Look at Ari Seth Cohen’sAdvanced Style. Fashion does take an interest in older women. We have a lot of incredibly chic women customers who are well over 40 at Barneys.”
So, what is the key to rocking it out as you get older?
“The key is not to try and look young, but to look like yourself. You have to find out who you are. That involves introspection and a comfort level.”
Who would you suggest as style inspiration for a 40-something woman?
“There are so many women rocking it into their 40s and beyond. Whether you are Anna Wintour or L’Wren Scott or Tilda Swinton, the key is to have your own individual look.”
Sarah Meikle, Fashion Market Director,Glamour
When do you think a woman should reassess her style?
“My whole wardrobe changed when I had kids; it became all about simplifying. Getting up in the morning, it’s not about mixing my prints and being super creative anymore. It’s all about having a uniform and putting it together. It’s all black, white, navy, and a few prints that are in the same tones. I don’t want to have to think about what goes with what. It all works together. “
How do you avoid playing it too safe?
“What I try to do is mix in something that is a little bit of a statement. A cobalt- blue leather skirt, a cute, leather short, a thick stripe, or a print. I add pieces that update my look, but go with everything already in my closet.”
What about accessories? Is it better to go younger with accessories or do the same rules apply as with clothes?
“Don’t go younger with accessories. As you get older, accessories are what really pull a look together and makes something sophisticated. Now, rather than look for something that is crazy embellished, I gravitate toward an amazing gold necklace or one great Hermès cuff. I want classic, cool statement pieces that are still young, but not trendy and embellished, or big and fancy.”
What do you avoid in terms of accessories now?
“In my 20s, I used to wear eyelet, rhinestone, bows, girly prints. I just don’t do that anymore in my 40s. I need streamlined. Occasionally, I will splurge on a fun pink shoe, like a Stella McCartney satin sandal, but it will still go with the navy, white, and black in my closet.”
Did your style change at all when you turned 40?
“The biggest shift for me was adding more kids to my family. One kid didn’t really change my life, but number two and three changed it in terms of shopping, finding time to shop, and prioritizing shopping. There is not a lot of time to hit the stores anymore. Now, I know what I’m looking for and when I see it; it’s done.”
How has your style evolved over the years?
“When I was young, all I bought was colorful, fun dresses, but that is just not my life anymore. I don’t go out as much. I’m working all the time. It is more about repurposing great staples, but also going out and buying the cute slit skirt from Band of Outsiders.”
How do you look grown-up without looking too granny?
“I still wear miniskirts all the time. I wear leather shorts. I go with more sophisticated, tailored, and modern, rather than girly and flippy. I will also add in a tough shoe or boot, something strappy or buckled or studded.”
Photographed by Christelle de Castro,
Photographed by Kava Gorna
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