What Does It Mean to ‘Dress Your Age’ in Your 30s and 40s?

Video: The Cut

It’s only around the time of your own birthday that you start to think, Wow, is it everyone’s birthday right now? But it really does seem like it’s everyone’s birthday right now. Restrictions are lifting and people are publicly throwing big parties for themselves again. And even if it’s not your birthday, spring can feel like something of a rebirth.

It’s the perfect recipe for an existential crisis. “I feel like I’ve come out of the pandemic just as I hit 30, and I don’t know how to dress anymore,” said one reader of her wardrobe. I’ve gotten a lot of questions like this lately: “Should your wardrobe change when you are about to turn 30?” asked another person. “I just turned 40 and have never thought much about my personal style,” said someone else. “Where do I start?”

It’s important to remember that birthdays don’t have to mean anything. They’re just one day. You can completely disregard them like Mariah Carey, who is 12. Or you can use them as an opportunity for a sort of annual review. It’s your life. I’m (clearly) a birthday person, and since my wardrobe is an extension of myself, I usually take a good, hard look at my closet every year. My most recent takeaway was “Wow, I’ve bought a lot of the same thing,” which made me feel kind of foolish for a second. But then I realized that this could actually be a good sign. Maybe, at the age of 30, I’ve finally figured out what I like and what works for me.

“The really fun part about one’s twenties is the discovery of personal style,” says designer Norma Kamali in her memoir-slash-self-help-book. “You have the freedom to dress any way you would like at this time, so experimenting is the way to do it.” Each chapter offers advice for a different decade of your life, so I revisited it this week, and this rank true for me. Ever since I first interviewed Kamali, who is now 76, five years ago, she’s served as my sort of style guru and age idol. I want to be her now, and forever, because she is ageless. “Phrases like ‘age-appropriate,’ ‘anti-wrinkle,’ and ‘anti-age’ aren’t in my vocabulary,” she writes.

Kamali was 19 when she first got married and 29 when she got divorced. When she decided to leave her husband and her company, Kamali, she had just $98 to her name, but she went out on her own anyway, starting a new line literally called OMO, for “on my own.” “The secret is to just keep developing and nurturing your true, authentic self,” she writes in the chapter on her 30s. “The benefit of self-esteem is that you do everything better when you have a healthy sense of who you are.”

In her 40s, Kamali bought an apartment and started spending her money (which she now had more of) on things other than clothes. In her 50s, she dyed her hair red. And in her 60s, she puts her soul mate. She’s living proof that there’s no right or wrong way to age — or to dress for your age. You can still wear a crop top in your 30s and a suit in your 20s, if that’s what you’re into. Instead of worrying about whether or not a garment is “fun” enough or “sophisticated” enough for a certain moment in your life, I think she’d tell you ask yourself instead: Is it me? There are a lot of things I’ve admired recently, like Chopova Lowena’s skirts, but ultimately didn’t add to my cart because I didn’t feel a personal connection to them.

As you figure out who you are, try to find designers and brands whose vision aligns with your own and whose clothes fit you well. Study them. Get to know them. Embody them. In the same way that you surround yourself with people who really get you as you get older, fill your closet with designers who really get it too. And everything else can go. For me, this means Kamali, of course, and I could afford her clothes in my 20s. I wore a red dress of hers to my 25th birthday, and I’ll be wearing one again for my 30th. (Maybe this a good tradition: buy yourself a sexy red dress every year or every five years.) I also idolize Miuccia Prada, who is 72, and it’s not a coincidence that she’s another female designer who isn’t defined by age. “I had this problem, worrying about looking old, when I was 33, and thank God I got over it and it never came back,” she once said. Her work reflects this, and I’ve been slowly amassing a collection of vintage over the years.

My personal goal is to only have like ten brand names max in my closet by the time I’m 60. My people! It’s not so much a uniform as it is — let’s call it style miming in Mrs. Prada’s honor. (She went to mime school once.) Who knows, though? Maybe I’ll change my mind. That’s life.

Norma Kamali Sweetheart Side Drape Dress
Very Good Deal

My best friend is taking me to La Grenouille on my birthday, so I want to wear this and match the red-velvet booths. To me, it’s a hotter version of the DVF wrap dress but still sophisticated. The neckline feels more ’80s, and the asymmetrical hem makes it more interesting — and sexier.

Rouge Hermès Satin Lipstick

Nice lipstick is a great present for yourself because it’s not wildly expensive, but it’s expensive enough that it feels like a treat. It also makes me feel older.

Miu Miu Two-Tone Patent Leather Pumps

If you really want to do something nice for yourself, maybe invest in a pair of grown-up shoes. These feel fun, and I think I could keep them in my closet for many years and they wouldn’t get old.

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