The Truly Rich Lady's Fashion Commandments on "Dressing Your Age" (If There Is Such a Thing)


To My Dearest Truly Rich Lady,

Hi. I am need of advice. Is there clothing that you shouldn’t wear beyond the age of 30, 40, 50, and above? I am in the “above” category. Also, I changed my clothes this morning because I saw your face.

Lovingly yours,

Not Your Mother


Dear NYM

Do we know each other?

Old Mother Wisdom, whom I hear is a total pill at parties, proclaims the following as off-limits once you have graduated from the age of full flowering: mini-skirts, daisy dukes, bandage dresses, leggings, sportswear when you are not playing sports, spiky heels that recall a corner worker, anything with bows, anything pink, and anything trendy.

In sum, she wants old people to dress old.

New Rule 1: 60 is the new 39.

But consider this: When Jennifer Lopez turned 50 this year, she wore to her big celebration a Versace gown with a bra-like construction that bared her chest and tummy, a slit that almost reached her hoo-ha, and straps that recall bondage. It was also in the audacious color of glitter, as in gold.

Despite the attire that may be more suited for someone half her age, I don’t think anyone in the world dared to say that these clothes did not suit La Lopez.

Take a look:

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Right?! What kind of age-defying sorcery is this? Singer of “Jenny from the Block,” please tell us which health store you source your supply of unicorn blood from?

The point is, 30 is the new 20, 40 is the new 30, 50 is also the new 30, 60 is the new 39. And being in your 20s is just stupid. Do you remember all the dumb mistakes you made like saying yes to a boy who turned out to be a liar. (I am not speaking from personal experience).


This backward shift in age is not just in the way a woman feels or thinks; it’s also in how she looks. More people are becoming attuned to taking care of the body that the period of youthful flowering is now longer. With help from science, it can even last forever.

As such, there is more leeway to dress in a gold Versace gown with barely-there coverage. I mean, if I looked like the 50-year-old J.Lo, I certainly wouldn’t deny the world my beauty by wearing a black car coat and sensible shoes.

New Rule 2: The Truly Old Lady has the license to not care.

How about a legitimately older example? Iris Apfel, the 98-year-old style icon, refuses to go gently into that good night. Even in her sunset years, she lives boldly, especially in the way she dresses.

Iris is like a rare bird—literally. See her in feathers, in bold, sometimes eye-searing colors, in clashing patterns, and with a pile of necklaces. It all works because, maybe, she just wears that jumble of clothes with full confidence.

One of the joys of getting is old is becoming more comfortable in your skin until finally, you learn not to care about the hurtful opinions of opinionated people. You, an old person, wake up one day and declare: “This is me, world! If you can’t love me in my pineapple-print, wide-leg trousers with matching blouson, you don’t deserve me at all. Good day!”

New Style Rule 3: What you wear should say something about you.

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Do you know that Anna Wintour, the pope of fashion and EIC of the bible (Vogue), dislikes the wearing of all-black ensembles. She would rather people wear clothing that says something about themselves, and that means a dose of color or a splash of creativity in how pieces are put together.

After all, what does a black dress with black tights and black pumps say about you? That you have lost your ability to determine colors because you are old? That you are playing it safe because you are old and scared? That you just wore what is easiest because you are old and tired?

Nuclear Wintour also emphasized, when asked about what to wear to an interview for the magazine, that people are hired for themselves and not their clothes. Taking off from her statement, which is law, by the way, it may be better to express yourself, as in wear what you want, rather than adhere to a set or don’ts prescribed by so-called experts in tastefulness.

So go ahead and wear pink, a skirt, or a frilly pink skirt—just, you know, make sure Anna approves of how you style it.

New Style Rule 4: Don’t think about the number.

Okay, if you came here looking for a hard-and-fast rule, here it is: When it comes to what to wear, forget about the number (of wrinkles), but rather focus on the situation.

The high slit on your well-toned stem is an empowering statement about your love for pilates, but it would be best to cover the revealing leg when, say, you are at the workplace.  Unleash the skin during your downtime like, say, when you are at the Important Party to be Seen.


Same goes for other articles that are deemed unacceptable by the style police, but you nevertheless like wearing. Please rethink the leggings and crop top when you’re, say, watching a ballet. There are certain boundaries we dare not cross like dress codes for formal affairs.

Finally, if you are here, shaking your head in anger or disappointment after reading these new style rules, I am not stopping you from dressing in a timeless manner, in all black, and in full cover (no skin please!). That is your expression. I fully support it.

One last thing, I made a face this morning because that pair of high-waisted jeans is, I think, mine, and I wanted to wear it to lunch. Anyway, you can keep it.


C.C. Coo

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