Old women dressing too young, young women dressing too old… pathetically, there are tons of women in Hollywood who do not seem to get how ridiculous they look, whether they are in their 60’s wearing skin-tight leopard print (not that anyone of any age should), or a teenager dressing as if they are a grown woman who has business looking like a street walker.
Here, we have found 15 ladies spanning the age range from 15 to 75, none of whom dress their own age, be it older or younger.
Read on, my friends, and prepare to learn all about dressing silly for your age in Hollywood, and probably to laugh a little, too, when you see some of these over-the-top, ridiculous outfits.
1. Kris Jenner – 61
This one is probably an obvious choice, hence its ranking on this list. The Kardashian mom-ager is known to act and dress younger than her 61 years, although I gotta hand it to her; she looks pretty damn good for 61.
In this photo, which was one of so many examples of her “youthful” style it is ridiculous, Kris wears a sheer, leopard-print, spaghetti-strap dress and tall boots. Her cleavage is more than apparent.
The fact that it is tight, revealing, above the knee, and somewhat see-through make this outfit, and others like it that Kris has been seen wearing, way too young for a woman in her sixties.
2. Mariah Carey – 47
Mariah Carey has the voice of an angel, and the body of a 25-year-old, even though she is 47 years young! Still, there is something to be said for modesty as you grow older, and I find it amusing that she dresses so provocatively as she nears 50.
Like Kris Jenner, there is example upon example of Mariah dressing in skimpy outfits, and she is notorious for flaunting her cleavage. This skin-tight getup is so short she can hardly move- much less bend over- without giving everyone a show. It barely even covers her hoo-ha!
Coupled with her long curls, fake tan, and bling, this outfit is more appropriate for a 19 or 20-year-old going out on the town, not a 40-something mother of two, although she did date a much younger man, so she is kind of a cougar. In that sense, her wardrobe makes sense.
3. Honey Boo Boo – 11
Let’s switch things up a bit, and look at one celebrity (if you can call her that) that is the opposite of Kris and Mariah, because instead of dressing too young, she dresses too old.
Alana Thompson, a.k.a. Honey Boo Boo, has been in the spotlight since she was a very little girl. Even if 11 was not too young to dress sexy, Alana has been doing so in pageants since she was seven in the show Toddlers and Tiaras.
After that, she was the star of Here Comes Honey BooBoo, in which her life and that of her overweight family was documented. Between the heavy makeup and the revealing costumes, Alana is a prime candidate for a position on this list.
Now 11, she is still seen often (though not nearly as much) prancing around in short-shorts, tube tops, tight clothing, and far too much makeup for any teeny-bopper.
4. Kylie Jenner – 19
You can’t have a list like this without at least a couple Kardashians or Jenners on it, am I right? So here is our second, little Miss Kylie Jenner, who just turned 19 but has been dressing scandalously for years. And continues to do so.
Even at 19, a young woman is still a teenager, and thus dressing the way Kylie does is very risqué. Kylie spent her teenage years dressing (and acting) like she was in her 20’s.
Take the above photo, for instance; Kylie looks waaaaay older than her actual age of 18 at the time (and she had literally just turned 18 days before). At the 2015 MTV Video Music Awards, Kylie showed up looking like a woman closer to 30 than 20.
Honestly, how can she even walk in heels that high and a dress that short? I bet if she turned around her butt would be hanging out. Just a guess.
5. Adele – 28
The beloved Adele, who is neither too old to dress young or too young to dress old in the sense we have been talking about thus far, earns her spot on this list for an entirely different reason: her frump.
That’s right; Adele who is loved by so many dresses like an elderly woman, and she does it often. She does look classier than most on this list, I will give her that. She is a beautiful woman, but she is only 28 years old. With so much life ahead of her, she should at least dress like it sometimes.
This dress, for instance, looks like it was made out of curtains or a tablecloth or something. The fabric and the print are not only unflattering, but they just look plain old, and not in the cute, vintage way.
But Adele considers her clothing elegant, not frumpy. She says, “Even if I did have, you know, a Sports Illustrated body, I’d still wear elegant clothes.”
6. Janice Dickinson – 61
Back to the older crowd now, we have the infamous writer and producer, Janice Dickinson, who is no stranger to dressing provocatively.
The 61-year-old who claims to be the “first supermodel” likes to think she is 25 or something, or at least that is how it appears from the way she dresses.
The above photo is just one of the many of Janice sporting tight clothing, cleavage, and making pouty fish faces at the camera. This photo is especially ridiculous simply because of the length (or lack thereof) of that teeny-tiny dress.
Paired with those street-walker boots, she definitely needs to take a step back, take a look in the mirror, and realize she is not 20. That was four decades ago, and although she looks great for her age, she looks nowhere near young enough to pull off a look like that with class.
7. Madonna – 58
This should come as no surprise. “The Material Girl” singer certainly prefers to wear less material, if you know what I am saying.
Showing some skin does not have to be sl*tty, and it does not mean you are trying to look young. But in a lot of these women’s cases, that is exactly how they come off. There is a way to look sexy and retain your class, but sadly Madonna did not get the memo on how to do that.
In 2013, for example, Madonna attended the Billboard Music Awards wearing this get-up. Yes, that was her actual outfit. If you know Madonna, you know this is not out of the ordinary for her, but that does not mean she should be dressing like this at 58 years old.
She was only 55 when this photo was taken, but still; you can order off the senior menu at 55, and even live in senior housing, so I think wearing fishnets and a garter belt (in public, no less) is a bit young for her. Or for anyone, really.
8. Charo – 75
Ok, maybe I am in the minority here, but until I started looking into ladies who dress inappropriately for their age, I had never even heard of Charo. But as it turns out, you cannot research this topic at all without finding her everywhere. That is because The Love Boat actress, who is 75, consistently dresses like she is 50 years younger.
From her flamenco dresses to little sequined numbers to anything with glitter, fringe, or a slit, Charo will wear it, and she will wear it proudly.
Oh, and with her signature half-ponytail lopped on top of her head, it is like she is living in the 1980’s (although, that would still make her in her 40’s, not her 20’s, but at least it is closer to her prime than it is now). Either way, Charo looks spunky and like she knows how to have a good time!
9. Pamela Anderson – 49
Here’s a no-brainer! Pamela Anderson of Baywatch fame is 49, but she is still a blonde bombshell and a total knockout. And she is a sex symbol, and probably always will be.
Anyway, Pamela is known for her big, bleach blonde hair and her even bigger boobs. Of those boobs, she says, “I don’t know now if I’d recommend surgery. Women’s bodies are beautiful. I’ve had a love/hate relationship with my breasts my whole life.”
That is funny; from like every picture I have ever seen of Pamela, she seems to be madly in love with her greatest assets. Or maybe she is simply in love with the exorbitant amount of attention they bring her.
Either way, she considers herself a feminist because “The true meaning of feminism is this: to use your strong womanly image to gain strong results in society.” Sure it is.
10. Bailee Madison – 17
Not so long ago, Bailee Madison was a cute little girl with baby fat who always played the sweet little sister type of character. Now she has come into her own, shed that baby fat, and is 17 years old. In fact, despite her baby face, that little girl is hardly recognizable under all the makeup.
Like most Hollywood youth, as she gets older, the sexier she begins to dress. It’s like there is something in the Hollywood water these girls drink; they all seem incapable of going through their teen years without dressing as sexy as they possibly can.
And like most of them, Bailee looks a decade older than she really is because of it. This photo makes her look so very much older not only because it is sexy, but she looks like she could be a 20-something professional on the way to work or something. Those legs and those heels only add to the image of an older woman, certainly older than 17.
11. Mayim Bialik – 40
Like Adele, and like her character Amy Farrah Fowler on The Big Bang Theory, actress Mayim Bialik dresses frumpily in her real life, too.
The former Blossom actress dresses like a grandmother at the tender young age of just 40. The vegan, neuroscientist, co-sleeping mom even admits it: “I don’t wear pants, or like them; I’m a Jewish woman who’s made the decision to wear skirts, so I wear mostly skirts past the knee… I like army boots, I like peasant skirts- sometimes together!”
She also admits to having a lot of stuff from when she was in high school. To me that means she does not care about style, and it shows. But she has made her own style out of the frump; I call it nerd meets peasant meets grandma meets someone who is definitely not 40. Hey, 40 is the new 30, right?
12. Rowan Blanchard – 15
She plays Riley, the daughter of Cory and Topanga on Girl Meets World, the “sequel” to Boy Meets World. Rowan Blanchard, 15, dresses as if she were about 40.
She wears stodgy patterns, frilly necklines, and suit-like apparel more suited to a middle-aged woman. Her clothes are a stark contrast to her very girlish face. She looks so young, in fact, that you can hardly help but notice the oppositeness in photos.
Rowan does not feel a need to define her style, though. She says “My style philosophy would be to never define your style. Be whatever you want!” Ah, she sounds just as young as she looks- minus the clothing, that is.
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