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. But oh, there is more. You see, when it comes to women and fashion, there is always more to get wrong than just age-appropriateness, or inappropriateness, for the sake of this list.
Besides age playing a factor in just how ridiculous some of these famous females look, there are other things to consider as well, such as frumpiness, for example. Although, that look is kind of “grandma”, so maybe in the end it all has to do with age, after all. But for the young girls who dress so much older than they actually are, it is not just that they look too sexy; some also dress like a professional or even a politician. And the ones that do may surprise you.
I have found 15 ladies spanning the age range from 15 to 75, none of whom dress their own age, be it older or younger. Who are they? I am sure you have some pretty good guesses, but I am equally sure that some of the women who have earned a place on this list will surprise you. 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.
15. 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. There is also the aspect of the show that focuses on Alana’s and her family’s weight problem, so having her walking around in skimpy outfits only draws more attention to her and that is not fair to her. 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.
14. 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.”
13. 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. But the funny thing is that I don’t see this as an outfit younger people would actually wear. It is not very stylish with the younger crowd (or at least, I never see them wear stuff like this), but 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.
12. 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! She wears it with shimmery nylons, high-heels, and a neckline that is as low as the skirt is high. 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 (Nick Cannon), so she is kind of a cougar. In that sense, her wardrobe makes sense.
11. Willow Smith – 16
Just as her famous father Will Smith is known for his kick-ass movies (and being the Fresh Prince of Bel-Air, of course), his daughter, Willow Smith, is known for her often-strange sense of style. And while her unique fashion sense is frequently in line with the modesty a girl of barely 16 should demonstrate, it just as frequently is not. Nowadays, it seems as if 16 has become the new 18 or 20 in terms of how girls dress, and Willow is no exception. She flaunts short skirts, low tops, astonishingly tight leather, and looks way more than 16 years old. Just weeks ago, actually, she was not even 16 years old, as her birthday was on Halloween. So tell me, do the photos above look like a girl who was 15 mere weeks ago? Does that outfit look like something you would want your 16-year-old daughter, niece, or sister wearing? I am sure it does not.
10. 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. Together with her sister Kendall, who turned 21 this month, 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.
9. 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.
8. 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.
7. 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 (born Maria del Rosario Mercedes Pilar Martínez Molina Baeza- whew!) 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!
6. 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. In fact, she and David Hasselhoff will be in the upcoming 2017 Baywatch movie. 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.
5. Kim Cattrall – 60
Known best for playing the promiscuous Samantha Jones for six seasons of Sex and the City (and two movies), Kim Cattrall dresses just as promiscuously in her real life. In a way, I admire her for doing what the hell she wants, just like her character Samantha does. In that way, I admire all of these women because they don’t care what people think of them. In other ways, however, I think they need to act/dress their own age. Kim turned 60 years old this year, and frequently wears low-cut, off-the-shoulder, slitted, form-fitting, or revealing outfits. Dressing sexy may just be in her blood by now, and maybe Samantha had a profound influence on her. Thankfully, more and more often as she ages, Kim is being seen wearing Hillary Clinton-style pantsuits, but she still has lapses into her past and dresses in Samantha-esque ensembles from time to time, and trust me when I say Hillary is much more flattering on her than Samantha.
4. 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.
3. 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 (mom to both human babies and the whale, wolf, and manatee she adopted) 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?
2. 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. Rowan is still playing the lead on Girl Meets World, and up next for the Spy Kid? She is currently filing the 2018 movie A Wrinkle in Time, based off the book of the same name. It will also star Chris Pine, Reese Witherspoon, and Zach Galifianakis.
1. Selena Gomez – 24
If any of the women on this list surprised me that they don’t dress their age, it was surely Selena Gomez. She is a 20-something, huge pop star. But she is shockingly modest when it comes to her clothing (well, most of the time). She may have some racy photoshoots and sexy stage outfits, but that is not Selena in her real life. She dresses rather stuffily if you ask me. Take this photo above, for example; she looks like a full-fledged adult, and not just one who is legally allowed to drink, smoke, and vote. Selena looks classy, which is not typical of someone her age, and especially not someone her age in Hollywood. She almost looks like she could be a lawyer on her way to court, or some other kind of hot-shot professional. But I must say, that is much preferred to babies dressing like street walkers, or quite the opposite, old ladies dressing like teenagers.