A Fatal Attraction to Cuteness
January 31, 2008 2:07 PM   Subscribe

My favorite styles of clothing and accessories tend to be whimsical, cute, and generally suited to children or teenagers... but I’m in my late twenties. I obviously need to outgrow this eventually, but I’m not sure when or how.

I love wearing things that are fun. I love cute. I love bright colors. I love Hello Kitty, neon eyeshadow, Claire’s Accessories, and dinosaur shoelaces. I even love Hot Topic. If there were no dress codes, I’d wear lobster-print pajama pants or deliberately mismatched flip-flops everywhere I went. This is not to say I can’t dress myself appropriately: I do have suits, and various Ann Taylor separates for work, but I don’t really like wearing them. I generally have the good sense not to do a full tilt boogie Harajuku Rainbow Brite Punky Brewster rollerskating in drag in space ensemble, but I like putting on a clump of plastic bracelets or a smidge of glitter eyeliner if I go out.

I have always known, in the back of my head, that the day will come when I can no longer pull off. I fear that day may be coming faster than I’m ready for, or that it may already be here. As much as I love Betsey Johnson’s spirit, I’m probably not going to be able to pull off her look at 35, never mind 65.

When is the time to put the cute stuff away and start dressing one’s age? Is it a numerical age, a change in one’s life (such as becoming a parent or getting a promotion), or the point when you start to notice wrinkles? Or is it one of those "I know it when I see it" things? Was it in fact five years ago, and no one told me? I very much doubt I’m going to wake up one morning, look at my closet of glitter and pink, and say, "Gee, I’m just too old for this and I don’t feel like wearing it anymore."

And how can I let the kiddie fashion go without tears? I have eclectic tastes and a good eye for style, so I know I’ll probably find things to wear that are both appealing and age-appropriate, but sometimes that plastic jewelry really does seem like the only thing standing between me and a slow slide into corporate casual, mom-jeans, three-shades-of-beige sartorial senility. And I can’t just decide to stop liking Hello Kitty… or can I?

(Please, please, please do not suggest that I watch "What Not to Wear" – even though I admit they sometimes have okay advice, overall I hate that show, I frequently disagree with their taste and half the time I’ve seen it they’re trying to get some poor soul to wear a blazer and heels to the supermarket.)
posted by Metroid Baby to Clothing, Beauty, & Fashion (27 answers total) 22 users marked this as a favorite
As long as you like it, go ahead and wear it.

But I imagine that the rest of the world will start to notice when you have the wrinkles and the saddlebags &c.

I don't think it's a numerical age, but when someone can look at you and "just tell" that you aren't in your 20s anymore, that's when they start to say things behind your back.
posted by kpmcguire at 2:17 PM on January 31, 2008

I know plenty of women my age (mid-thirties) with a flair for the cute and whimsical. It's all about work clothes vs. play clothes.

How can you tell when you're growing out of it...well...do you truly wish you still had your favorite skirt from when you were fourteen, or did you let some stuff go as you got older?

If you loyalty on principle to a thing greatly overshadows your ability to look in the mirror and actually see yourself, that's when you need to reassess. The middle-aged women that I see who are dressing way too cutesy for their age are wearing clothes that do not flatter or fit.
posted by desuetude at 2:26 PM on January 31, 2008

I'm 37 and a lot like you. Plus I have a job in finance and two small children. No Mom jeans here. But, I did realize that certain things start to look sorta ridiculous when you reach a certain "maturity." I look younger than my age so it took a little longer for me to figure this out.

What has worked for me is getting basics that have a slight edge and then adding maybe one funky/ punkrock/ bohemian/ artsy/ glam/ mod/ kiddie element. I have some nice, sleek, pants-suits that I can wear a cool t-shirt under with cute shoes, for example. And I wear my hair in a bit of a shag. Kind of Bowie-esque...

Anyway- there are ways to hang on without looking silly... you just have to tone it down a bit.
posted by mistsandrain at 2:27 PM on January 31, 2008

I'm forty-four, and I still wear pink, glittery, whimsical things, and Betsey Johnson is a favorite designer. Admittedly, 1) I have the personality to carry it off so far, 2) I'm a grad student and part-time consultant in a field where casual is the norm, and 3) I've been known to play the cancer card and say, "I've had a life-threatening illness. I'll wear whatever I damn well please because life is too short NOT to. Now get off my lawn, you kids, before I thwack you with my sparkly pink cane." YMMdefinitelyV.

I believe that many times it comes down to personality, not age. And there are those of us who don't like to be told "What Not To Wear"; especially because, IMO, dressing to stuffily or "elegantly" if that is not one's style can be aging.

So I think it's really up to you, and Trinny and Susannah can suck it. What kind of work do you do? Do you notice people sniggering at you behind your back? Have you been passed over for promotions? Have kindly, well-meaning higher-ups pulled you aside for a little chat on your sartorial preferences? Then maybe it's time to rethink, especially if you work in a conservative field. Otherwise, don't sweat it. If you are a Luna Lovegood type, then glory in your Luna-ness. Don't try to dress your age just because you "should," or, God forbid, some fashion authority decrees it.
posted by Rosie M. Banks at 2:27 PM on January 31, 2008

The time to get rid of anything in your wardrobe that makes you feel anything less than fabulous is right now. You must listen to how you feel in every item of clothing you own, and be ruthless in getting rid of the stuff you love for any reason other than that it makes the body you have look and feel fabulous. The thing I see a lot (on, yes, What Not to Wear) is people clinging to silly, crappy looking clothes as though their clothes are all they have. You are not your clothes. You can be crazy fun on the inside and look great on the outside- great in an objective way, not in a "BUT I LOVE my green shoes, orange socks and pink glitter suit" way. What are your career aspirations? What are your goals for life? Start dressing the part! If you don't like your work clothes, it probably shows. Start working on ways to inject your personality into your wardrobe for the life you have, instead of wishing you were still 14 (because, I'm sorry, that's the message plastic braclets or other Hot Topic crap screams to me whenever I see them on a grown person- "I have no sense of who I am now! I haven't changed since middle school!"). I think my wardrobe got more "grown up" naturally over time- I didn't throw out all my crazy vintage stuff all at once, I just realized as I wore each piece individually that they didn't fit and that I felt silly in them. So I got rid of them and replaced them with things that make me feel fabulous now.
posted by ThePinkSuperhero at 2:28 PM on January 31, 2008 [3 favorites]

As long as you can get away with it, go for it. I saw a woman on the beach wearing a neon green bikini not too long ago, and she was at least 70. You know what? She could get away with it. She was in better shape than a lot of women half her age. If you can figure out to wear to work that does not compromise a professional (promotable) image, then who cares what you wear on your off time?
posted by 45moore45 at 2:29 PM on January 31, 2008

When is the time to put the cute stuff away and start dressing one’s age?

If you care (and I hope you don't), some people probably already say mean things about your style, they don't wait for the wrinkles and saddlebags. People will always say mean things. They did in preschool and they probably do in the old people's home. Seems to me you're asking, "when will people disrespect me for my taste in clothing?" And the answer to that is, already and always. Knowing that, you can go on now, and keep dressing weird. The care-factor drops amazingly at age 30, and even more by 40 (at least it did for me.)

Of course, you know that your style might affect your career path, but if that doesn't bug you, then no problems.
posted by b33j at 2:34 PM on January 31, 2008 [2 favorites]

Why not intersperse cute stuff with adult stuff? What about wearing like most business-casual stuff with a printed t under a cardigan or blazer? Or a plain, sensible work dress but with pink shoes and Hello Kitty barrettes? You could wear fancy-colored socks underneath your sensible work pants (I do this). If you experiment, you can find a balance between Adult Clothes and fun stuff. Sometimes it looks a little silly but really, experiment, try on a bunch of stuff and see what it looks like.

As for when to give up the cute stuff... I don't know that you necessarily have to give up cute stuff for all time. But for me, at age 28, it gets grating after awhile to be mistaken for a high-schooler when I'm out working, trying to be taken seriously. I mean, I don't mind being carded if I go out, but it is annoying and difficult when I am working. So if that is an issue for you, it's something to consider.
posted by sutel at 2:34 PM on January 31, 2008 [1 favorite]

Lots of people older than "late twenties" still like Hello Kitty. Bangles and beads and catchy graphics for the most part aren't going to make anyone think you are immature, as long as you are self-confident (and you sound like you are).

Keep what you like, and experiment as you get older, maybe just making it a little more subtle. Over time, your cute and eclectic taste will become something people discover about you as they know you, rather than on first impression, and that's okay. You'll still be you. You don't have to go straight from cute and fun to beige and boring!
posted by misha at 2:37 PM on January 31, 2008

most people on the "what not to wear" show sound like you before going through the process- they disagree with the hosts' taste because they are wearing what not to and in the end they are always grateful for the transformation.

between hello kitty and ann taylor there is a full spectrum of clothes that are mature but have character. mixing vintage pieces with new ones or buying new ones that have an antique feel (think anthropologie) may help you avoid looking like a total yuppie. why do you have to let hello kitty go completely? you could pick just one thing that captures your sartorial character- bright shoes OR the glitter makeup, and stay true to your tastes.

when you decide to transform your sense of fashion is up to you, for most people this is a natural evolution. there is nothing inherently wrong with wearing age-inappropriate clothing, but if it interferes with your ability to be taken seriously at work, or if you begin to feel self conscious about the way others perceive you and this inhibits your ability to develop friendships with people your age (assuming you want to), then you have a choice to make about what is more important to you.

if you are asking this question here, you are obviously affected by the issue and it's unrealistic to think you can wear whatever you want and not be judged, and not be perturbed by those judgements- professionally and personally.
posted by flaneuse at 2:48 PM on January 31, 2008

Best answer: Somewhere along the way you got it into your head that that's what "you" look like. You probably do look much different than you think you do anyway-- most people do. And I can relate: as a person with gender ambiguities and fantastical interests firmly in place, half the time I can't even tell when I'm "in costume" and when I'm just wearing what I have laying around. "You" can really look however you want, and the best reason to broaden your taste isn't to for others' comfort, it's to continue to find what else will inspire you.

In my experience, people have found ways of telling me "you don't look the way you think you do in that." And I have to measure that based on how well they really know me, what I think of THEIR style, and the "reality" I see in the mirror. Sometimes they're right. Sometimes, fuck 'em. Being able to know the truth when I hear it has actually made me more creative, pushing me to find and try new things.

My main approach has been to choose my battles wisely. I have stripped my look down to the most basic attire (no more chandelier earrings, I'm afraid), counting on well-made, well-fitted garments to communicate the basic shape of my body and to broadcast my level of availability. On special occasions-- parties, holidays, fun outings-- all bets are off. Or when I am just going somewhere alone, and have only myself to embarrass. I'm always on the lookout for opportunities. But most other times, I go for the stripped down humanoid look (I even shaved my head) and consider it a challenge to let my personality grow and do the heavy lifting.

Essentially, my strategy has changed from "always catch 'em off guard" to "always keep 'em guessing."
posted by hermitosis at 3:16 PM on January 31, 2008 [2 favorites]

As long as you see it as "cute and whimsical," you can rest easy knowing that people who have a problem with it simply have no sense of humor (at the very least).
posted by rhizome at 3:34 PM on January 31, 2008

Speaking as a sartorially challenged guy, I don't see the problem here. You know when not to wear the lobster pajamas. The rest of the time, if it makes you happy, wear it. I think you sound great.

I've commented on this before, but it bears repeating especially here. A close friend of mine, a woman in her mid-40s, routinely wears outfits that on anyone else would almost be considered a costume—and she gets a lot of compliments from women who say "I wish I could wear that" (the only thing stopping them, of course, is that they think they can't). I should also mention that this friend only came to dress this way when she was already older than you—when she was in her early/mid 20s, she was a conservative preppy.
posted by adamrice at 3:37 PM on January 31, 2008 [1 favorite]

I can understand not wanting to decieve oneself - there's an acquaintance I know who said to tell her if she ever became a cougar. But that's impossible as she'd been one for quite a bit. And the aspie in me is still upset that because I knew her through ms. nobeagle I didn't feel free to tell her the truth.

Ultimately I think you need some introspection to see if you just like the cute, or if you're trying to look young. If you're trying to look young, you'll just continue to try harder, and it will be obvious to everyone. If you just like the cute, it will be obvious to many, and if you're ok with the occaisional gawkers or whispering, then live happy. Here's hoping for honest introspection.

Myself, I'm early 30's and occaisionally wondering just how much longer I can keep the dyed hair and facial piercings. As long as I can find employers who are fine with it, I don't feel the change in me yet. And as long as there are TCS's, Fleet Farms, and Value Village I'll always be able to supply myself with jeans, flannels and tshirts. I realize that my "fashion" is dated, but the jeans and tshirts are no longer from the 90's, and quite simply I look around, but only buy what I like.
posted by nobeagle at 3:43 PM on January 31, 2008

Chiming in with a "wear it". As others have said, you're already dressing appropriately for work.

There's a huge difference in the way someone presents themselves when they just happen to like Hello Kitty and are wearing it to please themselves than when someone's wearing Hello Kitty in a desperate attempt to look young and cute.

My friends have often remarked that I can "pull off" outfits they couldn't, and I'm pretty sure that the difference is that I don't think I'm pulling anything off... I'm just dressing how I like.

Last Halloween, I ran to the convenience store in the base of my Halloween costume, which was a teeny-weeny schoolgirl skirt and blouse. I'm in my early thirties, I'm starting to go gray... and yet, as I picked up my missing party supplies, I heard two other women in the store gossiping about me.

Not that I dressed too young for my age... they had assumed that I went to the nearby prep school and were complaining about how short "those girls" wore their skirts. I had looked these women full-on in the face earlier, so it wasn't a matter of them only seeing me from behind. They saw the uniform, and since I seemed to belong in it, they whacked a good fifteen years off my age. Not only did I get carded for cigarettes, the cashier argued with me over whether or not my ID was fake.

Enjoy your Rainbow Brite-wear as long as you can enjoy wearing it.
posted by Gianna at 4:10 PM on January 31, 2008 [2 favorites]

I am forty-nine years old, and I still wear my earrings with the little pink flamingoes on them.

Just not to church. ;-)

But to answer your question more fully-it has to do with your personality, I think. Where some people run into problems "dressing too young" is when they show too much skin when their bodies have aged out of looking good. Just dressing quirky is fine. If you have the style to carry it-and it sounds like you do-go for it.

But meanwhile do some shopping and buy some "older" stuff too. Because you need to give yourself permission to see if that starts working for you as well.
posted by konolia at 4:39 PM on January 31, 2008

Best answer: It sounds like you've already figured out that some clothes are work-appropriate and some aren't, so I'm assuming you're just talking about what you wear in your leisure time or to go out. In which case, it's a lot less important. If you really don't care what other people think, then wear the outfit you've got your heart set on.

But when I read your question, I get the feeling that you're starting to feel less comfortable in some of your younger, sillier clothes and accessories. It's hard to let go of things that have always made us feel good, but if you are having these small nagging feelings of discomfort, listen to them. It doesn't mean you have to pack up all your pink or all your Hello Kitty. It just means you'll probably start wearing them less and less, and that you will find other clothes and accessories that are funky but have more of a grown-up vibe, like vintage stuff or stuff from small, independent designers. You can still have style and not be boring, but look like a grownup.

I think for most people this is an organic, gradual process. I can't pinpoint the exact time when I started to wear more grown-up clothing, but it was probably in my mid to late twenties. I just noticed that I didn't feel comfortable in certain clothes anymore. They weren't *me*. I'd like to think I don't dress in an overly conservative or boring way, but I do wear stuff that's appropriate at work but that I feel good and attractive in. I don't really mourn the stuff I left behind.
posted by hurdy gurdy girl at 5:00 PM on January 31, 2008 [1 favorite]

My own feeling is that if you caught the wave of juvenile clothing in the early '90s (when it was cool to hang out at raves wearing too-small Care Bears or Hello Kitty T-shirts and sucking on a pacifier while high on E), if you were part of that, amd still dressing like it literally, you're now too old.

I don't quite have that feeling about you. But there are a lot of arty clothes that are graphic (in the sense of bold) and whimsical but don't make pop or girly references: think Garnet Hill or Marimekko.
posted by bad grammar at 5:09 PM on January 31, 2008

Well, there's a difference between dressing like a teenager and dressing like a whimsical adult.

I am 30ish, and occasionally I'll meet people my age who are dressed like a college freshman at Sunday breakfast, and it's super creepy.

It's neat and quirky to own Spongebob slippers. It's a little weird to have a Spongebob purse. Pink heart earings? Flair! Pink shoes? A little weird.

That said, dress how you want. Life is too short.
posted by gjc at 6:08 PM on January 31, 2008

I love Betsey Johnson too. I have a lot of vintage stuff. I generally wear it one piece at a time - that way it doesn't look too "costumey." But I, like you, love sticking out a bit and find it hard to resist going overboard. I save the full-on getups for places where other freaky people (artist, hipster, musician friends) will be, but I will wear the 40s suit jacket (with linebacker shoulderpads and wasp waist) to the mall with jeans and a nice tee, or to work with a silk blouse and dress pants.

All that said, here's what I came to decide some years ago after I saw two girls conspicuously laughing at my poncho (I was wearing a vintage one because I foresaw that they were about to come back into style, having I'd been looking at the runway shows online, and of course, three months later, everyone was wearing ponchos):

If the worst thing that happens to you all day is that someone laughs at what you're wearing, you have a pretty good life.
posted by jocelmeow at 7:13 PM on January 31, 2008

I'm 31 and I still love the whimsy! But yeah, around age 27, I consciously decided to cut out the outright childish stuff: Emily Strange shirts, Hello Kitty watches, anything blatantly ironic or gothic...I still do fun and girly but it's essential to:

1. Mix younger and older pieces together. One crazy accessory or funky pair of shoes is enough.
2. Step up the quality. There is a big difference between the material and cut of a Hot Topic find vs. Betsey Johnson. Or slapping on sparkles from Claire's vs. getting a Mac consultant to show you how to blend four shades of violet eyeshadow.

Honestly, life is short and you should wear what makes you happy. Personally, having a style grow along with me is important. It's not flattering to be stuck in a fashion rut from when you were a teenager.
posted by exquisite_deluxe at 9:20 PM on January 31, 2008 [2 favorites]

Oh, hell yes, girl. Rock on with your fine self. I dress like a candy-addled hyperactive 5 year old as well, and I guarantee you are making more people smile than laugh with derision.

As to how to gradually become more sophisticated:

Think "ladylike," not "boring grown up woman."

Think "twee," not "tat."

The wonderful Emily of Black Apple is always adorable, never costumey or over done.

I've got a few years of rainbow knee socks and Hello Kitty purses left in me, I think, but I hope someday I can be half as sophisticated as Piksi.
posted by Juliet Banana at 3:56 AM on February 1, 2008 [1 favorite]

Nthing if you can pull it off, keep it coming. If you're as self-aware and stylish as you sound, your look will change as you age, but you'll never have to abandon whimsy. Watch this for inspiration–it's an interview with Mary Baskett, whose collection of Japanese fashion was shown at the Cincinnati Art Museum. She's been know to wear this dress in public.
posted by generalist at 8:14 AM on February 1, 2008

Hmm. I'm middle-aged (nearly senior-hood) gray-haired female who occasionally wears her SpongeBob wristwatch with a business suit. Or my treasured red Keds (I will NOT give them up!) with black jeans and button-down shirt. Or my hot-pink panda socks under conservative slacks with loafers.

I'd suggest -- only suggest, mind you -- that you wear the lobster pants at home along with all the other fun, girly, glittery things that make you feel good. Or wear 'em when you go to the convenience store. Just not to work, probably.

That said -- enjoy your uniqueness, just don't overdo. I have, regrettably, had to give up wearing some of my favorite T-shirts in public; the slogans seem "unfitting" for someone of my vintage. (So I wear 'em at home or when in the company of fellow 1960s-era pals.)
posted by Smalltown Girl at 2:57 PM on February 2, 2008

Response by poster: Thanks, everyone! These are really all "best answers" and it's good to realize that I might not be as firmly stuck in fashion never-never-land as I thought.

I think the idea that this is an organic process - an evolution rather than an Extreme Makeover - is right, and the more I look at it the more I realize that my style has evolved, and will continue to evolve. I have a feeling I won't be throwing everything out all at once, but I'm going to be looking a lot more closely at the stuff I bring in from here on. The fact that I'm beginning to question my sparkle addiction is probably a sign in itself.
posted by Metroid Baby at 3:29 PM on February 4, 2008

Ah, I just stumbled on this post and I'm in love with your question. You sound exactly like me, and I'm so glad I'm not alone (I'm 26, by the way, and have begun to feel the pressure to change in the last couple years).

There's some truth to ignoring some of the shallower comments people will throw at you. A lot of the women I met when I moved to this city remind me of my sister, who is my complete opposite fashion-wise--not dowdy old maid, but hyper fixated on seeming "mature" in that supposedly classy, sexy (bo-ring) way. That's well and good and wouldn't bother me, but I find people with that fashion sense to act like snooty fashion police to girls who aren't down with that. I've had women say to my face condescendingly, pityingly, "well, you really need to buy some clothes made out of timeless fabrics" etc etc, less color, no more bright shoes, whatever. Screw them. It helps that whenever I glumly allude to these comments women we know make, my fiance acts flabbergasted and makes a point to tell me the way I dress is way cute and that their fashion sense bores the hell out of him and at worst veers on ugly. So.

I think the secret for me so far is to do what you've alluded to already--don't go all-out print pants and neon sneakers and day-glo hello kitty shirts anymore (ah high school and college), but have whispers of the kind of whimsy you love secretly rippling through your outfits. For me this means it's all in the little details. I wear classic silhouettes now--pencil skirts, "librarian"-ish tops and sweaters--but if a person pays attention they'll see my old affections in the details, like the fact my pencil skirt is cotton not crepe or whatever, or it's a unique but not fluorescent shade of blue as opposed to boring black or navy, the little buttons on the cuff of my sleeves that almost look like little red apples, the fact I'm not wearing a sleek pendant or strand of pearls but instead a little charm necklace with some quirky charm (a spoon, a hummingbird, whatever) in silver. I've got an amazingly classic wool ladycoat but it's in a quirky shade of burnt orange, and has two tiny tiny buttons on the breast that aren't lady-ish--My Bloody Valentine and Tin Tin, sometimes switched up with The Slits and Roy Lichtenstein. And my shoes are classier now, with fitted stockings, but there's still subtle details--I have these black boot shoes with silver-toned saddle shoe stitching, a hint of the past. I wear apron skirts sometimes, and you'd have to look up close to notice the pockets and detailing is "young." You can still have details you love but within the structure of a normal "grown up" outfit. That's been my answer, so far anyway.

And paint your toes crazy colors! Most people won't see 'em, but they'll make you smile.
posted by ifjuly at 10:47 AM on December 21, 2008 [1 favorite]

This tip might not be up your alley, but I found it helped me too: I found it was strangely easy to translate "kiddie cute" to "vintage femme" in a lot of ways, and for some reason the latter is more acceptable to mainstreamers. Dunno why. Like. Peter Pan collars on blouses, swiss dots, square pockets, nubby wool school kid cardigans, things like that.

You can do the "unique shade in a classic cut" approach, like french oxford work shirts but in brighter colors (I personally love this; I own like 7 oxfords in a rainbow of shades), or work the other way--subdued "mature" prints/colors/fabrics, but in a unique cut--black satin tulip skirts for nights out, circle skirts, etc. I have a gray velveteen A-line skirt from madewithlovebyhannah.com, and it has a handprint of a forest silhouette of black trees and a detachable pin at the bottom with a skunk (!) on it. It's classy fabric and the color is subdued, but the details, again the details...

Which reminds me: buying high quality handmade etsy-like stuff is a good way to stay unique and fun but still come off as "pretty" or "high-end" (which frankly ties in a lot with people's lame idea of "grown up." "Grown up" tends to imply "status-projecting." Dumb!).
posted by ifjuly at 10:58 AM on December 21, 2008 [1 favorite]

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