Too Old to Dress So Young?

Bubblegum popsters Debbie Gibson and Tiffany: 40-somethings who dress too young.

July 29, 2011

Tiffany and Debbie Gibson need some tips for dressing in age-appropriate looks

Source: Getty Images

Singers Tiffany (left) and Debbie Gibson look like they pulled these get-ups (ca. 1989?) from the mothballs for recent appearances.

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More than 20 years ago singers Tiffany and Debbie Gibson were the ultimate in bubblegum pop. Over the past few years these middle-aged women (both are about 40) have been doing projects — including hitting the stage — together again.

Honestly, I don't have a clue what either singer sings because I wasn't into that type of sugary music the first time around either. It's just that the fashion choices concern me (like the fact that 40-something Debbie Gibson was seen ontstage in a crop top – tummy bared – that had a giant red heart on it. Egads.)

Why is it that aging stars try to dress exactly like they used to? We've seen it with Cher who boldly re-wore a bodysuit from decades earlier. Note to Debbie,Tiffany: if even Cher can't get away with it, neither can you. Even Madonna is starting to look a little long in the tooth to carry off cone bras.

What's wrong with these pop stars aging with some dignity? There are plenty of cute, youthful styles out there that women of means (and with stylists) can take advantage of. Most of the time it's not what you wear, it's how you wear it.

Take for example Debbie Gibson's stage outfit in the above pic: she is wearing a belly-baring lime green top, pink feathers in her ear and white hip huggers. Tiffany is wearing a too-small leather vest and an armful of bangles. It doesn't help that both middle-aged ladies look like all of their accessories came off the markdown rack at Claire's. Even worse: both singers look like their wardrobes actually came from the '80s.

Learning how to dress youthful without looking too young takes some finesse. Most of all, it takes restraint. The best advice I can give women over 40 who want to dress younger is to take a youthful element – maybe it's a studded belt or a fedora, and mix it with a classic (dark, bootcut jeans, a basic tee shirt, a button-front shirt, etc.) When you start mixing young pieces with skin-baring looks – like Debbie Gibson and Tiffany – you start to look like, well, Debbie Gibson and Tiffany.

More about fashion over 40:

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Anonymous | May 4, 2012

I don't think she was TRYING to look younger or dress young, I believe she thought it looked great and she wore it... she wasn't comparing herself or hopeing to make anyone see her as younger!!! Why do people think she was trying to be youthful & that she was just wearing a cute fun quality hot outfit?? now if she was 80 bent over & sagging & wrinkled yep then I could understand

Anonymous | Nov 4, 2011

A lot of sensitivity and projection going on. This is exactly when women over 40 start to look ridiculous. We think we can carry the look when in reality it doesn't look good and isn't appropriate. Yes, yes, I'm in my 50s and I have people think I'm in my late 30s. Doesn't mean I should wear the same clothing as my 21 year old daughter-in-law. It's less, can I than should I. You end up looking like you're trying to hard.

Anonymous | Oct 26, 2011

they are just bad outfits. It has nothing to do with style. But the main complaint here is to call two attractive vibrant 40 year olds MIDDLE-AGED. Get real. Is the writer still living in the 1950s?

Anonymous | Feb 12, 2012

But they are in middle age. It cracks me up when people describe 60-year-olds as middle aged. It's doubtful they'll live to be 120.

Anonymous | Oct 17, 2011

As long as the woman are happy of what they are wearing who cares.

Anonymous | Oct 13, 2011

I am sure she feels the same about aging male rockers, but she's talking about females here. Not wearing looks that you wore in your 20s doesn't mean hanging it all up and having to dress like an old lady. These two women are still greatlooking, with fab figures, but I agree, what they're wearing in that picture,not good. Especially Tiffany. She's dressed like a 15 year old! That outfit Debbie Gibson is wearing is just plain hideous, on any age!

Anonymous | Oct 12, 2011

You say NOTHING regarding aging MEN rockers who are the WORST on trying to keep the appearence of still 20-something. It is so sad to see these guys wearing the grunge-look that in their 20s looked sexy, now they look like some old guy who isn't all there upstairs

Anonymous | Oct 12, 2011

Umm, the author obviously is not in her 40's yet. Let's she if she's ready to just hang it up when she turns 40. Don't talk the talk if you haven't walked the walk yet young lady. I'm 44 and I dress young because most people think I look about 29 and I have the body for it. I'll wear whatever I damn well please, thank you very much!! If you don't like what someone is wearing then you can always look the other direction!

Anonymous | Oct 9, 2011

in the land of the free and the home of the brave, let them wear whatever they want...it's their life not the author's.....

Anonymous | Oct 8, 2011

if you are in good shape you should wear what you feel good in not what others think you should wear, because who are you to tell others what they should wear