6 Signs You're Not Dressing Your Age

When you wear clothing made for a different generation, you're making yourself look older.

By Beth Levine

One day, you are going about your business when you catch sight of yourself wearing your favorite Hello Kitty t-shirt that always made you feel so free-spirited. Suddenly you think, “When did I turn into my Aunt Gladys?” Many of us fall into the trap of wearing clothes that are too young for us, thinking that the alternative is to wear dowdy, frumpy clothes.  But here’s the rub: Ironically, when you dress too young, you often make yourself look much older. And then there is the opposite trap of making yourself look older with dated trends. (Please, please, say goodbye to the 1980s Dynasty-style shoulder pads!)

“You always want to look modern, but that doesn’t mean forcing a trend that doesn’t match your body type and age,” says Samantha Brown, stylist, fashion expert, personal shopper and founder of the designer clothing consignment store, The Missing Piece. "You don’t want to look like you are trying too hard or holding on to a decade that’s past."

Other signs that you are not dressing your age...

#1. You are still shopping at trendy teen store.

“That’s a firm no. The clothing teens wear is not the clothing you should wear and vice versa.  The cuts are different, and their lifestyle is different than yours,” says Brown, owner of samanthabrownstyle.com. That’s said, trends are open to interpretation across the ages. The way a youth is doing the leopard print trend may not be the way you should. If she is doing leopard print leggings and you like leopard, translate the trend and get a kicky pair of leopard flats. And men, even if you can squeeze into young men’s low-slung pants, with your boxers hanging out, don’t. Just don’t. Stick with fitted flat-front pants. (Going in the opposite direction with dated pleated pants will age you.)

#2. Your drawers are full of graphic humor t-shirts with sayings like, “My get up and go got up and went.”

Know your audience. If you spend a lot of time with your grandkids and are wearing it for the purpose of entertaining, that’s appropriate. However, if you are interacting with people your age, it’s little juvenile and silly for day to day. Think of the real message you are conveying and the first impression you make. You want people to think that you are pulled together, creative, powerful, self-possessed. “Novelty t-shirts say you have a sense of humor but maybe you can project that in a different way, perhaps with a quirky piece of jewelry, whimsical prints, or bright colors.  That is a way to show that aspect of your personality that seems more mature,” says Brown.

#3. You like to show a lot of skin: low hanging pants, lots of leg, Real Housewives-ish décolleté

No, this is not about body-shaming. If you got it, flaunt it—but there are ways to do it so that it looks sexy and sensual, and not cheap. First, pick only one space to show. If you have a low cut dress, then keep the hem longer. If you are doing a short top, don’t show the belly button and pair it with long pants or a cool jacket. Be mindful of highlighting your best features. “A lot of designers are doing cutouts with sheer panels now. That is a really elegant, classy way to do it. There is still skin but there is still coverage. A sheer sleeve is still sexy but gives coverage,” says Brown.

#4. You still dress like you did ten years ago.

The quickest way to age yourself is to wear something out of date, unless it is a timeless classic silhouette. Looking modern is more important than looking trendy. This holds especially true for men who hold onto their suits for decades. Suit jackets have become more tailored. You should be able to fit only one fist in between your chest and the lapels when the jacket is buttoned. If there is more room, it’s probably too big and an older style.

Update your closet every few seasons. “If you are into vintage clothing, most look better when mixed with modern pieces, like a 70s long flowing dress with a new leather jacket. But be careful: getting the right fit is everything,” says Brown.

#5. You are still rebelling against The Man. 

You can remain true to who you are without looking like a Ramones roadie. “I will say that if you want to participate in that trend, it is weekend casual. It shouldn’t be worn to work,” says Brown. If you want to go bad-ass and edgy, wear one statement piece matched with more timeless wear. For example, if you are into the ripped denim trend, keep the rips minimal on the knees. (“No butt rips!” Brown state firmly) Then dress it up with a fitted jacket and top.

#6. Your swimsuit is from another era.

Even if you are not comfortable with your body, you don’t have to suffer in a frumpy burka-like ensemble. There are amazing one-pieces out there with cut outs, and nice shaping. Brown says to look for ruching (it’s a great to define a waist), a natural built-in waistline, and chest support. For men, Speedos are a hard no in the US. Also, make sure the suit doesn’t squeeze the waist into a muffin top and is something you can move in. “If you can’t stand up, sit down or swim, it’s probably not the right choice” says Brown.

Overall, Brown adds, “People over 50 shouldn’t shy away from participating in trends because they feel intimidated. Fashion and great style are for everyone.  There is no reason to wear your LL Bean turtleneck and shrink into the background. You can participate in trends but pay attention to cut, fit, style and how it fits into your lifestyle.”


Who wrote this? I wear what I want and what I'm comfortable in. Mostly jeans and T-shirt or leggings and T-shirts. Except for church, usually. After I retire, I will not have the resources to re-visit my wardrobe every season and upgrade it to "modern" Beth, join the real world.

emily_n@rogers.com on 2018-01-08 19:19:40

Great articles.

marvmari729@yahoo.com on 2017-05-16 05:47:52

I'm a soon to be retiree and I've finally reached the age where I'm comfortable in my own skin, and I dress the way I want regardless of what others think. The style I favor is something effortless and comfortable, but stylish. Comfort shoe brands, like Clarks and Naturalizer, for example, are making sexier shoes that are strappy or platformed with a higher heel, while still being comfortable. I love to pair them with casual rolled hem jeans and a button down blouse or loose, comfortable pullover sweater. Sometimes I'll wear this outfit with a comfortable kitten heel pump. Add a great hand bag and a pair of sterling silver hoop earrings, and you can be stylish and comfortable. Everything has stretch to them now, including jeans -- no need to sacrifice a youthful silhouette for comfort or style. Bottom line is to wear what makes you glow from within, despite what other people think.

1maile on 2016-08-29 03:29:58

Thank you bluemoonalone. I could not have said it better. Once most of us reach a certain age we feel like we have earned the right to dress as we wish - fashionable if we wish, comfortable if we wish, and yes, too young if we wish. We feel much freer to be ourselves and not worry about what others think. Earlier this summer I saw a woman who appeared to be in her 80's walking with her granddaughter's assistance into a trendy clothing store. She was immaculately groomed, very attractive for her age and was sporting short white lace shorts and a form fitting white top, an outfit that would traditionally be worn by a very young woman. After my mind recovered from it's first impression, my conclusion was that this woman had obviously taken very good care of herself, looked like a well aged beauty queen, and appeared very comfortable in her skin and her clothing. We should all look that good in that outfit at 80, or any age for that matter! Not to mention her self confidence! More power to her, and may every one of us feel free to be ourselves. But thanks to Beth for the suggestions. Some may find them useful.

CA Granny on 2016-07-30 15:59:54

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