The 6 Signs You're Not Dressing Appropriately For Your Age

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

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 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 10 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.”

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