What Not To Wear After 50

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People live longer now, which is usually a nice thing. And if they take good care of themselves, they might feel younger than their actual chronological age. But dressing as if you were decades younger does not fool anyone. They do it in Hollywood, sure, but that’s because you care about them.

For most of us regular folk, our kids or grandkids are even less likely to want to be seen with us in public when we dress inappropriately. We might even find friends our age canceling lunch plans. Here’s a quick guide to avoid some of these fashion faux pas.


Of course, you can wear a T-shirt, but you have to pick the right style. Pastels, solid colors, simple patterns—none of these display the real you. Shirts with sassy sayings or with pictures of teen idols are what you’re looking for. Shirts that brag about how much liquor you can hold are also perfect. Plain, bright colored shirts with a sensible scarf or jewelry or a jacket is exactly what you’re expected to wear. “World’s Best Grandma” or “Superdad” make better coffee mugs than T-shirts. Don’t be a sap.


After 50, any kind of fancy pants are totally perfect. Any kind of boring, practical jeans or slack are pretty worthless. Whether it’s sweats with words on the butt, brightly colored skinny jeans, frilled jeans, low-rise jeans with sequins and embroidery, or plaid pajama bottoms, you’re on the right track. If all you have is practical and modest jeans or slacks, burn them and head to Abercrombie & Fitch.

Boring Footwear

If you have heels with a wider base and a rubber sole, or maybe a little extra cushion inside the shoe, you’re doing it wrong. You should be wearing strappy platform heels or 5-inch stilettos. They might not be comfortable, but at least you look good in public. Boots that go up to your thigh are also fantastic.

Conventional Underwear

Most people of a certain age start to dress in such a way that their clothing covers their undergarments. This is a waste of time. Look for clothes that have skinny straps, are cut to show off your shoulders, and ride low enough that they could conceivably show bra straps or the waistband of your lingerie. While those in their teens and 20s can get away with conventional and conservative clothing, you can’t. Not anymore. For the more mature person, let it hang out. You’ve been here long enough.

Loud Handbags

Some suggest older women only use small clutches. But in truth, the size matters a lot less than the tone. Simple bags in neutral colors are out. You want something that shouts, “HELLO! I’m a purse and I’m alive!” Carry make-up, books, your phone and other practical items. Puppies are great on the outside or the inside of your bag. For accessories, jewelry that shows off cartoon characters or says “I Love Brad” in cursive is very chic right now.