Fashion & Beauty

Secrets to Dressing Beautifully Over 50

When I’m not writing, I’m managing the boutique I own. My customers are older, fifty plus, and they all have one thing in common. There is something about their body they hate.

This one’s hips are too big. That one has a shelf. Bat wing arms make them want to hide themselves. Some are so skinny that clothes hang like drapes. Some have tummies that jiggle and shake. Hair is thinning and graying. Skin is thickening and sagging. Legs have too many veins. The complaints are endless and often the same. Unfortunately, many older women think beauty belongs to youth, but it doesn’t. Youth possess one kind of beauty. Older women possess another.

It is said that butterflies can’t see their own wings. Though they are some of the most beautiful creatures, they are blind to themselves. So are my customers. Because they are older, they are more beautiful than they’ve ever been. They have character and strength. My store resonates with their laughter, compassion, wisdom, and grace.

My job is to remind them that young women show off their bodies. We decorate. Consequently, looking good over fifty is not hard if you’re brave. Many of us have been taught to wear age-appropriate clothing. We’re supposed to look respectable and hide body parts that no longer look young. Instead of reveling in our experience, we listen to the pundits and diminish ourselves. This needs to change.

Women over fifty are having second careers, traveling the world, and finding love. Gray hair is in, sexy is cool, and shopping has never been more fun because now many of us have the disposable income.

Our bodies are works of art. The textures and shapes tell the story of our lives. How we enhance them with color and line either muddies the canvas or makes it shine. Not everyone can wear a tunic, though they look great on some. I can’t wear short jackets, though I love them, because they just look wrong. The beautiful thing about fashion over fifty is we get to determine it for ourselves. We’ve grown past the trends. Now, we get to shop for items that reflect who we are instead of who we want to become. This requires bravery. If we refuse to become invisible as we age, we need to rethink how we dress.

Here are some tips:

1. Be comfortable.

If you’re wearing clothes that feel too tight, you’ll always be self-conscious about your weight. When you’re worried about your weight, you try to shrink yourself in other ways. Give your body room to move. Take up your space.

2. Don’t wear too much color.

Color is great, but when you wear too much of it at once, it’s hard to see you. Instead, try one bold piece at a time or wear neutral colors and accent them with bright scarves and jewelry. When you wear your clothes, you shine. When they wear you, you disappear.

3. Pay attention to line and texture.

Seams that run straight down the back are seldom flattering. Repetitive patterns look like wall paper – great in the bathroom, terrible on an older body. One way to break up patterns is to layer. That old vest in the back of your closet might look fantastic over the new tunic you just got. Clothes that are visually interesting enhance our beauty. Be unconventional and accept the compliments when they come.

4. If you like the way it looks on your body, you are never too old to wear it.

I have eighty-year old customers who look fabulous in mini-skirts and leggings. I know several twenty-year olds who don’t. This year, the trend is fringe. When I was at market in Las Vegas I had to laugh. Designers had sewn fringe onto just about everything, whether it belonged there or not. Just because we can doesn’t mean we should and just because we “should” doesn’t mean we will. Age-appropriate is so last century. It’s time to get over it.

5. It’s okay to dress according to your mood.

Hiding behind our clothes keeps us isolated and invisible. If you’re not feeling great and don’t want to make the effort to keep up appearances, that’s just fine. When people can see how we’re feeling, they’re more likely to inquire about our well-being. That gives us the opportunity to share stories, build relationships, and live richer lives.

Fashion is both a noun and a verb. We can buy into fashion trends and blandly acquiesce to conventional wisdom, or we can fashion ourselves.

Destiny Allison


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  • Cathie Jones

    What is a good website to look for fashion for women – well I’m 64. Tall slender but shapely. I like comfy casual and classy

  • Steve

    Great article. I read it over a few times and thought of some of the people that I have seen recently that really should be reading your article. Then I looked down at the worn out shirt and jeans I was wearing. How about some advise for men over 50?

    • Destiny Allison

      Well, Steve, I suppose the best advice would be to let go of your favorite, old shirt. I know it probably feels like a second skin, but when you wear it almost every day it gets a little old. You can keep it and wear it sometimes, but you probably should wear some of the nice shirts hanging in your closet. If you have a big belly, don’t tuck those shirts into your pants. Finally, It’s a good idea to look in the mirror before you leave the house, just to make sure you have remembered to comb your hair. I’m teasing, of course. Pretty much the same rules apply to men. Be comfortable, wear what makes you feel good, and don’t be afraid to add a little zest to your outfit. Good luck.

  • Mary

    Who cares about how they look once they are 50! Seriously, dress however you want, you have earned that. Why listen to this type of rhetoric at all. If you like it, wear it. Bright colors, tight jeans when you’re heavy, who cares? It’s all about you baby, and how YOU feel. If you are 50 and still looking for help on how to look better, I feel sorry for you. Someone is probably just trying to get you to buy their stuff!

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