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How to be One of Those Stylish Women Over 50

how to dress in your fifties

It took me a long time to feel confident about my style. I remember seeing women who looked like they had their act together and wondering. Would I ever find that kind of effortless style?

Having the confidence to wear what you want and what looks good on you is the secret to style at any age.

Which sounds a lot simpler than it is. How many times have we tried to talk ourselves into something because it’s on sale or we found our size on the rack? Woo hooo. Celebration time.

No matter what size you wear, I bet you find it challenging to find clothes that fit AND look good.

Color is a whole category on its own.

If your new top goes with anything you feel you’ve hit the jackpot but when it doesn’t work with anything? That’s how we end up with a closet full and nothing to wear!

The goal is getting all your clothes to play together in outfits, the ones you can grab in a hurry. Even better if you have options to put together a smokin’ look for every occasion.

Like the 9 hour flight or a 6 week vacation. That September cruise or the May outdoor wedding in the mountains. For me, travel style means keeping my color palette super simple to make it easier to put outfits together on the go.

If you’re asking yourself how should I dress after 50, the answer is simple.

Know your shape, height and coloring. Dress to flatter those qualities.

How Can I Look Stylish After 50?

  • Get a great haircut. Embrace trends but don’t be a slave. Softer longer layers flatter sagging jaw lines!
  • Don’t be afraid of color but don’t let it wear you. Brown or gray, not your beloved black, is more flattering to over 50 skin tones
  • Wear lighter brighter colors close to your face. Scarves are brilliant at this.

  • Accentuate your assets and conceal wobbly areas. A chic poncho can do wonders.
  • Invest in quality when it comes to shoes and outerwear.
  • Edit your closet often. Only keep what truly flatters your shape.
  • Keep patterns on the small side. Cabbage roses belong on the young or curtains.
  • Revisit your makeup routine. Lighten that heavy eyeliner or add a little if you’ve been makeup free.
  • Take care of your skin. One of my favorite lines is The Ordinary.
  • Invest in good quality eye glass frames. I prefer a light color to open up my eyes.

What NOT to wear after 50

Now this one is easy. There are no arbitrary rules about what you can and can’t wear after you turn 50. The reason this question comes up is that no one wants to feel foolish. We don’t want to be the last one who finds out we weren’t supposed to wear white jeans after September. By the way that rule is so not true.

There’s a British expression “mutton dressed as lamb” which is a rude way of saying an older women shouldn’t try to get away with wearing youthful clothes.

Funny there’s no similar term for men. Probably because they don’t care if they look ridiculous. Frankly very few men over 50 will try to get away with wearing a Speedo. But for the ones that do, no one thinks they’re sexy, just deluded.

Unfortunately women are much harsher critics of each other.

I’d say that if what you’re wearing makes you even slightly uncomfortable then that’s a sign. We can’t feel stylish if we’re in a dress that’s too small or a cut that’s too low.

How to dress in your fifties is up to you. Here’s some simple tips to keep in mind.

How to be a stylish woman over 50

Know your body shape:

Are you an Apple, pear or carrot (that’s a new one) shape? Find the fit that flatters your body shape.

  • Apple? Find clothes that loosely flow over your middle and emphasize your hips and legs
  • Pear? Emphasize your bust and shoulders to balance out your bottom half
  • Carrot? Create shape with a cinched waistline, show off good legs with just above knee skirts

Emphasize your best features and minimize little problem areas. When decolletage isn’t firm or smooth, cover up a little more but don’t be afraid of letting your bust shine.

Show off shapely legs with a hem just above your knees. Because my thighs are getting wrinkly, I make sure not too much skin shows.

A stylish woman over 50 knows her shape and dresses to flatter it, not cover it up.

Dress for your height:

Are you short, average or tall? Don’t settle for a just OK fit or length when shopping.

Fortunately a lot of women’s wear is now available in petite or tall sizing. Hallelujah! Even savvy workout wear retailers understand that fit is everything and offer petite and tall options.

  • Look for retailers like Athleta, Banana Republic, Loft who offer you a range of sizing and height options.
  • Find a good tailor who can alter pants, skirts and even jackets to fit your unique size
  • Keep proportion in mind. The same style that will overwhelm a petite figure may be perfect on a tall gal.

For every women who despairs at finding a pair of pants she doesn’t need to shorten, there’s another who wishes they would reach her ankles. Why not patronize stores that offer complimentary tailoring like Nordstrom and Athleta.

Know your coloring:

Color is always going to be your number one style accessory. Color makes or breaks an outfit. Find the colors that flatter your skin and hair to gain style points.

  • Dark skin or hair? You’re probably going to look best in warm colors with undertones of yellow or red. Think warm pink, orange, brown, golds and yellowy greens and blues. Bright or dramatic colors look fabulous on you too.
  • Medium skin tone and hair? If your hair has red or gold undertones then look for warm colors to complement. If your skin and hair are ashy or cool then look for cool colors like pink/red with a blue undertone, cool blues, grays or black.
  • Light skin and hair? If your hair is pale blonde or gray, then cool colors will be flattering. Deep gray is softer than black against mature skin.


Color is a funny thing. We all have our favorite colors and love to wear them. My wardrobe is full of blue and green as is my home!

Sometimes our favorite colors flatter us and sometimes they don’t. If you want to be stylish, then really look at the colors in your wardrobe under bright daylight and artificial light. Do they light you up or turn your complexion and hair drab?

Some colors speak very loudly. Ask yourself if you want to be stylish or stand out in a crowd. I never quite understood the red hat club.

Choosing what flatters you, not what gets you noticed is style.

One more element of style over 50.

Dress for the occasion. Isn’t that how we were brought up by our mothers? If we ever think it doesn’t matter how we look and start wearing sweats on the plane, we’ve forgotten those lessons. It doesn’t mean wearing gloves and pearls, but when we make an effort to look our best we feel more confident too.

You can never go wrong with a dress. Easy to throw on and look stylish on any occasion. Forgiving of tummies and bottoms too.

What to wear in your fifties is all about enjoying yourself and flattering what you’ve got.

Don’t forget your most devastating accessory. A smile!

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Tessa
Tessa

I created HOF to inspire women over 50 to follow their dreams. Whether you’d love to move abroad, travel to Europe or just reboot your midlife, it’s never too late to start over and create a life you love with style!

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