Over 50 style

How to Be One of Those Stylish Women Over 50

Updated August 3, 2023
women over 50

It wasn’t until I was over 50 that I felt more confident about my style.

I’d see women who looked stylish and wondered if I’d ever find that kind of effortless style?

No matter what size you wear, you may find it challenging to find clothes that fit AND look good.  Of course the goal is getting all your clothes to play together in easy outfits isn’t it?

For example a 9 hour flight or a 6 week vacation. That September cruise or the May outdoor wedding in the mountains.

The secret to being one of those over 50 women with style is this: Know what flatters your shape, height and coloring.

women over 50

Women Over 50 Style Secrets

  • Get a great haircut. Embrace trends but use face framing soft layers
  • Don’t be afraid of color but don’t let it wear you.
  • Black can be harsh. Brown, navy or gray are more flattering to over 50 skin tone.
  • Wear lighter brighter colors near your face. Scarves work wonders in a pinch.
  • 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 and only keep what flatters you and what you feel good in.
  • Revisit your makeup routine. Keep a light touch (although a little black eyeliner never hurt!).
  • Pamper your skin. One of my favorite lines is The Ordinary.
  • Invest in flattering eye glasses. A light color frame opens up my eyes.

Women Over 50 to Avoid

There’s no arbitrary rules about what to wear after you turn 50. Like you’re not supposed to wear white jeans after September. That rule is SO not true!

There’s a British expression “mutton dressed as lamb” which is a rude way of saying older women shouldn’t try to wear what a young girl does. Funny there’s no similar term for men. Probably because they don’t care if they look ridiculous!

My opinion is: if what you’re wearing makes you even slightly uncomfortable that’s a sign.

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

Women Over 50 Style Guide

1. Know Your 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.

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

2. Dress 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!

  • Look for retailers like Athleta, Banana Republic, Loft who offer 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?

3. Know Your Coloring:

Color makes or breaks an outfit. Find the colors that flatter your skin and hair.

  • 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 (and home) is full of blues and greens!

Sometimes our favorite colors flatter us and sometimes they don’t. 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. Is it your intention to get noticed or be stylish?

4. Women Over 50 Final Style Thoughts.

Always dress for the occasion. When in doubt it’s perfectly OK to add a bit more style to casual outfits. You  never know who you’ll bump into!

How we feel about ourselves is often a reflection of how we put ourselves together.  So why not make the effort!

It’s hard to go wrong with a dress. They’re easy to wear – less coordination needed and look stylish on any occasion. Forgiving of tummies and bottoms too. These days you can wear sneakers or a heel with a dress, mini, midi and everything in between.

Why not try one on and see how you feel?

Last but not least, don’t forget your most devastating accessory. A smile!

About Author

With over 30 years in a creative role in advertising and publishing, and a lifetime of journeys between the US and UK, I've created Hipoverfifty for you. I hope my journey and perspective will guide you on yours.