How to Nail Your Personal Style Over 50

It’s an often-repeated and common belief that we’re either born with great style or we’re not. That’s like thinking you’re either born with good manners or you’re not, which we all know is nonsense. I’m updating this post from last year with some new thoughts on how to develop your personal style over 50.

over 50 fashion blogger showing how she nails her personal style in white blazer and red jumpsuit

Style is a skill we can learn and like anything else, the more we practice, the more confident we become. If you’re lucky enough to be exposed to style and stylish people early on, your sartorial choices may feel easier. But what if you’re not? How do you develop your personal style and is it too late to develop it after 50?

row of pink blouses on closet rod

By the time we’re over 50, 60, 70, we’ve done a lot of living and want our personal style to reflect our confidence. Our clothes need to tell the world who we are now and allow us to step out in confidence.

Fashion advice for older women is everywhere but not all of it is relevant so here are a few ideas that may help you nail your personal style in midlife.


Jennifer Connolly wearing black victoria emerson bracelets

“If a woman has a closet full of clothes but nothing to wear, she doesn’t know herself very well.” – Bill Blass

  • Everything starts with self-knowledge. Who are you now and how do you want to been seen?
  • What’s your lifestyle? There’s no point in building a wardrobe for a sophisticated urbanite if you live in a rural area and need clothes for your casual activities.
  • Your wardrobe needs to be functional for your climate. If you live in Florida year-round, you don’t want a wardrobe of suede boots and faux fur jackets for winter.
  • Understand your body shape and dress to accentuate your best features and downplay the ones you’re not crazy about.
  • Buy what you love, and wear what fits your current shape. Wearing clothes that are too loose or too tight doesn’t give your body the respect it deserves.


Pay attention to the women around you. Are there certain looks you gravitate to over and over? Be aware of the colors you’re attracted to and the shapes you like.

styling a popped collar under a sweater

Start a Pinterest board and save images that appeal to you. After you have a large collection, go back through them and look for similarities. Are the colors similar? Do most of them have classic elements or are they more creative? Are the details feminine or dramatic? This helps train your eye to see what aspects of an outfit you admire.

AVOID RUTSpainting on hair color

We’ve all been there and no one wants to look like they’ve gotten stuck in a time warp. If you’ve always loved classic style be sure to keep it fresh and modern by styling pieces in new ways. Pop your collar. Half tuck your shirt. Stay abreast of trends but don’t be a slave to them or you risk looking tragic.


BE BRAVEshowing personal style combining leopard print with denim and multiple bracelets

Try new combinations and see what feels right. Take selfies in the mirror because they give you a totally different perspective on how things look on you. Do you recognize that woman in the mirror? Does she look the way you want to look? There are no wrong answers with fashion so don’t let fear stop you from trying.


ACCESSORIES MAKE THE WOMANwoamn walking down sgtrett in white shirt and jeans carrying bronze handbag

Personal Style is all about taking fashion and making it your own with personal touches only you can add. Be inspired by another womens style but give it your own twist to make it personal. Accessories are the game-changer here and will give your outfits personality. Collect ones that spark joy, then mix and match them to create your signature look.

And finally, know that great style can be found at every price point, so don’t feel limited by your budget.

How would you define your personal style?







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  1. Leslee
    September 13, 2021 / 6:29 am

    Love this post, great down to earth advice!

  2. beth byrd
    September 10, 2021 / 11:41 am

    It wasn’t until after my mom passed and my sisters and I were going through all the old photos that we realized what a fashionista she was! Growing up, I remember she was always well groomed and looked nice, but it took a look from a distance to realize how very stylish she was. I will be eternally grateful to her for instilling that desire in me to dress well … not expensively, but with much thought and pride in looking nice.

    My style keeps changing over the years. I’m still working and I really enjoying getting ‘dressed’ every day. Clothes excite me and I try to keep up on trends. Of course, your blog (and a couple of others) are so helpful in figuring out what looks best.

    Many thanks for all of your tips and encouragement to those of us over 50! Glad to be here!

    • Jennifer
      September 10, 2021 / 1:45 pm

      I’m so happy to have you as part of our community here, Beth

  3. Vee
    September 10, 2021 / 10:57 am

    Thanks for that comforting pep talk. It was just what I needed to hear as we move into my favorite season of Fall.

  4. Roberta
    September 10, 2021 / 7:44 am

    That first picture of you in the dark brown/rust with bright white jacket is the best picture I’ve ever seen of you. Strongly recommend you add more rust tones and bright whites to your wardrobe. I’ve always thought you look wonderful in wide leg pants. And your hair color seems slightly more golden which looks beautiful. Maybe it was just time of day photo was taken. Anyway you look great in first photo

    • Jennifer
      September 10, 2021 / 1:46 pm

      Thank you:)

  5. Karen
    September 10, 2021 / 6:57 am

    Great advice. Looking forward to fall looks.

  6. MRSBEN2
    September 10, 2021 / 5:55 am

    Excellent tips and advice, Jennifer! For myself I have always leaned towards classic cuts and being the fabric junkie that I am; choose those that offer texture, pattern (either in weave or print) with an added twist. (The latter – buttons, trim, color-blocked, fringed etc.) As to keeping my look updated; I do browse the internet to keep pace but mostly rely on accessories as do not necessarily follow garment trends. (For example being in my late seventies I’ll leave the wearing of mini skirts. cropped tops and platform footwear to my grand daughters …. lol!) All said; my personal style formula is ‘ I wear what makes me happy and gives me confidence’. -Brenda-

    • Jennifer
      September 10, 2021 / 1:47 pm

      I love your formula, Brenda

  7. Janice
    September 10, 2021 / 5:10 am

    I probably tend to wear too much black but I have added pink and white . I do wear jeans but still use my white and pink tops. I am short and constantly watch my weight. Keeping everything solid makes it easy to mix and match.

  8. Audrey
    September 9, 2021 / 6:01 pm

    Great post. I need to decide which items in my closet need to retire and then add updates. Always appreciate your blog.

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