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Dressing to Please Yourself: Style Tip of the Month

The older I get, the less I want to look like everyone else. During high school, it was critical that I blend in, wear what was popular and not stand out. I wasn’t one of those popular, cool kids who seemingly had no insecurities.

The older I get, the more secure I feel with my self-expression and the braver I become experimenting with different looks.

At 60, I wear what I love. I don’t always get it right but that’s part of the fun. Learning by experimenting.

Some day’s I want to look edgy, classic, creative or dramatic, but often it’s nothing you could label. What remains constant is my desire to dress with confidence.

I think the same is true for most women. They want to feel happy with their appearance and know their style is telling the world who they are.
Style and Lifestyle blog for women over 50

There are flowy, romantic looks I love and admire on other’s but know I could never wear because they would feel like a costume on me.

It’s easy to get stuck in a rut and wonder why others look better than we do. The truth is, they don’t look better unless we are unhappy with our appearance.

I encourage you to appreciate the style you admire in other women and if you like, try it on virtually. Imagine wearing that look. See yourself dressed that way. If that feels comfortable, start with one piece and wear it several ways.

Check in with yourself and ask, “Do I feel authentic? Does this feel like a costume on me? Am I comfortable with the attention this garment or look is attracting?”.

Pay attention to your comfort level, that is your guide. Listen to your instincts. You really do know best.

Then decide if this is how you want to look. Be inquisitive, be brave and most of all have fun with fashion.

Let’s go see Pam’s tip of the month.

What style have you been curious to try?

xo Jennifer





  1. Enjoy all the advice and comments. My charm bracelet has been sitting in a drawer for years, now I will turn it into a necklace. Thanks for all the tips.

    1. I thought my Mom was brilliant to do that with hers. Thank you for reading Diane!

  2. You nailed it when you said “style…is how you live your life.” You have style AND class. Don’t let the naysayers get you down. Rock on!

    1. Thank you Carol! I appreciate your support and encouragement.

  3. Dear Jennifer,

    Your blog is the bright spot of my day. I can’t get our much to,shop, so I rely on your suggestion that are available on-line. I admire your style- classic with a twist I call it.
    Keep up the good work

    1. Thank you, Eileen. I’m very happy to here you enjoy my blog!
      Classic with a twist, I like that! Great discription of how I like to style things. Some of the best things are available only on line. Have a lovely weekend!

  4. Please will you do a blog on silver versus gold jewelry. I know that so called summers are not supposed to wear gold. Do you subscribe to the ‘Seasons” idea? Thank you.

    1. Hi Jill. I do know the seasons concept and for a general color typing it works very well. Within each season are many variations but the warm vs cool remains the same. That’s a great idea for a blog post. I’ll write one soon touching on jewelry. The trend has recently been to combine the two, which I quite like. Thanks for the suggestion.

  5. I like wearing skinny jeans rolled up and Chelsea boots. They feel a bit edgy and somewhat rebellious when I wear them! Not at all a stereotypical 61 year old grandmother!
    We are so fortunate to have choices !
    I also like to put on a simple LBD with hose and kitten heels…we have many different options and for that I am very grateful

    1. I love switching it up too!!

  6. Great advice..it’s how I live now…too bad it took me nearly 3/4 of a century to have confidence in my ability to dress in a way that makes ME happy.

    1. Better late than never, Jan! Enjoy and spread the joy.

  7. I love the sweater you have on. Can you please let me know where I might find it?!!

    1. I bought it at Anthropologie 5-6 years ago. Back then, they did have styles I liked.

  8. Such good advice, Jennifer. Wearing what we love puts that confident smile on our faces.

    1. Confidence is the most attractive thing we can wear!

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