Behind The Chic

Jennifer Connolly

Jennifer Connolly, of the style blog A Well Styled Life, has the gift of knowing just how to pull an outfit together. And not just for herselfshe has an eye for always making people look their best. We spoke to her about why she started her blog, why she gives away the very advice that she used to get paid for, her favorite bloggers, and her fashion secrets.

Jennifer is pictured with: Caroline Pocket Shirt, Simone Bangles, Sondra Roberts Sally Studded Clutch.

Introduce yourself: Name, Age, Occupation.

I’m Jennifer Connolly, a devoted wife, mother, and grandmother. I will be 60 next month! I’m a personal stylist, image consultant, and the blogger behind A Well Styled Life—a lifestyle blog for women over 50.

What was your profession before you got into style blogging?

I was a homemaker and stay-at-home mom until my kids started high school. I’d always loved fashion and style so I took a part-time job selling women’s clothes. I quickly moved into management and became a lead buyer. I discovered that I really liked helping women choose clothes that made them feel confident about their appearance. So, I trained to become a certified Image Consultant and opened my own personal styling business. I wanted to be sure I had the proper tools and skills to give my clients good advice, and not just my opinion.

How did you end up blogging about style?

Eventually, I found that running my business was more than a full-time job, and I wanted some more flexibility in my life. I’d also discovered how many midlife women are struggling when it comes to their appearance. I started my blog to share my tips and ideas with women online. Blogging opened a whole new career path for me and allowed me to help women all over the globe.

Why is it important to share your knowledge? Especially with women who are a little bit older?

One thing I have noticed as I age is that lots of older women begin to feel invisible. For some, this happens over time, but for me, it was a precise moment, which feels like yesterday. I want to empower women to get back that visibility, and find their personal style and the confidence that comes with it.

What are your favorite blogs and bloggers?

Two of my favorite blogs are: Pam Lutrell of Over 50 Feeling 40. She shares her story of reinvention and encourages women to care for themselves and remember that they matter. Janice Riggs of The Vivienne Files. She shows color, pattern and style stories that help women learn what works well together.

What is your favorite social media platform and why?

Instagram: it’s visual and personal, a quick peek into one’s life. It’s also an excellent way to connect and build a community.

How would you describe your personal style?

I think of my personal style as a recipe. I like to combine the classic, the sporty, the dramatic, and the eclectic, depending on my mood. I like to look elegant no matter how casual my outfit is. I’m not afraid to wear a statement piece, and I know the value of an excellent accessory.

Why is style ageless?

There’s no expiration date on being stylish. Style has nothing to do with fashion—it’s how we present ourselves to the world. It’s the message you want people to hear. Fashion is the tool we use to show our personal style, and it ages as trends come and go. Your personal style is fluid and changes over time, but always should make you feel confident and unique.

What advice would you give your younger self?

Relax and lighten up. Much of what you worry about today won’t matter in the long run. Mistakes are just an opportunity to learn. Do your best, be kind, and wear sunscreen every day.

What do you enjoy about this particular moment in your life?

I am blessed to have a healthy, loving family and a grandson who brings me incredible joy. My husband just retired so we’re having fun traveling in our new little camper and exploring. I don’t take any of these things for granted.

What inspires you?

Strong, kind, courageous women like my mom and daughter. Both have taught me patience, and I’m in awe of their adventurous spirits and bravery. And, each email I get from my readers with feedback on how I have helped them feel more confident inspires me to share more!

What do you think about aging? The good, the bad, and the ugly…

The good: I love the wisdom that comes from age. Experience is a great teacher. It’s easier to know what I want, and what’s important.

The bad: My body is changing, and things aren’t in the same place nor do they look the way they used to, but I’m lucky to not have any serious health issues.

The ugly: Feet take a beating as we age and it’s hard to find comfortable shoes that are chic and don’t look like they belong on a gnome.

For more on Jennifer and her great eye, take a look at her blog, A Well Styled Life, and follow her on FacebookPinterestInstagram, and Twitter. We love what she has to say.

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62 Responses

    1. Ann Connelly

      Could you tell the powers that be to please put your turtle necks back in the winter line? They are my go to in the winter, and last year they were not in the line?.?.. The knit ones are just not the same. Thanks a bunch!, Ann Connelly. Winston Salem, NC. ( I see we have the same last name, just spelled a little differently.)

  1. plutrell

    Jennifer is amazing…she has a heart of gold and does truly want to help others. I am honored to have her as my friend and she wears Chico’s well…she is a great inspiration for the petite woman.

  2. Great job, Jennifer. You are a fabulous role model for women of a certain age and beyond. I’m into the beyond, but I still want to look fashionable and stylish. You exude that from every pore.

  3. So proud of all you strong beautiful smart women – who prove everyday that age is a state of mind.. This group is so strong and supportive and when was asked Chico’s to support our conference this group we knew they would love finding and working together with women like you…

  4. Laurel

    Lovely interview, Jennifer! You look amazing as always. And your blog has been a wonderful source of inspiration as well as comfortable stylish shoes and boots.

  5. Anne

    I’m glad Chicos recognized you! It’s great having a personal stylist online. Your honesty about recognizing the not so good parts of aging and suggesting work arounds (attractive, but comfortable shoes) is what I value most.

  6. Paula Moreshead

    I’ve been following your blog for a while, so it was interesting to read this interview and find out more about your personal history. You have a lovely style and inspiring blog!

  7. Pingback :A Well Styled Life Featured on Chico's New Blog! · A Well Styled Life®

  8. I have loved following Jennifer’s blog and now seeing a little bit more about her here is the icing on the cake. She has great style sense and is beautiful inside and outside!

  9. Sharon

    Interesting to learn a bit more about your background, Jennifer.

    I’ve been inspired to try new things because of your blog posts: I’m currently wearing the tinted sunscreen you recommended. I have other things in my closet that I learned about from you, too. I appreciate your honesty about the good and the bad of dressing at this stage of life, and I come away inspired.

  10. Martha

    What a great feature article about you, Jennifer! I am inspired every day as I read your blog. I also love Chicos and was thrilled to find that you are a shorter woman, wearing Chicos so well. It makes me feel like I can do this, too.
    Thank you!

  11. Pingback :Style For Women Over 50: It's Child's Play · A Well Styled Life®

  12. Anne

    Hi Jennifer – love your blog and your style! You have inspired me to dress better and I feel fabulous. Thanks!

  13. What great exposure for someone who deserves to be known far and wide. I should know, because I know how talented, creative and stylish you are, in addition to being a special friend who is generous to a fault with advice and knowledge. I’ve learned a great deal from you about the tender art of Blogging. You are a wonderful ambassador for Chicos. They are lucky to have you.

    Cheers, my friend,


  14. Marianne

    Thank You!, you just convinced me into wearing a red jumpsuit (from Chicos) to my 50th class reunion. I really wanted to, but was skeptical. Not so skeptical now!

  15. Jennifer Connolly. Would you tell the powers that be to please, please put the winter turtle necks back in this year’s winter line? They are my go to in the winter. The knit ones are just not the same. Thank you. I see we have the same last name , just spelled a little differently.. i tried to post once before, but it didn’t come up. Thank you sooooo much.

  16. Jennifer Connolly. Would you tell the powers that be to please, please put the winter turtle necks back in this year’s winter line? They are my go to in the winter. The knit ones are just not the same. Thank you. .