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 herself—she 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.
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.