The Latest
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Adventures in Singapore and a Packing Wakeup Call
A personal Singapore travel diary featuring Raffles Hotel, the National Orchid Garden, Marina Bay Sands, and lessons in dressing for humidity.
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Weekend Reading 05.16.26
We are off on our trip to Singapore and Bali! The plane seemed large enough until I realized I was sitting right behind a couple traveling with an infant and a child who looked to be about 4. It’s very hard to entertain young children for a 16-hour flight.
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After 20+ Years as a Stylist, These Are Clothes I’ll Never Wear
The longer I do this work, the more honest I get with myself about what actually works for my life versus what just looked good in the dressing room.
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How To Find Your Personal Contrast Level And Why It Matters
Most people focus on finding the right colors for their complexion, which makes sense. But your personal contrast level is just as important, and it’s often the missing piece when an outfit feels a little off but you can’t quite put your finger on why.
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The Best Shorts for Women Over 60 That Actually Fit
Can women over 60 still wear shorts? The answer is yes, if you want to. But the more useful question is what actually makes a pair of shorts work at this stage, because it’s not about age. It’s almost entirely about fit.
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Hi there!
I’m JENNIFER
Welcome to A Well Styled Life. I’m Jennifer Connolly, a certified image consultant and personal style expert who has been helping women dress with confidence for over 25 years. Read more…

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behind the blog
Hi, I’m Jennifer
It should be a joy to get dressed but after 50, too many women find it a challenge. Modern fashion seems aimed at the young and it can be hard to find what works for your body and lifestyle.
I started this blog to help women navigate the current fashion and understand how to make it work for them. What worked in our 30’s just doesn’t cut it over 50. I provide actionable tips and style advice so you can embrace midlife knowing you look your best.
I’m a wife, mom, and grandmother who likes nothing more than to share ideas about fashion, beauty, and all things that can make life enjoyable at this age.



