Posts tagged playful fashion
THE 90-YEAR-OLD IN HAPPY SOCKS; WHAT WE LEARNED ABOUT SHOPPING AFTER 55

We were standing in the Union League Club surrounded by gorgeous holiday finds, and we overheard a woman say, “Oh, I’m too old for something this fun.”

And we thought – says who? When did we decide that hitting 55, 65, 75 meant we stopped buying things that delight us?



So we walked through the holiday shopping event with fresh eyes, looking at what genuinely sparked joy instead of what we “should” buy.

Let us take you through what we discovered when we gave ourselves permission to be curious instead of careful.

We stopped at one of our favs – Lauren Lein – and she showed us the most incredible funky leggings. Patterns, colors, designs that made us smile. The old rule? “Women over a certain age should stick to black pants and neutral colors. Nothing too flashy below the waist.”

We talked with Lauren about how leggings are comfortable, practical, and can be absolutely fabulous. Why should younger women have all the fun with fashion? Who decided that turning “certain ages” meant trading personality for propriety? These leggings aren’t just clothing – they’re rebellion wrapped in comfort. They say, “I’m still here, still vibrant, still ME.”

We stopped at a pair of bold, dramatic earrings that caught the light beautifully. The old rule whispered in our ears: “older women should wear small, tasteful jewelry. Nothing too attention – grabbing.” But here’s what we’ve learned – why shouldn’t we grab attention?

Those earrings and others like them make us feel fabulous!

Then we discovered a French vendor with the coolest nylons we’ve ever seen. Not your grandmother’s pantyhose ( though honestly, why were we so boring about those too?) These were artistic, interesting, conversation-starting pieces.

There’s something particularly delicious about a French woman encouraging us to have more fun with our wardrobes. The French have never bought into this American notion that women expire at a certain age. They understand that style, sensuality, and self-expression are lifelong pursuits. These nylons reminded us that even the basics in our wardrobes can be sources of joy and creativity.

But our favorite discovery was Mary Mary, a shop that sells happy socks – colorful, whimsical, personality-packed socks that make you grin. The owner told us something that stopped us in our tracks: She has a client who is 90 years old, and he wears happy socks everywhere – even to black tie events.

Ninety years old. Black tie. Happy socks.

Let that sink in. Here’s a man who has lived nine decades and decided that formal doesn’t have to mean boring. That elegance and whimsy can coexist. That you can honor the occasion while still honoring yourself.

If a 90-year-old man can wear happy socks to a black tie event, what’s stopping the rest of us from adding a little joy to our everyday wardrobes?

Here’s what we took away from this holiday shopping event – the only shopping rule that matters after any age is this: Does it bring you joy? Does it make you feel the version of yourself you’ve always wanted to be?

What if the second half of life is about adding color back in? What if it’s about bold earrings and funky leggings and interesting nylons and happy socks?

This holiday season, we’re shopping with curiosity instead of caution. We’re asking “Why not?” instead of “Should we?’ Remembering that the best gift we can give ourselves is permission to be fully, vibrantly, unapologetically us.

Because at 90, we want to be the women in our equivalent of happy socks – sexy, sassy nylons – at the black tie event, choosing joy over judgment.

What “shopping rule” are you ready to break?

click to watch the video!