I don’t know about you but I could use a shot of frivolity. So this is a story about a dress. Or rather the buttery yellow two-piece number that I wore to my 50th birthday party.
When I told my family I wasn’t planning any major festivities for my big birthday, they went quiet. Then my brother reached out. Not on his watch. The evening my sister-in-law orchestrated for me was like…my wedding to myself. I highly recommend the experience.
Lest I digress, back to the dress. Putting clothes on is no easy task in the demi-elder echelon. (Check out my Substack, “How to be a hot-flash hottie” for more on the closet conundrum.) But this was a statement moment and I’d learned from experience that it deserves a statement outfit.
Ten years prior, I’d thrown myself a friend-filled 40th birthday celebration in Montauk that stretched over a full day, from beach-hang straight through to an after-hours dance party. That day was some of the most fun I’ve ever had.
I love that it happened before social media took over all our lives. We were wonderfully present. Candidly, I’m also glad few pictures of me from that night exist because I hadn’t given much thought to what I was wearing. At the time I was so monstrously busy grinding away at work that I just grabbed something from my closet. Multiple outfits over the day for different settings / activities. I looked presentable, sure, but not one of them amplified my joy, felt me-but-extra, or became part of a memory that makes me smile.
I wasn’t going to blow it this time. But what do you wear to a “beachy cocktail” evening on Shelter Island for a seated dinner when you’re single, child-free and 50?
I ruled out Black. This isn’t my funeral, thank you.
White? No way. Not my actual wedding. I might as well wear a veil for added pathos.
No to Pink. With all due respect to Barbie, it’s not my Quincincera.
Red? Too LOOK AT ME NOW. And doesn’t read “summer” to me.
What’s left?
I was at Aussie brand Zimmermann’s East Hampton boutique looking for an uncharacteristic dress for an upcoming “red party,” and came upon this ensemble. I don’t do ruffles. I don’t do yellow. And I definitely don’t do bralettes. I tried it on almost in spite of myself.
And the fit was great. Like, really great. I was physically comfortable. I could move freely, dance, lift my arms and I wasn’t worried about any extra bits making an uninvited appearance. The yellow didn’t feel over the top. It was feminine.
What’s more is, I could potentially rock an exposed midriff. That’s not something I could’ve done at 40 when I was too busy building a business to prioritize my own well-being. In some ways it’s analogous. I’ve since de-bloated my life and that’s showing up in my physical form.
The past several years I’ve prioritized taking care of myself. I leaned into pilates, committed to core workouts despite traditionally hating them, dropped excess bloating by curtailing my colitis, unintentionally got leaner by going fully gluten-free, and generally loved on myself. The result? I’m no Ninja Turtle, but I have some abs.
My sartorial hard stop is an exposed belly button. But a slice of torso somewhere above that and below a bra line is okay in my world. Even at 50. Maybe especially at 50. At 51? Who knows. I’m not there yet, so let’s not rush it.
I couldn’t commit right away to this flirty number. If it came across as too hot-to-trot there’d be a whiff of desperation emanating from my pulse points. I sent a short video of me in the forsythia-hued set to two dear friends, both of whom know me well and have great personal style.
Friend one (in her 50’s): Love it! Wouldn’t usually but this works.
Friend two (in her 30’s): That’s a hard no.
Hmmm. Needing a tie-breaker and some more courage - or a sanity check - over the coming days I ran the video by a couple of women who are older than I am, asking them if they felt that it was appropriate for the occasion. The unanimous answer was something akin to, “Please wear this. Because you can.”
And so I did. With mint-green snakeskin Manolo Blahniks I’ve had for 11 years - though I ditched them about 20 minutes into the cocktail hour and opted for barefoot glamour the rest of the night instead. Added a necklace designed by my great friend Meg from my jewelry box. And that’s it. I scraped my hair back in a bun, put on mascara and I was good to go.
In this outfit, I felt like a champagne coupe tower come to life, similar to the one I poured that very night. Effervescent, fun, celebratory, not an everyday occurrence. I was outside my comfort zone yet…comfortable. Which pretty much sums up my current state of life.
I’m sharing here the playlists my friend DJ Bonnie Thornton created for the evening. I hope you’ll put them on some night, along with an outfit that makes you happy, and dance around barefoot - with or without friends / a partner. Because sometimes we need a bit of frivolity to see us through.
If you found this at all helpful (or amusing), please give it a like or drop a comment below. And if you know someone that might enjoy my perspective, kindly forward it along. Your participation is everything.
Midriff Riff
I love this look and I feel like it’s a good reminder that we should dress for what makes us feel good rather than what we “should” wear
Wow! Thrilled to read how you said yes to the dress - but moreso to yourself as you entered this beautiful new decade 💛