There’s a shift that happens in your 40s. Suddenly, “cute” isn’t enough—you also want to feel comfortable, pulled-together, and just a little current without looking like you raided your daughter’s closet. You want that outfit that says, “I’ve still got it,” without saying “I’m trying too hard.”
And that was exactly my goal last weekend when we celebrated my friend’s birthday with brunch at Michael Angelo’s Winery in Richfield, Ohio. If you’ve never been, it’s a total gem. Gorgeous views, handcrafted wines, wood-fired pizzas, and a dreamy little garden patio that makes you feel like you’ve been transported to Napa—but with better Midwest charm.
Photo by Michael Angelo's Winery
It was one of those Ohio summer days where the temps start in the high 60s but hit the 80s by noon, which meant layers were essential. I needed a look that could take me from sipping rosé in the sun to snapping pics in the shaded vines—and still feel good.
Here’s what I wore, and why I’m fully convinced this might be the summer outfit formula for women over 40:
The Pretty Little Thing Floral Dress
This dress is pure joy in clothing form. The babydoll cut and smocked bodice mean it flatters without clinging, while the tiered skirt gives it just enough movement to feel fun and flirty. It’s feminine without feeling frilly, and the functional sleeve ties? A thoughtful little detail that gives your arms room to breathe (literally).
The floral print feels bright and celebratory—perfect for a brunch or vineyard vibe—and the elastic neckline makes it wearable off-the-shoulder or not, depending on your mood. Best part? It comes in sizes S to 3X and runs true to size. I wore a medium and had plenty of room for Chardonnay and the delicious brussel sprouts, drizzled with balsamic and to.die.for.
The Cropped White Denim Jacket
Let’s be honest—layering is a survival skill when you’re 40+. One second I’m roasting in the sun, the next I’m in full goosebumps under the shade. This white cropped denim jacket saved the day.
It’s structured with no stretch, which gives it a tailored, put-together look. The cropped cut hits right at the waist, balancing out the volume of the dress perfectly. And it comes in the cutest colors too—white was ideal for brunch, but I’ve got my eye on the lavender for early fall.
Pro tip: Toss it over your shoulders when you’re indoors and want that effortless, “I just threw this on” kind of cool.
The Clear Strap Block Heel Sandals
Okay, here’s where I made the fashion over function call—and I stand by it. These white block heels with a clear strap were the perfect finishing touch. They elevated the look just enough to feel dressed up, but with a block heel and cushioned insole, they were surprisingly walkable (even on winery gravel—no regrets).
Would I wear these to a standing-only concert? Absolutely not. But for a seated brunch where the vibe is “cute pictures and classy wine,” these shoes hit just right.
That said, if you’re not in the mood for heels, swap them out for sandals or neutral booties and the outfit still works—especially if you’re heading into fall.
The Sparkle: Moissanite Stud Earrings
You know I couldn’t resist a little sparkle. These 2.4 carat moissanite studs gave just the right amount of glam without going over the top. They look like real diamonds (no one at the table knew the difference), and the price point is way friendlier than the real thing.
Plus, they come with a certificate and a pretty little gift box—so if you’re celebrating a birthday, anniversary, or just want to feel like the polished queen you are, they’re the perfect touch.
Final Thoughts...Get Dessert
Listen, getting dressed in your 40s shouldn’t be a battle between fashion and function. It should feel like you—but elevated. A little playful, a little polished, and always prepared for whatever the day (or weather) throws at you.
So whether you’re headed to Michael Angelo’s Winery, a brunch with friends, or just want to feel fabulous on a random Wednesday—this outfit delivers. Strut in the heels for some dessert while you're there.
Photo by M affina