I'm 56, Live in NYC, and Wear These 7 Dress Outfits All the Time

We recently tapped 56-year-old New Yorker Elaine Davis for her advice on the easy and sleek items she added into her arsenal to upgrade her on-the-go wardrobe. And while age clearly has nothing to do with what you should or shouldn’t wear, we were curious about her expert style guidance as an over-50-year-old, in particular, given her years of sartorial experience. Well, after recently catching up again with the mastermind behind @squarepearls, she revealed that one of her key wardrobe staples just so happens to be the midi dress.

Here’s what she said: “I absolutely adore midi dresses. They’re a great length when you don’t want a maxi, but you do want a tad bit more length than what a just-below-the-knee dress offers. Midis can be flared, straight, tiered—you name it. They’re just so versatile.” So with that said, we thought there could be interest in the specific midi-dress outfits Davis swears by to look chic for her life in NYC.

With all that in mind, keep scrolling for seven stylish midi-dress looks, complete with visual and shopping inspiration.

"Wearing a fun floral midi, paired with a cute pair of sneakers is absolutely one of my favorite looks to wear year-round." — Davis

"Who doesn’t love a belted A-line dress styled with chic accessories for a classic daytime look?" — Davis

"Whether it’s a socially distanced summer brunch meetup or a casual meeting, I always feel ready in a midi that’s fun and professional." — Davis

"When I want that chic town-and-country look, I’ll wear a tiered midi along with a pair of statement trainers and one of my go-to totes." — Davis

"My go-to date-night outfit is always a black dress and a pair of heels. You just can’t go wrong with this combo." — Davis

"Off-the-shoulder smocked midi dresses and chunky sandals are a total vibe that I’m currently obsessed with right now." — Davis

"I love pairing a dreamy bubble-hem midi dress with a heel for a look that’s fit for a queen." — Davis

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