The 5 Dress Trends That Work for Everyone, According to a 66- and 26-Year-Old

Susan Feldman is the co-founder of One Kings Lane and In the Groove, a style destination where she shares her age-defying outfits and shopping tips. Feldman is also our resident style expert here at Who What Wear, and she's shared everything from her top spring shopping picks to the style mistakes she won't repeat. Today, we've tapped her to discuss dresses—specifically, the dress trends that work for every age, according to both her, a 66-year-old, and me, a 26-year-old.

I love this time of year. Everything is in full bloom, the days are longer, and the chill is nothing but a distant memory. Now that we're well into the summer, cheerful attire has become our go-to, and dresses have taken center stage in our wardrobes. After a long, pandemic-filled year, I'm taking this opportunity to blossom sartorially, and I plan to dress up and go out by throwing on a gorgeous dress. 

One pandemic style tip I'm taking with me in the future? I want to be comfortable. Easy dresses are a perfect way to transition out of athleisure and loungewear. The other great thing is how versatile they are—you can dress them up or down and wear them all around town. And we will be going out in the near future. 

All of the styles below will look great on anyone at any age.

1. Shirtdresses

Susan's take: "First up, the shirtdress. It's my go-to because you can wear it so many ways. Belted, not belted, and (my favorite way) open over a pair of jeans."

Susan's picks:

Anna's take: I have to agree with Susan here. Shirtdresses are oh so versatile. I always have at least one standard shirtdress in my arsenal, but this spring, there are so many creative ways designers are reworking the staple that I can't resist adding another in a fresh color or sleek leather coating to my closet.

Anna's picks:

2. Flowy Maxi Dresses

Susan's take: "It's a whole outfit in one piece! Just throw it on, add a pair of sneakers or sandals, and you're good to go. Maybe add a hat if you're feeling sassy."

Susan's picks:

Anna's take: There's a reason that these flowy frocks always come back around—they're just easy. It's as simple as that. I'm going for one that I can wear around the house for now but also dress up with some strappy sandals. 

Anna's picks:

3. Classic Wrap Dresses

Susan's take: "I started wearing this silhouette many moons ago because it was so flattering. And you know what? It still is! It's a classic for a reason. The wrap dress shows off the parts I want to show off and hides the rest, cinching in at my waist and camouflaging the rest."

Susan's picks:

Anna's take: The thing about wrap dresses is that they almost never look bad. Seriously, they just suit everyone so well, which I can't say of a lot of the trendier dresses of the moment. The type of wrap dress I'm drawn to right now, though, has charming puff sleeves and an eye-catching print that's an outfit all its own.

Anna's picks:

4. Breezy Minidresses

Susan's take: "I don't like my dresses too short, but if you can rock it, then go for it. These are perfect for those hot days when just the thought of getting dressed makes you sweat. I wear them as bathing suit cover-ups, too."

Susan's picks:

Anna's take: Each year, I crave a lightweight minidress as soon as the spring weather hits, so I always have at least one on hand (or two or three, if we're being honest). I'm with Susan on wearing them as beach cover-ups, too, so I'm shopping for one that does both.

Anna's picks:

5. Tank Dresses

Susan's take: "Tank dresses are a layering superstar. You can wear it with a sweater or blazer over, which comes in handy when you're running in and out of air conditioning."

Susan's picks:

Anna's take: I'm reaching for one of these minimalistic jersey dresses instead of leggings not only because they're just as comfortable but also because the spring '21 runways were filled with the everyday styles.

Anna's picks:

Next up, find out which three items Susan is retiring from her closet in 2021 (and what's staying).