29 Elegant and Cool Summer Dresses That Are On-Trend But Not Too Trendy

@styledsara outfit post in LPA linen midi dress.

(Image credit: @styledsara)

I feel like the title says it all, right? As much as I like to look forward and on-trend, I'm always weary of buying anything too trendy. That's especially true when it comes to dresses. The first issue that comes to mind, of course, is the inevitable buyer's remorse that comes along way too quickly with an overly of-the-moment purchase. Beyond that, there's the cringe factor! If I'm wearing a dress, odds are I will be asking my husband to take a picture of me, and what's worse than looking back on a not-so-distant memory and wondering, What in the world was I wearing?

Okay, enough of my inner monologue. Let's just get to the shopping. For all the reasons mentioned above and more, I decided to round up my favorite dresses of the moment that hit that sweet spot of cool but not too cool. As always, I ended up with more picks than can fit in my cart or closet. To see what made the cut, simply keep scrolling. Enjoy!

This story was published at an earlier date and has since been updated.

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Editor-at-Large

Since starting as an intern back in 2013, Nicole Akhtarzad Eshaghpour has held several roles here at Who What Wear, and she is currently Editor-at-Large. Upon joining, she was a senior about to graduate from business school at USC. Fast-forward to 2025, and she's moved to NYC from her hometown of Beverly Hills and spends her workdays a little differently from when she was just starting out. Currently, she focuses on a weekly mélange of shopping content and her Trust Me—Buy This newsletter. As far as her personal style goes, she's largely drawn to neutral, classic pieces but will always make an exception for something colorful or bejeweled as long as it's deemed worthy enough. After all, the only thing she loves more than a party is dressing up for one. On her downtime, she can usually be found at home eating something delicious and trying to force her husband to watch Summer House.