I'm So Sorry, But Wearing These 6 Things Could Be Dating Your Summer Outfits
Summer is basically here, which means that if you're a New Yorker like me you've recently gone through the process of transitioning your closet—AKA pulling out your warm-weather from storage and replacing it with your all your heavy winter items because the two can rarely coexist together. Personally-speaking, this specific task always forces me to do a seasonal audit and confront what I will (and won't) keep wearing from summers past.
When I sat down to evaluate the staples I used to wear between June and September, I realized they could largely use an update. Items like fitted denim cutoffs and kitschy colored-lens sunglasses that I clung to for years simply aren't resonating with my style anymore, and frankly, have begun to feel a little dated. With that, I'm making a few 2026 updates that will make all my summer outfits feel truer to the current moment and where my personal style is at now.
Ahead, the six specific summer pieces I'm transitioning away from, and what I'm leaning into instead.
Slightly Dated: Denim Cutoffs
More Forward: Taffeta Shorts and Pants
There will always be a time and a place for denim shorts, but I've realized that my fitted cutoffs with the fraying hems weren't making my outfits look fresh and forward anymore, and instead I've been eyeing the many pairs of silk taffeta pants and shorts that are emerging in pretty shades from brands like Chan Luu, Donni, and Reformation right now.
Slightly Dated: Cork Wedges
More Forward: Flip-Flop Wedges
Love them or hate them, there's no denying that wedges stir up many emotions. I, for one, used to be a wedge-sandal hater until recently when more designers began putting out sleek thong wedges that completely changed my tune. They're a modern update on the kitten-heel thong sandals that have ruled for a few seasons.
Slightly Dated: Bubble Skirts
More Forward: Balloon Pants
Bubble skirts are one of those trend pieces that isn't fully "out" but has past its peak. Instead, I'd suggest wearing a pair of balloon pants as a more updated base to casual-cool summer outfits.
Slightly Dated: Colored-Lens Sunglasses
More Forward: Slim Oval Sunglasses
One item I recently rid my closet of in the seasonal switch? Colored-lens sunglasses, the likes of which I used to hoard four to five years ago. Now, I'm more inclined to wear slim oval-shaped sunglasses that feel a tad retro but ultimately more timeless and chic.
Slightly Dated: Wraparound Bikinis
More Forward: Two-Tone Swimsuits
There are some swim trends that trend so hard one year that they'll always be associated with that summer, and to me, wraparound bikinis will forever remind me of the summer of 2021. This year, however, I'm placing bets on two-tone swimsuits becoming the It trend of the moment.
Slightly Dated: Shell Jewelry
More Forward: Elegant Pendants
It's not truly summer if my outfit rotation doesn't include a fun piece of jewelry or two and for a while that meant shell jewelry and underwater motifs. In 2026, however, elegant pendant necklaces are the piece I'm reaching for to add a little bit of whimsy and joy to my warm-weather looks.

Anna is an NYC-based senior fashion editor who has been a member of the Who What Wear team for over eight years, having begun her career in L.A. at brands like Michael Kors and A.L.C. As an editor, she has earned a reputation for her coverage of breaking trends, emerging brands, luxury shopping curations, fashion features, and more. Anna has penned a number Who What Wear cover interviews, including Megan Fox, Julia Garner, and Lilly Collins. She also leads the site’s emerging travel vertical that highlights all things travel and lifestyle through a fashion-person lens.