While the last year in fashion has largely been defined by comfort dressing, the fashion set is now returning to more directional looks as the world begins to reopen—and I’ve been paying close attention to the trendy summer outfits that are already emerging. I’m personally in need of some fresh inspiration for the new looks I’m wearing, and there is no shortage of cool ideas if you’re similarly wanting a dose of sartorial newness.
Taking a glimpse at the fashion unfolding among the coolest insiders, I’ve already flagged a number of outfits that I want to test-drive myself that hit on the season’s biggest trends. Pieces like oversize button-downs, crochet tops, and shorts sets are among the key buys this season, but the cool factor really comes down to some essential styling tricks. Ahead, let’s dive into the trendy summer outfits that will be huge this season and all of the core pieces you'll need to try them out.
Oversize Tailoring
Ever since Kendall Jenner stepped out onto the streets of NYC wearing a white button-down and a pair of slouchy trousers from The Row, her exact outfit has served as inspiration for countless looks spotted on the fashion set.
Shop the trend:
Matching Shorts Sets
One of the cool, cozy trends we’re seeing a lot of right now? Shorts sets. There are versions from practically every designer at the moment, so if you add one to your cart, you’ll want to make sure you have a bikini top to layer underneath.
Shop the trend:
Crochet Tops
Crochet has been really taking off this season, and I’m predicting that tops will be a huge trend for summer. Fashion people have been styling them with baggy denim pants or shorts and a great pair of sunglasses.
Shop the trend:
Colorful Button-Downs
One of the standout looks on the S/S 21 runways was at Valentino, where a model wore an oversize bubblegum-pink collared shirt with micro shorts. Ever since, the colorful button-down has been one of the pieces defining fashion this season.
Shop the trend:
Denim on Denim
Denim-on-denim looks were one of the key trends on the F/W 21 runways, and insiders are clearly getting an early start on the look. Opt for a denim shirt or jacket and straight-leg jeans plus a cool bag and loafers.
Shop the trend:
Next, shop 25 cool fashion finds I'm obsessing over right now.
-
This Dated Denim Pairing Is Suddenly the Chicest Way to Wear Jeans for Fall 2025Easy and stylish.
-
The Specific Way Everyone Stylish in NYC Will Be Wearing Boots With Jeans This FallIt's all about this styling trick.
-
I'm an NYC-Based Dad Who Is Always on the Move—This Is How I Redefined My Everyday WearEffortless, easy, and cool.
-
Ignore the Haters—I Still Love These Versatile and Comfy Pants and Bet You Do TooSee how fashion people from NYC to Paris to London wear them for fall.
-
This Classic Shoe Is Every Parisian's Secret to Making Jeans Look Elevated in FallAnd you probably already own it.
-
The Easy-Yet-Elevated Outfit Formula Fashion People Will Be Wearing Straight Into FallHere are seven takes on the chic look.
-
From Basic to Designer: This Outfit Trend Will Instantly Make Your T-Shirts Look The Row CodedPinky promise.
-
Here You Go: 5 Trend-Forward Fall Outfit Ideas I Think Are Wildly ChicThese looks get a yes.
