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5 Summer Outfits You Need to Wear Before the Season is Over
From shorts and heels to head-to-toe linen, make sure to cross these looks off your summer to-wear list before it’s too late.
It makes me sad to even say this, but the unofficial end of summer is quickly approaching. All the signs are there: the sun is setting a little earlier, back-to-school commercials are on the air, and the other day, I found myself mindlessly shopping online for sweaters. Whether I like it or not (I don’t—summer is by far my favorite season), this change is inevitable. And that’s why I have to make sure these last few weeks of sunshine, humidity, backyard barbeques, and beach-adjacent activities really count.
Here are the five outfits I plan on wearing—and I recommend you wear—before we say goodbye to summer.
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Summer Outfits to Wear Before the Season Is Over
A Celebratory Red Dress
My cousin Sadie is the best, and not just because she’s always keeping me up to date on what Gen Z is into. She’s also having a huge Bat Mitzvah at the end of the summer, meaning I’ll finally have a reason to bust out a vibrant, flame-colored dress (not that I need an occasion—the Ashley dress is machine-washable, wrinkle-resistant, and treated with an all-natural anti-odor finish called Polygiene, meaning it’s about as versatile as they come). I could pair it with heels, but for this party, I’ll be slipping on a pair of Rowan flats and trying to impress Sadie’s friends with my secret knowledge of TikTok dance moves. Bright red dresses don’t just belong in my summer wardrobe, and chances are, I’ll want to keep wearing this ultra-comfortable style throughout the colder months, too. To keep things cozy, I’ll add layers like the sharp Merritt jardigan and—when temperatures really drop—the cashmere Arbus sweater.
A Leggy Endeavor
Shorts and a pair of heels is a look that’s mega chic on people of all heights. As a petite person, I love the extra inches of leg provided by a pair of sturdy stilts, like the Ella sandals. The Sasha shorts in breeze are casually sophisticated, especially if worn with a simple but essential tank, like the Paige T-shirt. This is an outfit I’ll wear out to dinner, drinks, or even a summer Friday in the office. Many of the best cute summer outfits can be reimagined for fall, too. Come cooler weather, I can trade my shorts for equally comfortable pants like the Colbys and add the matching O’Hara blazer to create a complete suit.
A Nautical Manifestation
I haven’t made my way onto a yacht this summer, so I’m hoping this outfit will help me manifest an invitation. The Milo jeans in tusk have sailor-suit-meets-French-Riviera vibes, especially when paired with the Adele tank in a luxurious knit linen. Just in case it gets chilly out on the open waters, I’ll make sure to pack my Cookie cardigan in drift knit, which will keep me warm but not too hot. Now all I need is a cute hat and a glass of prosecco, and I’ll be on my way.
A Head-to-Toe Breeze
I was in the Hamptons last week, and the linen looks were flowy and plentiful. I had severe outfit envy, which could only be remedied by a head-to-toe set. A few of my favorites include: the Roo vest paired with the Shane pant in earthy acorn; the Mila shirt and Adina shorts in ultra-light cotton poplin; and the Avelyn top and Bia pants in machine-washable Air Twill. The Rowans in snakeskin and a pair of statement earrings elevate any Sag Harbor-ready ensemble.
A Perfect Date Night
When my family moved last summer, I was concerned that my husband and I wouldn’t have any go-to date spots in our new neighborhood. Luckily, our apartment is 10 minutes from one of the best Mexican restaurants in town, which means it’s easy to pop over whenever the mood for a margarita strikes. The right outfit can turn a random Tuesday into a special occasion, so next time we’re heading over, I’m going to slip into the silky Orchard skirt. The romantic vintage rose color pops when paired with the Vicky tank in pearl, and a matching pair of white sneakers (an essential shoe choice for the walk home) keep the outfit casual. (Bonus: For more outfit ideas featuring the Orchard skirt, check out this style guide.)