16+ Preppy Shorts Outfits For Summer 2025

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I’ve always loved the thrill of finding new outfits — especially when the seasons change and the sunshine practically begs you to refresh your wardrobe.

Summer, for me, is all about light, breezy looks that feel as good as they look.

And this year, I was determined to find the perfect shorts outfits — something fabulous that I could wear on a casual date, to brunch with friends, or even just strolling around town, feeling cute and confident.

At first, I’ll be honest — the search wasn’t as easy as I imagined.

I scrolled through dozens of options, tried on a few styles, and realized quickly that not every “trendy” piece actually felt like me.

Some were too much, others too plain. I wanted that sweet spot: outfits that were stylish but still comfortable, fun but still put-together.

After a bit of digging (and a few “nope, not for me” moments), I finally found what I was looking for: a collection of summer shorts outfits that hit all the right notes.

From classic denim shorts paired with a crisp white tank to linen sets that practically float in the summer breeze, each outfit felt like a piece of my personality — fresh, stylish, and ready for anything summer throws my way.

Now, I’m so excited to share my finds — the shorts outfits that I cannot wait to wear this season.

Whether it’s for a casual coffee date, a weekend road trip, or just a sunny afternoon out, these looks are officially on my must-try list for summer!

Tailored effortlessly chic look, H&M linen blue shirt and Reiss linen tailored shorts, styled with Hermes tan accessories.

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COS black tshirt, Nadine Merabi white skirt, Chanel ballet pumps and Hermes black birkin

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Lounging in holiday style with Reiss + silk satin shirt and tailored shorts + all white look with taupe Hermes accessories

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Chrissa Two Piece

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Warm days in NYC wearing a navy blue Tommy Hilfiger Cardigan with my Because of Alice Shorts and matching Tommy Accessories

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The perfect grey pinstriped set by lounge styled with white heels and my lady bag

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Pair Anabella Linen Dress+Santorini natural basket off-white smooth+MJ Cream Leather Ballet Pumps

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Pair Red western boots outfit+Morrina Beige Multi Floral Jacquard Barn Jacket+Denim Distressed Mini Skirt

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Denim Shorts + Brown Tank Top(Classic, simple, and effortless+Add sneakers or flat sandals and a crossbody bag)


Pair Knee-length shorts+Tailored suit waistcoat+ Sweet Little Hand Bag

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