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Summer in Shorts: How to Style Them with Confidence

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Let’s talk shorts.

For some women, they’re a summer staple. For others, they feel… complicated. Too casual. Too young. Not “office-ready.”

But here’s the secret: when styled with intention, shorts can be every bit as polished and powerful as tailored trousers or a chic midi dress. The magic isn’t just in what you wear—it’s in how you style it.

If you’ve followed along with my “Wearing vs. Styling” series on Instagram, you’ve already seen the transformation. Even the simplest pair of shorts can shift from “just okay” to “effortless and elevated” with a few thoughtful touches.

Here’s how you can do the same:

1. Start with the Right Fit

Look for shorts that skim your thighs instead of clinging. This keeps things flattering and comfortable—especially on hot summer days.

2. Think Longer, Relaxed & Modern

Trends are leaning toward longer silhouettes with clean finishes—like Bermuda shorts or tailored styles. They create a more intentional look and can transition from school runs to casual meetings with ease.

3. Add a Power Piece

This is the difference between “wearing” and “styling.” Add one standout element:

  • A blazer tossed over Bermudas.

  • A statement belt on boxer shorts.

  • A silk scarf tied at your neck or bag.

That single piece elevates the entire outfit.

4. Play with Pairings

Unexpected combos make shorts look sophisticated instead of sloppy:

  • Boxer shorts + crisp button-down (tucked, with sleeves rolled).

  • Denim A-line shorts + tailored vest + slides.

  • Bermudas + tank + longline kimono.

5. Accessorize with Intention

Shoes and accessories make or break the look. Trade flip-flops for sleek sandals, add layered gold hoops, or grab a structured bag. These “easy upgrades” are what pull the outfit together.

6. Make Shorts Work for Your Life

Shorts aren’t just for lounging—they can flex with your lifestyle:

  • Errands & pickups: Pair with sneakers and a linen button-up.

  • Dinner date: Swap sneakers for strappy sandals + bold earrings.

  • Casual office: Bermudas with a blazer and loafers.

👉 Want to see this in action?

Click here to view Wearing vs. Styling: The Shorts Edition Lookbook

 

STYLE RX: Swap distressed denim cutoffs for polished A-line denim or cotton poplin boxers. They instantly read more refined.

 

WHICH SUMMER IN SHORTS LOOK IS YOUR FAVORITE??

 

GET THE LOOK

Click the link HERE for the full Summer Summer in Shorts: Wearing vs. Styling Lookbook.

 

Loved these tips? Stay tuned for more style insights by subscribing to the newsletter and join the conversation by sharing your favorite tip in the comments below!

Happy Thursday GlamFam! This season has been full—from my daughter’s 9th birthday and our 22nd wedding anniversary to an Orlando family trip with 13 of us (!!). And in the middle of all that, I was reminded why intentional style matters. Until the next post….

 

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Hi, I'm Sam

Your Pharmacist turned Fashion Stylist, Confidence Curator, and Couture & Consignment Closet Bestie. I help heart-led women show up styled, confident, and camera ready.

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