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How to style denim shorts with confidence

Posted on September 12, 2025
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PICTURE: UNSPLASH/ JORTS

Just when you thought you’d left them in the 2000s, jorts – yes, longer length jean shorts – have made their way back into the fashion spotlight.

What used to be associated with DIY cut-offs and casual weekend wear is now being reimagined by designers and street-style stars as a statement piece. The modern take on jorts is less about sloppy cut denim and more about intentional tailoring, proportion play, and effortless cool.

So, if you’re curious about how to pull off jorts, here’s your style guide.

Fashion is cyclical, and denim is timeless. Jorts fit right into the current revival of early-2000s style, but they’ve also been given a more refined spin. Think structured silhouettes, longer hemlines, and elevated styling. Celebrities, models, and editors have been pairing jorts with everything from blazers to boots, proving that they’re not just for music festivals.

1. Balance proportions

Because jorts often have a boxy, looser cut, balance is key. If you’re wearing oversized denim shorts, pair them with a fitted or tucked-in top to create shape. For shorter, slimmer jorts, try an oversized button-up or blazer to give that cool, off-duty vibe.

2. Elevate with tailoring

One of the chicest ways to wear jorts is with tailored pieces. Think: a crisp white shirt tucked in, a structured blazer, or a fitted vest. This smart-casual mix instantly takes jorts from casual to polished.

3. Play with footwear

Jorts are versatile when it comes to shoes:

  • Sneakers keep the look laid-back.
  • Strappy sandals or mules add a feminine twist.
  • Knee-high boots or cowboy boots lean into street-style drama.
  • Chunky loafers or ballet flats create a preppy, fashion-editor finish.

4. Experiment with lengths

Not all jorts are made equal. Opt for:

  • Mid-thigh cuts for a universally flattering casual look.

  • Longer bermuda styles for a more polished, editorial vibe.

  • Micro cut-offs if you’re channeling festival energy.

5. Accessorize wisely

Because jorts can feel a little plain, accessories make all the difference. A statement belt, oversized sunglasses, or a mini crossbody bag will instantly lift the look.

6. Lean into denim-on-denim

Double denim is trending, and jorts are the perfect way to test it out. Pair your shorts with a matching denim shirt, vest, or jacket. To avoid feeling too “matchy-matchy,” mix washes or break it up with a bold belt.

Jorts are surprisingly versatile. They work for:

  • Weekend errands with sneakers and a tee.

  • Casual brunches with a blouse and sandals.

  • Fashion-forward nights out with boots, a blazer, and bold jewellery.

  • Vacation looks with bikinis or crop tops layered under linen shirts.

Jorts have graduated from their scrappy, DIY roots into a legit fashion staple. Whether you prefer polished and tailored or laid-back and cool, there’s a way to style jorts that works for you. The key is in the balance – play with proportions, elevate with accessories, and choose the right footwear to set the mood.

This season, don’t be afraid to give jorts a second chance – they might just become your most-worn piece.

First published by Woman & Home

Compiled by Amy Steenkamp

Also see: Must-have wardrobe basics fit for every season

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