How To Style Your Shorts 4 Different Ways

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Shorts have always been a hot topic in the fashion world. In fact, it's almost laughable how much this simple piece of clothing has sparked serious debate!

Questions like “Which shorts length is most flattering?” or “Can shorts be dressed up formally?” have made countless headlines, with people holding strong opinions on the matter. For men specifically, when shorts were first introduced, the debate stemmed from their association with boys' school uniforms, making them initially considered inappropriate for men.

Fast forward to today, and we LOVE shorts! They’re comfortable clothing items enjoyed by both men and women.

In celebration of letting our legs enjoy the season, we present a style guide for gents on how best to style your shorts!

1. The Street Look

If your fashion style leans towards an urban aesthetic, our Foundation Cargo Short in Deep Woodland Camo Aop is the perfect choice for you.

This bold camo print screams street fashion and pairs effortlessly with our Original Fit Logo Tee in Pitch Black/Trademark, creating that vibrant urban vibe streetwear is known for.

To truly embrace the street fashion aesthetic, don’t forget the accessories, as well as a bold, chunky pair of sneakers! Our iconic Intruders are perfect for the job.

Lastly, we’d recommend one of our eye-catching sunglasses or a beanie – whichever option best suits the weather, of course!

Street Look

2. The Sophisticated Look

If you prefer a more sophisticated look for your everyday style, we recommend styling the Foundation Cargo Short in Kelp. While it’s still a cargo short, you might not initially think it works for a semi-formal sophisticated look; however, the colour palette is everything!

Kelp is a lovely neutral tone that pairs well with other earthy colours, such as deep brown, sage green, white, and more.

For these particular shorts, we recommend pairing them with a white linen-blend button-up shirt (long sleeve or short sleeve), and our Pause Retro sneakers in Star White Barry/Lily White Jazz Suede. A simple chain and wristwatch would add that finer, elegant detail to the outfit.

3. The Edgy Look

For an edgy look, the key is to embrace black, be bold with your accessories, and never be afraid of some cool, chunky boots or sneakers!

To create your very own Caterpillar-inspired edgy look, we recommend starting with a pair of our Black Essential Stretch Shorts. Although these are workwear shorts, we believe they still rock the utility edge look – not to mention that they are incredibly comfortable, as they were designed to support gents for a full day of earthmoving labour!

Next, pair these shorts with our Pitch Black Advanced Reflective Logo Tee, and if it’s a chilly day, add our Foundation Bonded Insulated Vest as a stylish light layer. Finally, the boots will make or break this look, but luckily for you, there are two options we highly recommend: our Hardwear Mid, which offers that chunky feel, or our Colorado 2.0 Chelsea, perfect for those who want a quick and easy slip-on boot.

For some finer details, we definitely recommend wearing matching socks (either white or something bold for a pop of colour) and letting them peek through the top of your boots. Add a beanie to this look for the days you’re not feeling your hair, and finish with some funky shades.

Edgy Look

4. The Preppy Look

The preppy look is inspired by old-money Ivy League students, often characterised by their well-tailored garments, collared golf T-shirts, and knit sweater vests.

Today, this fashion style is enjoyed by many, with slightly modern tweaks. With our Caterpillar range, here’s how to create the perfect preppy look for shorts.

Begin with our Dusty Olive Foundation Cargo Shorts. Pair them with our Marshland Stripe Foundation Jersey Knit Polo. Layer this outfit with our Graphic French Terry Crewneck, and ensure that the collar of your knit jersey peeks through. Finally, you’ll need some footwear to complete the look, and for this, we recommend our Passport Rubber Cap or our Covert Low.

How Will You Be Styling Your Shorts This Season?

Now that you have four different looks to work with, we’d love to know how you'll be styling your shorts this season.
Did any of the fashion aesthetics mentioned above stand out to you? Or perhaps you have a completely different style combination you'd like to rock?
Be sure to tag us on social media so we can see how you’re styling your Cat Apparel shorts!

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