Ideas for Styling Tailored Shorts for a Casual Look

Summer’s here, meaning it’s time to bring out those shorts. But what if you want to maintain a touch of sophistication even in the heat? Enter tailored shorts. Unlike their laid-back cousins – think cutoffs or athletic shorts – tailored shorts keep it classy while letting you show off those legs. And the best part? They can be dressed for a breezy, casual look without losing that touch of elegance. Read on for cool ideas to style your tailored shorts for a casual outing.

Basic Tee + Tailored Shorts + Sneakers

There’s a reason why basics are classics. A simple white tee or any solid-coloured t-shirt paired with tailored shorts gives a relaxed vibe. Finish the look with your favourite sneakers, and you’re ready for a day out in the city or a casual brunch with friends.

Denim Jacket Layering

A tailored pair of shorts and a cool denim jacket is the perfect mix of polished and casual. Whether sporting a light wash or dark denim, the contrast with the tailored shorts is fresh and effortlessly stylish.

Off-Shoulder Top

For a more feminine touch, pair your shorts with an off-shoulder top. The playful nature of the top complements the structure of the shorts, creating a balanced and trendy look. Accessorise with a statement necklace or some layered bracelets to complete the outfit.

Boho Vibes with a Loose Blouse

A flowy, bohemian blouse can be a great companion to tailored shorts. The casual feel of the blouse, possibly with some lace or embroidery details, contrasts beautifully with the structured shorts.

Accessorise with a Hat

Whether it’s a Panama hat, a fedora, or a simple baseball cap, hats can add a new dimension to your casual tailored shorts outfit. They are also great for those days when you need extra protection from the sun.

Espadrilles or Sandals

While sneakers are a great choice, remember summer staples like espadrilles or sandals. They can add a relaxed feel to your outfit, making it perfect for a beach day or a stroll through a summer festival.

Lightweight Cardigan

For those slightly chillier summer evenings, throw on a lightweight cardigan over your casual ensemble. It adds a layer without overwhelming the breeziness of the shorts.

Belt It Out

A stylish belt can change the whole dynamic of your outfit. A thin, delicate belt or a chunkier statement piece can emphasise your waist and add character to your shorts.

Sling Bag or Backpack

Finish off your casual look with a trendy sling bag or a chic backpack. They’re not only practical but can also serve as the perfect accessory to elevate your style.

Roll the Hem

Try rolling the hem of your tailored shorts for a more relaxed look. This minor tweak can transform the appearance, making them look even more laid-back.

What About The Length Of Tailored Shorts?

The length of tailored shorts is a crucial factor to consider when choosing and styling them. The ideal size can vary depending on personal preference and body type, but here are some general guidelines to help you decide on the correct length for your tailored shorts:

Above the Knee

Tailored shorts typically end just above the knee for a classic and versatile look. This length is flattering for most body types and suitable for casual and slightly dressier occasions. It offers a balanced and polished appearance.


If you prefer a more relaxed and casual look, you can choose tailored shorts that hit mid-thigh. This shorter length is trendy for beachwear and straightforward settings. Remember that extremely short shorts may not be appropriate for all situations.


Tailored shorts are a good choice if you want a slightly longer and more conservative option. These shorts extend to just below the knee and provide more coverage. They can be a suitable option for more formal or modest occasions.

Inseam Measurement 

When shopping for tailored shorts, consider the inseam measurement, which determines the length from the crotch to the hem. Most men generally think shorts with a 7 to 9-inch inseam are a good size for tailored shorts, ending just above or at the knee.


Ultimately, the best length for your tailored shorts depends on your style and comfort level. It’s a good idea to try on different sizes to see what you feel most confident and comfortable in. Additionally, consider the occasion and the event’s formality when choosing the length of your shorts.

Can I Wear Tailored Shorts In Different Colours And Patterns?

Yes, you can wear tailored shorts in different colours and patterns. Tailored shorts let you express yourself and look unique with their many hues and patterns. Here are some considerations for wearing tailored shorts in different colours and patterns:

Solid Colours 

You can match various tops and shoes with timeless options like navy, khaki, grey, and olive in neutral solid colours. They provide a versatile and timeless look.

Bold Colours 

Choose vibrant colours like cobalt blue, red, or emerald green to make a statement. These can add colour to your outfit and work well in casual settings.


Tailored shorts are available in various patterns, including stripes, checks, plaids, floral prints, and more. Patterns can add a playful or stylish touch to your casual look. Just ensure that the design complements the rest of your outfit.

Printed Shorts 

For a more unique and eye-catching appearance, you can choose printed tailored shorts with designs like tropical prints, geometric patterns, or abstract motifs. These can be fun for summer or beach-inspired outfits.


Camouflage-patterned tailored shorts can give your outfit an edgy and casual vibe. Keep the spotlight on the shorts by wearing them with a simple t-shirt or tank top.

Colour Combinations

You can also experiment with colour combinations. For example, wear pastel-coloured tailored shorts with a complementary top for a fresh, summery look.

Final Thoughts

As we wrap up our sartorial journey, it’s clear that tailored shorts are the epitome of blending comfort with style. Effortlessly, they bridge the gap between formal and laid-back, showing they can redefine summer fashion rules with originality. So, as you bask in the summer sun, remember to let tailored shorts be your go-to companion, ensuring you remain chic, calm, and undeniably stylish.