Men's Leisurewear Shorts Quinn | Derek Rose

How to Style Men’s Shorts

Wondering how to wear a pair of shorts that feel both comfortable and stylish? Find out how to style men’s shorts so you can wear them with confidence.

As summer approaches in some parts of the world - bringing with it warmer weather, you may find yourself wondering how to wear a pair of shorts that feel both comfortable and stylish. Many men shy away from wearing shorts for fear that they don’t look quite right. But, with our help, a pair of shorts will quickly become your summer wardrobe staple.

Keep reading to find out how to style men’s shorts so you can wear them with confidence.

1. Wear Shorts that Suit your Legs

First of all, you’ll need to assess what style of shorts will suit your legs best. Men’s legs come in all shapes and sizes so there isn’t a one-size-fits-all when it comes to shorts. Having a better understanding of your leg shape will help you to make a better choice when choosing the style, length and colour of shorts. 

For example, if you have muscular legs, then a pair of slim-fit shorts will likely be uncomfortable. If you have shorter legs, you’ll want to choose a shorter pair of shorts so they don’t fall below your knee. For pale legs, avoid white or beige coloured shorts and instead choose darker colours for contrast.

2. The Best Colours for Shorts

For a truly versatile pair of shorts that you can wear with multiple different outfits for a variety of looks, choose timeless colours such as:

  • Blue: Whether it’s navy blue or light blue, this interchangeable colour will work with almost anything. A bright white T-shirt with navy blue shorts, for example, offers a relaxed and modern look.
  • Grey: From light grey to charcoal, this colour will match and look good with everything, so the options are endless. Grey is the perfect colour to choose if this is your first foray into styling shorts.
  • Brown: A popular choice for slightly more formal occasions or events, brown-coloured shorts is a simple yet extremely versatile colour that will pair with almost anything, such as blue, white, khaki green and black.

3. Shorts and a T-Shirt

A combination that never goes out of style is shorts and a T-shirt. For a relaxed and comfortable fit, our lounge shorts, made from finely woven cotton or silky smooth micro modal, can be paired with short-sleeve t-shirts to lounge around at home or to stroll along the beach. Pure comfort.

Either plain or patterned t-shirts also work well for tailored shorts as a way to create a more casual look. If you’re planning on tucking the t-shirt in, make sure to include a stylish belt. 

Men's Lounge Shorts | Derek Rose

4. Shorts and a Button-Down Shirt

Wearing a short-sleeve button-down shirt with shorts will instantly make you look well put-together effortlessly. With a plain pair of block-coloured shorts, you can pair any coloured or patterned shirt to add some colour and interest to your outfit. A smart casual shirt can help dress up a pair of shorts for events such as a family picnic, bbq, or a summer work party. Add a pair of sunglasses and some comfortable loafers to further elevate the look.

If you’re planning on wearing a shirt with shorts, we recommend short-sleeve shirts as they look much cleaner. Long-sleeve shirts with shorts can look awkward and unbalanced unless they are lightweight linen shirts with sleeves that can be rolled up.

5. Shorts and Polo Shirts

Polo shirts work well with chino shorts as it creates a slightly more formal look while still feeling relaxed and comfortable. If you want to keep it casual, leave the polo shirt out. But, if you want to look smarter, tuck the polo shirt in and add a belt. 

A polo shirt with athletic shorts can work for the ultimate leisurely look, but be careful that the loose clothing doesn’t look ill-fitting.

6. Shorts and Hoodies

If you’re wearing shorts to the gym (always recommended for leg day so you can visibly see the pump), a hoodie is an excellent choice to pair with them over a t-shirt. Hoodies are best worn with casual shorts worn around the house to run errands or to enjoy a long countryside walk.

If you’re wearing dressier shorts, such as linen or chinos, we’d recommend avoiding a hoodie but wearing a light jacket or bomber jacket instead. 

7. The Best Shoes to Wear with Shorts

Pairing shoes with shorts can be tricky. You want to avoid anything too clunky such as boots or big trainers, as this can make you look too bottom-heavy. Opt for lighter-weight shoes, such as:

  • Simple trainers. 
  • Slip-on trainers.
  • Boat shoes.
  • Espadrilles.
  • Loafers.
Take a look at our shorts collection made from a variety of fabrics with different colours, patterns and prints for a versatile look.