Freelance stylist C.K. Koo, 39, says shorts are a good choice in Singapore's weather, but finds that men here are "a little conservative and still think shorts are only for casual weekends".
He adds: "If you look at the men in Italy and France, they pair their shorts with a blazer for work on Fridays during the summer."
With a variety of shorts available in different materials and prints, there is no reason they should just be limited to casual Sunday brunch.
To err on the side of caution, your shorts should hit just above the knee and not be too fitting.
Here are Koo's tips on styling shorts for different occasions.
Casual: Try plain or printed shorts and match the material of your top and bottom - cotton shorts with cotton shirts and linen shorts with linen tops. For a layered style, wear a white T-shirt underneath the shirt.
Boat shoes or white canvas shoes go best with this look.
Smart casual: Go for tailored shorts. Try a lightweight linen blazer with checks or stripes in either a bright or subtle colour. This look goes best with suede loafers, casual Oxford shoes or even a pair of sneakers.
Experiment with silhouette: Keep it simple with a plain T-shirt in a nice cut, a tapered-fit shirt or layer it with a lightweight jacket. Just keep it clean and sleek.
Here are The Straits Times' picks:
White long-sleeved shirt, $44.90, from New Look; and black tailored shorts, $59.90, from H&M
Smart-casual occasions call for tailored separates.
Brown Brentham sailing jacket, $279, from Fred Perry; and patterned shorts in olive, $29.90, from Uniqlo
A pair of patterned shorts is much easier to pull off than you think. Just keep the top simple.
Navy blazer with elbow patch, $99.90, from Alcott from Zalora.sg; and brown shorts, $39.90, from Celio
Throw on a blazer to smarten your look instantly.
Black long-sleeved silk-feel shirt, $49.90, from Zara; and blue shorts, $29, from Forever 21
This look is still casual, but feels more luxe, thanks to the feel of the top.
Patent-leather white sneakers with croc-embossed pattern, $199.90, from Superga
These sneakers are great for casual and smart-casual occasions.
Tanned plain cap toe leather shoes, $250, from Benjamin Barker
Go for leather lace-ups for a smart-casual look.