Menswear (or fashion in general, rather) is very much a game of high risk/high reward.

Take a jacket + shorts look, for example. Although it is much easier to get the look “wrong”, if performed correctly it can be very chic and set you apart without looking out of place.

As the age old saying goes, “you have to know the rules, before you can break them.” That is to say, if you understand the basic elements of mens dress (fit, fabrics, pattern mixing, color coordination, accessorizing, seasonality, etc) there is a much better chance that you will be able to bend the rules to achieve a desired outcome. (Rules is italicized because there are no actual “rules”, only a heavy dose traditional conformity).

Here, some looks and tips to help you pull-off a jacket with shorts.

1. Heat Wave Business 

The trick is to have the proportions right. The jacket is an “modern” length (but not trendy short or “cropped”) so the shorts should have the same look and feel; about 1-2 inches above the knee.

The slimness of the shorts should also be cohesive with the jacket. They should be cut as if they are the matching pants of the suit, just chopped around the knee.

Bonus Tip: It’s already a look that can very easily look “affected”, so keep it simple with classic pieces, neutral colors and toned-done accessories.

Bonus Tip II: If the pieces aren’t tailored well it can look very amateur.

Bonus Tip III: Loafers are a lot easier than lace-ups. Think of shoes that look natural without socks.

Bonus Tip IV: Make sure the jacketing fabrics are summer appropriate. Think cottons, linens, tropical wools, etc.