How to Wear Shorts Without Looking Like a Dork

Let’s get this straight: Of course, you can wear shorts.

The cropped pair can be a point of contention in style with its undeniable association with a more youthful time in a man's life, as part of schoolboy uniforms. But the problem lies not in the garment itself but in how it’s styled. Think of the unflattering cargo shorts or the pair of basketball shorts worn on, say, the first date.

There are real, respectable ways to wear shorts proudly without sacrificing your dignity. Here, we’ve put together a guide for wearing shorts while still looking very much like a grown-up. 

1| Shorts are perfect for our tropical climate.

Shorts have been widely regarded as a garment for summer, and in this country where it’s warm almost all year round, there is no wrong time to wear shorts given the setting is appropriate. Remember: Shorts belong to casual wear. If your day involves leisure, you're in the right direction. 

2| Shorts should be short.

As with other garments, the right length and fit can make or break your shorts. Aim for the right length—your shorts should show your knees. You can go between two to three inches higher than the knee, depending on your height and figure. Shorter men can most definitely get away with three inches above the knee to create a vertical illusion, while taller men can wear shorts that hit just the knees to balance their figure.

Shorts are called shorts for a reason. Steer clear if they go past below the knee.  

3| Baggy and skinny shorts have no place in your closet.

Again, it’s all in the fit: Shorts should ride on the waist and have a straight cut from below the rear down to the knee for mobility. Baggy shorts do favors for no one as they add unnecessary bulk to your frame. Skinny shorts don't look good, too. The snug fit is a recipe for disaster, highlighting certain areas you wouldn’t want to draw attention to. Only your swimming trunks should be that tight. 


4| Chino shorts are the best way to go.

There are many different shorts to wear for several occasions like, say, board shorts for surfing or basketball shorts for that weekend game with your friends. Generally, the dressiest and most versatile option is a pair of chino shorts. The fabric and style offer structure to what is a generally carefree garment and its crisp feel pairs well with other polished items such as button-down shirts. You can tuck them in for a more refined look or pair with a plain white tee or a Henley shirt for laid-back situations. 

5| Socks and shorts sometimes don't go together.

The thing about visible socks is they interrupt a visual. Instead of making your leg look longer, they cut it. Of course, there are exceptions to this rule, such as when you have some height to spare, but when you’re wearing chinos with boat shoes or loafers, it is recommended to wear no-show socks to look taller.

7| Shorts can be cuffed.

This is a great way to make use of longer shorts that haven’t been altered (yet). You can cuff them to a more agreeable length by simply folding up the hem twice or thrice.  

8| Colorful shorts mean more casual.

Fashion-inclined men may enjoy the prospect of injecting more hues into their outfits by wearing shorts in punchier, brighter colors. Just take note that brighter colors invoke a more casual feel. Stroll down the shore in a seersucker shirt, red shorts, and flip-flops, but enjoy a beach-themed cocktail mixer in a pair of navy or khaki shorts.

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Sam Beltran
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