How To Wear Shorts the Chic Way

Tips for men on how to wear shorts in the chic and stylish ways.

How To Mens Shorts How To Wear Shorts The Chic Way

Shorts could be the most worn piece of garment in your entire life history if you’re living in Southeast Asia climate. As a person who works from home – which means a lot of time spent lounging around or typing away in boxers shorts – I couldn’t agree more.

Men Shorts Guide Style Fashion How To Wear Shorts The Chic Way

We don’t refer to those highly ventilating pieces we wear at home as “shorts” anymore since the term “loungewear” was coined. Loungewear are meant to stay inside the house, but you might notice a phenomenon here in Malaysia: a lot of men tend to wear almost loungewear-like shorts out in the nearest cafe, groceries, neighbour’s house, clinic or even for a stroll in the shopping malls.

And “a lot of men” included me. #IHaveSinned

Peroni Shorts How To Wear Shorts The Chic Way

(“Well, it’s just a few steps away! It’s not like everybody is looking at you… and you look fine in that shorts ok. You don’t have to change…” Yada yada. Guys, admit it! Haha)

But things changed one day when a female friend made a funny remark about it, and that’s when I realised it wasn’t a very pleasant sight. I might have been sacrificing too much for the sake of comfort (you don’t want to hear the full “uncle short pants” story).

Like choosing the perfect jeans, I believe one can wear shorts as chic as les Parisien hommes wearing their scarves, as long as he puts enough attention into the details. Here’s the tips I’ve learned:

Give Up Your Old Shorts

Regardless of how much money you’ve spent on them (or how much time you’ve spent in them), if they don’t look right to you at the end of this post, stop reminiscing the memories and do away with them.

They may be a gift from someone special, or maybe some really great quality pieces that you got under discounts, but that doesn’t justify having to wear them and not looking your best. (Deja vu? That might explain why your wardrobe is bloated. Cue: Rebuilding Wardrobe 101)

The Right Length

Men Shorts Length Guide How To Wear Shorts The Chic Way

The key to looking great and chic in shorts is the length of the shorts.

Referring to the illustration, A is definitely not a good look. Some shorts might be too long to be called “shorts”, and some might be too long for you. For the latter, I know it always happens to shorter men with certain brands (because it happened to me!)

B is the safest length for men – right about covering your knee cap. It works for 16 year old boy, as well as 70 year old men. Anything that expands below your knee cap will end up like A. On the other hand, 1 or 2 inches above your knee cap is still great.

Takahiro Kinoshita Style Shorts How To Wear Shorts The Chic Way

Takahiro Kinoshita, Editor of Popeye Magazine, Japan

C is an experimental length, and it’s becoming a trend in recently years. But here’s what a 60-year-old sartorial expert would tell you:

  1. Avoid it at all cost;
  2. Only your swimsuit, your sports shorts, and your boxers can look that short – nothing else!

He knows it’s difficult to translate that length to stylish and chic, but you can always give it a shot when you’re feeling adventurous.

Special note: it’ll require either one or born of these: (1) great confidence (2) great thighs.

Thesartorialist Shorts Sports How To Wear Shorts The Chic Way

Scott Schuman, “The Sartorialist” blogger, in his sports gear

Prada Burberry Dolce Gabbana Short Shorts Trend How To Wear Shorts The Chic Way

Short Shorts in Dolce & Gabbana Spring/Summer 2012

The Right Fit

Men Shorts Fit Guide How To Wear Shorts The Chic Way

After knowing the perfect length, you’ll need to pay attention to the fit. Fit is very crucial because it decides whether you’ll look masculine and chic or simply sluggish. Granted, off-the-racks don’t always fit normal men perfectly (well, so by abnormal I mean models aha) but you can always get a close fit.

Men Slim Shorts How To Wear Shorts The Chic Way

A good fit means it’s fitted around your thigh, crotch and your waistline. Unless you’re attempting a fashionable loose fitting or oversized look (which is a different story), there shouldn’t be too much excessive fabrics, or too much of anything. That, brings us to the next point…

Minimalistic Design

Men Shorts Minimalist Design How To Wear Shorts The Chic Way

Hackett Spring/Summer 2013

To create a clean and chic look, it is always best to keep the design of your shorts to minimum. Rule of thumb: beware of pockets, no pleats and avoid denim.

Cargo pants tend to have a lot of pockets, which add bulks to your lower silhouette. And when you have that much of pockets, it’s hard not to stuff things inside (or is it just me?) and that drags you even further from creating a clean, straight-line overall shape.

Denim shorts are usually too casual and it’s tacky if you want to create a polished look.

The Right Shoes

Men Shorts Chukka Suede How To Wear Shorts The Chic Way

Plait shorts, (Click to buy)

Instead of pairing shorts with slippers, try matching them with loafers, boat shoes, chukkas, sneakers or any shoes that carries more formality. People always look at your shoes, and you’ll be surprised by how much they elevate your overall look and feel.

In addition to great shoes, think about accessories like a belt or arm pieces.


This might be trivial, but it’s true that men with muscular thighs or legs tend to look better wearing shorts because the pants are filled up nicely. This resonates with “The Right Fit” theory.

Style Inspiration

Here are some great short looks that I love:

Takahiro Kinoshita Style Popeye Editor How To Wear Shorts The Chic Way

Carlo Alberto Pregnolato Fashion Editor Stylist How To Wear Shorts The Chic Way

Carlo Alberto Pregnolato, Fashion Editor / Stylist (Look at the white shorts at the back)

Yesstyle Men Shorts How To Wear Shorts The Chic Way

Vintage Brothers Flat Front Shorts (Click to Buy)

Men White Shorts Style How To Wear Shorts The Chic Way

White Shorts

Noah Mills HE Mango How To Wear Shorts The Chic Way

Noah Mills for HE by Mango (Click to shop at

Men Short Shorts Trend How To Wear Shorts The Chic Way

Short Shorts

Men Blazers Shorts How To Wear Shorts The Chic Way

Jackets & Shorts

Men Mint Green Shorts How To Wear Shorts The Chic Way

Mint Green

Men Blue Shirt White Shorts How To Wear Shorts The Chic Way

I hope the tips here can point you to the right direction the next time when you shop for shorts. In the end of the day, there are many ways to wear shorts, and it’s about discovering your personal style and having fun.

Bottom line: Keep your “loungewear” at home!

Hope you enjoy the post. 🙂

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