Image: Showbit

Here in Singapore, shorts function as much more than just beachwear or a comfy workout option. We practically live our lives in them! We have different styles for different occasions; short shorts for errands, denim ones for brunch, a tailored silhouette for drinks and sometimes even to work!

However, this innocuous and humble wardrobe essential can be the sartorial downfall of even the most confident women. I often see plenty of women strutting down Orchard Road in poorly styled shorts!

When it comes to baring your legs in shorts, people often neglect the importance of shoes. Sky high heels have the potential to come across as over the top; flats may lend the unfortunate illusion of stubby legs; and flip flops just makes everything look shoddy and sloppy.

We’ve been brushing up on our shorts 101 in the last couple of weeks (find out the best shorts for your body type and 3 classy ways to wear shorts) so we’ve decided to take it a step further. Here’s our guide on the best type of shoes to wear with the most popular shorts silhouettes.

1. Tailored shorts

Recommended shoes: Pointed toe low heels, masculine brogues

They’re probably one of the most versatile type of shorts that one can have. You can wear them to a brunch date, a party or even to the office if you enjoy a relaxed dress code. They’re smart and exude a polished vibe too, especially if you opt for expensive-looking shoes like pointed toe low heels or masculine brogues.

2. Denim shorts

Recommended shoes: Espadrilles, fancy flat shoes, platforms

Denims are my favourite type of shorts of all time. They are super chic, easy to wear and have never gone out of style. Put your strong shoe game on with trending styles like casual slip-on espadrilles and fancy flats or platform shoes!

3. Long shorts (or bermudas)

Recommended shoes: ballet flats, sandals with thin straps

Since these shorts hit lower at your knees, you should go for shoes with lower vamps and simpler designs. That will help to elongate your legs! Ballet flats or any sandals with thin straps will work really well! You can also opt for nude shoes that closely match your skin tone to maximise the leg lengthening effect.

4. High waisted shorts

Recommended shoes: Gladiator sandals, ankle boots or any high vamp shoes

These are flattering, stylish alternatives to your regular-waisted versions. It sits high at your waist, so that tricks the eye and creates the impression that your legs start where your waist does. With this silhouette, you have more allowance to attempt crazier shoes like gladiator sandals or boots that hit higher on the calves.