Dear Miss Glam,

I long for the four seasons in other countries. As I struggle with the stifling humidity in my homeland, my thoughts are on more pressing issues such as: Can I still wear calf length boots in Singapore and not look like an idiot? Please impart your wisdom so that I may also see the light.

Puss in Boots


Dear Puss in Boots,

What you can carry off will depend on how you wear it and your confidence level, not the weather. My advice is to go with your heart, and wear your boots with confidence. However, if you are planning on donning boots this fall, be sure to follow these simple fashion rules:

How to wear calf length boots

  •  Heels help: Heeled styles make you look taller and leaner. I wish this wasn’t the case, but unfortunately it’s a fact. However, low heels are fine and flat styles will also work if you follow some of the tips below.
  • Slouch styles are forgiving: Calf length boots that slouch are often more flattering because they add volume to the lower leg thereby balancing out proportions. Without the volume, you might look like you’ll topple over. Slouch boot volume bulks up a narrow calf, and can also flatten out a wider calf if the volume occurs underneath the widest part of the calf.
  • Find your sweet spot: Calf length boots vary in shaft height. Some styles work better when the tops finish under the calf, while others are best a little higher on the calf. Generally, wider calves look best when the shaft finishes under the widest part of the calf.
  • Raise the hemline: Exposing the knee cap is a must when wearing skirts and dresses. Going a little shorter is an option, but not a necessity.
  • Keep the boots tonal: Wear boots that are a similar colour to your legs, your hose or your tights. Wear skinnies and boots of a similar colour intensity. For example, the lighter wash jeans worn with grey boots below creates a continuous flowing line because the colour intensity of the two is similar. Pairing black calf length boots with black skinnies is a no-brainer.
  • Raise the waistline: add an empire cut dress or top, cinch in the smallest part of the waist with a belt, or tuck a top into high rise bottoms.

You won’t need to follow all of the tips at once to achieve a flattering leg line. I’m happy to keep calf length boots flat and a contrasting colour to my legs as long as my hemlines are raised.

It sounds like a lot of effort to get calf length boots to work but it will be worth the effort to keep these tips in mind. If you fancy the look, don’t give up yet!

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One thought on “Calf length boots?”

  1. All this calf length boots are so beautiful that I went and buy one for myself. Even wearing in Singapore it is not so weird as there are many who have it too. Wearing what you want is the best opinion.

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