Pointy-toe footwear was at the forefront of fashion for decades, until it completely disappeared in the ‘90s. It slowly made a comeback in the early ‘00s, gained its long lost momentum, and is once again completely mainstream. 

Pointy-toed footwear comes in a range of point shapes. From gentle almond toes and classic pointy toes, to toe boxes that are extremely long and pointy resembling witches shoes. Pointy-toe shoes and boots have their good and bad qualities.


  • Elegant, pretty, polished and dressy.
  • They create Modern Retro Charm.
  • Dramatic pointy toes add theatrical drama to an outfit.
  • They lengthen the leg line, which is especially effective when you wear low-vamp flats.
  • A great fit on narrow, low-volume feet.
  • Pointy toes look amazing peeking out from under long-length boot cuts, bell-bottoms and wide-leg pants.
  • They visually lengthen a short foot to create balanced proportions. This is visually effective when you are tall, and have relatively small feet for your height.


  • Uncomfortable fit on wide feet with short toes because toes are squashed into a too small space that is contrary to the shape of the foot.
  • They might cause long term foot pain and challenges when they are an unnatural fit for your foot.
  • In some settings they can be too elegant, pretty, polished or dressy.
  • Too much of a witchy vibe.
  • They make your feet look too long. This has been the case with some of my petite clients who have relatively large feet.

I LOVE the look of pointy-toe footwear because of my ‘80s and Modern Retro gene. I like gentle almond toes and classic points, but witchy pointy toes are not my thing. I can tick off the rest of their advantages in the above list too. I adore their dressy elegance and how they lengthen the leg line in flats. Most importantly, I have a small, narrow, low-volume, pointy foot which makes pointy-toed footwear an easy, natural fit. My long toes enjoy the length of the pointy toe box.

I don’t wear pointy toes exclusively because I like to mix it up, but most of my footwear has some sort of gentle or classic pointy toe box. Round-toe footwear is almost always too wide and short, unless I size up and get a narrow size. I’m very comfortable in pointy toes as long as they are flat or low-heeled.

Over to you. Do you wear and like pointy-toe footwear? Please add to my lists of pros and cons if you think they are incomplete.

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