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Think you can’t wear pointed-toe shoes? Why you might reconsider this stylish shoe option.

Posted by Christine Reicker on

Do you associate pointed-toe shoes with toes that are painfully squished together? That only women willing to ruin their feet for fashion’s sake would wear such torture devices? Or did you wear pointed-toe shoes years ago, but now your feet have spread, or you developed bunions, so now you don’t think you can no longer wear your favorite shoe style?

The part of a shoe that houses the toes is called a “toe box” (even if it’s round or ends in a point). With pointed-toe shoes, the pointed part extends past the main toe box. It might extend only ¼ inch past the tips of the toes, or in an extreme pointed-toe shoe, the pointed toe section can be up to three inches long! (Take care not to trip when wearing these babies.)

This pointed part of a toe box that extends past the toes is what gives the pointed-toe shoe its aesthetic. The pointed part is “empty” in that no part of the foot or toes fill it. Therefore, the tip of the point does not squash the toes. It’s the width and section of the shoe that spans the area where the toes begin in a pointed-toe shoe that usually determines if pointed-toe shoes will cram your toes together.   

You can probably wear this style of shoe even if you think your feet won’t allow you to. How is that?

Not all pointed-toe shoes are created equally.

Extreme pointed-toe shoe

ic: This pointed-toe adds inches to the foot

A pointed-toe section that’s over one inch past the toes probably means that the width of the shoe is wide enough to give your feet and toes plenty of room. Think of this type of point as being “tacked on” (it’s not) to the end of the shoe to give it an exaggerated appearance—extreme pointed-toe shoes do make a fashion statement.

Pointy-toe shoes that show toe cleavage

ic: An example of toe cleavage; the pointed-toe section extends about two inches past the tips of the toes

Did you know there’s such a thing as “toe cleavage?” That’s when the spaces between the toes are visible when a woman wears closed-toe shoes—pumps, flats, round toe, or pointed. Toe cleavage is a good indicator that this pointed-toe shoe might squish your toes together.

When toe cleavage is visible on a pointed-toe shoe, this can mean that the toe box is very short and narrow—meaning there might not be enough room for your toes to move around a little. This is especially true when there is toe cleavage and a short point (one-half inch or less past the tips of the toes).

In the photo above, the pointed-toe section looks as if it extends about two inches past the wearer's toes. Also the pinky toe appears that it is not squished towards the toe next to it. These pointed-toe shoes are probably comfortable. 

In the photo below, the pink pump has a smaller toe box than the black pumps (directly above) do. However, there still appears to be enough room to accommodate the width of the woman's feet. Both the black pump above and the pink shoe are cut quite low near the pinky toe, which might give some added room for the toes.  

ic: The width of this pink pump appears to accommodate her toes and feet

How do you comfortably wear this style of shoe if you really like the toe-cleavage look on a pointed-toe shoe? Try on a shoe that is one-half size bigger than you normally wear. I do this, and my shoes do not slip off my feet. The half-inch or less in shoe length provides for a slightly larger toe box, and thus more room for your toes. Of course, this also depends on the shoe designer or manufacturer. As with all clothing, sizes vary among brands. With boots, it's easier to go up a half-size because the ankle or leg material help hold your shoes onto your feet. That said, your feet should not be swimming in a pair of boots.

 Rounded pointed-toe

ic: Rounded pointed-toe

This style of pointed-toe is my favorite, and I have found that I often have to go up one-half size in this style. This is because the pointed-toe section is short and might only extend half an inch or so past the tips of the toes. Therefore, the part of the shoe leading up to the point—the same part of the shoe that houses the toes—narrows towards the point. The big toe and little toe often curve in towards the other toes, mimicking and accommodating the curve of the shoe. This is why a wider fit shoe or a shoe one-half size up is important. Squished toes can lead to foot problems later in life. 


Look for shoe designers who make widths in D (wide), or EE (extra wide).

  • Michael Kors
  • Stuart Weitzman
  • Sam Edelman
  • Steve Madden
  • Torrid


 Websites for shoes in wide widths:

  • Zappos
  • Nordstrom

 Go up one-half size.

I have found that shoes one-half size up do not slip off my feet. This depends on the manufacturer of course. You have probably experienced that not all manufacturer’s size 7 shoe fit the same, just as you might wear a size 8 dress by one designer and a size 6 from another. 

Wear only natural materials.

Wear only suede, leather, canvas, and other natural materials. They will stretch over time.

Avoid patent leather (unless you go up a half size or can find the shoe in “wide”). Patent leather is leather that has been coated in plastic, varnish, or lacquer to make it shiny. This coating prevents it from stretching.

These are a few tips so that hopefully all of us who are pointed-toe shoe fans can comfortably wear pointed-toe shoes.

If you have any suggestions  that I have not mentioned that work for you, please leave a comment. 


Feature Photo: Prada Sling Backs (

Extreme pointed-toe with metal accents: Tom Ford shoe, via PopSugar, 2019

Brown Boot: Cole Haan Vespa Bootie

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