The Pointy Toe

The pointy toe, or pointed toe if you’re a more sophisticated kind of folk, can be worn in many different ways.  Wear it right, and you’re saying, Don’t mess with me.  Seriously, don’t, I’ll kick your ass.  Wear it wrong and you might as well be screaming, Help, I lost my pantsuit! Does anybody know where it is?  And now, since the pointy toe has all of a sudden become trendy again, it’s important that you take a step back, and really think about which of these two options is most appealing to you.

While you can pair your pointy toe shoes with a skirt or a dress, they work best with pants (NOT a pantsuit, just in case you couldn’t sense my previous sarcasm).  A slim pant will create a sleek look, while a wide leg works best for a more professional, or trendier look.  Under absolutely no circumstances, and remember, no means no, should you ever wear a pointed toe heel with shorts.  You will look like a My-Size Barbie who got dressed in the dark.

Pointed Points:

  • Pointed flats are occasionally (as in probably not but there’s always a chance) tolerable, but if you’re going with heels, make sure they’re sky-high.  The only thing more irritating than sensible “mid- height heels” are kitten heels.  Avoid them both.
  • No pointed heels and shorts.  Just don’t.
  • Make sure they fit, cause squished toes aren’t cute.
  • Avoid shoes made in couch cushion prints.  Also tweed.
  • If you’re wearing them now (aka spring/summer months), pick colors that are also spring/summer colors.  Live a little.

Pointy-Toed Picks:


B Brian Atwood

Malika Patent Pointed-Toe Pump by B Brian Atwood

Available online from Bergdorf Goodman


Beverly Patent Leather T-Strap Pump by Gucci

Available online from Gucci


Kate Spade

Licorice Patented Pointed-Toe Pump by Kate Spade New York

Available online from Neiman Marcus

Christian Louboutin

Pivichic by Christian Louboutin

Available online from Christian Louboutin


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