If you've never worn pointed-toe shoes before, it would be understandable if you avoided them for fear that your toes would be crammed together in the pointed part of the shoe. This is not the case with shoes that are made today. The pointed-toe section extends beyond the tips of the toes, sometimes only by a half-inch or so, and sometimes by over an inch.
This pointed-toe section is essentially "empty;" that is, it extends beyond your toes and exists for fashion purposes. Pointed-toe shoes are sexy and make your legs look longer. But I digress. The important point is that the toes are not inside this narrow, pointy-toe section of the shoe.
That said, a shoe that ends in a point will narrow from the ball of the foot to the toes more severely than will a shoe that has a rounded or square "toe box." (The end of a shoe where the toes are is called a toe "box" even if it's round or pointed.) Therefore, pointed-toe shoes might fit a little more snugly in the toe area than a pair of rounded-toe shoes.
When the pointed section of a pointed-toe shoe measures over a half-inch or so, the shoe will be larger, and it will not narrow as quickly as a similar shoe with a shorter pointed section. These types of pointed-toe shoes (like the silver sling backs shown above) should feel as roomy as a round-toe shoe, but then there's the extra length to get used to walking in.
The same rules apply for when you buy other shoes: Buy shoes that fit and that are comfortable to walk in while you are trying them out in the store (or at home if you buy them online). If they aren't comfortable out of the box, then they most likely won't stretch enough to be comfortable later. When buying shoes with a longer pointed-toe section, you might need to go down a half-size.
As long as you buy shoes that fit, pointed-toe shoes should not hurt, unless you perhaps have bunions or other foot issues. Also, as with any other type of clothing, sizes vary among designers and manufacturers, so there may be some trial and error until you learn how a brand fits you.
Feature photo credit: Kelly Samuel