How to wear a hatpin

Wearing a hatpin is very basic. You simply pin it through the back band or lower crown of the hat, picking up a lock of hair as you pin it through. Here's a little tutorial:

For fine hair, a pin can slip a little. To prevent this, try crossing bobby pins at the back of your head, and pin through that AND your hair. Pins also work well if your hair is braided at the back. 
Pins work well in felt hats, and some fabric covered hats. Be cautious when pinning through straw, as some of the older straw hats can be brittle, and can't handle a pin. 
Of course wearing a wide brimmed hat on a breezy day is no good even with a hatpin. Pins don't secure a hat for high winds and dancing like a madman. They simply keep a hat from sliding off your head during normal movement. 


Here's an unusual wide brimmed, asymmetrical hat. Usually if something has a brim, and is asymmetrical, it has a base closer to the head for a better foundation. This is the case with this 1950s hat, and the brown 1930s hat below. With this hat I placed a hatpin on the side, under the brim and on the base. On the other side, just for good measure and because the area is hidden, I slipped a bobby pin.
  


This is also an asymmetrical brimmed hat with a base, but I placed a pin at the side, base of the crown.
 

On 1940s tilt hats, there's usually a band, or base at the back for support. These are perfect for slipping hidden bobby pins, and often don't need a hatpin.



Another little side tilt hat, but this time a hatpin goes on the top side.  

This one does sit on the back of the head, which usually just needs a pin in the back, but since it's a bonnet style with a brim at the front, an extra pin at the top is extra secure just in case there's a teeny breeze.   
Pillbox styles usually require a pin at the front or back, whichever is more comfortable. If you use a pin at the front, it's a great opportunity to use a fancy one!  

If you tilt it to the side, the pin goes on the top side. 
 {Hats from my own collection, not for sale. Brown 1930s hat from Poppycock Vintage. Others from Urban Eccentric Vintage} 
 Also see: History of Hatpins