I would browse their site for contact information and then send them some sample pictures letting them know you would like to be considered as a new Playmate.
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You can sign up for a for a casting call.

They have them in different cities throughout the year.
Some are coming up in NY and LA. Today and tomorrow they are holding them in Nashville.

Here is the main website:
http://www.playboy.com/specialeditions/casting/index.html

And here is some basic info:
http://www.playboy.com/specialeditions/casting/details.html

And here is a video about what happens during a casting call:
http://www.playboy.com/specialeditions/casting/video.html
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Step 1
Research photos of previous Playboy Playmates (http://playboyplaymatescenterfold.blogspot.com). Study the composition of the photos, different poses and the kinds of women who are featured as Playmates.
Step 2
Take your photos. You must send recent full-figure, nude photographs that show you in several different poses. You must also send close-up photographs that show your face well. The photos can be Polaroid, print, transparency or digital format.
Step 3
Write a brief biography for yourself. Include your height, weight, measurements, occupation, awards and hobbies.
Step 4
Prepare your identification. You must be at least 18 years old and provide proof (photocopies of two pieces of identification). Your name must be on both pieces of identification and one must have a current photo and your date of birth.
Step 5
Submit your materials. Email your photos, biography and proof of identification to playmateeditor@playboy.com. Put the following in the subject line: Attention Playmate Editor and your name. Alternately, mail your submission to: Attn Playmate Editor, P.E.I., 680 N. Lake Shore Drive, Chicago, IL 60611 USA.
Step 6
Know what happens next. If you impress the editors, they may call you to make an appointment for test shots. Hugh Hefner and the photography editors will judge these shots and Hef will decide if you have what it takes to become a Playboy Playmate.

# Do not send your photos in the form of CDs, discs or undeveloped film. Playboy does not accept these types of submissions.
# Playboy will accept the following documents as proof of identification and age: driver's license, passport, birth certificate, school identification, voter's registration, Social Security card, employee ID or state issued ID card.
# If you live in California, mail your submission materials to: Playmate Editor, Playboy Studio West, 2112 Broadway, Santa Monica, CA 90404.
# If someone else submits your photo to Playboy and you are chosen to become a Playboy Playmate, the person might receive a finder's fee of several thousand dollars.
# If you are chosen to become a Playboy Playmate, Playboy will contact you within three months. If you are not contacted within three months of your submission, you have not been selected.
# Playboy will return photos only if you include a self-addressed stamped envelope of the correct size with proper postage. If you do not include a return envelope, Playboy will destroy your photos.
Source(s):
http://www.ehow.com/how_2070427_become-playboy-playmate.html

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