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Going with friends? Make it a group thing
Going out on Halloween in a group could be a lifesaver. Not only is it more fun to bond with the guys at a party, but it can make dressing up even easier. You obviously don't want to copy your friends' exact costumes, but you can make them play off one another. Try going as a music group, or as part of the cast of a popular movie. If you mix your brains and ideas together, your costumes will likely turn out even better than if you went at it alone.
Stay up-to-date
Wearing a costume that relates to current events is a great way to attract attention. Since most people strike up conversations over current events as it is, being dressed as one should increase your popularity even more. Should you need some current ideas for who to impersonate, pick up the newest edition of the National Enquirer or something similar to find out who's the center of attention. When you do pick somebody, make sure your costume demonstrates their personality, and is not some club outfit that you copied from a photo of theirs.
Costumes to avoid
First and foremost, you should avoid any costumes that are too vulgar or offensive. Sure, you'll get attention, but you also may get yourself into a fight. Don't dress up in anything that has severe racial undertones, or, even worse, as a dead celebrity. As an example, dressing up as the Crocodile Hunter Steve Irwin after his untimely death did not demonstrate too much class.
Although not necessarily vulgar, dressing up as a woman is not the greatest idea. Many men have done this before, and while it's funny, it is very played out. Besides that, throwing on a wig, some makeup, and a dress could show that you're lazy and couldn't come up with a better idea.
Don't wait until the last minute
Waiting until the last minute is a common trap that many fall into when it comes to Halloween costumes. This is a bad idea for a couple of reasons. First, if you wait until the last minute, you will feel pressured. This will lead you to run to a costume store to find a run-of-the-mill outfit. Once you get there, however, you will realize that anything good has already been sold.
Planning ahead not only takes the stress out of the costume ordeal, but it also lets you brainstorm more. Also, if you plan ahead, you are less likely to buy an expensive costume. As you take your time, you will probably be able to find things around the house to make your costume complete.

Actual costume ideas
Have you gone through the listed tips and are still unsure of what to wear? Try going as Don Draper from the television series Mad Men. You could maybe even try dressing up as Mike “the Situation” from the MTV's the Jersey Shore. Movie characters to try include the Joker, Indiana Jones, Jason from Friday the 13th, and Freddy Krueger, to name a few. If you want to get political, try George W. Bush or Barack Obama.