How to cross-dress this halloween

Updated March 23, 2017

Isn't that devil costume getting a little tired? Men, why not take a walk on the wild side and be a glamour girl this Halloween? Cross-dressing is a fun and transformative All Hallow's Eve tradition. Here are some tips on getting out the door all dolled up, without breaking the bank.

Start with your figure. A strapless bra is best, as it gives the option of wearing a strapless dress. Enhance your figure with a garment that will slim your waist, such as extra tall shaping panties. Some such garments actually come with padded bottoms. One budget option is a one-piece shaping garment with built in padded bra.

Shop for your dress. It is the keystone of your outfit. No need to spend a lot. Haunt the discount stores like Ross, or proceed directly to Goodwill or your favourite second hand boutique.

Build your look around your dress. Pick a shade of pantyhose you think will work with it. Remember, dark shades will slim your legs, light shades will emphasise curves. Try Payless Shoes for an inexpensive pair of high heels. For your wig, try to find a wig store. Failing that, try the hip second-hand stores. The “Halloween Stores” are an option too, but the prices might not be as competitive.

Look for make-up. Go to the local drugstore, Target, Kmart or other discount joint. The full glam look demands foundation, eye shadow, eyeliner, mascara, lipstick, and maybe a sparkly powder puff.

Go home and get your girl on! You will need some practice with the whole process of pulling it together, let alone walking in those big shoes. Watch out for stairs and uneven surfaces. Feel the transformative magic of drag and go with it, darling!


Most stores have seen plenty of guys on similar missions, so don't be shy. With some selective shopping, your whole look can come together for £64 or less.


When headed out on your big night, exercise caution. Keep aware of your surroundings. Go with friends. Take those giant shoes off while you drive. Halloween is a very safe night for drag, but there are some narrow minded people out there who don't get it and never will.

Things You'll Need

  • Dress
  • Wig
  • High heels
  • Nylons
  • Makeup
  • Bra
  • Booty boosting undergarments
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About the Author

Nina Makofsky has been a professional writer for more than 20 years. She specializes in art, pop culture, education, travel and theater. She currently serves as a Mexican correspondent for "Aishti Magazine," covering everything from folk art to urban trends. She holds a Bachelor of Arts in English from Mills College.