How to Cross-Dress this Halloween

Isn't that devil costume getting a little tired? Men, why not take a walk on the wild side and be a glamor 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.

Things You'll Need

  • Dress

  • Wig

  • High heels

  • Nylons

  • Makeup

  • Bra

  • Booty boosting undergarments

Step 1

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.

Step 2

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 favorite second hand boutique.

Step 3

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 emphasize 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 secondhand stores. The “Halloween Stores” are an option too, but the prices might not be as competitive.

Step 4

Look for makeup. 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.

Step 5

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 $99 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.