My family has a strange and complicated relationship with costumes, and no month brings it out more than October. After all, October is when we all play dress up, from babies to grandparents to pets. Even the leaves on the trees put their regular outfits aside and change their look completely before they twirl and fly off to the party.

I probably should have seen warning signs back in college. My then boyfriend, now husband, used to show up at my apartment with his roommates—dressed in wigs and their latest Goodwill finds. Always on the lookout for costumes and props for Younglife skits, they prided themselves on outdoing one another, whether the contest was who could put the oddest combination together, or who looked funniest squeezed into something obviously not their size. Remember Chris Farley singing “fat guy in a little coat…?” You’ve got the picture.

Now, I love a costume, too; in fact, I grew up taking dance lessons and then moved into cheerleading. Often, my high school squad spent more time deciding on shoe inserts and hair bows for the upcoming game than we spent actually choosing the routines. On holidays, you could find us rummaging through the racks at our friend’s mom’s singing telegram business for something new to wear to costume parties—she had everything from Cupid to Santa’s elves to the Chiquita Banana lady.

No, the inherent problem in my family is not the costume per se, but that I am cheap. For instance, my argument with my husband’s current luchador mask collection is not that he has seven of them already, but that we are actually spending money on a Mexican wrestler’s accessory. You can imagine how well this tendency of mine goes over with my children at Halloween.

In the early years, it was easier. In fact, all three of my kids made use of the same hooded bath towel (Blue from “Blue’s Clues”) as a Halloween costume. Hooray for recycling, right? There was the year that I hot-glued a bunch of yellow felt and red yarn on some thrift-store oxfords and sent my oldest two out as Woody & Jessie from “Toy Story.”

However, there comes a time in every child’s life—no matter how careful you are—when your kids discover the polyester-filled costume aisle at Target. Or, worse yet, Halloween Express. I can still remember the shock and awe that my precious children experienced upon realizing that yes, you can actually go to the store and buy an official Disney/Star Wars/Indiana Jones character outfit. The wide-eyed amazement quickly turned into accusatory glares as they slowly realized I had been withholding this vital information.

Now my kids are teenagers, and on Halloween I am less concerned with costume buying and more preoccupied with preventing possible property damage. Still, last year my daughter’s school had a dress-up spirit week, and she decided to participate. I couldn’t have been more proud. She borrowed a man’s vest and bowtie, popped the lenses out of some leftover 3D glasses, and made a Grape Crush bottle cap pin. She was the cutest Carl Frederickson (“Up”) that I’ve ever seen. Now, if I could just convince my youngest son to stop scaring the living daylights out of me with that horrible mask he bought last year at Halloween Express…

Sarabeth Jones is a creative at Fellowship North who enjoys all kinds of artistic work: writing, directing, acting, design, photography and the occasional flash mob. She lives in Sherwood with her husband, Bryan, and their kids, Elizabeth, Jonathan, and Will, and blogs at TheDramatic.com.