Halloween costumes for old people: 6 surefire rules for dressing up

Oct 30, 2025 - 08:28
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Halloween costumes for old people: 6 surefire rules for dressing up


Let's face it: Halloween is only fun if you're a kid. If I had my way, I'd spend the evening at home with all the lights off and a pile of newspapers on the doorstep so nobody thinks there's any free candy to be had.

But I have children of my own, which means I've got to roam the streets with all the other middle-aged walking dead and their spawn. Now I can either do this in the time-honored dad uniform of jeans and quarter-zip sweater, or I can dispense with pretensions to dignity and wear a costume of my own. Years of experience has taught me that option number two is the only way to go.

Investing in a basic theatrical makeup kit can ensure that your costume is at least as frightening as the obsessive amounts of time and energy that clearly went into it.

Look, I hate dressing up for Halloween. It's not so much that I mind wearing a costume; it's the hassle of deciding upon one and then procuring the necessary pieces to make it happen. School just started and "the holidays" loom; who needs another decision to make?

But I've come to see it as my duty. You see, every adult standing around like a dork in their street clothes makes the occasion that much less Halloween-y. You get a critical mass of such wallflowers, and the night is ruined. So each year, a certain number of us must take it upon ourselves to do what other parents can't or won't.

I'm no hero. Or if I am, I'm a reluctant one. Every time Halloween comes around, I tell myself I'm going to sit this one out. But in the end, I always suit up. I like having a job to do. Over time, I've compiled a list of simple rules to help me do that job. Maybe they can be of use to you.

1. DON'T pick something you have to explain

Matt Himes

I threw this together at the last minute with an old dress shirt and and my son's debate trophy. The key is confidence. Walk around with an indifferent swagger, NOT as if you're pleading with people to guess who you are. They know who you are — and if they don't, that's their problem. The startled laughs and nods of appreciation that trailed in my wake as I moved through the crowd told me all I needed to know. Remember: A good Halloween costume is all punchline, no setup.

Here's an example of a costume that didn't work because I violated this rule:

Matt Himes

New York City, 2008 (that's my friend Robin as "Sarah Palin" next to me), and I'm dressed as ... what? An Islamic terrorist? Well, yes, but he's also an Obama supporter, as explained by the cover of "Rolling Jihad" taped to my chest. Instead of going with something timeless and elegant like "Jäger bomber" I've turned myself into a walking political cartoon (the ones that nobody gets). Do this, and you'll have people puzzling over your little commentary (or threatening to beat the s**t out of you on the F train) all night.

2. DO team up with your kids while you still can

Matt Himes

That kid in the striped shirt? He's 12 now. This year, he's going as a disgusting zombie and hanging out with his boys. But once upon a time, we were best friends, just like the duo we portray in this picture. Enjoy it while it lasts: At a certain point, childhood ends, and Hobbes has to step aside.

Here's an even older one with my daughter. She's applying to college this year as I quietly sob into my laptop.

Matt Himes

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Sunset Boulevard/Getty Images

3. DON'T prioritize 'originality' over recognizability

Matt Himes

You may pride yourself on your refined taste in music, art, and movies, but Halloween is not a time to show it off. Nothing kills a costume concept like the desire to be "original." I thought I had a brilliant idea for my wife a few years back: Stevie Nicks. Not too mainstream or obvious but oh so clever and niche. And who doesn't love Stevie Nicks? A better question to ask would have been who recognizes Steve Nicks? Nobody who saw the above ensemble (right) did, that's for sure. I thought this look would hit like the opening arpeggiated synth bass line of "Stand Back," but my ego wrote a check my eye for scarf-and-hat coordination couldn't cash.

Unlike Stevie's Prince-inspired 1983 banger, "Bohemian Rhapsody" is not a song I ever need to listen to again. But like I said, when it comes to costumes, it helps to go for the big hits.

Matt Himes

Do I like Queen? They're OK. I'd rather listen to Steely Dan, but Donald Fagen isn't going to make for much of a costume, now is he? So Freddie Mercury it is. He's like Donald Trump: You may not like him, but there's no mistaking his signature style.

Not a huge "grunge" fan, but the same thinking guided my choice to be Nirvana frontman Kurt Cobain. In this case, it helped that I, too, have fair skin and hair. Also this particular image is well-known enough that you can type in "Kurt Cobain sunglasses," for example, and the internet knows exactly what you're talking about.

Matt Himes

Admittedly, Sid Vicious and Nancy Spungen is a bit of a "deep cut," but anyone who didn't get it just assumed we were generic punks — itself a valid costume. Although sharp-eyed readers will notice that I nailed the details.

Matt Himes

4. DO get way too into it

Let's zoom out on that Stevie Nicks photo:

Matt Himes

That "authentic Gene Simmons KISS demon" costume cost me something like $300; it had reviews from professional KISS cover band guys raving about how it gets "every last grommet" correct.

I also spent an hour and a half figuring out how to do my own face paint, hunched over the bathroom sink while watching Simmons himself demonstrate on his daughter.

Overkill? You bet. But sometimes you have to take one for the team. Plus now I have an heirloom-quality codpiece to pass down to my children and grandchildren.

Matt Himes

Investing in a basic theatrical makeup kit can ensure that your costume is at least as frightening as the obsessive amounts of time and energy that clearly went into it:

Matt Himes

5. DON'T overshadow your wife

When the Gene Simmons idea got ahold of me, I was planning to do something to go along with my wife's Stevie Nicks. Tom Petty? I can't remember, but the result would no doubt have been uninspiring. I'm glad I made the choice I did, but I do regret leaving her in the lurch. While there's no rule that says couples have to coordinate costumes, I did have a responsibility to make sure she was properly sorted before getting myself ready. It's like in those airline safety videos when the oxygen masks drop.

My showboating tendency is still kind of an issue in this Boy George/Cyndi Lauper combo, but I like to think I did right by her — and the "Girls Just Wanna Have Fun" songstress.

Matt Himes

And the year we showed up as these two, I think she got the better part of the deal (that mask was hot):

Matt Himes

Some people say my wife's clenched fist and rigid posture is a sign of distress; I just a see a woman grateful to submit to her husband's God-given role as Halloween creative director:

Matt Himes

When you marry a marine biologist's daughter:

Matt Himes

One year, I had an idea of being a head louse. Didn't quite come off (see rule 1 above) ...

Matt Himes

... but I did get this photo of my wife as a school nurse that I will treasure until my dying day:

Matt Himes

6. DO strut your stuff

As the father of two daughters, I'll be the first to say that Halloween costumes have gotten way too revealing. But that doesn't mean all nudity is gratuitous; sometimes the "role" calls for a little sex appeal.

Matt Himes

You're not going to have this lithe, youthful body forever — if you've got it, flaunt it! That said, keep in mind that you will be around children and old people. When my wife wanted to leave the house in this "sexy squirrel" getup, I had to put my foot down. Some looks need to stay in the strip club.

Matt Himes

Happy Halloween to you and yours.

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Fibis I am just an average American. My teen years were in the late 70s and I participated in all that that decade offered. Started working young, too young. Then I joined the Army before I graduated High School. I spent 25 years in, mostly in Infantry units. Since then I've worked in information technology positions all at small family owned companies. At this rate I'll never be a tech millionaire. When I was young I rode horses as much as I could. I do believe I should have been a cowboy. I'm getting in the saddle again by taking riding lessons and see where it goes.