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Classic Guys’ Halloween Costumes That Always Hit

It's possible. today, my fictional sports heroes

by Megan Collins Updated: October 13, 2023

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I’m not big on Halloween. Well, that’s not totally true—I love helping my niece and nephew pick their costumes (she’s going to be Ariel. He’s the Hulk). And I love the decorations that pop up around the city and on neighbors’ doors. Oh, and I definitely love the bags of candy offered at 90% off at Duane Reade the day after.

But after attending college, where female students took any costume idea as a chance to put the word “naughty” in front of it, and guys—weirdly—all seemed to jump at the chance to wear women’s clothing (what is that about, anyway?), I’ve soured some on the holiday for grownups.

Halloween is an opportunity, in my opinion, to wear something that actually makes you look better—cooler, suaver, hipper—than you usually do. I honestly don’t understand why every guy who owns a tux doesn’t just grab a water pistol in one hand and martini glass in the other and go as James Bond.

Short of that, I came up with some no-fail, easy-peasy, unoffensive, and simple to assemble costumes, and I’ll be sharing them through the rest of the week.

Today’s theme for last-minute Halloween costumes for guys?

Three last-minute Halloween costumes for guys: fictional sports stars edition

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Coach Eric Taylor (Kyle Chandler) from “Friday Night Lights”

Wear it Well: To watch Friday Night Lights is to love Coach Taylor—including his straightforward style. Coach figured out his look early and stuck with it—which means it’s super identifiable, at least among “FNL” fans, who are exactly the sort of people you want to hang out with.

You already have the khakis, so all you need is to declare your allegiance – are you a Panther or a Lion?

For this look, we went with a royal-blue windbreaker, a Dillons Panther tee, and—the magic ingredient—some Croakies. Extra credit for hot-glueing the “P” to the windbreaker.

// Shop the Costume //

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Rocky Balboa (Sylvester Stallone) in “Rocky”

Wear it Well: It literally doesn’t get easier than boxer Rocky Balboa’s training outfit: gray sweats and black cold-weather gear. Tons of bonus points for outfitting your own small dog in a matching gray tee.

Besides the hat, all the accessorizing you’ll need is a glass filled with raw eggs, the 1976 version of juicing.

// Shop the Costume //

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Dave Stoller (Dennis Christopher) in “Breaking Away”

Wear it Well: If you’re a cyclist, you probably have most of this in your closet—not least because “Breaking Away,” the 1979 movie that made the Cutters famous, is maybe the best biking movie ever.

All you need for a credible Dave Stoller is the tee, plus his super-distinctive yellow cap—the rest (biking shorts, gloves) you already have.

// Shop the Costume //

For more #SGapproved costume coverage, look here. 

Megan Collins

I started Style Girlfriend to help guys look, feel, and act their best.

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