Halloween H20

Look of the Week: '90s teen style in Halloween H20: 20 Years Later

Contributed by
Aug 12, 2018

Welcome back to Look of the Week, celebrating the best in TV and film sartorial excellence, past and present across sci-fi, horror, fantasy, and other genre classics!

When the next installment of Halloween is released in theaters this fall, it will have been 40 years since Jamie Lee Curtis first played Laurie Strode. Anniversaries are important in the Halloween-verse. Twenty years ago, in the summer of 1998, Halloween H20: 20 Years Later hit theaters. Eschewing the end of October release seems like an odd marketing strategy, but the movie did considerably well at the box office.

Halloween H20
High-waisted flared jeans and a button-down shirt have been replaced for sensible pencil skirts and a sweater draped over Laurie Strode’s shoulders in Halloween H20. She has faked her death, changed her name and is now the principal at a boarding school in the middle of nowhere.

Halloween H20
When Laurie changes out of her stiff work attire for jeans and a sweater and starts swinging vodka straight from the bottle it signals the impending arrival of her personal boogeyman. Final Girl attire is as consistent as Michael’s desire to kill Laurie.

When Jamie Lee Curtis returns to play this iconic character in October it will be as if Halloween H20 and every other sequel never happened. Michael is not Laurie’s brother and Laurie no longer has a son; instead, the new Halloween will see three generations of Strode women coming up against Myers. But while there is no longer a place for Josh Hartnett as Laurie Strode’s son John Tate, Halloween H20 will always have a special place in my heart. Nostalgia drives a lot of these feelings, so strap in for a Look of the Week focusing on the teens of Halloween H20 and ‘90s fashion.

Halloween H20
Jamie Lee Curtis is undoubtedly the star of this film, but she was not the reason why I went to see this movie on its opening weekend. Instead, Michelle Williams was the big-name draw for me, as Dawson’s Creek had debuted earlier that same year and Jen Lindley was my favorite character. Jen is the reformed bad girl of Dawson’s Creek, whereas here, John’s friends are rebellious without being too wild. The biggest mistake they make is ditching the school camping trip to Yosemite for a night of Halloween shenanigans on what they believe is a mostly empty campus. What they don’t bank on is the appearance of Michael Myers.

The teen group dynamic in Halloween H20 is interesting because they don’t fall into one typical social clique or another. None of these kids are particularly popular, but they aren’t super nerdy or outcasts either. They smoke, drink, hook-up and watch horror movies on Halloween — Scream 2 if you were wondering.

Halloween H20
For all the cliché traps and horror tropes this film falls into, the representation of the teen characters is not one of them. The same can be said for their style, which ticks several big ‘90s trends boxes without looking like a fashion magazine from this period threw up on them.  

I wore a uniform to school throughout the ‘90s — including a necktie — until I was 18 years old, so I am fully aware of the many ways you could attempt to individualize your daily attire. The dress code at Hillcrest Academy is particularly relaxed because Sarah (Jodi Lyn O’Keefe) is wearing a striped turtleneck instead of a shirt and tie. She has paired this with baggy pants, a wallet chain and the Hillcrest blazer to give some semblance of school uniform.

Halloween H20
The following year, O’Keefe would be playing super mean girl Taylor Vaughn in She’s All That; this skater-adjacent look is something her future character would sneer at.  

Meanwhile, Williams' Molly has got a whole Gordon Gekko Wall Street vibe going on in a pinstripe shirt and suspenders. The bottom half of her ensemble is more Clueless; a pleated skirt and knee-high socks.

Halloween H20
Sensible flat shoes are an indicator that Molly isn’t quite as fashion forward as Cher Horowitz. I have a very strong memory of wanting to recreate this look for school, but the uniform code was far stricter than Laurie Strode’s domain — I would’ve been sent home immediately.

The school uniform is one way to reveal character through style choices and costume designer Deborah Everton is no stranger to this — she also worked on The Craft. John wears his shirt super baggy, untucked and with a loose tie. He avoids the puka shell trend for a black shoestring necklace that could’ve been swiped from Molly’s dresser. He is that kind of boyfriend, which makes this ensemble extra hot.

Halloween H20

His hair looks like Michael Myers himself has taken a knife to it, but even that is part of his charm. In the opening credits of Halloween H20, Hartnett gets the “introducing” credit, his first in a run of teen heartthrob parts with a bad-boy edge. In the late ‘90s, Hartnett ruled the corridors of high school movies.

The string-thin choker is a look Michelle Williams opted for at the Halloween H20 premiere. Red carpet flashbacks are always fascinating to see how much styles have changed.

Halloween H20
Williams’ satin strapless black dress is very late ‘90s — I had a very similar looking skirt, which instantly creased as soon as I put it on. Janet Leigh (in one scene in Halloween H20, there are at least three nods to her film Psycho) and daughter Jamie Lee Curtis look pretty timeless in comparison.      

Back to the movie, rounding out this friendship and the cozy foursome is Charlie (Adam Hann-Byrd). His style can be best described as that time Twin Peaks did a fashion show; for the secret Halloween rendezvous, he wears a chunky turtleneck with a plaid shirt.

Halloween H20
This is not the kind of party that requires fancy dress. Instead, Sarah wears an outfit I am all too familiar with: a print tight top paired with a grungy maxi skirt, offering up a cool vibe while also showing off your figure. Part boho, part skater, part rocker chick. She's unsure if she wants to be Courtney Love or Gwen Stefani, so why not try both?  

Meanwhile, Molly is a little bit more low-key in a suede jacket, a plain v-neck shirt, and baggy pants. Again, she doesn’t look like she is trying too hard. Molly also has the quintessential ‘90s brown shade of lipstick to jazz up her look, plus some super thin brows.

Halloween H20
This eyebrow trend, like most of the relics from this decade, is threatening to make a comeback. Her relatively plain outfit has some elements of Final Girl attire about it, and her BFF Sarah is the cooler of the pair. And we all know how things end up for this kind of character.  

Charlie is the first of the friends to encounter Michael Myers after going on the hunt for a bottle opener — a bottle opener that ends up as a neck accessory. This is why a screw top is always better because you will never have a reason to split from the group as the booze is instantly accessible. Sarah is not too far behind and an unfortunate incident with the dumbwaiter lift gives quite the disturbing close-up of her highly covetable Dr. Martens boots.

There is a mirroring in costuming between John and his mom, both in v-neck sweaters and jeans — all the better for running away in. Laurie will always be the Final Girl, but it is good to know that she passed on these survival skills to her son. I have a feeling the new generations of Strode women in the forthcoming film will also possess these abilities to protect themselves against Michael Myers. (And the teens won’t be wearing suspenders to school.)