5 Awesomely Awkward ‘90s Style Staples From ‘The To Do List’

’The To Do List.’
Photo: Courtesy of CBSFilms

The To Do List hit me right in the feels for a lot of different reasons. I realized my intense love for Donald Glover after watching him dance in yellow overalls. I had a sudden desire to throw away all my purses and just carry a Trapper Keeper to my next party. And yeah, for the first time ever, I found myself thinking, “Hmm, maybe I should buy a pair of skorts.”

Aside from the A+ incredible cast (Aubrey Plaza, you just may have redeemed yourself from that whole MTV Movie Awards Will Ferrell stage-crash thing) and cringe-worthy sex jokes, the real star of The To Do List is the throwback ’90s fashion. The characters aren’t just wearing crop tops and cut-offs; they’re using those crop tops and cut-offs to tell a story. A story about just how embarrassing high school is. Deep, right? My favorite ’90s staples are used here to make me simultaneously yearn for the bodacious decade AND praise Alanis that I made it out of there alive. So, here are the 5 most awkward ’90s style staples, as told by The To Do List (also, real life).


Underwear in ’The To Do List.’
Photo: Courtesy of CBSFilms

Type-A valedictorian Brandy (Aubrey Plaza) finally decides to let loose and experience all the things she’s missed over the past 18 years. First stop: keg stand. Her hair is messy, her cleavage is showing, her dress is over her head, and… She’s wearing her Saturday granny panties. Archetypal sexually uninhibited ladies don’t wear day-of-the-week panties. Now, I don’t want to get too symbolic up in here, but OK, actually, yes I do. This moment, these giant floppy underpants, all of it represents the fact that Brandy and all the other “good girls” of the world can do all the (literal and figurative) keg stands they want, but it can’t hide who they are at the core. I know, I know—who knew underwear could be so profound?


Skorts in ’The To Do List.’
Photo: Courtesy of CBSFilms

In Brandy’s first attempt to cross an item off her to do list, she decides to go to third base with sweet-faced Cameron (Johnny Simmons). Things are progressing typically enough until Cameron moves to unzip Brandy’s skirt, and *drumrollll* finds another layer of denim.

Cameron: Is this shorts or a skirt?

Brandy: Neither, they’re skorts.

Unless you’re Molly Ringwald, first hook-ups are never cute. So, thank you, skorts, for keeping it real and making this fact even more glaringly obvious.


Aubrey Plaza and her Trapper Keeper in ’The To Do List.’
Photo: Courtesy of MovieWeb

You wouldn’t normally think of a Trapper Keeper as an accessory, but trust me, it’s the most important one in this entire movie. I mean, it stores THE to do list (y’know, like the TITLE?). Brandy uses the glorified binder in 50% of the scenes and carries it like it’s the Celine Trapeze Bag. Every time you hear the rip of that Velcro flap, you just know that something big is about to go down. Including the pivotal moment wherein the list falls into the hands of the ABSOLUTE wrong person. That kind of plot twist just doesn’t happen with password-protected smartphones.


Aubrey Plaza in ’The To Do List.’
Photo: Courtesy of CBSFilms

The To Do List takes place in 1993, right when Baywatch was in its Pamela Anderson/David Hasselhoff prime. Brandy gets a summer job working at the same pool as hunky Rusty Waters (Scott Porter), her sexual white whale. Cut to her trying to be seductive. All. The. Time. Luckily, the pool issues out red one-piece swimsuits to all the lifeguards, so one slow mo Baywatch strut is all it takes to get Rusty’s attention for good. Oh, she also tries to seductively eat a popsicle on her lifeguard stand, but as it turns out, brain freeze is not all that alluring.


Flannel in ’The To Do List.’
Photo: Courtesy of CBSFilms

Oh, flannel. Glorious, grungy, Kurt Cobain-y waist-tied flannel. There is something undeniably appealing about a brooding, plaid-wearing musician who refuses to be bothered with any issues less important than genocide. Brandy learns this when she spies Van (Andy Samberg) at a dimly-lit concert and instantly decides that he will be her next sexploit. But here’s the thing about flannel—once the boy loses his shirt, he also loses very important appeal points. I won’t spoil the atrocity of the *achem* climactic Brandy-Van scene, but I will tell you that it involves a shower and some extremely UN-waterproof hair dye. But heed these words: don’t always trust a dude in flannel.

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