Look of the Week: The kids and the adults of It

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! 

Looking back at the clothes you wore as a kid can be an enlightening, humbling, and often surprising experience. There are some garments you would wear in a heartbeat if they still fit, but the decade you grew up in will likely determine the embarrassment levels. Fashion is cyclical, so there is a good chance the style of your youth will make a comeback at some point. A period of 27 years has passed since the events of the first It movie, which means we get to see the grown-up versions of the Losers' Club — including what the costume design says about how fashion and their wardrobes have changed (or not).

Also up for discussion: who wore it better, the pre-teens or their adult counterparts? 

Spoilers for It Chapter Two ahead.

The shorts are shorter and the tube socks pulled up higher in the summer of ‘89, but the attire of the younger self-appointed Losers is pretty timeless, avoiding fads that defined this decade of excess. In fact, if you were to glance at the kids, you could easily think it was set in the original '50s period of Stephen King's book.

There are clear pop culture references that betray the timewarp aesthetic, like Eddie Kaspbrak (Jack Dylan Grazer) wearing an excellent blue Thundercats T-shirt that would no doubt fly off the shelves if Urban Outfitters or Target stocked it now. Short shorts and cartoon tees don’t fit in with adult Eddie’s (James Ransone) sensible adult polo shirt attire, but who knows what he ended up packing in his two massive suitcases? There's more than enough room for sentimentality.

King of patterned shirts Richie Tozier (Finn Wolfhard, no stranger to the '80s) is also fond of pairing it with another clashing garment. This aspect matches his penchant for wisecracks, which ensures he stands out in a group. The signature specs are not the only sartorial link, as adult Richie (Bill Hader) is still doing the short sleeve shirt thing but the print is muted in comparison to his childhood wardrobe.

The leather jacket he wears acts as armor and artifice, a barrier between the persona he thinks he is meant to display in his standup routine on stage and the person he is. After trying to administer first aid using this garment, it is poignant that he leaves the jacket behind with Eddie. It is a futile gesture, but far from an empty one.

Beverly Marsh (Jessica Chastain) has ditched the short overalls of her childhood for ripped jeans, a tank, and a black blazer. She packs in a hurry, fleeing her abusive husband in the rain after Mike Hanlon (Isaiah Mustafa) makes his "come home to Derry" call. The key young Beverly (Sophia Lillis) wears around her neck has been replaced by two necklaces, a token that she finds hidden in the wall along with her beloved postcard poem. Again, this is a muted look in comparison to her teen years.

One of the signature costume colors of her youth, courtesy of costume designer Janie Bryant in the first installment (Luis Sequeira took over for Chapter Two), is red. Older Bev’s tank starts white, but by the end of the movie, it mirrors her younger counterpart's closet. (We don’t recommend the method she undergoes to achieve this look.) On a boat with Ben Hanscom (Jay Ryan) after the horrors of Derry, she has let crimson back into her closet in a more serene manner via a floral dress.

Bold pattern and color features in the childhood clothing of Eddie, Richie, and Beverly, but no one comes close to Ben’s (Jeremy Ray Taylor) horse shirt. He is incredibly sweet and starry-eyed, which is evident in the galaxy print tee he wears during the first chapter.

Of course, Ben gets the glow-up which involves the patented CW dreamboat grey henley (with a hot guy denim shirt worn over the top). Objectively, this is a better look as a henley is always a good choice, but wistful young Ben is working a dream-inspired aesthetic that is much more daring and therefore endearing. 

Young Bill Denbrough (Jaeden Martell) and Mike (Chosen Jacobs) are easily the most timeless of the Losers’ Club in a rotation of jeans, tees, raglan shirts, plaid overshirts, and button-downs. Their closet in 1989 veers closest to 2016, and basic garments like this endure. Mike lost everything in a fire at a young age, so he's unlikely to put much stock in flashy attire. Meanwhile, Bill is the stoic leader of the group, but he isn’t one for wanting to stand out. In this case, it isn’t who wore it better, as they wore it the same.

It is brief, but adult Stanley Uris (Andy Bean) shares a love for the patterned tailored looks of his pre-teen self. Young Stanley’s (Wyatt Oleff) horizontal striped pastel button-down and polo shirts are once again more colorful than his adult wardrobe. When they moved away from Derry, their memories of this time faded and so did the desire to wear bold shades.

The only people who still dress exactly the same as they did 27 years ago are Pennywise (Bill Skarsgård) in all his ruffled glory and Georgie (Jackson Robert Scott), perpetually tied to his yellow raincoat. Not everyone can move on or grow up. 

A clear throughline exists between who the Losers' Club were back in 1989 and who they are in the present. The casting is one of the highlights of this franchise, and the costume design underscores this strength — but in a “Who Wore it Better?” debate, the kids take the sartorial prize across the board.