In this episode of Why’d They Wear That?, Stacy London and Clinton Kelly revisit When Harry Met Sally and break down the film’s fashion across twelve years of changing style. From Sally’s preppy late 70s looks and early yuppie polish to oversized denim, off the shoulder party dresses, wedding fashion disasters, and Harry’s truly unfortunate sweaters, they unpack how the wardrobe reflects real people living through real time.

This is less about high fashion and more about character, era, and the kind of styling that quietly supports one of the most famous romantic comedies ever made.

Special Thanks to Our Sponsor:

The Knickerbocker Hotel → A legendary New York landmark reborn as the first luxury hotel in Times Square. https://www.theknickerbocker.com/

Produced by Simple Alien → https://www.simplealien.com/

Camera, Audio and Crew provided by TV Boy → https://tvboynyc.com/

About Why'd They Wear That?:

A pop-culture and fashion commentary show where Stacy London and Clinton Kelly break down the on-screen looks that sparked trends, started debates and occasionally made audiences ask, "Why'd They Wear THAT?"

→ https://www.whydtheywearthat.com/

Find out more @ ALL CHEWED UP Channel → https://www.allchewedup.com/

In this episode of Why’d They Wear That?, Stacy London and Clinton Kelly break down the style of One Battle After Another through eight key looks. From Teyana Taylor’s instantly iconic revolutionary wardrobe to the thrifted, lived in realism of the supporting cast, they unpack how the costume design builds character without ever pulling focus. 

Along the way, they talk subtle styling, class signals, camouflage, denim, boots, political archetypes, and why Colleen Atwood’s work here is so impressive precisely because it feels so invisible. 

Produced by Simple Alien → https://www.simplealien.com/

Camera, Audio and Crew provided by TV Boy → https://tvboynyc.com/

About Why'd They Wear That?: A pop-culture and fashion commentary show where Stacy London and Clinton Kelly break down the on-screen looks that sparked trends, started debates and occasionally made audiences ask, "Why'd They Wear THAT?"

→ https://www.whydtheywearthat.com/

Find out more @ ALL CHEWED UP Channel → https://www.allchewedup.com/

In this episode of Why’d They Wear That?, Stacy London and Clinton Kelly break down the style of Wednesday through one of the show’s most visually playful episodes. From Wednesday suddenly wearing color to the purple-and-black Nevermore uniforms, Hester’s sharp gothic tailoring, Lady Gaga’s ghostly cameo, and the recurring silhouette choices for Larissa, they unpack what works, what misses, and what the costumes are telling us before the plot does.

Along the way, they get into character styling, makeup, tailoring, gothic imagery, and the challenge of making fashion feel specific inside a world that already has such a strong visual identity.

Produced by Simple Alien → https://www.simplealien.com/

Camera, Audio and Crew provided by TV Boy → https://tvboynyc.com/

About Why'd They Wear That?: A pop-culture and fashion commentary show where Stacy London and Clinton Kelly break down the on-screen looks that sparked trends, started debates and occasionally made audiences ask, "Why'd They Wear THAT?"

→ https://www.whydtheywearthat.com/

Find out more @ ALL CHEWED UP Channel → https://www.allchewedup.com/

In this episode of Why’d They Wear That?, Stacy London and Clinton Kelly revisit Working Girl and break down the film’s unforgettable late 80s style one scene at a time. From commuter sneakers, big Staten Island hair, and mismatched office accessories to Sigourney Weaver’s sculptural power looks and Tess’s full corporate makeover, they unpack how the clothes tell the story. 

Along the way, they talk shoulder pads, brooches, green eyeshadow, fuzzy jackets, wedding fashion disasters, and the strange idea of success that shaped office style in the late 1980s. 

Produced by Simple Alien → https://www.simplealien.com/

Camera, Audio and Crew provided by TV Boy → https://tvboynyc.com/

About Why'd They Wear That?:

A pop-culture and fashion commentary show where Stacy London and Clinton Kelly break down the on-screen looks that sparked trends, started debates and occasionally made audiences ask, "Why'd They Wear THAT?"

→ https://www.whydtheywearthat.com/

Find out more @ ALL CHEWED UP Channel → https://www.allchewedup.com/

In this episode of Why’d They Wear That?, Stacy London and Clinton Kelly revisit Scarface and break down the movie’s unforgettable fashion one scene at a time. From Michelle Pfeiffer’s liquid silk gowns and icy all white looks to Manny’s tuxedos, layered chains, and full Miami excess, they dig into what made this movie feel so glamorous, dangerous, and instantly iconic. 

Along the way, they talk costume design, silhouette, chest hair, 1980s masculinity, and why Elvira remains one of the most memorable style presences in movie history.

Produced by Simple Alien → https://www.simplealien.com/

Camera, Audio and Crew provided by TV Boy → https://tvboynyc.com/

About Why'd They Wear That?:

A pop-culture and fashion commentary show where Stacy London and Clinton Kelly break down the on-screen looks that sparked trends, started debates and occasionally made audiences ask, "Why'd They Wear THAT?"

→ https://www.whydtheywearthat.com/

Find out more @ ALL CHEWED UP Channel → https://www.allchewedup.com/

In this episode of Why’d They Wear That?, Stacy London and Clinton Kelly revisit Tootsie and break down the film’s fashion one look at a time. From Dorothy Michaels’ endless high neck blouses and flowing skirts to Teri Garr’s unexpectedly chic wardrobe and Jessica Lange’s soft, effortless glamour, they dig into what works, what does not, and why the movie’s costume montage changes everything. 

Along the way, they talk silhouettes, styling tricks, 1980s fashion logic, and the costume choices that helped define one of the most iconic movie transformations of its era. 

Produced by Simple Alien → https://www.simplealien.com/

Camera, Audio and Crew provided by TV Boy → https://tvboynyc.com/

About Why'd They Wear That?:

A pop-culture and fashion commentary show where Stacy London and Clinton Kelly break down the on-screen looks that sparked trends, started debates and occasionally made audiences ask, "Why'd They Wear THAT?"

→ https://www.whydtheywearthat.com/

Find out more @ ALL CHEWED UP Channel → https://www.allchewedup.com/

In this episode of Why’d They Wear That?, Stacy London and Clinton Kelly revisit 9 to 5 and break down the movie’s unforgettable fashion one look at a time. From Jane Fonda’s overaccessorized first day suit to Lily Tomlin’s razor sharp office style and Dolly Parton’s impossible to ignore silhouette, they unpack how costume design helped define each woman’s character. 

Along the way, they get into 1980s power dressing, pussy bow blouses, office kimonos, giant wigs, red accessories, and the details that still make this movie feel stylish decades later. 

Produced by Simple Alien → https://www.simplealien.com/

Camera, Audio and Crew provided by TV Boy → https://tvboynyc.com/

About Why'd They Wear That?:

A pop-culture and fashion commentary show where Stacy London and Clinton Kelly break down the on-screen looks that sparked trends, started debates and occasionally made audiences ask, "Why'd They Wear THAT?"

→ https://www.whydtheywearthat.com/

Find out more @ ALL CHEWED UP Channel → https://www.allchewedup.com/

In this episode of Why’d They Wear That?, Stacy London and Clinton Kelly revisit Weird Science and rank Kelly LeBrock’s most iconic looks from the film. From the unforgettable doorway reveal to the hot pink lamé dress, the punk mall look, and the surprisingly polished goodbye outfit, they break down what works, what dates the movie, and why these costumes still leave an impression. 

Along the way, they get into 1980s fashion, brooch overload, teen fantasy styling, and how costume design helps shape Lisa’s character arc from objectified fantasy to something far more interesting.

Produced by Simple Alien → https://www.simplealien.com/

Camera, Audio and Crew provided by TV Boy → https://tvboynyc.com/

About Why'd They Wear That?:

A pop-culture and fashion commentary show where Stacy London and Clinton Kelly break down the on-screen looks that sparked trends, started debates and occasionally made audiences ask, "Why'd They Wear THAT?"

→ https://www.whydtheywearthat.com/

Find out more @ ALL CHEWED UP Channel → https://www.allchewedup.com/

In this special Scene Stealers episode of Why’d They Wear That?, Stacy London and Clinton Kelly each choose three unforgettable leading lady looks that made an instant emotional impact and never left them. From Moonstruck and The Shining to Grease 2, Rear Window, The Grifters, and Xanadu, they break down the outfits, styling choices, proportions, and fashion moments that still live rent free in their heads.

Produced by Simple Alien → https://www.simplealien.com/

Camera, Audio and Crew provided by TV Boy → https://tvboynyc.com/

About Why'd They Wear That?:

A pop-culture and fashion commentary show where Stacy London and Clinton Kelly break down the on-screen looks that sparked trends, started debates and occasionally made audiences ask, "Why'd They Wear THAT?"

→ https://www.whydtheywearthat.com/

Find out more @ ALL CHEWED UP Channel → https://www.allchewedup.com/

Clinton Kelly and Stacy London rewatch Poltergeist with a totally different lens: the fashion. From JoBeth Williams’ suburban mom looks to Tangina’s ghostly dress, awkward school uniforms, prairie skirts, popcorn sweaters, and some truly chaotic styling choices, they break down the most memorable outfits from the movie one look at a time. 

Along the way, they revisit one of their favorite movies, quote iconic scenes, argue over what works and what absolutely does not, and ask the only question that really matters: why’d they wear that?

Special Thanks to Our Sponsor:

The Knickerbocker Hotel → A legendary New York landmark reborn as the first luxury hotel in Times Square. https://www.theknickerbocker.com/

Produced by Simple Alien → https://www.simplealien.com/

Camera, Audio and Crew provided by TV Boy → https://tvboynyc.com/

About Why'd They Wear That?:

A pop-culture and fashion commentary show where Stacy London and Clinton Kelly break down the on-screen looks that sparked trends, started debates and occasionally made audiences ask, "Why'd They Wear THAT?"

→ https://www.whydtheywearthat.com/

Find out more @ ALL CHEWED UP Channel → https://www.allchewedup.com/