Fashion, Lookbook

The breakout star of ‘Always Be My Maybe’ is actually Ali Wong’s wardrobe

Through her ever-evolving style, Wong's character Sasha pays homage to her predecessors while making the genre her own.

When one thinks of the quintessential rom-com, a few attributes immediately come to mind. There’s the flawed yet lovable protagonist, the charming love interest (or two), the funny best friend, the colorful setting, and, of course, numerous eye-catching, enviable outfits. While costume design is important in any film, it functions nearly on the level of another character in romantic comedies.

Sometimes it’s crucial to the plot, as with Julia Roberts in Pretty Woman or Katherine Heigl in 27 Dresses. Sometimes it’s more understated, as with the dedicated career woman Sandra Bullock plays in The Proposal. Yet, however prominently it may appear, the clothing a rom-com protagonist wears gives us great insight into their character.  

Nowhere is this more apparent than in the recent Netflix release Always Be My Maybe, starring comedian Ali Wong and Fresh Off The Boat’s Randall Park. The film breaks new ground for representation by focusing on an Asian-American heroine with an Asian-American love interest. Featuring diverse supporting characters and a cameo by Keanu Reeves, Nahnatchka Khan’s directorial debut is an enjoyable watch crafted with care.

Undeniably, the heart of the movie is Ali Wong’s character, Sasha Tran. Her vivacious nature and drive to succeed make Sasha an easy character to root for. Sasha is the latest addition to a small but growing group of Asian American rom-com protagonists. Other members include Lara Jean Covey from To All The Boys I’ve Loved Before and Rachel Chu from Crazy Rich Asians. For all of these characters, fashion functions as a conduit through which they express themselves and explore new possibilities. Naturally, their personal styles couldn’t be more different. 

In an interview with Entertainment Weekly, costume designer, Leesa Evans, states that Sasha’s wardrobe was inspired by classic rom-com heroines. While Sally Albright’s style in When Harry Met Sally prizes her New York roots, Sasha’s is shaped by her hometown of San Francisco. Evans explains that “a lot of the clothes that Ali wears in the movie […] either have an architectural element, or they have an edge to them.” 

Forming Impressions

The character Sasha Tran played by Ali Wong stands facing the camera, wearing a full-sleeved red dress and a silver necklace.
[Image description: The character Sasha Tran, played by Ali Wong, stands facing the camera, wearing a full-sleeved red dress and a silver necklace.] Via Ed Araquel for Netflix.
The film hinges on the premise of Sasha, a successful chef, returning to her hometown to open a restaurant. Like most homecomings, she encounters reunions both expected and unforeseen. Not only must she interact with her once distant parents, she also runs into her former best friend, Marcus. Played by Randall Park, Marcus works for and lives with his dad, though his real passion is music. While Sasha left her home behind long ago, Marcus still shies away from breaking out of his familiar world. 

Before this happens, the audience is introduced to Sasha through her childhood outfits. As a child, her style is full of pastels and unique patterns. After she reaches adolescence, the edge Evans mentions starts taking shape. Teenage Sasha pairs her braces, bangs and wire rim glasses with dissonant pieces like overalls, plaid, and fishnet stockings.

When we see her as an adult sixteen years later, however, she looks very different. Clad in expensive fabrics and monochrome tones, the Sasha who has attained success displays her achievements through her clothing. Even at home with her fiancé, played by Daniel Dae Kim, she prizes appearance over comfort. Her gaudy cheetah print glasses are the sole concession to creativity in these outfits. 

A San-Fran Induced Style Shift

Sasha Tran, played by Ali Wong, and Marcus Kim, played by Randall Park, walk on a street side by side. Sasha is wearing white jeans, a white graphic shirt and a red cardigan, while Marcus wears a light blue shirt and a dark gray jacket.
[Image description: Sasha Tran, played by Ali Wong, and Marcus Kim, played by Randall Park, walk on a street side by side. Sasha is wearing white jeans, a white graphic shirt and a red cardigan, while Marcus wears a light blue shirt and a dark gray jacket.] Via Ed Araquel for Netflix.
Once she returns to San Francisco, however, a more playful side of Sasha surfaces. When she’s still resisting the newly warm embrace of her family and uncomfortably interacting with Marcus, her clothes are mainly in block colors with muted flourishes. But as she starts to open up to the prospect of reconciliation, her style also undergoes something of a transformation. 

A few scenes into her return, Sasha begins wearing lighter colors and prints reminiscent of her upbringing. Even when she’s attending high society events, she incorporates funky patterns and pastel shades. And one can clearly see the influence of her hometown and Marcus in the graphic t-shirts she newly sports.

Her wardrobe throughout the film thus demonstrates the two lives she moves between. She’s both the celebrity chef with an image to uphold, and the San Francisco native who loves to experiment. There are dramatic silhouettes and offbeat suspenders, metallic fabrics and cozy cardigans. This newfound stylistic fluidity shows how, in coming home, Sasha discovers the courage to imagine a life of more than lonely material success.

By the closing scene of the film (which I won’t spoil but will say is deeply satisfying), Sasha is wearing a white jumpsuit that she looks both comfortable and striking in. It’s a skilful visualization of those two seemingly disparate lives fusing with each other. 

Ultimately, Sasha’s path throughout the movie is about coming home, discovering the potential for love there, and learning how to carry it with her. Although her journey involves much more than fashion, the depth it brings to her story makes the film that much more fulfilling to watch.