Anna Kendrick's Outfits Change Based on Her Relationships in HBO's Love Life

Published on June 10, 2020 at 4:30 PM

Anna Kendrick plays Darby in HBO Max's Love Life, a series that spotlights none other than the main character's love life over the course of eight years (2012-2020). Though it sounds like a pretty straightforward storyline, it's complex in that it challenges you to look within, because actually, a lot of the phases Darby goes through are pretty relatable — and that extends to her closet and the outfits she puts on based on who she's with or what she's doing.

I talked to costume designer Jackie Demeterio about the process of dressing Kendrick, along with the other characters in the show — Zoe Chao plays Sara, Darby's roommate — who was amazing to dress in her own right. "She had that downtown party girl thing and it just worked so well on her," Jackie told me. But I was really interested in the way Darby's wardrobe was crafted.

"When [Bradley and Darby] start dating, she starts to become what she thinks is more sophisticated and cooler and wears what will fit into HIS world."

"In the first episode, creator/director Sam [Boyd] had said to me he would like for me to keep [Darby] in flats. I knew she was going to try and get more sophisticated for Bradley in episode two and I had to have her start out in a place so we could see her evolve over time. At the beginning, the flats for me symbolized her youth and beginnings in NYC as well as her quirky sensibility," Jackie said.

She also elaborated on the pieces Kendrick was excited to wear — even keep! — like a pair of zip-up Rag and Bone boots and her distressed Converse All Stars, along with the looks she enjoyed styling on Kendrick: a Victoria Beckham coat she wears to the Gramercy Park Hotel and a red Rick Owens dress from the 10th episode.

"When she sees Bradley in episode two and visits him at his apartment she is still very youthful wearing a Hawaiian-print shirt, a short skirt, and her All Stars. When they start dating she starts to become what she thinks is more sophisticated and cooler and wears what will fit into HIS world," Jackie emphasized, touching on the fact that, as people who feel vulnerable in new relationships, we may subconsciously alter the way we present ourselves without even knowing it.

Ahead, get a breakdown of Darby's many New York City fashion moments, a lot of which you'll definitely be able to appreciate, seeing as that you probably have similar pieces sitting in the back of your closet that you wore during past relationships.

Darby's Overall Personal Style

"Darby's personal style has a constant classic base that evolves over time. She looks good in reds and oranges, and she wears a lot of beautiful pieces that pop on camera, [specifically in episode six]. Anna liked a lot of Darby's outfits and she did take home quite a few pieces from her wardrobe. I know she really liked a lot of the boots that she wore. There were a pair of zip-up Rag and Bone black boots from the first episode that she liked, and she also loved her distressed Converse All Stars."

Darby's At-Home Style

"Darby starts out casual, wearing a lot of vintage sweats and T-shirts at home, hanging out with her roommates and waiting for Augie to call. Once she starts dating him, you can see her wardrobe starts to reflect what is going on. She looks cute and a little preppy with a quirk on their dates together but isn't trying too hard — just what feels good and natural."

Darby's Casual, Going-Out Style

"[Throughout the seasons] you see the changes and evolution in Darby's clothing, but they always have a classic sensibility to them," Jackie said. Darby wears the same floral summer dress we've all got hanging in our closets, easy to team up with a denim jacket and crossbody bag for a day party, and her striped sweaters run the gamut — perfect for print mixing.

Darby's Business Outfits

"Darby definitely becomes chicer and a bit more conservative when she starts becoming more successful at the auction house. Later, when she works at the art gallery, her choices become more fashionable, but still with classic cuts and shapes . . . I have received some DMs [on Instagram] asking specifically about the leather Dior perforated vest that she wears in episode six and a couple of her dresses."

Darby's Halloween Costume

"Anna Kendrick absolutely LOVED Darby's Black Swan Halloween costume from the first episode. She was very happy in that costume! It's too bad you only saw it for a couple seconds."

Darby's Party Style

While I asked Jackie about the dress and oxfords combination Darby wears to Bradley's wedding in the first episode (who hasn't chosen flats over heels for comfort reasons?), there's a clear distinction from this sophisticated number she wears later in the season. "The season spans from 2012 to 2020, and I wanted to be able to show the different phases of Darby's life through her wardrobe," Jackie said. "The oxfords [in episode one] were definitely a choice. I tried heels on with the dress and that just seemed liked the obvious straightforward selection. The oxfords to me told a much more interesting story about Darby . . ."

"In [Kendrick's] first fitting I had a pair of vintage Robert Clergerie oxfords that my shopper Karena found at a thrift store. They were so perfect, but unfortunately way too small on Anna. I was obsessed with finding the perfect pair of oxfords to replicate those vintage Clergeries. We bought a pair of Crocket and Jones in the same color and I sent them to my ager/distresser to have them almost match those Clergeries. They ended up being the perfect choice with the dress that she wears to Bradley's wedding."