Montage Interviews Courtney Wheeler for FX’s The Bear Season 3

I had a lovely chat with Courtney Wheeler about menswear, brand collabs, vintage finds, and how to build a wardrobe.

After absolutely tearing through Season 3 of FX’s The Bear when it came out in June (then tearing through ample discourse on the ‘fits, Carmy + Syd will-they-won’t-they, and restaurant review speculation), I had the pleasure to speak with the show’s Emmy-nominated costume designer Courtney Wheeler. I first met Courtney virtually right after Season 2 premiered, so it was a treat to pick back up with her for a chat about breakdowns from this season’s best looks, how her costuming process has evolved, and advice she has for anyone trying to build a timeless wardrobe.

Sydney is a high-low queen

One of my favorite aspects of The Bear is its ability to balance the high tempo frenzy of an ensemble cast interacting in tight quarters with delicate moments of individual character exposition. We see that most notably with Marcus, Richie, and Tina who all have dedicated episodes in Seasons 2 & 3. A lovely element of Courtney’s work on this show is being able to illustrate character growth through wardrobe. Last season the internet delighted in Richie’s emboldening “I wear suits now” moment, but this season my favorite sartorial blossoming came from Sydney.  In Seasons 1 & 2 Sydney sported a variety of fun pieces including a patchwork Paloma Wool puffer and white workwear overalls paired with Nike sneakers. In Season 3, though, we see Sydney shoulder the increasing weight of responsibility at The Bear, battle stressful career indecision, and break bread with an utterly nutso table of culinary greats (imagine sharing dinner with Christina Tosi, Malcolm Livingston II, and Genie Kwon). Serious times call for serious drip.

“She still is very much herself and has her same point of view. It’s just we’re seeing her in situations that require a certain finesse and polish and so we saw fewer vintage tees and more structured matching sets. She is entering the world putting her best foot forward as she meets legends of the industry,” says Courtney on Sydney’s style evolution this season. Or maybe it isn’t an evolution after all. As Courtney reflected, perhaps this structured style is where Sydney’s been at all along, but only now does she get to show the world who she is outside of the kitchen.

We went deep on one of Sydney’s outfits in particular – the Comme des Garcons Girl sailor jacket and matching shorts ensemble she wore in Episode 7. “I do think Sydney is absolutely someone with great taste who would pick out something like this.” Courtney sees Sydney as someone who enjoys investing in a few staples from affordable luxury brands and balancing that with playful pieces and secondhand finds. “A lot of her wardrobe is high low. For every $400 piece there is probably a vintage piece or something that was passed down from her mother or father.” This level of thoughtfulness about the why and how each character would dress is one of many things that make Courtney so good at what she does. But Courtney isn’t the only one who has opinions about characters’ choice of brands. Half of the fun of this show is digging through the trove of fan theories deep in the comment threads on Reddit and Instagram. In a recent Instagram post about Sydney’s $450 Comme de Garcons jacket, folks sounded off in the comments about whether this purchase seems realistic for someone of Sydney’s industry. People always have their opinions on this topic (same with Carmy and his $100 t-shirts), but my favorite comment was from one person speculating “lowkey Syd seems like the kinda girl to be on depop/ssense/grailed.” Agreed.

The Bear x J. Crew – A Natural Collaboration

I was stoked to learn of J. Crew’s collaboration with The Bear this season for an exclusive menswear collection. Shortly after Season 3 aired, the classic American brand revealed news of the collab which includes four pieces – a work jacket, crewneck sweatshirt, trucker hat, and t shirt. The design straddles an interesting line between everyday workwear and overt show merch. The lovable handymen Fak brothers inspired the designs, with their Matter of Fak logo plastered across the gear.  

“It was definitely the brainchild of Chris Black (friend of Chris Storer, founder of Done to Death Projects and one half of How Long Gone) who came on board to help the show facilitate brand collaboration.” At the time Black had been working with J. Crew through Done to Death. Regardless, the brand was a natural fit for the show especially as Courtney had used several J. Crew sweaters for Carmy already.

Brands’ eagerness for collaboration speaks not just to the appealing stylistic universe Courtney has created but also more broadly to the role of TV characters as compelling billboards for clothing brands. Particularly if they look like Jeremy Allen White or Ayo Edebiri. As one proxy for the juice The Bear generated for J. Crew, recent Instagram posts about the collab from the brand’s menswear account generated 5-10x more engagement compared to typical J. Crew menswear posts. It’s also worth mentioning the collection initially sold out within days. J. Crew has since restocked.             

Since Season 1 aired Courtney and her team have received inbound requests from countless brands to be featured on the show. They can’t work with everyone, but Courtney notes “it’s fun to find smaller labels to feature.”

Building out from the basics

With a creative team like Courtney, Chris and Courtney Storer, and Matty Matheson, it’s no coincidence that The Bear has been such a beacon for men’s style. “We all love menswear and playing with clothes and the language of clothes. It’s important to us. That’s why the show looks like it does, because everyone has a point of view whether they’re behind or in front of the camera.”

I would love to be able to quantify the direct impact Courtney and her team have had on the evolution of men’s style since June 2022. “It’s been awesome and mind-blowing and kind of surreal to see people connect to costumes in such a way.” Courtney’s influence extends beyond the stoking of any desire to throw on a loop wheeled white t-shirt or grey cable knit sweater a la Carmy’s standbys. Her use of specific well-crafted brands like Scandi-based NN07 have stirred wider consideration about the quality of clothing as a worthy and baseline criteria. “It is cool that men seem to be paying attention to what they put on their bodies, and considering quality which should be talked about and is important.”

I asked Courtney for her advice to anyone attempting to build a wardrobe. “Start with the basics like a good pair of pants then go from there. Go to the good vintage store that carries nice jeans.” Secondhand stores tend to be a good resource for denim as older pairs are 100% cotton whereas newer pairs tend to be made with synthetics. “Then you can add a nice button down. And once you find a good color and cut that suit you, everything comes easier and you can start to have fun and buy more color and texture.” On finding the right fit for one’s body, Courtney reminded me that many retail stores – ranging from Bergdorf Goodman to Uniqlo – have in-house tailors. In an age of fast trend cycles and dizzying options, it’s helpful to be reminded of the foundations for good style.

This Week’s Montage: Courtney’s Vintage Shoutouts

One thing to know about Courtney is that if you name a Chicago vintage shop, she has most likely scoured their back room or basement. In fact, a lot of The Bear’s costuming is sourced secondhand (sorry to all of the fans of Carmy’s Filson flyfishing vest from that blink-and-you’ll-miss it Scandi bridge scene, that was an eBay find!!). Some of my favorite vintage pieces from this season include Sydney’s 90’s Chicago Symphony Orchestra tee and her Ralph Lauren chunky sweater.

The queen of the secondhand hunt was kind enough to share some of her favorite vintage spots with us:

-          Fine and Dandy in New York

-          Goody Vault in Chicago

-          Shudio in Chicago

-          Layers in Chicago

-          Able Shoppe in Chicago

I can’t wait to see what Courtney and her team have in store for the future. In the meantime, stream Season 3 of FX’s The Bear on Hulu and then head to Montage to explore Courtney’s costume design work.