Cottagecore Ganni & Vintage Escada: Unpacking The Fashion Of “The Bear” Season 4

Like previous seasons, Wheeler and her assistant costume designer Lariana Santiago spent weeks sourcing outfits, carefully working with vintage stores across Chicago and scouring eBay for rare finds. And sometimes, like in the case above, the look just comes together on its own.

“We try not to overthink everything, and we're really collaborative with the actors and what they want to wear,” Wheeler says. “We want them to put on what feels true to their character.”

If you’ve followed "The Bear" since the beginning, you know that each character brings their own layered, lived-in aesthetic to the table. There’s Carmy and his classic menswear looks, consisting of sweaters from J.Crew and denim from the '50s; Sydney, who pairs an amazing vintage t-shirt collection with an equally enviable jacket archive (this season, the notable silhouette was an Escada vintage jacket sourced at Some Like Us); Marcus (Lionel Boyce), who’s still mixing his affection for American streetwear with Copenhagen style codes; and, of course, Richie (Ebon Moss-Bachrach), who’s leaning into a tailored suits era that acts as a “kind of an armor,” Wheeler says.

There’s also Donna, the mother of Carmy, who undergoes one of the most significant style evolutions. “This season, you could see Donna trying to feel lighter and not as heavy as seasons past,” Wheeler shares. “One of my favorite looks is the powder blue suit she wears in the open house scene, which reflects this shift.”

Like in seasons past, The Bear isn’t just serving up high-stakes drama—it’s plating some of the best styles we’ve seen on TV. Ahead, we chat with Wheeler to get all those style IDs we’ve been searching Reddit for—from where to get Sydney’s hot dog bandana to Francine and Sugar’s matching cottagecore wedding dresses.

Congratulations on another great season! Having worked with the cast since season one, who would you say had the biggest style evolution this season?

Courtney Wheeler: "Thank you. There are definitely a few characters that have had significant evolutions this season. One of them is Sydney. She's always been playful, but this season you see her more in her in spaces, and more comfortable with her POV. I think Carmy notices this shift, too. This season, she attends a wedding wearing a really cool, water-blurred camo two-piece set.

You also have Richie, who, when we first met him, was more of a defensive character, always wearing the same thing he has always worn. He was kind of stuck in a rut, wearing his old t-shirts. He was wearing a lot of “The Beef” tees—stubbornly holding on to the past. But now, he's wearing these suits and it makes him feel good—it's kind of an armor, [but] not a defense mechanism. It makes him feel so good. I think his arc is one of my favorites. I hope everyone can see that, if they watch season one or even two, how much the characters’ styles change."

I also wanted to ask you about Sydney and the brands you were gravitating towards for her this season. What were some brands that you were excited to pull for her?

CW: "She's such a fun character to work on. Like most people, she doesn’t have all designer items in her closet. She has a few little pieces and gems, but she also wears a lot of vintage and secondhand pieces. We found this great Escada vintage jacket, which we sourced at Some Like Us in Pilsen, that she's wearing throughout the season, and we love it so much. A lot of her sweaters are from Norse Projects, and she wears a lot of vintage Gap, so she's a true mix. For her bandanas, we’ve pulled them from practically everywhere—RRL, Mur by Ayca, Eloi, Kapital, Echo New York, Cai & Jo, and One Ear Brand.

I think, as a Black woman, moving through the spaces she does where she's the only person who looks like her, she’s always had to bring a part of herself and her opinion when she could. Even if she’s had to stay silent, she's making sure that she stays true to herself and what she wears. This season, we have a lot of Black American-based T-shirts. She's wearing a Negro league sweatshirt in one of the episodes. She has the Smithsonian one. She's just someone who likes to collect, whether through her father or her mother, who passed away. I think clothes help ground her and convey her point of view."

The whole cast is very stylish. How did you work with each of them this season?

CW: "My assistant costume designer, Lariana Santiago, and I have a lot of fun sourcing the looks. And then, once we’re filming, we set them up and we just let the cast go to town. We ask them, 'What are you feeling today? How do you think your character is feeling?' We try not to overthink everything, and we're really collaborative with the actors and what they want to wear. We want them to put on what feels true to their character."

Where’s the most unexpected place you've sourced a look from this season?

CW: "A lot of these local Chicago-based vintage shops let us visit their warehouses. And it’s when we’re digging through those bins that we find the best stuff. It’s really a great feeling to have all these amazing fashion people in Chicago trusting our vision and letting us into their spaces."

Do you have one grailed item that you can't believe you found?

CW: "The Negro league sweatshirt Syd wears is definitely one of my favorites. Our friend Manny of Goody Vault had it on display, and we were like, 'Can we take this?' And he's like, 'Of course, you got it.'

Another rare find was this Michael Jordan restaurant T-shirt that we didn't get to use this season, and we're so sad because it was for Marcus. Lionel loves it. He told us he has an obsession with that restaurant, and it's supposed to be a callback to something that happened. We're hoping to work it in next season, but we'll see."

That would be iconic. I wanted to ask you about the wedding scene this season. Do you have a favorite look from the episode?

CW: 'My favorite looks are actually Francine and Sugar's. There's a very much light cottage-core vibe happening, and we thought it would be so funny if they wore these sweeter silhouettes, because they are absolutely trash-talking the sh*t out of each other. Francine’s wedding dress is from Silkie and Sugar’s wedding dress is from Ganni.'

What’s one unexpected detail that people might overlook, but you're obsessed with?

CW: "That's really hard. If I had to pick, I’d say any of Donna’s looks this season. She means a lot to me as a character, and working with Jamie Lee Curtis was such a treat. She's so in tune with her characters and takes so much care with Donna. There were so many instances where she’d be like, 'Hey, I was on eBay and I saw these. What do you think?'

This season, you could see Donna trying to feel lighter and less heavy than in seasons past. One of my favorite looks is the powder blue suit she wears in the open house scene, which reflects this shift. It's funny because I had all of these more muted tones in the fitting, but I had this suit in my back pocket. We had put it outside the room, and when Jamie walked in, she said, 'How about that one?' That was our wild card and that's exactly why you should always have a wild card because you never know when it's going to work. That suit is so special to me because I'm very attached to Donna as a character."

Are there any pieces that the cast loved so much that they took off-set?

CW: "They haven't taken anything yet… But it’s probably because they know that they’ll have to use it the next time they're in. But there was a funny instance with Jeremy’s sneakers because they both wear Nike Cortez. So one time he was like, 'Are those mine, or are those Carmys?'"