“It’s like cooking. It either tastes good or it doesn’t.” That’s how Sophie De Rakoff describes costuming Reese Witherspoon—and she should know, having done the job for over 20 years, on numerous productions since and including 2001’s Legally Blonde. When you’ve been good at something for that long, an instinctual secondhand takes over. Fellow costume designer Debra McGuire had similar things to say about working with Jennifer Aniston over the last 30 years. (McGuire and Aniston first met on the set of Friends.) “There’s just this flow to it that doesn’t exist with other actors,” she told us.

It’s rare in Hollywood for a costume designer to have worked so extensively with a single actor, and it’s even rarer for two such designers to work together on a single production. The costuming of season three of The Morning Show is therefore unique: De Rakoff designed three entire episodes of the Apple TV+ drama, as well everything for Witherspoon’s character, Bradley Jackson. McGuire handled Aniston’s character, Alex Levy, exclusively. And a third designer, Beth Lancaster, supported on everything else. This collaborative environment, and the nature of having known your colleagues for over two decades, made for some interesting behind-the-scenes anecdotes—like how the designers were trusted enough to pull pieces from the actors’ personal closets, or how McGuire collaborated with Valentino to re-create one of Aniston’s most iconic red-carpet moments for Alex.

They say if you want to go fast, you go alone; and if you want to go far, you go together. Here, we caught up with De Rakoff and McGuire to learn more about how far things can go when creatives get to collaborate.

How do we see the style of Jennifer Aniston’s character, Alex Levy, change in season three?

Debra McGuire: We meet Alex in the first season and she’s wearing a lot of buttoned-up suits and pussy bows, and she’s very professional and very sort of hidden in a way. It’s not until the second season and there was a baring of the soul when the wardrobe follows suit, and there’s a different kind of vulnerability. We get into the third season and there’s a confidence that is much more pronounced, and consequently, she doesn’t have to put on a jacket to feel powerful. We see a lot of skin, a lot of arms, a lot of V-necks, more shoulders.

Are there any style moments you’re especially proud of?

DM: Alex wears a Khaite jumpsuit that is strapless, and is pretty amazing. There is an Alexander McQueen pantsuit that is incredible. And when Alex wears a Saint Laurent turtleneck with anything, it’s amazing. We also see Alex in a Valentino gown that was made to be like a gown Jennifer had worn years ago—and because that dress didn’t exist anymore, Valentino made the dress for us again.

Debra, you’ve worked with Jennifer Aniston for almost 30 years, all the way back to Friends. What’s it like as a creative person to collaborate with someone for that long?

DM: Here’s the thing: Jennifer is one of the very few actors who really knows herself in terms of her physicality. Often actors will tell you what looks good on them, and as designers, we know that’s not always what is actually the best look for them. But Jennifer is quite exceptional in that she knows exactly what works. I trust her instincts in a way that I [don’t] with any other actor. Just look at her personal decisions she’s made in terms of her red-carpet looks—she’s never had a mistake. You can’t say that about most celebrities, if you look at the longevity of their career!

How do we see the style of Reese Witherspoon as Bradley Jackson transform this season?

Sophie De Rakoff: When we first meet Bradley, she’s a regional field reporter in West Virginia. They dress themselves, they don’t have a budget; she would’ve been shopping at Macy’s and Kohl’s. In season three, she is [a national] evening news anchor, and it’s the position she’s always dreamed of. She’s moved into a very different arena emotionally and professionally. I would say her anchor look is split, intentionally, to reflect Bradley’s duality. One of the reasons she is successful is she is purple—she can talk to the left and to the right. She’s split between traditional and elevated pantsuits. A wide pant and a fitted jacket is something she’ll alternate with a shorter skirt. Her costumes speak to the duality of masculine and feminine, the left and the right, what’s expected and what isn’t. She crosses back and forth on that fence. It’s intentional.

Are there any style moments you’re particularly proud of?

SDR: We collaborated with Lafayette 148 for some custom-made suits. I couldn’t find what I wanted in the right palette, knowing we were moving her into this wider-leg, higher-waisted silhouette. They worked out really well. We also used a lot of McQueen on her for anchor wear. It hit all the right boxes of elevation, name recognition, and a sharp silhouette. In terms of her off-duty wear, it’s always been jeans, boots, T-shirts, leather jackets. But this season we put her in these Frame leather jeans with pumps, and that was a nice twist—another sign of her elevation. She’s stepping into her confidence and much more secure about her own identity.

You’ve worked with Reese for over 20 years, most iconically on Legally Blonde. What is that like for you as a creative person?

SDR: A lot of times, designers will click with a director and that collaboration keeps on. At this point, my core collaboration has been Reese, and we have a complete shorthand. We’ve been friends for 20 years, so there’s this warm familiarity that makes everything come back to this idea of family.

It’s very unusual to have costume design structured as it was on this production—the two leads having their own primary designer—plus, Sophie, you also did three episodes on your own, and a third designer supported on the remaining episodes. How did that process work for you?

DM: I think something that most people don’t know is that designers don’t have the opportunity to work with other designers, for the most part. If we know them, we know them socially. This was a unique situation.

SDR: It’s very unusual to work like this, but Debra and I are happy to talk about it, so we can be an example for other designers that it can take a village and be done collaboratively. It’s a big show, and there are a lot of characters. It’s a lot of designing. But the big difference between features and episodic is, it’s very different time management—very often we don’t have all the scripts at the beginning of a season, so you’re constantly making decisions quickly, pivoting, designing, and executing very quickly … but [the third costume designer] and I share an office, and Debra is right next door, so. We are in constant communication. It’s very enjoyable.

The Morning Show wardrobe has a lot of great pieces in it—was there anything your actors tried to steal?

DM: We don’t have that situation. We actually steal more from Jen’s closet than Jen would steal from us! We do fittings at her home, and every so often I’ll put her in a Saint Laurent pant and she’ll say, “I have one from three seasons ago that will work better.” And often it does. There are several pants this season, and maybe some jewelry, that’s personally hers. We love to open her jewelry drawers!

This interview has been edited and condensed for clarity.

Todd Plummer is a Boston based journalist covering culture and lifestyle. He is a seasoned entertainment reporter, travel writer, and is an alumnus of McGill University and St. John’s University School of Law.