Cazzie David On The Perfect Pair Of Jeans & Dating Guys With Bad Style

Cazzie David doesn’t like wearing jeans. Whenever possible, she prioritizes comfort, as she tells NYLON: “I’ve never gone home and not immediately put sweatpants on, because I hate the feeling of being in regular clothes.” But Madewell has made the two-time published author a changed woman: Not only was she wearing a Madewell striped shirt when we got on the phone, but she stressed that the denim from its Fall 2026 campaign is so easy to wear, she finds herself lounging in it while working from home.

It’s a testament not only to the denim Madewell uses, which handily straddles the line of stretch and rigidity, but the fits it has perfected in its Fall 2026 collection, of which David is the campaign star. Highlights include The Low-Slung Baggy Jean — a favorite of stomach-issue-inclined girlies like David — and The Relaxed Bootcut Jean, the latter of which David would wear for a night out with her friends: “It’s just a perfect pair of pants that happens to be jeans.” The rest of the collection includes the basics you’ll fall back on when you’re in an outfit-equation rut, like the layering pointelle camis, striped sweaters, and a preppy wool polo in a cheeky lemon yellow that is dying to be worn with mid-wash blue jeans.

Ever a woman of many words, David plays the role of “Denim Expert” in the campaign, fielding calls and dishing out advice. When someone asks how they’ll know when they’ve found “the one,” she gamely replies, “You’ll just know. They’ll lift you up, you’ll reach for them every day and miss them when they’re not around.” It’s an editorial that not only serves to show how versatile the latest denim is, but how David’s signature dry humor and wit can serve as both relationship and jean-picking advice. “How about trying one with deep pockets, if you know what I mean?” Relatable.

After a summer spent on Martha’s Vineyard, David dialed in from Los Angeles to talk about her newfound love of wearing jeans inside, her song of the summer, and why dating someone with bad style is a plus.

This campaign fits your personal style super well. Tell me about shooting the campaign and what pair of denim went home with you from set.

It’s interesting because usually you don’t get 30 pairs of jeans to choose from. They were all great. I’m really not just saying this, I’ve had one pair of jeans my whole life and I’ve never chosen a different pair of jeans to wear. It’s very rare to have an assortment of jeans to choose from and like all of them equally. I didn’t care which ones I was wearing because they all fit well and were so comfortable. The shoot was super collaborative, and that was great. You can feel like a prop doing stuff like this, and it was a great experience because I was able to contribute creatively and not just speak to the product, if that makes sense.

Putting on a good pair of jeans and making people laugh is a good way to do that. Is there anything else besides the jeans that caught your eye and will make its way into your wardrobe this fall?

The jeans are so good that it doesn’t really matter what top you’re wearing, which is rare. Usually you have to put in equal effort. I love all the striped stuff. Embarrassingly enough, I’m wearing this shirt and I was like, “Do I change before?” because it’s so on the nose for me to be wearing a Madewell shirt. It’s going to seem like I did it on purpose. The striped stuff is really cute, and the sweaters. There are a lot of fun layering options.

I love that. It’s giving brand ambassador.

I’m going to try and sell the sh*t out of them. I’ve never gotten home and not immediately put sweatpants on, because I hate the feeling of being in regular clothes and I hate the feeling of being in jeans, honestly. I put on these jeans, and it feels the same as wearing sweatpants. You can actually lounge in them. For me to be able to do that has been a game changer, to feel more like a human when you’re in the house. It makes a huge difference to not be in pajamas all day.

Is dating someone with a bad sense of style a deal breaker for you?

No, and I actually get annoyed when my friends who are single will go on a date and be like, “I can’t go on another date. Their style was so bad.” That is something you can change. The only reason any straight man has bad style is because they don’t have a girlfriend that’s helping them behind the scenes. For me, not a deal breaker, but it’s definitely a plus if they do have it.

It’s a plus. I look at it as a fun project.

Totally. That’s part of the deal of dating: You’re going to have to dress them like a baby. It’s your fault if you have not intervened and your boyfriend still looks bad.

If you were to give a pair of jeans to anyone in your life, who would you give them to and what pair are they getting?

I would give them to my sister because anytime I give her something, it goes a long way for me. She’ll be like, “Wow, that’s so nice. I wasn’t expecting you to do something nice for me.” I would do something low-waisted because she has stomach problems. Maybe a white jean for summer.

I have a pair of the Madewell white jeans. They’re good.

They’re really good. They’re not embarrassing. It’s an under-the-radar white. I feel like sometimes when I wear white pants, it’s too much attention.

What’s on your reading list for fall?

I’m excited to read Anna Konkle’s book, The Sane One. I only want to finish that. I think she’s brilliant and hilarious.

What is your song of the summer?

OK, so I jokingly posted on my Substack that The Odyssey rap is the song of the summer. Did you hear the Jimmy Fallon thing? It got so stuck in my head to the point where I had the urge to memorize it like I was 14 again, when you used to memorize songs as an activity. That is what I want to do with The Odyssey rap.

In the campaign, you were taking calls as the Denim Expert, so I’m going to give you some scenarios and I would love to know what jeans you would wear. Number one: getting a bagel when you’re hungover on a Saturday morning.

First of all, low-waisted, because if you’re eating a bagel, you might get a little bloated. You don’t want high-waisted, and you don’t want to be unbuttoning the pants. If you’re a girl with stomach issues like me, usually I choose low-waisted and baggy.

Next scenario: You’re going somewhere and you know your ex is going to be there.

OK. You need something that’s going to accentuate the butt. Put on the pair that makes your butt look the best — but you don’t want to look like you’re trying too hard, so I would say something that’s not a baggy jean, but a straight leg where the ass looks really good. Maybe a dark wash.

Next scenario: family brunch on a Sunday.

I’m going to go again for the low-waist baggy, because I don’t give my family anything. I actually dress down for them on purpose. They don’t deserve me at my best.

My last scenario: Friday-night drinks in New York with the girls.

There’s this pair of jeans called the classic vintage something, but they’re just the perfect pair of jeans that you could wear with anything. I would choose that. It doesn’t make your outfit look too much like you’re wearing denim, if that makes sense. It’s just a perfect pair of pants that happens to be jeans.

The Madewell Fall 2026 collection is now available in Madewell stores and online at madewell.com. See our favorites below: