New York’s Best Pizza Meets Australia’s Best Jeans

In partnership with Rolla’s.

Allow me to present a theory I have been diligently working on for the past few years: We are living in the golden age of pizza. There are so many varieties! So many interesting toppings! So many options catering to different dietary restrictions and preferences! We are spoiled with choices. I mean, cauliflower pizza crust? What a world!

Given my occupation and passion for pizza, I have been enlisted to help solve one of the single most common pizza-related quandaries: What’s the best thing to wear while eating a slice or two or few? Something that says, “I honor and respect this pizza restaurant” but doesn’t get in the way of enjoying the experience. Like sugar in tomato sauce, Australia-based brand Rolla’s jeans are the secret ingredient that makes a trip to the very best pizza parlor look like an event but feel like a breeze. They’re comfortable, cute, and come with just the right amount of stretch to let you indulge in laid-back luxury.

The first step: I put together a list of Team Man Repeller’s fave NYC pizza spots. Step 2: Harling Ross whipped up three outfits showcasing Rolla’s jeans that were inspired by my pizza picks. Step 3: Model Isabella Carr test-drove said outfits at Motorino—one of our favorite spots—for stretch, style, and general deliciousness. Results below!

When the moon hits your eye: The best date-night look for amore

Rolla's Eastcoast Flare Karen Blue Jean styled with Uniqlo denim shirt, Opening Ceremony mesh tank, Tory Burch shoes, Squar'd Away headscarfRolla's Eastcoast Flare Karen Blue Jean styled with Uniqlo denim shirt, Opening Ceremony mesh tank, Tory Burch shoes, Squar'd Away headscarf

Pizza might just be the perfect first-date food: It starts with a bonding exercise in the form of selecting the perfect toppings, maybe a witty tête-à-tête over the merits of anchovies. Then it ends with cute banter about leftovers or the warm afterglow that can only come from polishing off a whole pie together. Here, Isabella exhibits a perfectly constructed date outfit, where the pants have enough stretch to handle even the most serious of toppings (meatballs, anyone?) while she stays looking like a pretty lil’ pepperoni.

Rolla’s Eastcoast Flare Blue Jeans

Harling’s recipe: “The classic flare silhouette coupled with a medium wash made me want to lean into the timelessness of a denim-on-denim look (the sartorial equivalent of a Margherita pizza, if you will). I paired them with a denim shirt that I left unbuttoned to show off a plaid mock-neck underneath and topped the whole thing off with a silk head scarf because I find that when you’re deep in the pizza consumption zone, it’s preferable to have your hair out of your face.”

Shared superlative: A perfect fitRolla’s jeans are designed to fit the body they’re on, so they kind of, sort of, feel like your soulmate. This particular silhouette acts like a high-rise skinny up top (ideal) and flares out at the bottom (even more ideal), thus turning on the charm in multiple respects. They also feature Rolla’s signature deck stitch on the back–a stamp of approval on your best asset. Other than your personality.

Best date night pizza spots: Ops (very cozy), Motorino’s (I mean, look at it), Emily (beautiful, just like you two), Barbancino (classic), Lucali (if you want a lot of time to talk).

Easy as pie: A laidback look for the most casual pizza outing

Rolla’s Eastcoast Flare Bordeaux Cord styled with Kule T-shirt, Kule cardigan, Tory Burch shoes, Safsafu earringsRolla’s Eastcoast Flare Bordeaux Cord styled with Kule T-shirt, Kule cardigan, Tory Burch shoes, Safsafu earrings

While the current avant-garde pizza climate is full of off-the-wall ingredients, beautifully constructed wood pizza ovens the size of studio apartments, and so many status tote bags, it’s important not to overlook one of pizza’s best qualities, its ease. Some days you’re too tired to cook, or go out, or flirt, and just want to order in or roll up to your usual spot to get your usual thing with your best friend. This look is all about deceptive relaxation—the bold-colored cords say, “I’ve got my life together!” while the comfort and stretch say, “I’m going to watch five hours of TV while also texting!” Life’s about balance, ya know.

Rolla’s Eastcoast Flare Cords

Harling’s recipe: “In addition to looking great, these flared corduroys are also insanely comfortable—so much so that I rolled with that element and styled the outfit according to my favorite “aesthetically pleasing but still cozy” outfit template: the aforementioned pants, a striped T-shirt, and an almost-as-delicious-as-mozz cardigan.”

Shared superlative: Business in the streets, totally fine to wear in the sheets—You could 100% get into bed with these cords and a slice of pizza, they’re that comfortable. You’ve already put your best flared foot forward for the world, relax a little.

Best all-purpose pizza spots: Artichoke Pizza (you already know), John’s on Bleeker (like being on the set of a fictional pizzeria), Lombardi’s (same), San Matteo Pizza and Espresso bar (let’s hear it for uptown options!), Best Pizza (they have a special that’s a six-pack and a pie), and whatever slice spot is closest to your home.

Serious pizza for a serious woman: Cozy style and comfort food

Rolla's Eastcoast Flare Galaxy Black Jean styled with Ganni vest over Live The Process knit cardigan, Clergerie shoesRolla's Eastcoast Flare Galaxy Black Jean styled with Ganni vest over Live The Process knit cardigan, Clergerie shoes

Grandma pie is like that super smart, no-nonsense friend —salty, kinda rigid, but ultimately a source of comfort for her buddies who are maybe not quite as together. The square grandma slice is one of the all-time top comfort foods, especially as we head into colder months, so Isabella is dressed for maximum coziness. And like that friend we all turn to for support, Rolla’s jeans are surprisingly tough and can stand up to spills, washes, and wears, so if you drop a little pepperoni cup on your thigh, don’t worry about it, she’s got you covered.

Rolla’s Eastcoast Flare Galaxy Black Jean and Black Cord

Harling’s recipe:Black jeans are the sleekest of blank canvases, so the world was really my oyster for look #2. I decided to contrast them with a grandpa-inspired combination of long-sleeved knit polo, sweater vest, and white brogues. You know what else black jeans are great for? Masking the inevitable tomato sauce splatter from enthusiastic pizza bites.”

Shared superlative: Perfectly cheesy—A grandma slice has to have the exact right amount of stretchy cheese action to work, just like Rolla’s have the right amount of stretch to maintain the shape of the jeans, without feeling too restrictive. You don’t want too much stretch or cheese, but you’ve got to have enough.

Best grandma slices: Prince Street Pizza (those pepperoni cups though!), Emmy Squared (technically Detroit-style, but basically the same thing), L&B Spumoni Gardens (the OG).

You can shop Rolla’s online at Rolla’ and Free People online. If you’d like to try on Rolla’s in person (maybe on the way to a pizza joint?) you can also find them at select Free Peoples store near you.

Photographer: Sabrina Santiago
Stylist: Harling Ross
Market:  Elizabeth Tamkin
Model: Isabella Carr at Wilhelmina
Hair and Makeup Arist: Shideh Kafei
Stylist Assistant: Jean Pflum 

Nora Taylor

Nora Taylor

Nora Taylor is the Editor of Clever. She can frequently be found knocking things over in the greater New York City area.

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