How 6 Celebrity Stylists Would Wear Baggy Jeans

If the thought of squeezing into a pair of skinny jeans horrifies you, you’re in luck: Big, baggy denim is in this year. Soon after skinnies were deemed cheugy in 2021, a slew of stylish stars and models were spotted in the antithesis of pin-thin denim. Hailey Bieber, for instance, leaned into the grungy look and paired oversized jeans with an equally large bomber jacket and dad hat. Balenciaga also made the silhouette its signature (its spring 2022 collection saw them styled with moto jackets and turtlenecks, for one). 

If straight-leg jeans are more your vibe, slipping into a more voluminous silhouette can be a somewhat scary idea. You go too baggy and you suddenly look like you’re rocking parachute pants. But fear not. Below, six powerhouse Hollywood stylists shared how they would style the look for their clients. From pairing them with fitted tank tops to matching the vibe with oversized hoodies, it turns out that you can wear them with practically everything. They may even become your new winter staple—because if they’re good enough for Rihanna, they’re probably good enough for all of us. 

Karla Welch

Clients: Justin and Hailey Bieber, Tracee Ellis Ross, Ruth Negga

My favorite [baggy jeans] are by Balenciaga. You can do it two ways—fitted on top or all oversized. They both work. Just yesterday I wore huge The Row jeans with an oversized sweatshirt, and it felt exactly right. Today, I styled a client in a fitted Lycra tank and massively oversized Balenciaga jeans. The key to pulling it off is confidence—and the correct length. You still have to be able to walk and not drag your pants and get tripped, but they definitely need to hit the floor.

The Row cotton-jersey hoodie

Saint Laurent cat-eye sunglasses

Erin Walsh

Clients: Anne Hathaway, Ashley Park, Lucy Hale

I love B-Sides baggy jeans lately. It’s all about proportion and occasion. For more casual, I love it with a more fitted top with shoulder pads, like a Frankie Shop tee or a Dries Van Noten or Khaite blouse. (Aritzia does great ones too.) I think you also have to go big with the shoe. A super-chunky sneaker like Golden Goose or a giant platform Versace will do. Aldo has great options in that department as well. A fitted crisp tweed jacket à la Chanel will always work with that shape—look for a bold shoulder and a lean cut so your frame doesn’t get overwhelmed. Options I love include Iro, Isabel Marant, and Veronica Beard. You have to put together the silhouette properly and own it. Also, don’t show your bum. Never do that. Adding feminine details tends to work, like statement jewelry à la my fave Jennifer Fisher. I am loving Eliou’s statement necklaces these days, and a neck scarf always looks great. Tove and Le Scarf have great ones. I also love a La Ligne striped sweater tied around the shoulders with literally everything.

Khaite Rosy ruche twill top

B Sides vintage lasso jeans

Ilaria Urbinati

Clients: Ben Affleck, Jon Bernthal, Charlie Puth

Right now, we are styling baggy jeans on our guys a little grunge with oversized knits, Isabel Marant men’s mohair sweaters, and Doc Martens–style boots or Blundstone work boots. We’re also styling them with more preppy vibes, such as sweaters over button-ups and white high-top sneakers. It’s all about getting the proportions right: You can’t put a slim shoe on a baggy pant, and the overall vibe needs to feel relaxed.

Isabel Marant mohair-blend sweater

Acne Studios wide-leg jeans

Tommy Hilfiger black tank top (3-set)

Blundstone Original 500 boots

Jason Bolden

Clients: Cynthia Erivo, Storm Reid, Alicia Keys, Taraji P. Henson

I like to style baggy jeans with super-classic things on top, from turtlenecks to proper blazers, like how I styled Demi Singleton in all Celine. The key to pulling off a baggy jean is to make sure it lands on your waist properly. 

Another Tomorrow cotton-blend blazer

Uniqlo Heattech turtleneck

Celine large flared jeans

& Other Stories croc-embossed leather tote

Thomas Christos Kikis

Clients: Gabrielle Union, Amelie Zilber, AnnaSophia Robb

The key to a baggy jean is pairing it with extreme proportions on top—either an oversized blazer or long coat, or shrunken and cropped. I would style my favorite baggy jeans—the Bella by Grlfrnd—with this cropped Prada jacket and Rich Paul’s 550s sneakers.

Prada cropped poplin jacket

Grlfrnd Bella low-rise jeans

New Balance Rich Paul 550 sneakers

Elizabeth Stewart

Clients: Jessica Chastain, Amanda Seyfried, Gal Gadot

I’d style baggy jeans with a sharply tailored jacket that is cropped to show the waist, cinched with a good belt. Contrast is great, so [try] a feminine ruffled blouse or an embellished sweater. And play with shape: It can be balanced with a tighter top, or go big over big with a great coat.

Mango faux-leather blazer

Frame high-waist baggy jeans