There is something deeply satisfying about watching a celebrity step out in sweatpants and look like they belong on the cover of a magazine. No effort, apparently. No overthinking. Just a pair of sweats and the kind of effortless cool that makes the rest of us immediately open a shopping app.

But here is what those looks actually require: intention. The celebrities who make sweatpants look extraordinary are not just throwing on whatever is nearest and walking out the door. They are making very specific styling choices about proportion, contrast, footwear, and accessories. The sweatpants are the starting point, not the entire idea.

Here is the full story of how sweatpants became a fashion statement, why they are still one of the most culturally significant items in a wardrobe, and exactly how to wear them like the celebrities who do it best.

The History: From Athletic Necessity to Fashion Essential

Sweatpants were not always a style choice. When Emile Camuset, founder of French sports brand Le Coq Sportif, created the first pair in the 1920s, they were purely functional. Simple gray cotton trousers designed to absorb sweat and keep athletes comfortable during training. Utilitarian, unglamorous, and entirely practical.

They remained that way for decades. By the 1930s they had made their way to the Olympics. By the 1970s, hip-hop culture and street style were beginning to claim them as something more expressive. And then 1980 arrived, and everything changed.

The fitness boom of the 1980s brought sweatpants out of the gym and onto the street. Jane Fonda's iconic 1982 workout video helped cement the idea that athletic clothing could be aspirational. Rocky had already made the gray sweatsuit culturally iconic in 1976. And as gym culture exploded, sweatpants followed, moving from sports-specific context into general leisurewear for the first time.

The 1990s deepened the shift. Hip-hop artists and skate culture had been wearing sweats as everyday clothing for years, and as streetwear moved into the mainstream, the idea that comfortable athletic clothing could be genuinely fashionable began to take hold. Calvin Klein, Ralph Lauren and Tommy Hilfiger started infusing their collections with sportswear elements. The lines between formal and casual were softening.

Then, in 2001, Juicy Couture introduced the velour tracksuit, and the fashion world was never the same.

The Juicy Couture tracksuit, with its plush velour, feminine colors, and Swarovski-studded logo across the seat, was something genuinely new: it took sweatpants and turned them into luxury. "That cushy velour connotes the concept of, 'I have so much money, I can essentially wear pajamas out,'" Vogue senior fashion writer Liana Satenstein has observed. Juicy sent their tracksuits directly to celebrities, seeding what we now recognize as influencer culture. Britney Spears, Jennifer Lopez, Madonna, Paris Hilton, Kim Kardashian: all were photographed in matching Juicy sets, and the tracksuit became the defining fashion item of the early 2000s.

The financial crisis of 2008 quieted the trend temporarily. But the athleisure wave of the 2010s brought sweatpants back, this time in a more sophisticated form. High fashion labels including Chanel, Fendi, and Prada began issuing designer tracksuits. In 2013, Donald Glover released a hit single called "Sweatpants" and explained the title simply: "Rich people wear whatever they want." That same year, denim sales began to decline, a trend that has continued ever since.

Then COVID-19 arrived in 2020, and sweatpants were no longer a fashion choice. They were a necessity. The pandemic accelerated the complete normalization of comfortable clothing across every context, with remote work making it not just acceptable but expected to wear sweats throughout a working day. When the world reopened, people brought their sweatpants with them, and the fashion industry adapted accordingly.

In 2026, sweatpants are not just acceptable. They are a genuine style statement when worn correctly. And the celebrities who have always known that are the ones to learn from.

The Celebrity Playbook: Who Wears Sweatpants Best and How

Emily Ratajkowski: The Model Off-Duty Formula

Emily Ratajkowski is one of the most consistently referenced names when it comes to making sweatpants look effortlessly good, and her approach is worth studying closely. The formula is almost always the same: slim or straight-leg sweatpants in a neutral color, a fitted top that creates proportion contrast, and a shoe that elevates the whole thing. White sneakers, loafers, sandals or ballet flats. Never too much on top. Let the contrast between the relaxed bottom and the polished shoe do the work.

Bella Hadid: The Street Style Approach

Bella Hadid has been photographed in sweatpants countless times, and her approach leans into the off-duty model aesthetic with complete commitment. Oversized sweatpants worn low, a cropped or fitted top, and sneakers or slides. The key to her version is the confidence with which the slouchy fit is worn. The sweatpants are not fighting the outfit. They are the outfit. Everything else is there to support them.

Hailey Bieber: Elevated Basics

Hailey Bieber's take on sweatpants leans into quiet luxury. Matching sets in neutral tones, worn with a simple top and clean white sneakers or classic loafers. The monochromatic approach, wearing coordinating shades of the same color from top to bottom, gives even the most casual sweatpants a polished, considered quality. This is the version that looks most intentional and most expensive without requiring anything complicated.

Rihanna: The Unexpected Contrast

Rihanna has worn sweatpants with fur coats, with heels, with sharp tailoring, and with full glamour accessories. Her approach is the most advanced on this list, but it teaches the most important lesson: sweatpants work at their most interesting when they are contrasted with something that has no business being near them. A luxurious coat over a casual sweat. A structured bag against a soft, relaxed pant. The contrast is the point.

Kim Kardashian: The Monochrome Set

Kim Kardashian's most successful sweatpant moments have almost always been monochromatic. Head-to-toe neutral, often in the kind of sculpted, high-quality sweats that blur the line between loungewear and fashion. It is the approach that most directly continues the Juicy Couture legacy while updating it for a different era: the tracksuit as status symbol, expressed through restraint rather than bedazzlement.

The Rules: How to Style Sweatpants Like a Celebrity

The celebrities who make sweatpants look extraordinary are all, without exception, working with a version of the same playbook. Here it is, broken down.

Rule 1: Proportion Is Everything

The most common sweatpant styling mistake is wearing a large, baggy sweatpant with an equally large, baggy top. The result reads as genuinely unintentional because there is no contrast and no structure. The celebrity approach is almost always to balance a relaxed bottom with something fitted or structured on top, or vice versa. A fitted ribbed tank with wide, relaxed sweatpants. An oversized coat over a slim-cut sweat. The contrast between the two creates an outfit rather than just a comfortable set of clothes.

Rule 2: The Shoe Makes Everything

Nothing elevates a pair of sweatpants faster than the right shoe. Clean white sneakers add casual polish. Loafers add a smart-casual sophistication that no one expects with sweats and is therefore extremely effective. Ballet flats bring a feminine, editorial quality to the combination. Even a simple slide can work if the rest of the look is considered. What does not work: ratty sneakers, chunky athletic shoes that match the energy of the sweatpants rather than contrasting it, or shoes that look like you genuinely just rolled out of bed.

Rule 3: Invest in the Sweatpant Itself

The quality of the sweatpant matters more than almost any other styling decision you can make. A well-made sweatpant in a quality fabric, with a clean silhouette, a proportionate fit, and a color that works with the rest of your wardrobe, is the foundation of every great sweatpant look. A cheap, misshapen, or poorly fitting sweatpant will read as exactly that, regardless of how good the shoes are. Celebrities are wearing well-made sweats. That is a significant part of why they look good.

Rule 4: Tonal Dressing Is Your Best Friend

When in doubt, wear one color head to toe. All grey with silver jewelry. All chocolate brown with suede boots. All black with black shoes and minimal accessories. Monochromatic sweatpant dressing is one of the most reliable ways to look intentional, expensive, and put-together without any complicated styling decisions. The sweatpants look like a choice rather than a default.

Rule 5: One Elevated Piece Changes Everything

A trench coat. A structured blazer. A sharp leather jacket. A great bag. One elevated piece worn over or alongside sweatpants shifts the entire register of the outfit. The contrast between the casualness of the sweats and the polish of that one elevated element creates exactly the kind of interesting tension that makes an outfit look genuinely fashionable. This is the secret weapon of almost every great celebrity sweatpant look: there is always one thing in the outfit that has no business being there, and that is precisely why it works.

Rule 6: Keep Accessories Clean and Deliberate

Chunky gold earrings with grey sweats. A structured tote with a matching set. A sleek pulled-back ponytail that says "I meant to look like this." The accessories in a great sweatpant outfit are never an afterthought. They are the detail that signals to everyone else that this is a considered look, not a lazy one.

The Combinations That Always Work

A few specific styling formulas that are consistently worth reaching for:

Sweatpants and a blazer. The juxtaposition of a sharp blazer against the softness of sweatpants is one of the most reliably fashion-forward combinations available. Wear it open, add a simple fitted top underneath, and finish with loafers or clean sneakers.

Sweatpants and a trench coat. Sweatpants underneath a classic belted trench coat is the airport-to-errand formula that every well-dressed off-duty celebrity knows by heart. It is comfortable, it looks polished, and it works for almost every occasion short of a black-tie event.

Sweatpants and ballet flats. One of 2025 and 2026's most referenced celebrity styling choices is sweatpants paired with classic flat shoes rather than sneakers. The unexpected formality of the flat shoe against the relaxed sweatpant creates something that feels editorial and intentional.

The matching set. Coordinating sweatpants and sweatshirt in the same fabric and color is the contemporary equivalent of the Juicy Couture tracksuit: simple, deliberate, and more stylish than it has any right to be when done with care.

Sweatpants tucked into boots. A slightly wider sweatpant or jogger tucked into knee-high boots creates an unexpected and genuinely interesting silhouette. The fullness of the sweat creates a slight puff above the boot that is very much intentional.

The Bottom Line

Sweatpants went from athletic necessity to cultural status symbol over the course of about a century, and their journey is not finished. They are embedded in the vocabulary of fashion in a way that no amount of trend cycling is likely to undo, because comfort is not a trend. It is a direction of travel.

The celebrities who wear sweatpants best are not wearing them because it is easy. They are wearing them because they know exactly how to make comfort look intentional. And with the right shoe, the right top, the right coat, and the right level of confidence, so can you.