Jeans are one of the most tried and true styles out there for a reason. Whether you prefer a wide-leg or flares, there are so many stylish pairs out there just waiting to be worn. No matter the season, there’s also always a way to wear them that’s chic, polished, sophisticated or even casual-yet-cute. Celebrity stylists love styling denim because there are endless wardrobe essentials to pair them with—from ballet flats to ankle boots. And more recently, they say there’s one niche style in particular that’s ready to take the season by storm: low-rise baggy jeans.
While this style lost a bit of favor after the early 2000s, celebrity stylist Mickey Freemanswears that they’re back and better than ever. He loves styling them for his celebrity clients—which includes Keke Palmer, Peyton List, Dasha Polanco, Kyla Pratt and Paige Buckner—and he’s giving the inside scoop on how you can rock this style here in 2026, too.
Think oversized tees, varsity jackets, sheer tops and ’90s accessories. Even if you never wore this look back in the day, now is the time to try since Freeman says they’re about to be everywhere for spring. To find out how to style low-rise baggy jeans and get all his best styling advice, along with seven outfit ideas, read on.
Related: Here’s Exactly How To Style Straight-Leg Jeans, According to Celebrity Stylists
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How To Style Low-Rise Baggy Jeans
Stylists like Freeman say low-rise baggy jeans are one of spring’s most versatile trends. For starters, there are so many ways to dress them up or down, and you can build out a wardrobe that contains a variety of pieces that they pair well with.
“It’s essential to invest in unique pieces like elaborately embellished or embroidered tops and accessories such as silk scarves, corsets, iconic jackets, clutches, statement jewelry, gloves and belts,” the stylist says. “[You’ll also want to invest in] stylish footwear like boots, clogs or mules, as the trend of mixing high and low-value items continues to rise.”
One of his favorite approaches is balancing masculine and feminine elements in the same outfit.
“[This is where] garments above the jeans’ waistline convey feminine energy, while those below offer a masculine touch,” Freeman adds. “To achieve this, first identify the pants’ waistline, which serves as a guide to separate the two styles in your outfit.”
A successfully balanced look can be created by pairing low-rise baggy jeans with classic styles like Timberland boots (Freeman says he prefers the classic Nubuck ones), and a white fitted tank top made from delicate fabrics like silk, satin or lace.
“Bralettes are also a great option, especially when crafted from delicate materials, and for added flair, consider more rigid fabrics—denim on denim works wonderfully,” he continues.
For a trendier, summer-ready look, Freeman also says you can style low-rise baggy jeans with a one-piece swimsuit or a bathing suit top. He says you can even add a pair of Crocs if you’re into the look.
“Pair a matching denim bralette with a cropped denim jacket for cooler evenings, and complete the look with denim chunky boots or patchwork denim booties for a striking monochromatic effect,” he suggests. “This balance not only channels your inner Aaliyah, but also adds an edgy flair by transforming a fitted white T-shirt into a DIY cropped top, which can be paired with Dr. Martens combat boots for a bold statement.”
Related: 7 Best Jeans for Curvy Women, According to Celebrity Stylists
How To Avoid Looking Frumpy in Baggy Jeans
While low-rise baggy jeans are one of the season’s biggest style hits, it’s easy to get swallowed up by fabric if you don’t have the right tips. To avoid looking frumpy when wearing baggy jeans, Freeman says to consider incorporating a corset into your outfit. He even says this is set to be a significant trend in 2026.
“Corsets offer timelessness, sexiness and versatility, making them suitable for various occasions and body types,” he shares. “Whether worn under or over a top, or even by itself, a corset can enhance your silhouette and provide an immediate flattering shape. This stylish addition can be paired with sneakers for a casual look or chic boots for a night out, allowing for personal expression and thoughtful wardrobe choices.”
He also adds that choosing the right corset or shapewear can breathe life into your experience with baggy jeans. The same goes for your intimates.
“Many women and men make the mistake of not paying attention to their choice of undergarments every day,” he warns. “The type of intimates one chooses can completely alter how an undergarment fits and, most importantly, affect overall comfort. By making these thoughtful choices, you can elevate your style and avoid the frumpy look often associated with baggy jeans.”
Related: 9 Best Jeans for Short Women, According to a Celebrity Stylist
7 Best Ways To Style Low-Rise Baggy Jeans, According to a Celebrity Stylist1. With a sporty-chic hoodie or jacket
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Pairing your low-rise baggy jeans with an oversized top, hoodie or jacket can create a sporty-chic look.
“This ’90s revival style is appealing because it blends comfort and a laid-back vibe,” Freeman says. “To achieve this look, opt for neutral colors or fun patterns that reflect your personality. My styling tip is to accessorize with chunky sneakers or combat boots to complete the tomboy essence.”
2. With early 2000s accessories and graphic prints
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According to Freeman, incorporating a bejeweled choker, oversized tee and fishnet stockings creates a cool early 2000s emo aesthetic when styled with low-rise baggy jeans.
“I love this look for its edgy and expressive nature,” he shares. “Perfect for making a bold statement.”
To style this look effectively, he says to ensure your oversized tee has a unique graphic or message, and mix textures by adding a leather jacket.
“Don’t forget to layer on the accessories for that quintessential emo flair,” he adds.
3. With an oversized tee
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Similar to the punk-feminine look, Freeman says going for the skater boy aesthetic is another perfect pairing with this style. For this, he says to try an oversized tee paired with your low-rise baggy jeans.
“I appreciate this style for its casual and carefree attitude,” he explains. “When styling, choose vibrant colors or fun graphics on your tee to inject energy into your outfit. Pair it with skate shoes for an authentic vibe, and consider adding a snapback hat for a touch of flair.”
4. Layered with a kilt or skirt
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This might be a little out there for some, but if you’re feeling adventurous, Freeman says this is a total look.
“Adding a kilt or skirt over low-rise baggy jeans is a fresh way to layer and style your outfit,” he says. “I find this combination intriguing because it blurs traditional gender lines and encourages creativity. When layering, choose complementary colors and patterns, and consider contrasting fabrics for added interest. A fitted top can help maintain balance in the silhouette.”
5. With a dress shirt and tie
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For a more work-appropriate outfit, Freeman says to try styling your low-rise baggy jeans with an oversized or tailored dress shirt and tie. This can easily be taken from the office to after-work drinks or dinner, too.
“[This look] creates a chic and polished vibe,” he states. “I love this combination for its unique blend of versatility. For styling, ensure the dress shirt is slightly longer, and consider rolling up the sleeves for a relaxed feel. Pair this look with loafers or sleek sneakers to maintain that chic aesthetic. And don’t forget a belt!”
6. With a team jersey or varsity jacket
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For a fun and youthful take on low-rise baggy jeans, Freeman says to try incorporating a team jersey or varsity jacket.
“I enjoy this style because it embodies a playful spirit and can be very comfortable,” he adds. “When styling, choose bright colors or graphic prints that represent your favorite team or sport. Finish the look with sporty sneakers or slip-on shoes to enhance the overall casual vibe.”
7. With a sheer top
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Like Freeman mentioned above, adding a feminine flair to a traditionally masculine silhouette works really well here. He loves adding a sheer top or camisole to a low-rise baggy jeans look.
“Embrace an ultra-sheer top with low-rise baggy jeans for a sexy and chic statement,” he explains. “I love this look for its boldness and confidence it conveys.”
In terms of styling, he also says to choose slightly translucent tops, allowing a hint of skin while still being tasteful.
“Complement this look with simple jewelry and sleek sandals or ankle boots, striving for an effortlessly stylish appearance,” he notes. “And, a spring fur coat for layering for those cooler nights!”
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Related: Cuffed Jeans Are Trending for Spring—a Celebrity Stylist Shares the 7 Best Ways To Style Them
Source:
Mickey Freeman is a celebrity stylist who works with clients like Keke Palmer, Peyton List, Dasha Polanco, Kyla Pratt and Paige Buckner.
This story was originally published by Parade on Apr 12, 2026, where it first appeared in the Life section. Add Parade as a Preferred Source by clicking here.