Celebrity Stylist Shares the 7 Best Shoes To Wear With Baggy Jeans Morgan McMurrinOctober 5, 2025 at 9:10 PM 0 Shorts season is coming to a close, and it's officially time to welcome jeans season back. This means there's a whole new world of styles to explore.
- - Celebrity Stylist Shares the 7 Best Shoes To Wear With Baggy Jeans
Morgan McMurrinOctober 5, 2025 at 9:10 PM
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Shorts season is coming to a close, and it's officially time to welcome jeans season back. This means there's a whole new world of styles to explore. One of the hottest trends this fall? Baggy jeans. While their loose, relaxed fit can sometimes feel intimidating to add to your wardrobe, that's usually because people aren't sure what to pair them with—whether that means tops or footwear. To help you figure it out, we've gathered the best shoes to wear with baggy jeans, straight from a celebrity stylist's playbook.With decades of fashion experience in Hollywood dressing celebs like Fran Drescher, Jamie Lee Curtis and Molly Shannon, stylist and authorBrenda Cooper has mastered the art of styling A-listers. Thanks to her unmatched ability to blend textures, silhouettes and accessories, she's the perfect person to get advice from. She not only breaks down what types of shoes look great with loose denim, but she also reveals some dos and don'ts on how you can style baggy jeans too.That way, the next time you pull out a pair of these bottoms from your closet, you'll know exactly what you should wear with them. Whether you're going for a laid-back vibe or something more polished, you'll feel confident in your choice. So, what are you waiting for? Find out everything there is to know about baggy jeans below!Related: 7 Best Ways To Style Wide-Leg Jeans at Any Age, According to a Stylist
How To Style Baggy JeansAs a layered outfit
When it comes to styling baggy jeans in general, you can't go wrong with layers. Which is also perfect for those brisk fall days."A layered look is good because baggy jeans provide a beautiful, relaxed canvas, almost like a blank slate," Cooper tells Parade. "When you layer on a fitted tee with a great cardigan, a blazer or even a chic trench, it adds a sense of deliberate complexity."She says that "because of this, you get to play with different fabrics, lengths and textures, creating a dynamic look that's both effortless and incredibly stylish." She also shares that baggy jeans give you a great base that you can add onto."The jeans keep you grounded and cool, while the layers let you express your personality and play with different silhouettes," she explains. "It's like painting with clothes—the jeans are your canvas, and the layers are your masterpiece."
With slightly rolled up bottoms
A lot of people have strong opinions on cuffing (or even double-cuffing) jeans. But Cooper shares that "slightly rolling the bottom of baggy jeans is a quick and effective styling trick" that adds a new element to your 'fit."It elevates the look from sloppy to effortlessly cool," she explains. "Intentionality is key, as baggy jeans that are too long can look ill-fitting. A simple cuff creates a clean, intentional hemline that balances proportions. And because baggy jeans have a lot of volume, cuffing them creates a visual anchor at the ankle, which helps to balance the silhouette and prevents the frame from being overwhelmed by the fabric."
But, do not wear with an oversized top
Of course, you can do whatever you'd like when it comes to your personal style. But if you're looking for an expert's opinion? Stay away from baggy tops with your baggy jeans."The biggest no-no is wearing baggy jeans with an oversized, shapeless top," Cooper advises. "I call this the 'lost in the laundry basket' look. It's a style crime! You lose all sense of your silhouette, and it just looks like you're wearing clothes that don't fit. You're not a tent, so don't dress like one!"Related: A Celebrity Stylist Is Begging Women To Follow the '3-Color Rule'
What Do Baggy Jeans Look Good With?A fitted top
Okay, so if baggy jeans don't look great with an oversized top, then, of course, it makes sense that they do look good with the opposite."This is a beautiful contradiction, a high-fashion tug-of-war of sorts," Cooper says about this duo. "Since baggy jeans are all about that effortless attitude—with their relaxed fit and cool-girl slouch—and a fitted top is a confident, polished counterpoint as it hugs your body and defines your waist, together they create the perfect yin and yang of an outfit."Again, it's all about equilibrium in your outfit, and these two do well in that department."The volume of the jeans is balanced by the sleekness of the top, so you get the best of both worlds: a look that's comfortable and casual, but also chic and put-together," she shares.
A belt
Even if you don't like belts or don't really need one to keep your baggy jeans up, they do add a great focal point that elevates your outfit."A belt is your secret weapon for creating a waistline," Cooper reveals. "Baggy jeans are all about volume, but without a point of definition, you can lose your shape entirely. Cinching with a belt gives you a perfect hourglass silhouette."Related: 7 Best Ways To Style a Jean Jacket, According to a Celebrity Stylist
7 Best Shoes To Wear With Baggy Jeans, According to a Celebrity Stylist1. Black tie-up boots
Now that you know the basics about styling a look with baggy jeans, you'll want to pick out the best shoes for your outfit. The first expert-approved shoes for baggy jeans are black tie-up boots."These boots demonstrate the perfect way to keep a casual outfit elevated," Cooper notes. "It's all about adding a touch of refinement to a relaxed silhouette. But the absolute key is managing the proportions—the sweatshirt or the pants can be baggy, but not too baggy. We want effortless style, not a tsunami of fabric where the clothes are wearing you."She tells Parade that, in her opinion, there are two great ways to style this look."I think the best way to pair baggy jeans with combat boots is to make sure you can actually see the boot. After all, the boot is the anchor of the look, and you can't lose it," she states. "You can do a simple tuck, though, by pushing the hem of the jeans right into the top of the boots. Or, for a more deliberate, funky look, you can take a ribbon and tie it around the bottom of your baggy jeans at the ankle. This secures the fabric and creates a great shape, guaranteeing your shoe to be the star. It's that little detail that makes the whole outfit look intentional."
2. Ballet flats
Ballet flats are having a serious comeback at the moment. But for Cooper, they never went out of style. And that's thanks to the fact that they're so versatile (which is why they also pair well with baggy jeans)."In my book and style system, The Silhouette Solution, I've got eight shoes to help you build your basic wardrobe, and of those, one of my favorite shoes is the classic ballet flat," she notes. "I love that they are so versatile that they can be paired perfectly with baggy jeans. I especially love the balance of this outfit. The only thing I might change would be adding a pair of gold or red ballet flats instead. They would just add a pop of color, shine and femininity that's actually very elegant."Related: 8 Things You Need To Build a Capsule Wardrobe, According to a Celebrity Stylist
3. Sneakers
Sometimes, when figuring out an outfit, it's best not to overthink things. And this can mean going back to the basics with sneakers. Be mindful, though."When styling baggy jeans with sneakers, you must think in terms of balance," Cooper instructs. "A platform sneaker with a bit of a heel isn't just a suggestion—it's a necessity and the secret to elevating the entire silhouette and preventing the look from feeling bulky."She does note that "an outfit without polish is just... clothes," so it's important to "add some pizzazz" to your look. "Wearing a scarf in a bold, contrasting color—think a vibrant cobalt blue, a sunny yellow or a shocking pink—is an absolute non-negotiable," she suggests. "A multi-layered necklace would also add some subtle drama to the overall look, creating a focal point that's both elegant and entirely unexpected with a pair of baggy jeans."
4. Pastel pointed pumps
If you love heels and want to dress your jeans up a bit, then some pointed pumps will do the trick."A monochromatic look with sharp, pointed pumps is absolutely divine—it's sleek, elegant and elongating," Cooper reveals.Don't stop there! She says that by incorporating some accessories, you can make your baggy jeans look even more chic."Adding a big, bold flower brooch or a charming pocket scarf is the perfect way to bring in personality and 'oomph' to the look," she shares. "It creates a beautiful point of interest and breaks up the clean lines with a touch of fun. It's all about adding that perfect finishing touch."Related: 6 Best Ways for Women To Style a 'Barn Jacket' This Fall, According to a Celebrity Stylist
5. UGGs
Say what you want about UGG boots, but they're not only comfortable, they also go great with baggy jeans."This look shows the brilliant, often-overlooked secret to mastering bulk," Cooper says about this outfit. "The genius of this look is the knitted vest paired with the baggy jeans and UGGs. It's not about adding; it's about editing. The vest slices through the weight of the bulkiness and creates a completely new, polished silhouette. It adds a whisper of texture without a single ounce of heaviness, showing you the right way to wear UGGs with baggy jeans."She says that she likes the style so much that she would only make one small fix."I would just tie something around the ankles of the baggy jeans to give this a more blouson look," she tells Parade.
6. Loafers
"This outfit is the perfect example of the core style principle that your shoe choice is the message of your outfit," Cooper explains. "In this look, the loafers are a statement. That single element immediately tells a story. Pairing those loafers with baggy jeans and a jacket instantly creates a very preppy, very classic look. It's clean, it's smart and it's a great foundation."When it comes to styling this look herself, she reveals that she would add a couple more pieces."If I were to add anything to this outfit, it would be a shirt and tie," she dishes. "The tie would lean into the collegiate feel, making it even more preppy, but it would also add that little funky element. It's that unexpected twist that would create a look with a unique personality."
7. Wedged shoes
Combining a couple of shoes we already mentioned—platform sneakers and UGGs—this look incorporates tall, wedged shoes to make your baggy jeans stand out. You can choose anything from platform clogs to wedged heels and more to achieve this look."Jennifer [Lopez] really hit it out of the park with this look, didn't she? A perfect 10," Cooper exclaims. "I absolutely love how she's paired that elegant, form-fitting top and wedged shoes with her baggy jeans. It's a fantastic contrast that works so well, creating a look that's both polished and effortlessly cool."When it comes to her own styling of this look, she shares that she would add a classic accessory."If I were to add a little something, it would be a belt that matches her purse," she shares. "I don't care what anyone says—matching your belt to your purse gives a traditional look a sense of polish and a finished, intentional feel. It's a small detail that makes a big impact."Up Next:
Related: 7 Best Ways To Style a Vest in 2025, According to a Celebrity Stylist
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Brenda Cooper is a celebrity stylist who's dressed celebs like Jamie Lee Curtis, Molly Shannon and Fran Drescher.
This story was originally reported by Parade on Oct 5, 2025, where it first appeared in the Life section. Add Parade as a Preferred Source by clicking here.
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