I Spent a Decade Perfecting How to Style Boyfriend Jeans—Here's What I Learned

I learned how to style boyfriend jeans long before they were trendy (and before I had a boyfriend to steal jeans from). My preteen self used to scour the men’s rack to buy pairs of baggy jeans because the women’s department mostly displayed straight-leg or skinny jean styles—silhouettes that didn’t align with my tomboy aesthetic.

I eventually became known for my too-large pants that, without the help of a belt, easily slid down my hips. So needless to say, I was grateful when boyfriend jeans gained popularity, and denim brands started manufacturing a slouchy silhouette with a woman’s physique in mind. This is my very long-winded way of saying: I’ve been wearing boyfriend jeans for over a decade, and I have a wealth of knowledge when it comes to tips and tricks on how to style them.

But first, it’s important to distinguish the difference between mom jeans and boyfriend jeans. Mom jeans resemble those ’80s high-waisted, classic Levi’s jeans that are neither too slim nor too baggy. They taper in at the hem yet are a little roomier than a straight-leg jean. Boyfriend jeans, on the other hand, are baggy jeans that typically hang off the hips—much like you would find on men’s jeans—though more modern iterations offer high-waisted versions as well. Think of them as extra-wide-leg jeans, providing optimal comfort and endless styling potential.

Most styling tricks for boyfriend jeans are quite simple, because the statement jeans already carry the weight of the outfit. A look can be as simple as starting with a white long-sleeve tee, slipping into an oversized blazer, and draping a sweater over the shoulders.

How I style boyfriend jeans with a blazer

How I style boyfriend jeans with a leather jacket

How I style boyfriend jeans from day to night

Want more? Here are 10 more ways to wear boyfriend jeans this fall.

Preppy With a Striped Polo

Preppy chic continues to reign in 2026, and striped polos happen to pair perfectly with this denim style. Whether you opt for high-rise jeans with a cropped top, as shown above, or low-rise boyfriend jeans with a slouchy sweater is up to you—both styles make for great fall outfits. Finish with some comfortable sneakers and a statement earring or sunglasses.

With a Model-Off-Duty Leather Jacket

Fall is when all the lightweight jackets come out to play: that’s your blazer, your trench, and of course, your leather jacket. The combination of jeans and leather creates a much-loved model-off-duty look that’s both practical and effortless. I’ve been swapping out my pullovers for button-up cardigans lately—something that would layer well in this casual look.

The Office Boyfriend Jeans Outfit

You can always rely on your wardrobe classics, like a crisp button-down, to pair well with jeans. I love a loose fit on both the top and bottom. But if you want to create a little shape, simply tuck the top into your waistline or rely on a belt to visually break up the top and bottom halves. Because the outfit is more relaxed, balance your look with a more polished accessories.

With Chic Cardigans

While boyfriend jeans may look inherently more masculine, you can absolutely create a feminine ensemble by opting for a dainty top. Button-up cardigans, particularly figure-hugging ones, give you a ladylike appearance even with baggier jeans. Just make sure to opt for ballerinas, heels, or loafers to really drive home the look.

The Date Night Look

With boyfriend jeans, oftentimes the bottoms serve as the outfit itself. So keep the rest simple by opting for a white tank, tee, or long-sleeve T-shirt and heels. It keeps the attention on the pants, offering a ’90s look that remains as loved today as it was three decades ago. It’s surprisingly chic for a night out too, though the heels can be swapped for sneakers for a more casual everyday fit. And considering these oversized pants tend to be extra long, the added elevation is as much a practical choice as it is a stylish one.

Denim-on-Denim, the Perfect Pair

An underrated yet comically easy look to pull off is the denim-on-denim trend. The key here is to opt for darker denim, think indigo or even black, in order to achieve a more polished appearance. An oversized denim button-down is an excellent choice, but the jean jacket currently hanging in your closet will do just as well. Just make sure to pick pieces that match in hue as closely as possible. Lastly, pointed ankle boots and a top-handle bag give it that editorial finish.

The Airport Chic Look

On a recent flight back to New York, the stewardess complimented my travel outfit, and I never felt more seen. I was wearing high-waisted boyfriend jeans, a sweatshirt, and an overcoat—nothing worth writing about, but chic enough to feel put together in a public space. The best airport outfits are just that: comfortable but not sloppy, and styling your boyfriend jeans correctly will win you major travel points.

With a Fall-Appropriate Turtleneck Sweater

Once sweater weather arrives, it's time to bring out the knits and turtlenecks and style them with boyfriend jeans. A blazer or leather jacket layers nicely over the combo, too. Since the outfit is rather simple, accessorize with some sunglasses, earrings, or hats to add a little visual flair.

The Power Blazer

I’ve worn this formula plenty of times before: the fitted T-shirt, baggy jeans, and blazer combo. It’s that laid-back, borrowed-from-the-boys style that wouldn’t be half as cool without the boyfriend jeans. Finding the right blazer is important here too. You don’t want anything too fitted—oversized and boxy is the way to go.

With Pops of Color

My preference is to not mix too many colors in one outfit (though I know plenty of stylish women who would disagree). And because blue jeans count as a color, if I wish to wear, say, a bright striped button-down on top, then I would opt for gray, black, or dark indigo jeans. The street-style star here demonstrates this theory perfectly: The red stripes truly pop when styled with a darker pair of boyfriend jeans. Any colorful blouse will do, but you can try a similar look yourself with the picks below.