Isn’t there something so freeing about wearing clothes that are meant for men? Whether you’re into the “let’s borrow from the boys” idea of womenswear inspired by menswear, you shop in the men’s section, or you just straight-out steal from your partner’s wardrobe, we can all agree that the menswear aesthetic is just as fitting on women as it is on men. So that’s why androgynous aesthetic of boyfriend jeans is one of those “wow, I wish I’d thought of that myself” things. A pair of jeans, designed for women, but inspired by menswear fits. Why didn’t we think of this sooner? The answer is: we did.

Although many people believe boyfriend jeans are a fairly new trend, this loose-fit denim actually goes all the way back to the 1960s when Marilyn Monroe was spotted in relaxed boyfriend jeans on the set of her film, Misfits. That wasn’t the first time Marilyn’s style was a bit off-kilter, but people all over the globe were shocked by her shift in style, a far cry from the starlette’s figure-hugging and revealing outfits. Though the boyfriend jeans didn’t become extremely popular at the time, Marilyn brought the style into the mainstream world of her era and showed that women can look beautiful without the body-clinging fits and tight clothing that she was usually known for wearing.

Boyfriend jeans send a subtle-yet-powerful statement of equality. They show that women can (literally) “wear the pants” and express themselves freely too, but most importantly, boyfriend jeans are comfortable. And they look good.

A handful of decades after Miss Monroe shocked the world in her menswear-inspired denim, boyfriend jeans garnered a whole new wave of popularity by another popular trendsetter: Katie Holmes. In 2009, Holmes was strutting around NYC after a dress rehearsal, and the one thing everyone noticed about her outfit was her extremely loose-fitting jeans, which she had actually stolen from husband Tom Cruise’s closet. At that moment, the term “boyfriend jeans” was born, and the style rapidly became one of the most sought-after denim looks for women. Even now, you can catch all of the hottest it-girls and style influencers snapping photos of themselves in a pair of boyfriend jeans.

With all the democracy in denim today, which boyfriend jeans will you choose: a pair marketed for women, or a pair snagged from the men’s section?

Whichever you prefer, there are plenty of boyfriend jeans out there, so we’ve narrowed down the list to show you the best of the best.

3X1 Burke Embellished High-rise Boyfriend Jeans


Woman Burke Embellished High-rise Boyfriend Jeans Mid Denim Size 28

$425 $191

A high-waisted pair of boyfriend jeans to give off that laid-back vibe at the hips, with a vintage-inspired embellishment and crop ankle finish to keep a feminine edge in the look. Team with pair with some classic loafers.

AG Jeans The Ex-Boyfriend Slim Jeans


The Ex-Boyfriend slim jeans

$338 $236

A more slimming take on the favored style, this pair features a mid-wash with a slightly distressed finish and cuffed ankles. This jean pairs perfectly with a knitted sweater and Chelsea boots.

Ei8ht Dreams Distressed Slim Boyfriend Jeans


Distressed Slim Boyfriend Jeans

$270 $83.99

A light-wash jean with exaggerated ankle cuffs and an understatedly distressed finish. This boyfriend jean is a great piece to wear when you need an easy go-to look, and you want to highlight some simple basics. Wear this jean with a plain white t-shirt and a neutral color pump.

Frame Denim Le Garcon Boyfriend Jeans


Le Garcon Boyfriend Jeans in Silva


Perfect for an all-out relaxed vibe, this medium wash pair of jeans works just as well with a thin canvas sneaker or dad sneaker as it does with a feminine pair of ballet flats or kitten heel. Wear this jean with literally any top, because its wash and cut are so versatile that you can.

7 For All Mankind Josefina High Waist Boyfriend Jeans


Josefina High Waist Boyfriend Jeans

$219 $86.99

The iconic boyfriend jean style takes a turn toward the trends with this pair from 7FAM. Its high length and dramatic rip detailing join forces with a high waist to allow for an utterly distinctive look. Wear this pair with a black turtleneck and animal print flats for maximum effect.

Citizens of Humanity Liya High Waist Boyfriend Jeans


Liya High Waist Boyfriend Jeans, Size 30 - Blue


shredding cotton denim pair with an authentic vintage look, these boyfriend jeans give off a slouchy feel at the legs with a cuffed, ankle-grazing hems to tie the look together. This pair looks awesome with loafers and a basic top.

Citizens of Humanity Liya High Waist Slim Boyfriend Jean


Liya High Waist Slim Boyfriend Jeans, Size 26 - Red

$258 $154.8

Done in red, Citizens of Humanity’s Liya jean is completely different from its gray counterpart. This pair makes a statement for you, no work necessary. Just slide into the relaxed fit and pick a dark pump or loafer to pair with the ankle-grazing hem.

Replay High Waist Slouchy Boyfriend Jean


High Waist Slouchy Boyfriend Jean with Slogan Back Pocket - Blue

$198 $79

A light wash pair with the ultimate relaxed leg for impeccable laissez-faire style. With a greater length than most boyfriend jeans, this pair by Replay still features the same accentuated high waist. Try wearing this one with a slightly cropped top and a pair of canvas sneakers to complete the look.

Paige Denim Brigitte Transcend Vintage High Waist Crop Boyfriend


Brigitte Transcend Vintage High Waist Crop Boyfriend Jeans, Size 23 - Blue

$219 $118.2

A sleek pair in a dark wash with contrasting cuffed hems and a high waisted finish. This pair boasts a modern, sophisticated take on the iconic boyfriend style.

And if you’re sold enough on boyfriend jeans and actually ready to borrow from the boys…

Jack & Jones Intelligence Jeans in Loose Fit


Intelligence Jeans in Loose Fit - Blue

$103 $41

A classic jean in a medium wash with a simple fit on the leg and a cuffed ankle. If this men’s style fits too long, try rolling the cuffed ankles up a bit more. Make this men’s style the contrasting centerpiece to an on-trend womenswear look by teaming it with D’Orsay pumps and a tucked-in top.

Topman Crop Wide Leg Jeans


Crop Wide Leg Jeans

$75 $18.75

A dark-washed jean with a wide fit and straight cuffed ankle. Unlike our previous menswear piece, this Topman style is designed with a wide leg, allowing an ultra-wide leg when used as a womenswear style. This boyfriend jean looks great with flats, but if the jean is too long, pair it with a pointed-toe pair of pumps. Play into this jean’s overtly relaxed fit by teaming it with a cozy knit sweater, perfect for early fall days and on-trend looks.

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