How to Wear Boyfriend Jeans: Outfit Ideas

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What to Wear With Boyfriend Jeans

Street style boyfriend jeans and tweed jacket
Christian Vierig/Getty Images

Boyfriend jeans may have started as a trend, but today the boyfriend is a staple jean in many women’s wardrobes. Boyfriend jeans can be baggy or slim, cuffed or not. This jean style is typically fitted at the hips, with a more relaxed fit through the legs. You can style boyfriend jeans to create plenty of fashionable outfits, from the ultra-casual to dressier ensembles that work for date night. Take a look at these stylish outfit ideas for what to wear with boyfriend jeans now. Before you buy a new pair, learn which boyfriend jeans flatter your body type.

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Boyfriend Jeans With a Button-Down Shirt

Street style ripped jeans
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This easy, sexy look is a great reminder of why we started stealing jeans from our boyfriends in the first place. A crisp, white button-down shirt looks downright alluring when paired with slim boyfriend jeans, like the ultra-distressed, cuffed denim style pictured here. Add some accessory love, in the form of a fabulous shoulder bag and statement shoes, for a cheeky girl-meets-boy outfit.

Shop for distressed boyfriend jeans on Amazon.

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Boyfriend Jeans With a Bold Top

Street style in jeans
Edward Berthelot/Getty Images

What could be easier for casual denim days at work than a buttoned shirt and blue jeans? We love the way these high-waisted boyfriend jeans look with a boldly patterned shirt. Tuck in the shirt to highlight your waist and add a matchy-matchy leather purse and shoes for a simple, pulled-together look you can wear easily to work.

Shop for high-waisted boyfriend jeans on Amazon.

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Boyfriend Jeans With a Black Leather Jacket

Street style leathe jacket and jeans
Vanni Bassetti/Getty Images

Blue jeans and a leather jacket have been cool since the days of James Dean and Marlon Brando in the 1950s. Look like a beautiful rebel in a fitted motorcycle jacket, striped T-shirt, and relaxed boyfriend jeans, like this high-waist, distressed pair. Classic black sunglasses and basic white sneakers are the perfect additions to this casually cool look that's perfect for weekends.

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Boyfriend Jeans With a Beige Leather Jacket

Street style jeans and leather jacket
Christian Vierig/Getty Images

Here’s the classic jeans-and-leather jacket-combo again, just styled in a different way. Take a look at how swapping out the black motorcycle-style topper for a ladylike, buttery beige leather jacket instantly changes this look into something more special. Wear this comfortable fashion combination on a movie date, gallery hopping, or out shopping with friends.

Buy a beige leather jacket on Amazon.

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Boyfriend Jeans With a Sweater

Street style jeans and sweater
Christian Vierig/Getty Images

Guys pull on jeans and a sweater and go, so why not you? Boyfriend jeans, like this clean-cut, dark wash pair, and a sporty striped sweater make an easy, trendy weekend outfit. Add a dose of style while keeping things comfortable with metallic loafers and a colorful bucket bag.

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Boyfriend Jeans With a Tailored Jacket

Street style jeans and designer purse
Christian Vierig/Getty Images

Slouchy boyfriend jeans can look surprisingly office-appropriate, as seen in this street-style outfit. If you work in a more creative field, you can wear boyfriend jeans to work by dressing them up with a tailored jacket, a simple top, and black leather ankle boots. Finish your office ensemble with expensive-looking extras like an oversized statement bag that shows you mean business.

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Boyfriend Jeans With a Cropped Jacket

Street style jeans and tweed jacket
Timur Emek/Getty Images

.Here's another look at how even vintage-inspired boyfriend jeans in a lighter wash can look appropriate for work and later. Create an outfit you can wear to the office and then out for after-five cocktails with straight-leg boyfriend jeans, a spaghetti-strap tank top, cropped tweed jacket, and high-heeled shoes. Carry a large leather tote bag for office hours, then swap it out for a smaller clutch when you're ready to hit the bar with friends. 

Shop for tweed jackets on Amazon.

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Boyfriend Jeans With a Boyfriend Blazer

Street style boyfriend jeans
Edward Berthelot/Getty Images

Play with a stylish menswear look in full-length, boyfriend-fit jeans topped with a turtleneck sweater and menswear-inspired blazer. A leather crossbody bag, ladylike watch, and ankle boots are the perfect finishing touches.

Shop for crossbody bags on Amazon.

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Boyfriend Jeans With a Bomber Jacket

Street style boyfriend jeans
Edward Berthelot/Getty Images

Want a great, tomboy-chic weekend outfit that pulls off the perfect balance of casual and put-together? Take a pair of cropped boyfriend jeans with rolled cuffs, layer on a crisp white shirt, and top it all with a colorful bomber jacket. Finish your trendy outfit with a crossbody bag and wear it with casual sneakers. Or for a next-level look, mix things up by adding sexy, strappy high heel sandals.

Shop for women's bomber jackets on Amazon.

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Boyfriend Jeans With a Floral Blouse

Street style boyfriend jeans
Christian Vierig/Getty Images

Mixing male and female fashion influences is a great recipe for a stylish outfit. Pair relaxed, high-waisted boyfriend jeans with a feminine floral blouse and high-heeled ankle boots for a pretty, easy look you can wear on dates or out to brunch. 

Shop for high-waisted boyfriend jeans on Amazon.

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Boyfriend Jeans With a Feminine Top

Street style ripped jeans
Vanni Bassetti/Getty Images

A lacy, ruffled, feminine blouse makes a fun, sexy counterpoint to distressed, relaxed-fit jeans. Add an eye-catching statement shoulder bag and exotic animal-print boots, and you've got a great outfit you can wear gallery hopping, out to dinner, and on date night.

Shop for distressed boyfriend jeans on Amazon.

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Boyfriend Jeans With Denim on Top

Street style double denim
Claudio Lavena/Getty Images

Double denim is a major trend in women’s fashion that keeps on going strong. For a classic, all-American take on this fashion trend, pair slim-fitting, high-waisted boyfriend jeans with a basic denim jacket and colorful red, white, and blue sweater. If you’re tall and slender, you can get away with wearing a similar wash (color of denim) on the top and bottom. To camouflage a bottom-heavy figure, wear dark-wash boyfriends with a lighter jacket fabric.

Shop for denim jackets on Amazon.