30 Outfits To Check Before Wearing Your Boyfriend Jeans

By Kaia Saunders / February 16, 2017
Chic woman in pale pink blazer and boyfriend jeans

If there is one trend that continues to baffle fashion designers year after year, it has to be boyfriend jeans. Who would have thought that a baggy, over-sized style of clothing would remain popular for so long? Yet, nearly three decades after making its way onto the mainstream fashion scene, this tomboyish style is more on-trend than ever.

The truth is that boyfriend jeans have been around since the very beginning of denim back in the 1800s. Think of those classic Levi’s 501 jeans. The same comfortable, loose-fitting style so popular among the working class of the American public has not changed much over the years. What has changed, however, is the way that we style them.

Fast forward some 200 years and such jeans have become the hottest clothing item in the modern woman’s wardrobe. They are the go-to style choice when we want to look laidback and relaxed yet still modern and edgy. We can style them casually with a cotton T-shirt and sneakers or, for a more dressed up effect, with a leather jacket and stilettos.

But don’t just take our word for it. We’ve collected some of the trendiest styles of boyfriend jeans with the latest tips and tricks to make 2017 your most stylish year yet.

Boyfriend Jeans Can Be Chic & Sophisticated Too

1) A Vision in White

Stylish blonde in white boyfriend jeans and a lace top

An outfit of pure white gets edgy with lacy black stilettos (photo: tuulavintage.com)

Nobody can resist the classic allure of pure white. Indulge in the simple elegance and wear the color from head to toe, leading down to strappy lace-up stiletto sandals in contrasting black.

The rest of the outfit consists of high-waisted boyfriend jeans in ripped white denim plus a white mesh top adorned in lace and ruffles. This outfit strikes a fine balance between ultra-feminine and edgy – perfect for those days that call for a little sweet and sexy.

2) Studded Style

Chic brunette in studded jacket and ripped blue boyfriend jeans

Go back to black in an outfit of edgy studs and boyfriend jeans (photo: ashley-ringmybell.com)

What is your go-to outfit when you’ve got nothing to wear? If your immediate answer is ‘anything black’, may we suggest an update? Check out this pair: your choice of denim needn’t be overly baggy and ripped all over.

We love this sleek, elegant cut that still retains that trademark boyfriend fit. With only one rip along the right knee, this style is chic and elegant with a cuffed hem adding to the allure. Pair your denims with a simple black T-shirt and a fitted bomber jacket covered in studs. You can’t forget the accessories, of course. We simply adore these Christian Louboutin Pigalle heels and Alexander McQueen clutch purse.

3) Diamanté Darling

Stylish brunette in sequined top and blue boyfriend jeans

Sequins are always a good idea, especially when wearing boyfriend jeans (photo: andeelayne.com)

Those who prefer feminine, ladylike clothing needn’t be wary of the boyfriend trend. Make the baggy, loose-fitting style work for you by pairing your denims with the most sparkly accessories you own. Case in point: this brightly adorned diamanté off-the-shoulder top. It makes the ideal companion to cuffed, slightly ripped boyfriend denims. Nude-colored ankle strap stiletto sandals complete the glamorous ensemble, along with fine metallic jewelry.

4) Simple Classics

Brunette in blue boyfriend jeans and white blouse

Keep it cool and classic in basic blue denims and a crisp white shirt (photo: ashley-ringmybell.com)

Few outfit combinations can come close to the simple elegance of blue denim worn with classic white. Part-glamorous, part-tomboyish, this outfit playfully combines stonewashed blue jeans from H&M with a loose-fitting white button-up shirt. Round off this effortless ensemble with a dainty pair of Yves Saint Laurent ankle-strap sandals and fine gold jewelry to match.

5) Rosy Elegance

Chic woman in pale pink blazer and boyfriend jeans

A touch of baby pink adds a feminine touch to casual boyfriend jeans (photo: songofstyle.com)

If you tend to go for the finer things in life, boyfriend jeans may not be your natural first choice. We often think of them as being casual, laid-back and slightly tomboyish. This outfit, though, seen here on blogger Aimee Song, shows us how to put a feminine spin on the trend.

She opts for more fitted boyfriend denims featuring light rips on the knees and haphazard cuffs on the ankles. A light V-neck cotton T-shirt adorns the top, underneath a beautiful tailored blazer in baby pink. Adding to the girly persona, lace-up pointy stiletto heels tie it all together elegantly.

6) Yes, Pleats!

Stylish woman in white pleated top and cuffed boyfriend jeans

Show off a taut midriff in a pleated crop top and boyfriend jeans (photo: micahgianneli.com)

Chic and sophisticated doesn’t have to mean covered-up and conservative. Take a peek at this trendy street look, for example. The star of this outfit is a beautiful white box pleated silk top cut right above the navel.

This style is ideal for ladies keen to show off a toned midriff and a killer tan. Cuffed jeans sit easily just above the hips, leading down into nude-colored pointy stiletto heels. This look screams casual elegance with a side of attitude.

7) Black and Blue

Brunette in blue jeans
Brunette in blue relaxed jeans (photo: chicisimo.com)

Nice and comfortable combination for a stylish everyday look.

Casual Looks With Your Favorite Jeans

8) Cuffs and Stripes

Trendy blonde in white sneakers and boyfriend jeans

Take it easy in horizontal stripes and easy-fit denims (photo: vanilla-andvelvet.blogspot.com)

This look is designed for casual girls who like to take it easy and look good at the same time. Here we have an outfit made up of clean, crisp basics paired together effortlessly. An easy-fit striped sweater is the perfect match for loose boyfriend jeans cuffed right above the ankle. Finish off the daytime look with a pair of white platform sneakers and black round sunglasses.

9) Scarf Styling

Chic woman in boyfriend jeans and patterned scarf

Quirky Aztec print adds fun and dimension to this easy-going look (photo: polienne1.rssing.com)

If you find yourself gravitating toward loose-fitting clothing, this ensemble was made for you. A baggy white woolen short-sleeved sweater is roomy and comfortable but still stylish. Jeans here are cuffed above the ankles, showing off black and metallic strappy flat sandals. To add some color to the look, wrap an Aztec-patterned scarf around your neck. Polish off the easy-going ensemble with a cute black sling handbag.

10) Khaki Queen

Trendy woman in ripped boyfriend jeans and khaki shirt

A khaki shirt is the season’s most coveted casual style item (photo: polienne1.rssing.com)

The simplest outfits are usually the best outfits. When you’re looking for an easy-going, all-purpose ensemble, you can’t go wrong with ripped boyfriend jeans and a white vest.

This look goes one step further by throwing in a trendy touch – a parka-style khaki shirt. Whether you choose to wear it buttoned-up or hanging open like this, this is one style item that is sure to be around for many seasons to come. Spice it up by choosing a tasseled sling handbag in blush pink plus pretty beaded flat sandals.

11) Pretty and Petite

Cute brunette in acid wash boyfriend jeans and Birkenstocks

Petite frames get more definition thanks to clever styling tricks (photo: thriftsandthreads.com)

This look is ideal for women with a smaller, more petite frame. The key is to add shape and dimension in your slimmest areas to create the illusion of curves.

A top like this one highlights the shape of the shoulders, making them appear broader and more toned. These boyfriend jeans are also on the more petite side, with rips and rouging along the thighs and knees to create some more shape in this area. This easy-going ensemble is rounded off perfectly with a pair of Birkenstock sandals.

12) Perfectly Peplum

Stylish woman in blue boyfriend jeans and peplum top

A peplum blouse creates curves in all the right places (photo: thriftsandthreads.com)

Is there anything cuter and more ladylike than a peplum top? This outfit perfectly combines a bit of feminine finesse with the casual style of denims. Here we see a collared black peplum blouse worn with a pair of cuffed denims.

This style is particularly flattering for taller girls looking to create some curves around the hip area. Tying it all together is a trendy pair of peep-toe block wedge sandals from Zara. This ensemble would work equally well for a relaxed barbecue with friends or a day spent window shopping at the mall.

13) A French Affair

Trendy blonde in striped top and ripped boyfriend jeans

Get inspired by the French in classic stripes and dainty heels (photo: ahouseinthehills.com)

When the day calls for simplicity and style, look no further than the simple combination of denim and stripes. A black-and-white Breton-striped top will see you stylishly through many seasons and goes perfectly with any type of denim out there.

This pair of boyfriend jeans, for example, provides an edgy update to the classic Breton. The bold rips and distressed treatment provide a nice twist, especially when worn with dainty strappy stiletto sandals. Add a further daring element with a fold-over clutch purse covered in eye-catching leopard print.

14) Dusty Rose & Brown Leather

Stylish woman in pink cotton top and boyfriend jeans

Shades of brown and pink combine in a sweetly feminine ensemble (photo: wendyslookbook.com)

The boyish look may have been inspired by our love for baggy boyish fashion, but that doesn’t mean we can’t inject some feminine charm now and then too. This ensemble features classic boyfriend jeans cuffed above the ankles plus a brown leather belt tied around the waist.

For a ladylike touch, a longer-length cotton T-shirt in soft dusty pink is draped across the body and tucked in casually at the hips. Block sandals from Yves Saint Laurent complete the look as well as a matching handbag in brown leather by Mulberry.

15) Superstar Style

Trendy brunette in Adidas Superstar sneakers and boyfriend jeans

Channel your inner tomboy with boyfriend jeans and Superstar sneakers (photo: fustany.com)

Own the androgynous, boyfriend style by channeling some masculine energy into your ensemble. This pair is styled using typical male pieces. We love the simplicity of pure white Adidas Superstar sneakers for a sporty effect which fit perfectly with baggy cuffed boyfriend denims.

On top, a loose white cotton T-shirt is worn beneath a structured black blazer cuffed casually at the sleeves. The overall effect is athletic and trendy – perfect for an easy day spent with friends.

16) Lily of the Valley

Pretty blonde wearing a black hat, dressed up in lace-up bodysuit and ripped and cuffed boyfriend jeans

Show some skin if you dare in a V-neck lace-up bodysuit and blue jeans (photo: blameitonbarneys.com)

Check this ensemble – it’s laidback and easy-going while still incorporating two of the hottest trends right now – boyfriend jeans and lace-up necklines.

Trendy denims feature big, uneven rips right on the knees as well as jagged cuffs above the ankles. She complements them with a black bodysuit complete with a daring deep V-neck lace-up motif.

Get Urban and Edgy in Ripped Boyfriend Jeans

17) Black Leather Babe

Edgy brunette in black leather jacket and ripped boyfriend jeans

Let your inner rock chick run free in black leather and ripped denim (photo: trendytaste.com)

Who doesn’t love a bit of drama now and then? This outfit combines some rock star edge with a devil-may-care attitude. Looking at this ensemble, the eye is instantly drawn downwards to large, dramatic rips on the knees and upper thighs. This leads down to black lace-up sandals with a solid block heel.

On the top half of the body, we find a khaki-colored cotton vest worn underneath an edgy black leather jacket. This daring look gets even more edgy with a black leather sling handbag lavishly adorned in long leather tassels.

18) Brown elegance

Elegant woman in coat and jeans
Elegant woman in coat and jeans (photo: chicisimo.com)

19) Mellow Yellow

Edgy brunette in yellow camisole and ripped boyfriend jeans

A blend of soft yellow and gold jewelry adds sparkle to distressed denim (photo: ashley-ringmybell.com)

There’s something undeniably sexy about ripped boyfriend jeans and strappy barely-there heels. We love this look on style blogger and actress, Ashley Madekwe. She combines destroyed Ralph Lauren cuffed boyfriend jeans with a slip camisole in soft yellow and a thick brown leather belt across her hips.

A pair of Yves Saint Laurent ankle strap sandals ties it all together. This look is the perfect choice for a cheeky dinner date out on the town.

20) Cleverly Layered

Trendy blonde in black leather jacket and boyfriend jeans

The clever use of layering adds to the unique charm of the ensemble (photo: thebohoflow.com)

Layering different pieces of clothing is an art in itself. When the individual items are slouchy, however, it becomes even trickier. Take a style lesson from fashion blogger, Cristina Monti. Here, she wears a classic pair of distressed jeans cuffed above the ankles.

On top, we see multiple layers worn together at once: a long white T-shirt, a thick grey sweatshirt, and a black leather moto jacket. What makes this outfit work, is the clever combination of baggy and structured pieces worn in layers. For a more girly touch, floral-printed espadrille wedge sneakers and a suede leather handbag tie it all together.

21) Strappy Statement

Trendy woman in black strappy sandals and boyfriend jeans

The perfect accessory to boyfriend jeans: lace-up stiletto heels! (photo: songofstyle.com)

Edgy, urban and artsy – that’s the motive behind this cool city look. Pick out your most creative T-shirt or cut-off vest and style it with a pair of fool-proof slouchy boyfriend jeans. Whether it’s a T-shirt showing off your favorite musician or a souvenir from one of your travels, a graphic tee is a great way to inject some personality into your ensemble.

Then, to polish off the look, throw in some unexpected glamour in the form of sexy statement heels. We love this pair of strappy Giuseppe Zanotti lace-up stiletto sandals. For some extra oomph, choose a matching belt and chain-strap black leather handbag.

22) Ripped to the Max

Trendy woman in grey boyfriend jeans and pointy stiletto heels

The larger the rips, the better when wearing boyfriend jeans (photo: alex-closet.com)

Go big or go home – that’s the idea when it comes to ripping these slouchy boyfriend jeans. In a stonewashed dark grey color, this pair of denims provides all the drama you need in one look. All that is needed to complete the outfit is a loose-fitting light grey cotton T-shirt and pointy-toed stiletto heels. Complement these neutral colors with a simple black handbag featuring slight metallic touches.

23) Textured Tease

Edgy blonde in cuffed boyfriend jeans and black leather jacket

Throw on your favorite draped basics for an easy, comfortable day look (photo: fashioncorner.net)

Check out the different textures, layers, and fabrics in this look. An outfit like this one is the ideal choice when you’re looking for comfort without compromising on style and edgy appeal. The eye is instantly drawn down to huge rips right above the knees on cuffed stonewashed boyfriend jeans.

A loose-fitting white cotton T-shirt drapes easily across the body, peeking out beneath a black biker-style moto leather jacket. A pair of worn-in Converse sneakers and a large black carry-all tote bag finish off the look. Easy, edgy and cool!

Accessorize Your Denims like a Pro

24) Ethnic Effect

Trendy brunette in black blazer and ripped boyfriend jeans

An ethnic necklace provides the focal point for this simple look (photo: trendytaste.com)

Structured with a twist – that’s the effect when you combine loose-fitting boyfriend jeans with a fitted, men’s style blazer. This look is made up of eclectic parts that, when worn together, create a unique, trendy ensemble. On the bottom half, we find a pair of destroyed jeans, cuffed once right on the ankles.

A simple white cotton T-shirt is worn underneath a black suede blazer. But it’s an ethnic patchwork-style necklace that ties it all together. Pointy stiletto pumps and a black leather handbag complete this chic city look.

25) Color Craze

Trendy brunette in white T-shirt and ripped boyfriend jeans

A touch of red and green spice up this outfit of basics (photo: ashley-ringmybell.com)

So you’ve got a few accessories in bold, daring colors but don’t know how to style them? Easy – wear them with a basic outfit of blue boyfriend jeans and a simple white T-shirt. This outfit perfectly strikes the balance between casual and quirky by simply adding a bright red Chanel handbag plus a coat in deep emerald green. Give the look an unexpected elegant touch with a pair of gorgeous black Christian Louboutin heels.

26) Dimension Diva

Woman in blue jeans
Woman in blue jeans and over sized woolen sweater (photo: whaelse.com)

Don’t be afraid to play with different dimensions and angles when styling your boyfriend jeans. The natural tendency may be to pair baggy bottoms with more fitted tops, but this outfit shows us just how chic and stylish a voluminous top can be. Here, a pair of ripped jeans is worn with a woolen sweater.

27) Bright Supreme

Woman in bright outfit with jeans
Woman in bright outfit with jeans (photo: estefaniaacuna.com)

28) Loose Chic

Woman in loose boyfriend jeans
Woman in loose boyfriend jeans (photo: chicisimo.com)

 

29) A Lesson in Primary Style

Trendy brunette in red stiletto sandals and boyfriend jeans

When red meets blue, the result is a fashion triumph! (photo: songofstyle.com)

Here’s one for the style risk takers. Boyfriend jeans provide the perfect opportunity to play around with bright, bold colors – the more daring the blend of shades, the better. We love this eclectic mix of primary colors. A royal blue camisole top is offset beautifully by scarlet red ankle-strap sandals and a matching red sling handbag. Tying it all together is a pair of cuffed jeans ripped all along the legs. Perfect!

30) Creative Counsel

Stylish woman in burgundy hat and boyfriend jeans

A draped black top adds volume and shape to boyfriend jeans (photo: brokebutbougie.com)

We’ve all got a few style items in our closets that speak to our personality and bring out our fun, quirky side. This look shows us just how to style them for maximum effect. The trick to wearing them is by combining the items in a way that’s classy, elegant and in proportion.

A longer-length draped sweater in solid black is tucked into the waistband of a pair of cuffed boyfriend jeans. Peeking out underneath is a leather belt with a large metallic buckle. Leading the eye downwards is a pair of elegant black stiletto heels, picking up the sleek black found in the rest of the outfit. Add some extra spice to the look with a statement tiger-striped handbag and a floppy burgundy hat.