How to Wear Boyfriend Jeans

Fashion-Week Attendee Wearing Distressed Jeans And Half Zip Oversized Jump
Credit: Farfetch

Is it possible to have a love affair with a pair of jeans? If it was, we’d be guilty. We just can’t get enough of boyfriend jeans; they’re practically perfect in every way a pair of jeans possibly could be. They’re comfortable, a little bit edgy, and they are beyond versatile. It’s hard to go wrong with these beauties, but we want to show you all the different looks you can achieve with these loose jeans. Follow our style tips and you’ll soon be able to master outfits from casual through to polished, just by the clothes and accessories you pair with your jeans.

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What are Boyfriend Jeans?

Boyfriend jeans stand out in the sea of skinny jeans you see many women wearing today. They’re inspired by menswear, but created for the female form. The cut of the jeans is relaxed and slouchy, but they’re still feminine in their tailoring.

In the 1960s, Marilyn Monroe was spotted wearing loose fitting jeans on the set of Misfits or Clash by Night, so we can largely thank her for starting the boyfriend jeans craze. She was known for her feminine appearance, but she managed to add an element of measured masculinity by donning looser jeans with her shirts and blouses.

Marilyn Monroe Boyfriend Jeans Misfits
Credit: Marilyn Monroe, Pinterest

But Marilyn Monroe isn’t the only style icon associated with this style; the petite Katie Holmes helped them make a comeback decades later after leaving a dress rehearsal in New York City wearing Tom Cruise’s jeans. It didn’t take long for a long list of celebrities to join her in wearing a more relaxed fit of jeans, and they’re very much still on the catwalks and runways today.

The good news for all of us is that there are more styles of boyfriend jeans available than ever before, so they can look flattering on most body types. Whilst they’re meant to be worn fairly slouchy, with the right outfit they never cross over into looking sloppy.

Reasons Why You’ll Love Them

With all the newer styles of boyfriend jeans available, you can choose a pair that best suits your shape and size. Despite the name, boyfriend jeans don’t have to be worn extra baggy. In fact, there are plenty of designers who are creating slimmer and more structured pairs; perfect if you prefer a more fitted look. If you do dare to go baggy, avoid choosing a slim cut, and even think about choosing the next size up so they sit a little lower on your hips.

Model mixing Up Casual Faded Blue Jeans With A Yellow JacketModel Wearing Simple White Mom Jeans OutfitModel Wearing Faded Blue Classy Mom Jeans
Credit: Matches Fashion

Whether you choose a looser or more tailored pair of jeans, you’ll still be falling in love with them for the same reasons. Firstly, they’re comfortable. They won’t be clinging to your legs like your skinny jeans do, making movement and relaxing just that little bit easier. But most importantly? They’re the new king of your wardrobe. They can help you to pull off any look you throw at them, whether it’s bohemian, casual, or ultra-feminine. And yes, that is possible even with a touch of their boyish charm.

How to Style Boyfriend Jeans?

This is the pair of jeans that will take you from day into evening with minimal effort. It’s all about the tops and accessories that you choose to wear with them. We’ve picked seven different styles to inspire you to pick a pair of the cuffed jeans we love so much. It’s time to give those skinny jeans a rest and give the boyfriend fit a go; you’ll have the celeb look down in no time at all.

The Femine Look

Think you can only pull off the most feminine looks with pearls and soft pastel pinks? Think again, as you can do it with a pair of loose fitting black jeans, complete with rips and frayed hems. Monse boyfriend jeans are the thing of dreams, and they definitely throw a curveball into the definition of traditional feminine attire.

To get the look, first choose a pair of black boyfriend jeans; these ones work so well as they are cropped to just the right height, and have a skewed waistband which adds a bit of edginess into the design. Next you can look for the perfect top or blouse that complements the jeans you’ve chosen. We like ruffles and silky fabrics for a touch of elegance. Finally, pick some pointed pumps or heels to add the feminine touch as the silhouette here makes all the difference. A The Row clutch bag finishes off the look, even if you are tempted to use your bigger than average jean pockets.

The Bohemian Look

Become the coolest kid on the block when you choose to go boho with your boyfriend jeans. If you’re testing the waters, start with a looser fit of cuffed jeans and add a crop top that suits your style preferences. But we’ll let you in on a little secret: the real fun starts when you’re brave enough to venture out of your usual comfort zone.

We love Sacai jeans, so why not give them a go for a look you’ve probably never tried before? What more could you want? They are deconstructed, asymmetric, and have fabric peeking out from under the cuffs. They couldn’t be more cool if they tried. With a simple t-shirt and a Marques' Almeida casual jacket, the outfit is so easy to put together, you’ll wonder why you haven’t gone bohemian before.

The Polished Look

You don’t have to pick a pair of black jeans to achieve a smarter look; with our tips you can rely on blue jeans to see you through to the evening and beyond. The best part is, you probably already have most of the ingredients in your wardrobe: a white blouse, classic pumps or heels, and a matching clutch bag.

We’re fans of Dolce & Gabbana blue jeans as they have been artfully distressed, but still look impeccably put together. The cut is flattering, but it made even more so when elongated with heels featuring a pointed toe. The hemlines are kept intact, allowing them to be cuffed with straight lines. All of these elements result in an effortless, yet polished, style.

The Autumnal Look

Boyfriend jeans will see you through most of the year; you can style them for spring, summer, and even autumn. As they’re going to be hovering above your ankle, you’ll need to wear some extra layers to counteract the cooler weather in the autumn. We think that makes for an excellent excuse to invest in a new trench coat to wear with your jeans, along with a chunky scarf.

This pair of mid-rise stretch denim cropped jeans from Current/Elliott is an autumnal wardrobe staple. The simple style works well with a whole heap of accessories, coats and shoes, so they’ll see you through the whole season with many different looks.

The Stylish Look

Not every outfit is designed for everyday wear though; sometimes you need something just that little bit more special. A big night out, a red carpet event with cameras flashing; whatever it is, you need to look a million bucks. If it’s not quite formal dress, let a more tailored pair of boyfriend jeans take you to style heaven instead.

We can’t think of any better pair for this than a TRE paneled boyfriend jeans. After all, the designer Natalie Ratabesi is said to “treat denim like haute couture”, so what more could you want? The slimming effect looks sublime with a tight crop top and matching boots. It’s very much a take-over-the-world worthy outfit.

The Casual Look

For all of the days in between the big nights, you can soften the look with a simple t-shirt and jacket. One of our greatest tips is to choose a fitted top when you’re wearing looser jeans, but you can still pull off a longer or more boxy shirt as long as you tuck it in at the waist. Even better, add a belt. This will help to bring your outfit together, making casual still look incredibly stylish.

Classic Straight-Leg Jeans From Need In 96
Credit: Need Supply Co.

Go for a light blue pair of jeans to master the casual look. A pair of low-rise Current/Elliott jeans looks just the part. They can sit low on the waist and have a ripped and torn effect at the knee; they manage to look both effortless and chic at the same time. The perfect pair for your next trip to the shops, or an evening at the cinema.

The Romantic Look

If you’re looking for a way to wear boyfriend jeans for a hot date, we’ve got the tips to make it happen. This time it’s all about the slim fit jeans, and the other clothes and accessories you choose to wear with them. Try a tucked in vest top, or a slinky bodysuit if you want to keep your clothes tight to your body. We’ll give you bonus points if you find a lace-up or one shoulder top for that extra sexy something.

A pair of jeans from cult denim brand GRLFRND is sure to see you on your way. This pair is stonewashed in light blue denim, and looks striking when paired with all black accessories. Get an added boost of femininity with a pair of Cult Gaia stilettos. We love ones with slender ties that take them up around the ankle, meeting the bottom of the cropped jeans.

How to Avoid Boyfriend Jeans Fashion Faux Pas?

Now you know all about the different styles you can pull off with boyfriend jeans, we thought we should add a few points about how not to wear them if you still want to keep that feminine feel to your outfit. We know that boyfriend jeans come in many different fits and shapes, but you’ll still want to avoid going for an outfit that’s too baggy.

You might choose a pair that has a more relaxed fit, and sits lower on the waist. These are incredibly comfortable, and perfect for pulling off the casual look. But you’ll want to keep your top tighter so your outfit doesn’t look too boxy with your looser jeans. We’re also fans of adding a belt to help sharpen the look, and add some definition at the waistline.

Another potential faux pas can be through the shoes you wear with your boyfriend jeans. Again, it’s really hard to get it wrong, but the only shoes you may want to shy away from are UGG boots and knee-high boots. This is simply because you lose the shape and elegance that help boyfriend jeans to look feminine through their cut and tailoring.

Speaking of tailoring, remember that you can buy boyfriend jeans in many cuts and styles. Look for tapered legs on your jeans if you want to create that narrow-ankle appearance, and you can also use shoes to complete the effect. Heels and pumps with pointed toes help to elongate the leg, especially when combined with your cropped jeans.

Quick Tips for Wearing Boyfriend Jeans

  • Go wild choosing a pair of shoes to wear with your boyfriend jeans. The only styles we think don’t work so well are UGG boots and high cut boots.
  • When wearing a looser fit of jeans, you can choose other pieces like crop tops and pointed toe pumps for the feminine touch.
  • Add the right pair of heels and a matching clutch bag and you can get away with wearing boyfriend jeans for your evening wear.
  • Look cool in an instant by pairing your cuffed jeans with a plain t-shirt and a belt; if your top is loose fitting, tuck it in at your waist.

On That Note

We think we’ve probably convinced you by now that boyfriend jeans are worthy of being a staple item in your wardrobe. When something is comfortable, a little bit edgy, and incredibly versatile, how can you possibly go wrong? We’re sure you’re going to be reaching for your boyfriend cut jeans just as much as your trusted skinny jeans from now on! You’ll have a lot of fun styling them, whether it’s a boho look you’re after, or a polished one for a top night out.

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