How to Wear Boyfriend Jeans

How to Wear Boyfriend Jeans - The Well Dressed Life

Today, we’re breaking down how to wear boyfriend jeans, specifically for the grown up crowd.

If you’re looking for a jean that is chic, casual and comfortable, look no further than a boyfriend jean.  Admittedly, we feature a lot of skinny jeans, especially in the winter because they pair so easily with boots.  But, maybe skinny jeans are not your favorite, or you are just ready for some variety.


Boyfriend JeansHow to Wear Boyfriend Jeans - The Well Dressed LifeModern Boyfriend Jeans, Everlane: $68

There are many options when it comes to boyfriend jeans. Generally, they will be loose fitting, and the hem will stop around your ankles.  The most flattering fits will have classic 5-pocket styling, and a relaxed yet slim leg. 

Some variations will have distressing around the knee and hem.  I happen to like that look, but I know many readers aren’t into it. 

For the purpose of today’s post, I picked these Modern Boyfriend Jeans by Everlane.  I like the quality, color of the denim and price. These are a more traditional denim, meaning there is not much stretch so keep that in mind. 

 This darker wash by Madewell are easy to wear and look great with everything. Plus size?  I like these by KUT.  Petite?  Take a look at these from NYDJ.

Shop these other options in all sizes:


You can make boyfriend jeans super casual or date night ready. They are a comfy alternative to leggings, especially if you work from home but want to feel a bit more pulled together. 

I created three different looks with a variety of items you may already have in your closet. 

Three Ways to Wear Boyfriend Jeans 

How to Wear Boyfriend Jeans - The Well Dressed Life

Let’s break down each outfit.

Outfit One

Top, $50  |  Sneaker, $65  |  Bag, $22

Boyfriend jeans are ideal for casual looks.  Here, we paired them with this updated striped top from J.Crew.  The tie at the waist puts a fun twist on an otherwise classic top. 

If you wear the tie, skip a necklace.  To keep the look modern, roll the hem of the jean and wear a pair of fresh white sneakers.  Superga is a popular and affordable option.  They have a low profile, so they complement where the hem will hit you on your calf and the width of the jean leg.

I found this red bag at Target.  It’s a sweet little pick me up for the warmer weather, also available in black and soft blush.

Outfit Two

Jacket, $98  |  Clutch, $149  |  Heel, $96

For nights out  a moto jacket is where it’s at and the boyfriend jean pairs perfectly.  There is a wonderful contrast between the sleekness of the jacket with the slouch of the jean, yet they “go” together because they are both still casual. 

I’m of the opinion that when you wear a moto jacket, the jacket is the outfit and you don’t take it off.  Keep the under piece simple, like your favorite white tee shirt, or a tank and leave the jacket unzipped to create longer line of the body.

Here’s where it gets fun. Pair your jeans with a ladylike pump. This helps elongate your leg, gives you some height and feels dressed up.  These beige Sam Edelman pumps are divine and under $100.  Because you’re going out, I added this small Clare V. pouch.

Outfit Three

 Sweater, $13  |  Heel, $70  |  Bag, $140

In our last outfit we kept the whole look cozy.  First of all, this sweater by H&M is $13, and as I write this, most of the sizes are still available. We featured the gray, but I was close to using the navy – hard choices. 

The heels are by Franco Sarto. From my experience, they are crazy comfortable. Once the weather warms up, even the tiniest bit, I would pull these out. The shoe is still substantial, even though it has an open toe and the block heel works well with the shape of the jean.

Finally, we found a wear-with-everything crossbody, in a remarkably similar color to the shoe. Not that it has to match, but when you’re going for easy and casual, it helps.

Tips on How to Wear Boyfriend Jeans

  •  You can wear any shoe from strapy stilettos to flip flops. Take your height into consideration. If you’re tall, a pointed toe flat will look lovely if you roll the hem of the jean. If you’re short, a wedge will help elongate your leg.
  • To dress up the jeans, think in terms of contrast. Add a fitted blazer, a blouse with lace detail or a pump with some embellishment. Pieces with some kind of luxe detailing elevates the look instantly.
  • Avoid capri style boyfriend jeans.  You want these to hit at or close to your ankle.  Mid calf is the least flattering place for a pant to hit on your leg. (See my unfiltered thoughts on capris here.)




How to Wear Boyfriend Jeans

22 thoughts on “How to Wear Boyfriend Jeans”

  1. Hi Meg,
    Can you also explain the right length and if you should cuff, how to cuff and how many rolls in the cuff? I’m pushing 50 (ugh!) but wear jeans a lot. I found rules for wearing a bootie with skinny jeans but I’m not sure what to do with a looser jean. Thanks!

    • Hi Jen! The cuff is really what makes the jean a “boyfriend” jean so I would always wear them cuffed. You want the jean, once cuffed to hit at or right above your ankle. I wouldn’t cuff it more than twice, because it will get too thick and heavy. How wide of a cuff will depend on your height and proportions. Generally speaking no more than 2″. Your best bet is to play with it until it feels right. Hope that helps!!!

  2. Hi Megan, I love these looks. You just posted something about Stitch Fix which I recently subscribed to. Since they use Pinterest is it possible to save suggestions like today’s to our Pinterest Page for our stylist?

    • Hi Lois! Yes, at bottom of each post is a Pinterest icon. Click on that and it will help you link it to one of your boards. We create a hidden image on every post, that works best on Pinterest. It will show up automatically, it will be the longest image.

  3. I have been wanting to order from Everlane. I bought a pair of great flats off their website, but I have been hesitant to purchase clothing. Most of their models are extremely thin, and they photograph great- but I can’t tell if the clothing is cut for a junior, or if a size 10-12 misses can appreciate them, too. Do you or your readers have experience with them?

    • Hi Kathryn, Everlane is definitely not juniors cut. I just ordered these in a size 29, and I typically wear between a 6 – 8. Once I get them I’ll let you know how they fit!

  4. I read that women over 60 should not wear jeans. Do you agree? And if so, perhaps you can do a blog about casual looks for this age group. Most other pants are trouser style and the material seems better suited to office wear.

    • Hey Mary, I think that’s crazy! I don’t believe in limiting what women wear based on age. You should choose pieces that work best for your body type and lifestyle, certainly, but age should play no role. Every outfit we feature is meant to serve as inspiration regardless of age, but to give some context to our demographic, most of our readers are between the ages of 35 – 70+. If you focus on classic styling, with a modern twist you’re pretty much guaranteed to look timeless and ageless. 🙂

  5. A silly question—what is the difference between a Boyfriend Jean and straight leg jean? I just bought the Paige Skinny Straight Horton Jean. It is somewhere between skinny and boyfriend, and can’t decide where to hem it. I tried rolling the hem (like a boyfriend) and it looked terrible. Help!

    • Not silly at all. Retailers and brands call things by the wrong name all the time. Traditionally boyfriends will have a wider leg and hit at or just above the ankle. If I’m guessing, the “Skinny Straight” is more of a skinny that isn’t skin tight and you’re right, looks silly with a cuff.
      I would keep them to the very top of your ankle. You can probably pair them lots of shoes shoe options: flats, pumps, ankles and knee hight boots.

      A traditional straight leg is just that, tends to have have a standard length that would break on top of your shoe.
      Hope that helps!

  6. Hi,
    In my opinion Articles of Society skinny Jeans have a terrible fit. I wear 30/31 in Jeans and I bought these in a 30. The crotch came halfway down to my knees and the butt sagged so bad that I only wore them once. I’m 5’6 and even though they are skinny and are supposed to come to the ankle, a 30 R came about 3 inches above my ankle. I really believe you get what you pay for. I will try the Paige jeans next time.

    • I’m confused by this comment because I don’t mention Articles of Society jeans in this post at all and this is about boyfriend jeans, not skinny jeans.

  7. Thank you for this post! And for your update on the Everlane denim. When I asked about their sizing awhile back, your response was helpful. I have since ordered several pieces from them (ironically, not yet denim) and been happy with nearly all of them.
    I have one pair of boyfriend jeans and I wear them with my oxfords/brogues. I never could figure out how else to wear them. This post helps.

  8. Hi Megan, I am going on a river cruise in May from Nuremberg to Budapest. I would like to look stylish but casual. What would be your suggestions please? Should I wear boyfriend jeans and a blazer, or do you think it is too formal?

  9. I have mixed feelings about boyfriend jeans…I like the look in theory but I’m plus sized and tall (6′) with a big butt, a fairly small waist and long legs and I just think they’re completely the wrong cut and shape on me. The relaxed fit makes legs look bigger and the cuffing shortens them, plus they take away from waist definition. How do you style boyfriend jeans to make them flattering on curves?

    • I would say not every style is going to work for every body type so if it doesn’t feel right on, I would skip it. There are lots of looks I like in theory but can’t pull off 😉 Instead of a boyfriend, look for a straight ankle length jean, in a dark wash, it will flatter your curves without making you look bigger than you are. And yes, skip the cuff, it adds bulk and cuts your long legs off.

  10. Hi Megan. The boyfriend jeans are definitely on my list to buy, but it’s cold here in Canada for bare
    ankles. Do I have to wait for summer or how can I do this with socks?


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