How to Wear Boyfriend Jeans

How to Wear Boyfriend Jeans - The Well Dressed Life

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 with spring around the corner we’re ready for some variety. Today, we’re breaking down how to wear boyfriend jeans, specifically for the grown up crowd.

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.  Looking for plus size?  I like these by Levi’s.  Petite?  Take a look at these from NYDJ.

How to Wear Boyfriend Jeans 

How to Wear Boyfriend Jeans - The Well Dressed Life

How great is this?  Let’s break down each outfit.

Outfit OneTop, $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 TwoJacket, $98  |  Clutch, $135  |  Heel, $96

For nights out in nice weather, 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.

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 ThreeSweater, $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.


  •  You can wear any shoe from strappy 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.)

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Thank you to our reader Missy who submitted her question about boyfriends jeans on a previous post.  We love getting comments and questions so keep them coming.  We use everything you share with us to help inspire daily content you want to see!  Have a great weekend! xx Meg

Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

  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!

    1. 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?

    1. 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?

    1. 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.

    1. 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. 🙂

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