How to Wear Boyfriend Jeans

After my post yesterday on how to wear different styles of jeans, many of you are asking for more info on boyfriend jeans. First, let me say that I’m not cool enough to pull off this look, but I’m happy to tell you what they are and how to wear them if you want to take the plunge.

What are Boyfriend Jeans?

Boyfriend jeans are a loose, relaxed fit and often have some distressing. They have a cool, tomboy vibe that is super fun if you can pull it off. Usually you wear them rolled at the ankle.

You can find slimmer styles and baggier styles; it’s all about the look you are going for. They aren’t the most figure flattering style of jean, but they have an edgy, modern vibe that is pretty appealing anyway.

Here are a few examples.


How to Wear Boyfriend Jeans

As I said yesterday, boyfriend jeans tend to look best with tops that are tucked in but not too tidy. You often see them worn with a feminine blouse and heels. And because they’re pretty baggy, they’re usually worn with a belt. 

The idea is to pair the boyish style jeans with feminine accents. If you get the right combination, it’s really a fun look. I went to Pinterest to find some examples to show you.

Here they are paired with a simple blouse. The animal-print shoes make the look super chic.

boyfriend jeans with blousesource

I like how she paired them with a blazer in this photo.

boyfriend jeanssource

These boyfriend jeans have a slimmer cut which is a bit more flattering than the typical baggy styles. I like how she puts them with a basic gray tee and a black jacket and statement necklace. This look I could almost pull off!

slim boyfriend jeanssource

I looked and looked and never found a pair of boyfriend jeans on Pinterest paired with flats or sneakers. I actually think boyfriend jeans could be really cute with a pair of fashion sneakers and a casual tee. I’m not sure why I didn’t find any examples.

Ooooh! Flats! But still a dressy look.

boyfriend jeans with flatssource

I could go on and on finding cute looks on Pinterest.

I did finally get a couple pairs of boyfriend jeans. Here’s my version of the look.

Fashion Over 40 | How To Wear Boyfriend Jeans

And a more casual take:

boyfriend jeans

So tell me, are you running out to buy a pair right now? Or are you sitting this trend out?

Also, if you’re looking for help building your wardrobe, I highly recommend Trunk Club, a personal shopping service by Nordstrom.

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23 thoughts on “How to Wear Boyfriend Jeans

    1. Disagree age doesn’t matter anyone can ware boyfriend style jean! It really depends on the person and whether they can pull off the look, I’m 62 and rock it, no problem!
      Love the boyfriend jean styling I see on Pinterest, very cool, modern, and casual fun!

      1. I agree. there is almost no look that can’t work on any age group if done right. In any case, people over 50 is much too large a group[ of people to say what looks good on all of them! I can’t think of anything sexier then an older women, with naturally grey hair wearing worn in jeans. Ive seen it done beautifully. Actually, i am NOT over 50. But…My suggestion is to go for mom jeans. they are just like boyfriend jeans, but higher waisted. Wear them like boyfriend jeans, a bit loose rolled up. That gives the waist some definition. Tuck in the t shirt, at least in front. Show off the ankles. You will never be as young as you are today!

        1. Agree. I’ve seen it done well too. There’s a lady who works at Gap. She is grey and over 50, I’m sure, but so trendy and cute. She pulls off the “younger” styles with panache. 🙂 I think it depends more on your personal style aesthetic than age.

  1. Not my style either since I’m also in the over 50 group. The only time I wear distressed baggy jeans is while gardening.

  2. I have some, and I only ever wear them with converse. I just don’t think I can pull off the heels look. Mine are gap sexy boyfriend. Love them.

    1. Give it a try with a wedge or low kitten heel but not to high of a heel.
      I’m over 60, although everyone can’t believe it & tell me I look late forties or fifty.
      Whenever I’ve worn my distressed boyfriend jeans younger and mature women compliment the look.

      Bottom line, it truly depends on the individual woman.

  3. You are the best….thanks for posting about these. Though I think you could wear these. I LOVE the looks on the models….not sure if I can wear them or not. Thank you to the person who mentioned she got hers from the Gap….I may need to try them. I actually love the rolled up part….especially in the fall:) Here is to shopping and seeing if I can actually pull them off:)

  4. I saw a woman (mother of 2) this weekend wearing them with ankle-high converse, rolled of course. She teamed them with a casual blazer and t-shirt. Looked very cool. For those on the go a lot, wearing them with flats is still an on-trend look and SO much more practical. I am hoping I’ll be able to pull the look off once I have had no. 2 & shed the excess!

  5. I don’t have them like you I don’t think I’m cool alone for them either. However, the ladies on pinterest wears the look effortlessly and I love it when appropriately paired with heels.

  6. Have them. Wear them. I do the front tuck w belt usually. Love them w sandals but wearing them w flats for fall. The key is to juxtapose the casual, boyish vibe with very girly everything else.

  7. Coincidentally, I’m wearing them in my style post today. Love them. AND, they look great on bigger sizes too. Wendy and co here are all a size zero and in their twenties but I think they’re universal if you balance your proportions.

    1. Thanks for this comment. I was going to say that they are much more flattering for some figures, than skinny jeans are. 🙂 Some of us just can’t pull off skinny jeans.

      🙂 🙂 🙂

  8. I like Jag Jeans Tommy Skinny Boyfriend. They are loose enough in the waist and hip but more fitted in the legs (my thin body parts!). I am 49 and find this a cute, casual style if paired with a neater, more classic top (I like a simple fitted dark tee). I think ballet flats or smoking slippers look good with this style. Love your website btw.

  9. I’m 62 and have several pairs, though I do tend to avoid the extremely distressed kind. I wear mine with booties, flats, heels. I wouldn’t let age stop you if you like the fit/look.

  10. Wish I were skinnier so I could rock these. I have a pair and they just make my body look fatter and kinda dumpy. I’m pretty much a skinny jeans girl. Though I do like how these look on other people.

    1. Honestly, I don’t care for them on me either. I think they’re hard to wear unless you have a boyish figure… or you have to be willing to wear stilettos, which, yeah. Not my bag. LOL.

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