How to Wear Boyfriend Jeans This Spring

Over the years I’ve struggled a bit with the boyfriend jean, but now that cropped straight jeans are trending, I’ve decided I’m ready to embrace the boyfriend. Haha! Why am I always a year or two behind on these things?

A boyfriend jean is about the same length as the cropped straight, but with a more flattering silhouette. I prefer how boyfriend jeans follow the line of the body as it naturally tapers towards the ankle area, whereas the straight leg style hangs straight down from the hips and then cuts your leg off an an awkward place.

Here, let me show you what I mean. On the right, I’m wearing a cropped straight style from Madewell.

Granted, my boyfriend jeans are a “slim boyfriend” style, so not as baggy through the thigh area as some, but you get the point. I definitely think they create a more flattering silhouette than the cropped straight pair in the picture on the right.

I’ve tried the boyfriend jeans with slides and with booties, but my favorite way to wear them is with a fashion sneaker like Converse or Vans. The slouchy fit seems more conducive to a casual look. (See all my looks with boyfriend jeans HERE.)

I’m loving these updated Vans classic slip-ons right now. I’ve tried various fashion sneakers over the years, and I always end up passing them down to one of my daughters and going back to my trusty Converse Shorelines, but these are mine, all mine!

I hate futzing with laces, so I only seem to hold onto the slip-on style sneakers, and these were super comfortable right out of the box. I wore them all day after shooting this look, and I never got a blister or felt uncomfortable in any way.

They have a padded collar and footbed for added comfort as well as cotton drill lining for breathability, and the slim profile is flattering.

These are the (Pinked Suede) Silver Lining/Blanc De Blanc in a Women’s 8 Medium, and the fit is perfect. I typically wear an 8 or 8.5 in fashion sneakers and a 9 in Nikes, for reference.

I actually thought they were going to have a blush tint to them, but they’re pretty much straight-up silver/grey, which is fine. Either way, they work well with this outfit.

Now let’s discuss this top! This is another Treasure & Bond athletic tee, and I love this color combination for spring.

With the last Treasure&Bond sporty tee I featured, I had some questions about the stripe on the sleeve. You can see that look HERE.

On this top, the white stripe is screen print and the pink stripes are the same cotton material as the rest of the shirt. The screen print stripe doesn’t bother me, but I know that was a deal breaker for some of you, so I wanted to point it out.

It’s a nice quality tee, and the material feels good on. The v-neckline is flattering as well.

For size reference, this is a small, and it’s plenty big. It has a slightly curved hemline, but it’s very subtle.

I like it best with a front-tuck, especially since these jeans are cropped, which has a way of visually shortening the line of the leg. By front-tucking the top, it shortens the top and allows you to see more length in the pants, which helps achieve that pleasing 1/3  to 2/3 overall proportion.

I carried my new R Minkoff Darren shoulder bag with this outfit. I absolutely adore this bag, and the putty color works perfectly with this outfit.

For accessories, I kept it simple with silver hoops and my favorite silver link bracelet.

This outfit is perfect for weekend wear or casual days at home when you want to feel comfortable but look put-together and on trend.

sporty v-neck tee // Citizens slim boyfriend jeans (similar for less here, here, here) // Vans slip-ons // R Minkoff shoulder bag // silver triad hoops // silver link bracelet (option)

Be sure to visit Cyndi and see the spring outfit she’s styling today!

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59 thoughts on “How to Wear Boyfriend Jeans This Spring

  1. Super cute outfit and I like how you styled your hair 🙂 I have a pair of those shoes on my wishlist for the spring!

    1. They are good!!! I have these and a pair of their cropped straight that I picked up on the Shopbop sale. Their material is a tad thicker than some of the other brands I normally buy, but still very soft and molds to your body in a good way. 🙂

  2. So cute! I do like how the boyfriend jeans taper more toward the ankle compared to the other cropped straight jeans. Also love the color combination with gray and light pink.

    1. Very cute & comfy. Must have those shoes. Not pricey as I thought. Love bag but not in my price range. 🙂

      1. The bag is high… but I got it 25% off. 🙂 It will go on sale again. I love her bags, and they really are a good value for the price. The quality is fantastic – every bit as nice as Tory Burch, but the prices on those has really skyrocketed in recent years.

  3.  I love this look! It just looks comfy and springy and awesome! And I see what you mean about the comparison of the two pants. I’m with you on these crop jeans they just I don’t know just don’t look right? And I’m a straight leg jeans kind of person. But yeah they just seem awkward. . I hope you have a great day! 

  4. Love, love, love the outfit! I especially love boyfriend jeans. 😊 And the boyfriend jeans look much more flattering than the cropped straights. I haven’t been able to embrace that trend. I may have to look into that top and the Van’s. They’re really cute. I have several pairs of Converse, but the Shoreline are my favorites too.

    So ready for spring. I just checked the 15-day forecast for my area in northern Illinois, and there’s one day that hits 50. The rest are 30s and 40s with quite a few days of rain. (one day says snow showers.) We have spring break coming up in another week, so I’m hoping the forecast changes. 😊

    1. Yep, ours is similar. Highs in the 40s and lows in the 20s for the foreseeable future. It’s the 20s that kill me because I like to run in the mornings, and it’s just. so. cold. That plus the wind chill… UGH.

  5. Love the shoes! Are they more comfortable than the converse shorelines? I have a pair of those and they can be scratchy and less supportive.

    1. Yes, out of box, I would say these Vans are more comfortable than my Converse. I had to break my Converse in a little bit, and they are kind of stratchy inside. The Vans are softer, and that padding around the heel and ankle is nice.

  6. I have been in funk of late; back problems not allowing me to workout and the weather, so when I opened your email this morning it immediately cheered me up! Funny how the little things can improve a mood! I love this outfit combo, it looks so cute and screams spring is coming! I may have to order the shirt, is it lightweight or a thicker cotton Blend? Have a great day!

    1. I’d say it’s kind of in-between. It’s not that thin slub cotton, nor is it that thick, stretchy pima cotton. It’s just a nice crisp mid-weight cotton that isn’t see-through.

    2. Hey Ginger….I think we are having the same morning.  I too am having lower back problem and feeling in the funk but made myself go out to walk a little and the fresh air and then Jo-Lynne’s email cheered me up. Ha Ha.  Have a good rest of your day.  

  7. Cute! For some reason your emails the last 3 days have stopped going into my primary inbox and are going into my promotions so I have to dig them out. I have no idea why and can’t seem to figure out how to fix it. Any suggestions?

    1. That is happening to me too! (I get my own emails, lol.) Probably has to do with the format change, maybe it seems more “newslettery” than it used to? I don’t know. Between the stupid algorithms on the social networks and email providers deciding where your email should go, I am about ready to give up. Why can’t anything just be?

      So if you’re in gmail, you should be able to filter all my emails to go where you want them to go. Be sure you’re on on a web browser – and then go into my latest email, and click the MORE button up at the top, and you will get a pop-up box.

      Put [email protected] in the From: box, and then click Create a filter with this search in the bottom right.

      Select Categorize As and choose Personal. Then Apply.

      Or you can create a Folder for it if you want, and then my emails will always go into that folder. If you subscribe to other blogs, you can create a Blog folder, and put them all in there, and then go thru and read all your blog emails at once! 🙂 That means also that my replies to your comments on my blog will go to that folder, though. Just as an FYI. 🙂

      I hope that wasn’t information overload!

      1. Thanks for the info as the same thing was happening with my email: your posts started going to promotions.
        A great casual look!

  8. Hi. I love your posts every day!  Question about bathing suit and cover ups.  What do you think of lands end. Are they too “old lady” looking. I’m thinking of getting shorts as cover up over my suit. Getting rid of all the tankiini skirts😉
    Thank you!

  9. Thanks for the reminder that it’s time to change out my jeans.  We still have a foot of snow here in MN, but it’s not so cold I can’t show a little ankle.  I’m also ready to move to cute spring casual tennis shoes.  I’m off to dig in my closet.  Have an awesome day! 

  10. Love the outfit! Boyfriend jeans are so comfy! The bag is my favorite but might have to save up for that! I qould love to see you style some of the embroidery jeans and florals coming out. Oh what about styling a floral purse?

    1. Yeah, I’m not a big fan of the embroidery. I can appreciate it for others, but I haven’t found any that I really like on me. I can try some on at the mall, though, and take pictures. 🙂 I haven’t really noticed many out there yet… or maybe I’m just looking right over them since they don’t really call my name. Haha! I’ll keep an eye out.

  11. Have you tried sizing down in boyfriend jeans? Besides making you feel better about buying a smaller size, they are less baggy but still looser than your skinny jeans. And I think you are just looking to vary your everyday denim uniform so this would accomplish that. Also wearing them with some kind of heel makes them more flattering. I love that you keep showing us new styles even if you may not be that comfortable in them. Headed up your way this weekend so please have it get warmer!

    1. I can’t size down – they are already snug in the waist. 🙂 And yeah, I’ve worn them with a low heel too. Check out the two posts I linked – with slides and with ankle boots. 🙂 I like them both ways! I’ve been wearing them more this spring (I often wear them to the salon to get my pedicure, lol, b/c they are the only jeans I have that I can actually get up over my calf) and I’m definitely getting more used to the look. Definitely a nice way to vary my everyday uniform!

  12. I’m really liking the look of the slim boyfriend jeans! I’ve only worn skinnies for years, though I have one pair of boyfriend style from WHBM that I’ve worn to death. Hmmm. I might be on the hunt for a pair of boyfriend slims. I am also loving the Treasure & Bond sporty tees. After seeing your earlier post on one of them, I ordered 3, to decide which I liked best. Ordered 2 V-neck and 1 crew because I couldn’t resist the green crew. All three are hanging in my closet, lol. I couldn’t decide which one to give up! And the shoes are perfect with this outfit! Vans have never been a good fit for me, but I found Toms Avalon. They have much more support than the original Tom styles and I personally like the shape of the vamp, particularly for larger feet as I wear a 10. Thanks, Jo-Lynne!

  13. Have you tried either jean with heels?  They look super cute with a blazer and heels–one of my favorite “casual Friday” work looks.  I alway feel a bit self conscious about the slim boyfriend/girlfriend jean on me looking like an ice cream cone, which is partially why I like the straight crop…  just a different perspective!

    1. Yep, I have. I like the boyfriend jeans with heels a lot but I’m not sure I have anywhere to wear them that way. For some reason skinny jeans and heels feels safer to me. Ha!

  14. I love that entire outfit. You look so comfortable and relaxed 🙂 I ordered the top, great for Spring which is coming…….eventually. I’m in Idaho and we’ve had a mild winter but for those of you back East I feel for you.

  15. I have a pair of perforated black classic vans that I use as my “commuting shoe” now that I work in the city. I have a shoe bag that looks like a lunch box that I carry my heels in. I also have a blush perforated pair that I got last spring and wore all over Ireland!

  16. It was interesting to read difference between crop and boyfriend jeans. I clearly saw the difference. I so much prefer the boyfriend 

  17. You look so cute in this outfit. I love the jeans on you. The boyfriend style is definitely growing on me too and these jeans are amazing.

  18. Love this outfit! Those boyfriend jeans are just perfect on you! Thanks for pointing out the difference in them and the straight cropped style. I’ve actually been scratching my head over that difference for a while. And yay for Vans! They are my favorite brand of slip-on sneaker and the lace-up kind are really cute as well. The Vans I have are all so comfortable right out of the box and they have such a huge variety of colors and patterns. My favorites are navy/white striped canvas that I got last summer and wore constantly. They are just the right extra touch for any basic outfit that works with sneakers.

  19. These Vans say they are suede. Did you spray them with some kind of protector? Do you do that on your suede booties? If so, is there a kind you recommend? I ordered one on Amazon but haven’t used it yet so haven’t worn the shoes. Seems like they all have mixed reviews. 

  20. So helpful to read and see the pictures between the 2 kinds of jeans. I’ve been wondering about all that.  I love the look of the boy friend jeans on you but at age 56 yrs. old I’m just not thinking I can go there.  I hope skinnies don’t go out but with the new crop straight out…. if many start wearing them, then our eye will go toward that and pretty soon we won’t desire the skinny. I always say, “I’ll never wear bell jeans or never wear skinny jeans and then there I am wearing them.”  Fashion…..can make a person crazy sometimes.  LOL Have a blessed day and hope you warm up more.  

  21. Love!! I like the boyfriend cut better too! I also like the darker wash better. I think overall, I like a darker wash in most denim pieces, but specifically jeans. I guess it doesn’t have to be a dark wash, but at least a medium wash. Anyway, I love the top and your sneaks as well. I have been look for a pair of slip ons that feel good and fit well, but so far haven’t found the perfect thing. I’m sure it is out there somewhere! Ha, ha. – Amy

  22. When I look at the straight crop jeans 2 things stand out to me.  First, the wash.  Light wash jeans are generally not as flattering as darker wash jeans.  Second, my eye is drawn to the zipper.  To me, it would look better if there was a long zipper.  The space below the bottom of the zipper seems big, and that is throwing me.

    1. Yes, I totally see that space under the zipper now! That is partly what makes these look so odd. I like a lighter wash, but I think it’s more flattering on skinnies or bootcut somehow. I think it needs to be tight in the thigh area.

  23. I have to ask you about your Vans. I always have trouble with new shoes causes blisters on my heels. Have you found that the Vans are less likely to do that? I think that is why I never buy new shoes because it is so uncomfortable with blisters.

  24. Love this outfit! the purse the shoes and the shirt….. adorable. I think the “pinked” on the sneaker refers to the zig zag edge, I think. I want it all.

    1. Yes, it does! That is so funny – I was trying to figure that out – pinking shears… yes!!! But in the picture on Zappo’s, they seemed to have a blush cast to them. Oh well, I like them anyway! 🙂 And I do love the zig zag edge.

  25. I’m so glad you put the two jean styles side by side; I clearly see what you mean! I learn so much from you. Many times you have saved me from “the frump.” lol

  26. This is another great casual spring outfit. I really like the colors in the top against that shade of denim. 

  27. I LOVE this outfit on you and the overall look.  Now I want to try on slim boyfriend jeans that are high waisted and the regular length as well as cropped.

  28. You look great in everything but I am not a fan of the boyfriend straight. I have a pair of Old Navy boyfriend skinny that I like and wear often. I look better in a skinny jean in general.

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