Stripe Top + Boyfriend Jeans

Alright, I tried them again. THIS time, I actually did wear this outfit all day without changing to my skinnies. Yay for progress!

Yes, the boyfriend jeans are back, and this time I styled them with ankle boots and this great little striped bateau top from Old Navy.

This top is currently on sale for $24, and you can get an additional 20% off thru end of day today (9/20) if you click on that deal at the bottom of the page. That brings it down to just $19. For that price, you may want two! In addition to this navy with red stripes, it also comes in white with navy stripes as well as a solid grey heather and a solid fir green.

I love that it has a straight hem, and the length is nice for leaving untucked. The side slits are a nice detail, and even though it has a dropped shoulder, it doesn’t seem to add bulk like some do.

Usually the rule of thumb with boyfriend jeans is to wear something more fitted on top but I don’t like things too tight through my waist because I tend to carry a little extra weight there, so this top is perfect. It has some shape to it without being clingy. For size reference, this is a small.

I’m cuffed my jeans twice this time instead of once, as pictured on the website. I feel like this is a better length for wearing with the booties. When I wore my slides, the single cuff was fine because they have a much lower shaft. You can see that outfit HERE if you missed it or want to reference it for any reason.

These boyfriend jeans are slimmer than some, and I really like the cut — especially the rear view. Most boyfriend jeans make me look wide and flat, but these actually have a nice shape to them, and the slimmer cut overall is slenderizing.

They’re spendy so I linked to a few other options in the widget at the end of the post, but I can’t vouch for how they fit. The LOFT ones are 40% off, though, so definitely worth a try!

I carried my Lucky Brand bucket bag in the brindle color because I love how it coordinates with the ankle boots and the casual vibe works well with this outfit. It’s on sale at Amazon right now.

I kept my accessories simple — these winding arrow earrings and a few Alex and Ani bangles.

top // jeans (option) // boots // bag // earrings // bracelets // watch

Be sure to visit Cyndi and see the fall outfit she’s styling today.

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50 Responses

      1. Do you remember the Loft turtleneck you styled last winter?  It was a neutral tone.  You forced me to purchase it!! ????  Anyway, that would look super cute with these jeans and boots.

  1. I wasn’t sure about the jeans, but when you show the back view, they look great!  All my boyfreind jeans leave me looking wide and flat from behind too.  You look so good in your skinnies, but this is a great casual alternative.

      1. I was going to suggest the J. Crew ones. I noticed in their store they said they were more slim cut than regular boyfriend jeans but did not have a chance to try them on. I forgot you had already styled them.

  2. Cute!  I just bought the Old Navy Field Utility Jacket and love it, along with the fitted V-neck sweaters.  Surprisingly flattering.

    Question for you.  Do you cut your jean hems to make them ankle length, or are you buying them already cut?  I bought a ton of the booties/shooties and love them — but the hem of my pants are too long to show off the details.  I’d rather give my older jeans a haircut to bring them into the here and now than trying to buy new ones.


    1. I haven’t cut mine b/c I like the length – most of mine that I wear with ankle boots have a 28″ inseam – but I would if I were shorter. Sometimes I cuff them if the booties are taller.

  3. You look great!  I hope to make it to the ON store today.  If not, I will be placing an order tonight.  That top is on my list.  

    Have a blessed day!

  4. Another great one with these jeans! I honestly think they work so well on you, even though you still may not be the most comfortable in them. I hope you continue to work with them. I’m also very tempted by this bag! I’ve actually been looking for a casual one in a lighter color like this. And I already have some LB booties in brindle, which makes it all the more tempting, lol.

  5. Love the top and am really kind of liking the jeans. Might have to give that style a try again! Definitely like the slimmer fit of these. I’m just not a fan of the boots in this situation. I liked the slides before, or would probably even go with dressy cute sneaker type shoes or loafers to try a different look for me.

    1. I think you could do any of the above with this. I like the ankle boots okay but I wore Converse Shoreline with these pants and this top to a high school football game, and I thought that was cute too.

  6. I agree with everyone else. I think you look great in those boyfriend jeans. They look comfortable and stylish, doesn’t get any better than that. I’m glad you kept trying different looks with them instead of returning them or pushing them to the back of your closet. Super cute!!! I just purchased a pair of Frye slouchy booties, Nordstrom had them on sale for 1/3 off. I’ve never pulled the trigger on Frye’s but this time I had to do it. I’ll need help on how and what to wear them with. Could you share some looks with slouchy booties if you have a pair? Thanks for all your great ideas.

  7. Jo-Lynne – I agree with everyone else, you really do look great in these jeans! They look very comfortable and casual but not frumpy. And I love the striped top! Thank you for continuing to try things for the rest of us. I really do appreciate what you do!

    Cathy V.

  8. I am currently taking the adore your wardrobe eclass as you suggested. My body type is short-waist pear. Do you mind telling me your body type, I really like your casual style but not sure if it fits with my suggested wardrobe options. I love skinny jeans but the eclass says i should wear straight or boot cut :(.

    1. Sure, I’m a short-waisted curvy so skinnies are technically allowed according to AYW rules. 🙂 I think that’s the piece of Kelly’s advice I have the biggest struggle with. I totally see what she means, but I think it would be really hard for me to give up my skinnies b/c they’re so practical and work so well with current shoe trends. I definitely encourage you to try the recommended styles and see how it goes. I also encourage people to take course 2 because Kelly shows you some ways you can cheat some of the rules with accessories and color play. I hope you’re enjoying it so far.

  9. I agree, such a cute outfit… You and Cyndi sure present Old Navy clothes much better than they can actually look:) They are starting to come along with some better quality on some items too. The jeans look great, and there are those days we just want a baggy pant, without looking oversized. I have a pair and enjoy pulling them out every so often.
    Have a great day.

  10. Stripes are so fun and add energy to “looks”.  Having choices are great and boyfriend jeans are an option I often choose to wear in our Oregon horizontal rain, which we get to enjoy every season of the year!  Plus, jeans help my legs stay warm.  I like your bangles, too.  I wear a watch, and I have a few bangles, but honestly, I never wear them.  I need a lesson!  You look fabulous in this casual look! 

    1. I used to love wearing knee length skirts. But nowadays I find them so difficult because I’m too short waisted and big chested to tuck a top in, and most tops are too long and/or voluminous to work untucked. Back in the 90s, tops were made to work so well with pencil skirts, and I wore them a lot. I have styled a denim skirt a few times in the last year or two: https://jolynneshane.com/tag/denim-skirt

      I was just at LOFT and tried on a couple of skirts but couldn’t find a top to work with them. 🙁

  11. I like the jeans on you too & that shirt is great (stripes make me so happy!). I recently bought a pair of Loft boyfriend jeans & like them very much! They are slightly more fitted than they were a few years ago so they look better & not overly baggy. I often wear them with slip-on sneakers on weekends since my lifestyle is fairly casual.  I think I’ll give booties a try once the weather cools off.

  12. Jolynne, I was probably the only one who didn’t like the way you styled the boyfriend jeans last time. But this time I love it, to me this is how they should be worn – casual without fuss, that’s what you did here.  Personally as I can’t wear heels due to needing an ankle recon I would go with converse, which I think you wore to a football game in one of your comments? Spot on!

  13. The jeans look great on you. I like the double cuff.  I bought some jeans several years ago from Loft that look very similar and they are not skinnies but don’t know at the time what they were called. They are lighter wash and I love them rolled once with slip on tennishoes and flat sandals.  I like the casual look like these jeans are for you.  I think you shouldn’t ever hesitate to wear them. Yes, the key is a short enough top.  

  14. Cute Jo-Lynne!  I’m only 5’3″ and have shied away from boyfriend jeans but I like these! I have had good luck with Gap girlfriend jeans ????  Love this cute top!

  15. Love this look on you!! I’m glad you are stretching yourself and trying to style different jeans in different ways.  I ended up ordering a similar sweater pattern from Loft. 

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