How To Style Boyfriend Jeans


Well, two things we have strong opinions on are pantyhose and boyfriend jeans! I loved reading all your comments and I love that your honest with me but in a very nice way.

Here’s the picture I showed yesterday. It was quite controversial, even on Instagram. How To Style Boyfriend Jeans

I’ve said many times, just because something is “trendy” doesn’t mean we need to wear it. I probably need to listen to my own advice and ditch the boyfriend jeans.

But I wanted to try them, they’re comfortable and that’s really all I can say. I do think mine are a little big, hence the name, boyfriend jeans. It does seem that they’re supposed to look a little big.

How To Style Boyfriend Jeans


I really want to call them “husband” jeans. I don’t have a boyfriend and I don’t want one. I’m happily married! Ha!

Anyway, I styled them again but a little more dressed up this time. Again, I think they’re a little too big. Here they are with a white blouse and I added my Stella & Dot necklace that I love! I also added these Steve Madden wedge sandals, similar here.

How To Style Boyfriend Jeans

The blouse hangs longer in the back. It’s kind of an updated white button down.

How To Style Boyfriend Jeans

One of you suggested I wear them with my chevron top tucked in with a belt. I like this and I added my Stella & Dot chandelier earrings.

How To Style Boyfriend Jeans

Okay, I may not wear them on the blog again but that’s how I would style them.

I’m not sure if I should ask this, but should I keep them or ditch them?

Beauty For the Heart~~This is a good reminder for all of us! But the Lord said to Samuel, “Do not look on his appearance or on the height of his stature, because I have rejected him. For the Lord sees not as man sees: man looks on the outward appearance, but the Lord looks on the heart.”

Have a blessed day!

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  1. Love them with the white button down and heels! You could always take to local Tailor and have the legs brought in just a little. It should cost 15 max

  2. Hi again Cyndi! I prefer the outfit with the white shirt myself :0) To me there’s something way off with the chevron shirt. I like the shirt but not with the BF jeans. I’m just not a fan of BF jeans. One of my fashion rules is if you don’t love it then lose it. Have a super day! Hugs your way.

  3. Hmmm, keep them or ditch them? My opinion is ditch them. My problem with them is the “ripped/frayed” areas. I am 50 and really think no one over 35 should wear that look. I think that needs to stay with the younger ones. If I had my way I’d do with out the “ripped/frayed” look all together.
    I do like it with the Chevron shirt best on you, though. Thanks for the discussion. Blessings.

  4. I like the white button down with heels! I tried these jeans also and husband ask I not wear them again. I am tall, so I thought that might help- they look good on super models and they are tall, lol. Ok guess not. 🙁 So off to the thrift store they went.

  5. Ditch them. Women over 40 (even 30!) should not be wearing “deconstructed” jeans. You are a beautiful woman and the jeans, especially with the chevron top, do nothing to enhance your natural beauty. The cut is not bad with the white shirt; but I just can’t get beyond the rips and tears.

  6. I love the boyfriend jeans on you, but you are correct, they are a little too big. I always go one size down from my regular size when ordering pants in the “boyfriend” cut. I think if you try them one size smaller, you might really like them.

  7. I don’t like the frayed jeans either… for our age. At this point in life we should be able to afford jeans that don’t look like hand me downs. I love ankle jeans though, NO crops, they must hit below the calf to make you look taller and not frumpy! I also love the look with the white button down and wedges.

  8. I love the boyfriend jeans on the right person. I am definitely not that person. When I try them on, they look more like “grandpa jeans” and I am talking an 80 year old grandpa….
    I think from the pictures that you look cute in them. I like the way you styled them today and if you feel comfortable in them, keep them. But if you are not comfortable because of the size, I think they are a cute look for you so maybe try smaller…thanks for the fun of being part of a debate =0)

  9. The jeans are stylish but in my opionion not very flattering on you. I think you have to be really super slender and not have many girly curves at all for them to be attractive. I just think you have a lot of other things that look so much better on you!

  10. I like these options better, especially the white blouse. And I love, love those sandals!!! As always, you look super cute in whatever.

  11. Cyndi, you are just too too cute! I love the white blouse, I love the necklace, I love the chevron top! But I still say the jeans would be great for fishing or camping with Wayne… After all they are “husband” jeans:) Have a great day! Krista

  12. I love your style 99% of the time, but have to be super honest with you on this one. Give that baseball tee style to Courtney. I would love those boyfriend jeans if they were at least one size smaller and preferably white (like the ones at Loft). I think the deconstructed look doesn’t look as worn out in the white ones (if that makes sense). Most people probably don’t even get past your beautiful face n smile!

  13. I am “torn” on the boyfriend/husband jeans. I think you’re right, yours are just a size too big. Seeing you encourages me not to order any online but to try on first. I really want to try them but I think I will try to find a pair that aren’t torn. Thanks for all your advice!

  14. The white shirt with the boyfriend jeans is adorable on you. What a great post to us all it is okay to be a bit daring even if not a total win.

  15. Hi All! I just discovered boyfriend jeans and love them. Cyndi, I am with you and would rather call mine husband jeans because I am happily married and certainly don’t want a boyfriend or his jeans! I think your pair might be a little loose on you but still very cute and comfy looking. I really like them paired with the white blouse and wedges.
    While I think of myself as a girly-girl (grandma), I also think I don’t have to look feminine all the time to be a lady. So I am keeping and wearing my Old Navy cuffed and cropped pairs of husband jeans. Hope you will wear yours for us again soon. Thank you for your wonderful posts.

  16. The What Not to Wear People say that we should NOT wear capris…or shorts… I usually don’t, unless I’m at the beach…then I wear shorts… I don’t love Capris, but I do love the “ankle” jeans… maybe you could describe the difference 🙂 one of your commenters mentioned to either love it or lose it… I fall into that category now…if I don’t love it… I lose it! and I tend to be less adventurous now with my clothes– but, I love that red chevron shirt!
    can you tell me the brand? it would be darling with white jeans!
    you are gorgeous no matter what you wear!

  17. I say keep them even if just for a walk in the woods with hubby or a day on the couch reading a good book. Some days, they just feel good.

  18. Keep them. I love them on you. I want some and I am 42. They look great. So where can I find some? Should I just walk in a store and ask for “boyfriend” jeans (HA) Like them with both tops.

    Again, I love you posts each day and I can’t wait to hear what you have to say about capris.

  19. I agree the BF jeans with the white button down and heels looks the best! I also agree that the BF’s are too big and that maybe they’re a bit too frayed, but thanks for hitting this subject, inquiring minds wanted to know and we’re not as brave as you! 🙂

  20. I like them. I have seen on other sites where women will get a size or two smaller than normal so they fit better. I haven’t tried them yet.

  21. I say keep them, but I like them better with the flip flops than with the wedges. I think I’ve said this before – you look good no matter what you’re wearing. I saw your sister’s comment about you looking adorable. In my wildest dreams, I cannot imagine one of my sisters telling me I look adorable. Count your blessings!!!

  22. I am 46 and love deconstructed jeans! Sheaffer on Pinterest told me to” blog wears hers constantly! Granted she’s in her 30’s, but so what. I think you’re cute no matter what, but this particular pair might be a bit too big for you. I think you could size down. 🙂 You have a darling figure and shouldn’t “drown it”, if that makes sense. 🙂 Above all, wear what makes YOU feel great, inside and out!

  23. Cyndi- I think you look SUPER cute in anything u wear. Some people can just pull anything off simply because of who they are. With that said, I like the white shirt better, but I am wondering if a more form fitting shirt would go better with the BF jeans. Or maybe a super cute blazer and heels? Just my two cents. BUT- I think they’re cute. I have no problem at all with the rips and I’m 42. Nothing wrong with “our age” wearing rips and tears that are trendy. That’s just my opinion. To sum it all up, you’re a doll. I’ve only been following u for a short time and already love you! ❤️❤️

  24. I think they look fine. I especially love the white shirt outfit and those shoes. It’s just a different look that we may not be used to. I am usually slower to warm up to trends but often end up joining in — just before the next one hits!
    That said, it sounds like you aren’t comfortable in this look. If so, ditch ’em. But I agree with so many others, you look beautiful in whatever you wear.
    Thanks for your style and spiritual inspiration. <3

  25. I LOVE how you styled them today. They do look adorable and young, but not as if you’re TRYING to look young. Maybe I should say youthful. Definitely a keeper.

  26. I love the BF jeans with the white top and wedge shoes —- they are adorable. I think perhaps it’s just something out of your comfort zone and they are less structured than you are used to wearing. I think peronsally think you should keep wearing them – trying them with different things until you get used to seeing yourself in them. Also, if you’re like me – anytime you wear a wedge you feel a bit more “dressed up”. And as for pantyhose – a big no for this girl 🙂

  27. I’m late, but, KEEP them! Very cute, especially with the red chevron and brown strappy heels! The fact the shirt is a bit tucked makes the baggy Jean not overwhelming on you. And, I’m old enough to have a “boyfriend” sweater from the 60’s. You look adorable, so go for it!

  28. I also love boyfriend jeans and I am 53. I wear them for the simple reason that they are just so darn comfortable! They are great for long distance drives or just to hang out around the house in. I usually pair mine with a fitted tea and Tom’s.

  29. So many opinions…don’t you love us, when you ask a question and your get answers. I think the boyfriend jean is OK if they are not too baggy (these are on you). Also no frays (these have them). You have a wonderful shape and these outfits do nothing to highlight how pretty you are. Now I’m not saying skin tight or anything. I do know you’re a pastors wife 🙂
    I think a fitted shirt would be better. A few of your tops lately don’t flatter your shape.
    I have found Eddie Bauer has some great boyfriend jeans that are a little more fitted and without the fraying! They have a great white pair and usually you can’t find white boyfriends that don’t have fraying. That said they look better dressed up than with flip flops.
    I’m 48 and love my boyfriends, that are more fitted and not fraying. They are VERY comfy and look styled with the right shoes and top.
    Ditch this pair, find a more fitted pair, if you plan to go with the style.

  30. I tried on some BF jeans a while back and thought, wow, these make me look boxy and immediately took them off. When I saw you in yours yesterday I thought..I guess that’s how they are suppose to look so in my opinion, I don’t care for them but if you decide to keep them, I like the look today better then yesterdays look. I think if you are comfortable in them, you will fill good going out in them.

  31. Cyndi,

    I think if you feel good in them, then you should keep them. I LOVE the white blouse and SUPER CUTE sandals. They give the outfit a “pulled together” look. I also think that we obviously wouldn’t wear BF jeans to church, but for a fun daytime outing . . . why not? Follow your heart – you won’t go wrong!

  32. They look cute with the white top and shoes the best! But I agree with the others, the ripped look is best for the younger gals. Maybe trying them without the rips and a size smaller would be great! Thx fir sharing. Looking forward to hearing about capris 🙂

  33. Cyndi,

    I love your style and I love most of the outfits you wear. However, I don’t think these boyfriend jeans look good on you. They make you look heavier than you are and they don’t look as polished as you usually look. If I had to pick one of these outfits I would pick the white shirt one as the best one. The chevron one does not look good at all. I like the chevron blouse with the jeans you showed yesterday, but definitely not with the boyfriend jeans. But I would still keep the jeans to wear on a casual day.

  34. I am 51 and I have a pair of boyfriend jeans from Ann Taylor. I sized down one size and chose a pair that were not destructed mainly because I got teased about women my age wearing jeans with holes in them. I think they look much better with heels and with a tighter fitting top since they are somewhat slouchy. I also believe pants should be worn to the ankle because cropped pants/capris make your legs look shorter. I think if you are comfortable in them, you should go ahead and wear them. If not, send them packing.

  35. First of all, let me say that you always look beautiful. 🙂

    As for the restyle on the boyfriend/husband jeans. I love the look with the white shirt and wedges. Too cute. As for the chevron shirt, I would untuck the back and just have a loose front tuck and maybe a slightly wider belt. That’s just me. I think you would absolutely love Boyfriend jeans if yours were maybe one size smaller and maybe a darker wash. The darker wash dresses them up a little. Old Navy has some that are cute and affordable.

    As I said, you always look beautiful. 🙂

    Thanks for sharing.

    P.S. Capris…not for me, but I’m interested in what you have to say about them. I do love slim fitting ankle pants, but only the skinny style. Can’t wait to read your post.

  36. I work super hard at keeping my figure, so anything that makes me look bigger is out for me. Since these jeans are baggy, I wouldn’t wear them personally. I don’t wear super tight clothes either, but just don’t need help looking larger! I like my clothes to fit me right, I guess .

  37. Ok, so here’s the thing… I always think it’s great to have a super comfy pair of jeans you can throw on with your tank top and flip flops OR a long sleeve and chucks. For me that’s my boyfriend jeans! I LOVE them, but I wouldn’t wear them everywhere. I’ve had mine for 3 years now (LOFT has the best, I think) and wouldn’t trade them anywhere. Great for beach walking, too… just saying. 🙂 My vote is keep ’em if they’re comfy.
    xo Heidi

  38. You just need a smaller size! I’m 45 and I bought a pair of faded boyfriend jeans last summer at the Loft. My husband loves how they look on me! We aren’t too old for this style!

  39. I think you should keep them! They look very cute and casual! I love them with the white shirt and heels. I think it’s very flattering on you!!

  40. Cyndi, I usually love, love, love all the outfits you feature, but on this particular item I vote for ditching the boyfriend jeans. I don’t think they would look flattering on anyone. Just my two cents!

  41. Cyndi: LOVE the “husband” jeans with the white top and strappy wedge sandals…you look great in that outfit! Once you said they were comfy on, then my vote is KEEP them…women always need that COMFY pair of jeans in their wardrobe. Great scripture verse today! Thank goodness our Creator looks at our heart…I like the balance you strive to create in your life…bless you! 🙂

  42. They do look best with the white blouse but with that said….I would ditch them. You have such a beautiful figure and IMO those jeans don’t show it off like your other clothes do. Maybe I am just not a fan of those type jeans, but I just think there are so many other jeans out there that look so much more flattering.

  43. I think the boyfriend jeans are cute and appropriate for your age. I am 50 and I wear them all the time. I just didn’t care for the flip flops you wore them with. i like the wedges!

  44. Yea! I am 45 and love my snug fitting deconstructed jeans from white house black market. On myself, I don’t like boyfriends, but I am short. I need to follow this scheaffer person 🙂

  45. How immensely encouraging it must be to be told after every picture you post how adorable and cute you are!

  46. All my comment didn’t post above this! I went on to say that I like the white shirt best with the jeans. The jeans aren’t my favorite, but we all have our likes and opinions. It’s what makes us unique!

  47. Boyfriend jeans aren’t my favorite , but I do think that your styling with the black and white tops are both much more flattering than the tucked in verson with the chevron top. You are such a sport to challenge yourself and try the suggestion from readers!

  48. Hi Cyndi, I agree that just because something is in style doesn’t mean we have to wear it. That being said, I don’t think age is the deciding factor for BF jeans but instead, as most have stated these are just are too big and, personally, I don’t care for the destructed look myself. I have a pair and I agree they are so comfy; although I did go down one size. An item that is oversized needs to be balanced with something more fitted, especially for us petite gals. Try a fitted t-shirt and lightweight blazer with the sleeves pushed up (to make it casual). The strappy sandals are a little heavy; try nude ballet flats or some pointy-toe pumps. That’s just my 2 cents, but you still look adorable. P.S. of all the tops I liked the Chevron best, with some nude or orange shoes.

  49. I may be in the minority, but I like boyfriend jeans. When I hit 40, it was not my style to start buying elastic waist pants, cut my hair short, buy clunky tennis shoes, and wear holiday themed sweatshirts…on the other hand, I didn’t start wearing mini skirts and tank tops either. Boyfriend jeans may not be for everyone, but if I were you, I would totally rock the white shirt combo! It’s classy and cute with a teeny bit of edginess.. The tee shirt and flip flops are not bad for a super casual day… I didn’t think that the tucked in chevron shirt was as flattering as the white shirt… My view now is wear what makes me feel good, not what others say I should wear. That is what is great about getting older…

  50. You are right but I will say these frayed jeans were not cheap. They may look like hand me downs but they weren’t priced that way. Thankfully I had credit and didn’t spend the money on them.
    Thanks so much for stopping by!

  51. Ok here’s my 2 cents!!! I think you’re boyfriend/husband 🙂 jeans are too big for you! Just get a size smaller….and here’s another thing……(because I LOVE my boyfriend/husband jeans.. and I have about 6 pair) the ones with stretch are best!!! I got mine at Forever 21 and never mind that I work there (haha) but I’ve had some from Old Navy and The Loft and I find the ones with stretch are great! …I wear mine dressed down with converse tennys and a cute top and I’ve dressed them up with wedges and a flowy top…so there you go!!! Also I walked into my doctors office and had them on and my Dr. thought they were darn cute and she said how lucky I was to get away looking cute in them at 53!!! LOL!!!

  52. t.ey will be comfortable for cleaning house, yard work, and painting and DIY projects. Otherwise, goodbye. You are too classy to wear these in public.

  53. Hi Cindy, I’m just turned 63 and I have two pair of the boyfriend jeans and think they are so comfy!
    You look adorable especially in the white blouse, keep them you look so up to date!

  54. Cyndi I am in the group that loves them on you. They look stylish but also comfy. I always go by the rule that if I wear loose bottoms I wear a more fitted top and vise versa as loose tops with leggings. It seems to work better for me. Enjoy the jeans, besides. I seen baggy jeans on some of the fashion blogs and even read where the skinnys are on the way out.

  55. You always look so cute. You must have a HUGE closet! In my opinion these particular boyfriend jeans are a little too big on you. I’m guessing you are on the petite side? I am 5ft.4in. & found the perfect pair of Kut (brand) Catherine boyfriend jeans. They are still comfy but a little more fitted. I think those would work great on you. I really love mine.

  56. Cyndi…l think the white shirt style is cute and you are right, the white shirt dresses the boyfriends up. I have looked up “Fashion for women over 60” on Pinterest. I especially love the women who have not had surgery and dress like they mean it. I was inspired by them and by you. (I am in my 60’s). I don’t know how to dress myself and I don’t want to be a frumpy old lady! You are helping me learn. MP

  57. I ditto this comment… you have inspired me to go look at our local (small town, florence, SC) JC Penney store. I actually bought a pair of their boyfriend/husband jeans before this post and have enjoyed wearing them! I love your stella and dot necklace and white shirt. can you share from where the white shirt came? i look forward to your posts each week. thank you for sharing your talents!!

  58. I think they look a little big on you which might be why you are not the most thrilled with them. Get a size smaller. I love love love mine. I feel younger and just happy when I wear them…hence they are my saturday jeans….every saturday.

  59. I love the white shirt! Please share where you got it! I still think boyfriend jeans are great. Maybe it depends on your body shape. I feel best when I am wearing my boyfriend jeans and I am a banana

  60. Hi Cyndi

    Have to agree with you on the image sent through yesterday – I think the look looked very comfortable and probably great for a day spent around the home and garden. Definitely prefer the look today (white shirt and tan wedge sandals) – classier but relaxed at the same time. I would definitely consider this look for a casual day out. Love your blog and inspirational message!

    Grantham UK

  61. Thank you for showing us how to dress up the boyfriend jean look. I recently purchased a pair from Macy’s (INC Brand) that fits a little tighter without any holes and I love them. I do wear these types of jeans only on days where I am basically around the house, running errands etc.

  62. I think the boyfriend jean style is for a casual look so I would stick with a casual shoe like Toms or maybe even your gold ballet flats. I’m not a fan of chunky sandals (even though I know they’re in style).

  63. I think you look great in the boyfriend jeans. My favorite style is with the white shirt. My second favorite would be with the black t-shirt for a more casual look. I would definitely keep them. 🙂

  64. Ditch them! In my opinion, they are not flattering. Sorry, I usually love your outfits, but these are not a winner…..kind of frumpy.
    I agree with Sandy, they are too boxy for most women to pull off.

  65. Cyndi, I love them with the white blouse and the black blouse too!!! You rock them with style! Yes, I would wear them like this out to town( I generally wear mine around the farm). I will have to try this look!! I love them as capri pants!
    Thank you for this blog about the boyfriend jeans!!

  66. Oh and I would wear mine with flats… I do not wear heels when wearing casual outfits. You look very sexy and hot in these boyfriend jeans!! It must be in your “jeans” !! 😉

  67. Cyndi – you look GREAT in everything. Go with your heart – if you are comfortable and like what you see – just wear it! I have pair of BF jeans from Kohls – they have two tiny rips by the pockets so not too distressed – and I wear them to church! It’s easily the Piece of clothing in my cupboard that has gotten the MOST wear. While I don’t think we should rock the HOLE-y jeans – to each his own. You look fabulous!

  68. Cyndi,
    I think style has so much to do with our attitude when we wear something. You aren’t trying to dress or act as if you’re 21, and I think your humbleness and sweetness shows through no matter what you wear. I like the “slightly” distressed look and think us middle aged gals can pull it off. It’s not like you’re walking around with large rips or holes in the knees. I agree that they are too big and you might try a smaller size. I own a couple of pair and I think the key is more in the leg opening. I like a slimmer, skinnier leg at the bottom. I have found this helps more with not making me look heavier than I am, and giving an overall slimmer and finished appearance :)) Kelly

  69. The white shirt came from Stitch Fix. The brand is bella dahl.
    I’m sorry I can’t be more help!
    Thanks so much for stopping by,

  70. Cyndi – I think you look adorable with the “husband” jeans and white shirt — for me, that was the best styling. They certainly aren’t something to wear everywhere, but a nice comfy pair of jeans should be in everyone’s closet! Love your blog — because of you, I’ve decided to try Stitch Fix — my first fix is scheduled for May 1! Can’t wait! Thanks!

  71. yes, I have those Catherine style boyfriend jeans from KUT from the Kloth as well… super cute, and a bit more fitted. Love those, and also the Vigoss brand (Nordstrom often has then on sale for around $38).

  72. Keep them. I like them with the chevron top and white blouse. I would just change the shoes either a nude flat or pumps.

  73. Keep em! They look great on you & they are so comfy! I’m 61 and I have a pair…..they are my go to jeans cause you can dress them up or down and they look great either way.

  74. The question is, should “anyone” wear them? They seem to look stylish on 6 ft size 0 models, but only if we are discussing style, and not figure flattering. They make no one look better, and 99.9 percent of ladies look far worse. ( and i am referring only to the true loose boyfriend fit, not cuffed slim fits masquerading as boyfriend)

    You look better than most in yours.

  75. I was 67 on Feb 2 and think I would like a pair of boyfriend jeans…..where shall I shop for them. I might be old, but I don’t dress, think or act old. Your daily blessings are such an inspiration to me. Having been a fashion design major before I majored in Education, I love fashion. How many hours can one spend looking at outfits! My precious mother passed away two years ago and I miss her dearly. After all, she was the only one who cared what I was cooking for supper and she always wanted to know what I was wearing. Blessings to you! And thank you. You are a blessing to many.

  76. I love the boyfriend jean look. I am 43 and wear them all the time. You look fabulous in most of the pictures. I am not a fan of the chevron tucked in look but all the others I love! Keep on rocking this look!!!

  77. Hi I just wanted to say that I liked the way the boyfriend jeans looked on you and you should keep them. It’s a good look.

  78. You are so small and can pull off the skinny jean thing so well…ditch the boyfriend jeans. You don’t need the extra fabric and you’re much too cute to wear these baggy jeans!

  79. You are adorable, I don’t know how old this post is but I hope you kept the boyfriend jeans. I’m 57 and love my boyfriend jeans. They are my go to for those days I just want comfort. We all need a jean that we play in. Do we have to be stuffy all the time? Own it, And be confident in them you look great.