I’ve always loved the combination of grey denim and burgundy—it’s a timeless pairing that never goes out of style. Today, I’m giving an old favorite outfit a modern update. This look features my new MOTHER Weekenders in the Wanted! wash, which feel so much more current compared to my original grey skinny jeans.
THEN (2017): cowl neck tunic (S) // grey skinny jeans // rag & bone booties (39) // Rebecca Minkoff satchel // wrap bracelet // similar sunnies
NOW (2025): cable knit flare cuff sweater (S) // MOTHER Weekender in Wanted! (29) (option) // Franco Sarto Vianca (8) // Quince box bag // hoop earrings // YSL sunnies
One big difference between the old 2017 look and the new is the proportions. The tunic with the skinny jeans cuts me in half vertically, making my overall silhouette look shorter and less balanced. Additionally, the exaggerated cowl with the drop sleeve, along with the booties featuring a dipped front, were on-trend at the time but now give the outfit a dated feel. I still like it, but I wouldn’t wear it today. I also doubt it would be as flattering on me now, as I’ve experienced some weight gain and redistribution over the past seven years, not to mention my breast reduction surgery.
For this updated look, I chose a burgundy cable knit sweater with on-trend flared sleeves and a more subtle cowl neck. I actually found this sweater at Talbots! Compared to the thinner fabric of the original tunic sweater, this cashmere knit is a definite upgrade—luxuriously soft, plush, and made to last. I also love the pretty cable knit pattern, and the flared sleeves with wide ribbed cuffs add a modern twist. Plus, the 23″ length paired with full-length flare jeans creates that pleasing 1/3 to 2/3 proportion.
These grey flares probably need no introduction—I’ve been wearing them on repeat this winter! Not only are they stylish and on-trend, but they’re also incredibly flattering and leg-lengthening. I kept black boots with this updated outfit, and I love how they work with my dark hair to ‘bookend’ the look. These black Franco Sarto Chelsea boots feature a slender square toe and a sculpted 2″ block heel that’s both stylish and practical. They feel much more modern than the original pair, with the low shaft and dipped front detail.
Finally, bold hoop earrings and the Quince box bag add a sleek, polished touch. Together, they’re more current and streamlined alternatives to the accessories in the original look… although I did love that satchel, and it’s a fairly classic design. Still, the box bag feels a bit more of-the-moment and complements this updated outfit perfectly.
I hope you like this outfit update! It’s always fun to revisit old favorite looks and give them a fresh, modern twist. I have a few other “Then & Now” posts, but they are old. I’ll try to do some more of these as we transition from winter to spring!
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63 Responses
This post is so helpful. I struggle to see trends and then to see how I need to swap my own clothing to be more current. You broke it down and the side-by-side pictures really helped. Thank you!
I saw something online yesterday that skinny jeans are back for 2025. So I googled it, and found several sources stating the same. Care to comment on that? And, if they are, then are the tops changing? I really don’t care which jeans are more on point as I kept some skinnies and also bought new jeans, so I have both. I don’t need to be fashion foward; I just want to not be fashion behind.
Yep, I actually addressed this in my Saturday email. Here’s my take, for those who missed it: There’s been buzz about the return of skinny jeans for a while now. At first, it was fringe sources predicting a comeback, but more recently, a few everyday style influencers have started hinting at their resurgence. I do think skinny jeans are on their way back as an option, but I don’t see them dominating like they did in the 2010s. The beauty of today’s denim trends is the variety—flares, straight-leg, and wide-leg styles all feel current, and women are embracing what works best for their personal style. I see skinny jeans making a quiet comeback over the next few seasons, but styled in fresh, modern ways. 🙂
Thank you for replying! This take is super helpful. If you kept your skinny jeans and decide to pull them out, I’d be interested to see what your fresh, modern styling is. I’ll keep wearing my newer jeans because I like them, but adding my skinny jeans back into the rotation would just be another option. I was never a ride or die on skinny jeans. Or, well, any jeans. Trends come and go.
I did not keep any. I assume washes and proportions will be different when they come back around again, but I’ll keep an eye on my favorite stores and see what I find. 🙂
I have a hard time with “skinny jeans are back” as it feels like they never completely left. While I ditched mine entirely about 3 years ago (which isn’t that long for a trend to be gone on its own) many of my friends and neighbors and community members are still wearing the pairs from 2019. A lot of people everywhere I go. So how can something be “back” when it still hadn’t fully left the mainstream yet? I do not live in some podunk town either- I’m in a suburban sprawl in an area that is sometimes said to be on top of trends.
Totally agree! I honestly think the fashion industry – especially the “fast fashion” sector – is trying to cycle the trends thru faster in an attempt to make more sales. But I expect it to backfire as many women will still have the items that are coming back “in.”
I agree. They never went away. I think most women now just wear what they like especially if they don’t care about fashion trends. I got rid of mine since I never really liked them. I’m hanging on to my flares and wide legs like some do with their skinnies.
When I say things are back (or they left), I’m speaking in broad generalities. Sure, skinny jeans have been around—some women still wear them, and some stores still sell them—but that doesn’t necessarily make them a ‘current’ look in the broader sense of fashion trends. And different regions definitely experience the trend cycle at different times. When I talk about styles having a moment or looking current or dated, I’m not only speaking about what I see what I see where I live. I’m also speaking to what I see and hear from other “influencers” who are more informed than I am, and style experts like Jen at Everyday Style School, who are also looking at the broader landscape of fashion trends across different regions and demographics. That’s why something like skinny jeans might not feel ‘back’ to everyone—it’s more about the overall conversation in the fashion world. I hope that helps! 🙂
Jolynne do you expect them to be more slim fitting straight or “cigarette” style? I would consider that but honestly don’t know if I can force myself to go back to the tight begging style!
*jegging ha!
At the moment, yes, that is what I’m seeing (if I see any at all; I really don’t see them yet, it’s more or less just chatter.) I did see the tight legging style pop up at Gap Factory, but I’m not sure that’s due to the trends. It could just be that they tend to keep every style option and these happen to be in the new arrivals at the moment. Does that make sense? I do not see legging jeans making a comeback any time soon, and if they do, I don’t think women our age will be embracing them. It’s too soon, and we wore them for too long.
Really fun post. So interesting how what seemed so fresh then looks so dated now, especially the proportions. Who knows what we’ll be thinking in five years about what we are currently wearing!
I always wonder that!
Fun post!
I love the comparisons!!! What fun and it sparks my imagination!!
Hi – What is your lipcolor you are wearing?
That day, I’m pretty sure I reverted to my old “lip trio” — some colors may be discontinued.
I love the “then and now” pictures!! It helps me see how dated some of my things are…and how I would look if I wore them! Thank you!
Thanks for this Then & Now post. I always think back to my skinny jeans and longer/tunic top days as things I miss, but when I see see the then & now, I think wow, we’ve come a long way! What were we thinking back then!!
Love this post and hope you’ll make Then & Nows a regular. Back in the day I purchased so many things based on your suggestions and loved them. Figuring out what to keep and why remains a challenge. Seeing the side by sides is especially helpful. I had moved my skinny jeans to the bin at the top of the closet for awhile now but kept a few of the better ones knowing that trends always come back around and the idea of having a pair or two as options with knee high boots warms my preppy-JCrew-loving heart. Also embracing less-is-more with higher quality classic purchases that will hold up over time when the trend does swing back around. I don’t think any of the fast-fashion sweaters, tops and jeans I was buying back in the day would even still be in good enough condition to wear again. Trends change but colors that work for you don’t (if you didn’t change your haircolor) and this combo is a winner. Now of course we’d all like to see an update of the gold sweater-leopard print scarf combo that so many of us, myself included, initially found you from. Happy Monday!
Haha! That look was one of my best ever. Not even sure that color combo could look current now… at least, not for for my personal style. I would not wear a leopard scarf, or any indoor accessory scarf, and I probably wouldn’t wear that mustard color right now. It did feel fun and fresh at the time, though!
I think you hit the nail on the head about the what to keep and why – the higher quality items in more classic styles that can be reimagined for current outfits are worth keeping – if you still love them, of course. The fast fashion stuff is not really worth keeping, unless it is something you absolutely love and cannot find now in a better quality version.
I love these types of posts!
I think I probably began following you around the time that look was “in,” and I felt ever so modern buying booties that were similar with the dip in the front…. and perforated ones too. Blast from the past indeed!
But my absolute favorite was the mustard sweater with the leopard scarf. I felt so brave stepping out of my comfort zone with the mustard AND the leopard…..I felt completely modern and thrilled with myself at the time. 🙂 So funny to look back on those outfits and how far I’ve come thanks mostly to this blog and the work you do.
Morning Jolynne! I love this post! But I have to say you look wonderful in the cowlneck/tunic and skinny jeans. And I prefer that look on you. It’s very slimming and still a good look. However, I completely understand weight distribution. It would be interesting if you recreated the look. Maybe you have.
I still wear cowl necks and tunics but skinny jeans never were a good look for me. You always looked fantastic in them and I don’t see the look as outdated. Thank you!
I so agree with you!
I read so much about proportions these days. Was that not a thing 7 years ago or did we just ignore it for fashion’s sake?
Honestly, I’m not sure, lol!
I really like the then and now post. More please
Agree with this!!
What a great post! Those jeans ! I want them badly! If they do go on sale by my birthday in June I am going for it. Think I will have them for years! Even if skinny jeans return I will not jump on the band wagon. I can’t stand the restricted feeling!
I liked this then and now! Also, just a note for others re gray jeans: I purchased the WHBM gray jeans and they were perfect and fit much like the Mother Wanted jeans. Thanks Jo-Lynne!
So happy to hear that!
I absolutely love the box purse in your 2025 update!
I really liked this post and it helps to see what has changed. I also started reading your blog in 2017, so the look is familiar. I do remember that because of you, I purchased some Rebecca Minkoff bags and a Tory Burch, both of which you carried quite a bit. Thanks for the memories!
Yes! Two of my favorite handbag brands.
Love the update! However, I don’t know about anyone else but while the updated look definitely reads as “gray” jeans, the original reads as blue in every picture on my monitor, so its not an apples to apples comparison. But I would love more of these!
They were definitely grey, but those photos did make them look blue. I even mentioned it in that post. And that sweater was burgundy, not plum, as it appears in those pictures. My husband took those photos (that was before I had Alison!) And I remember trying to fix the white balance, but those colors never did look accurate. 🙂
Love the analysis in this Then and Now post. A great idea as we “ shop our closet”. Very helpful.
I agree with the posts below! It would be fun to pull a photo from 8-10 years ago and create an outfit that’s similar but updated!
That original post was 8 years ago! (Almost, 7 1/2.) 🙂
Love the new versus the old. My first thought was did we actually wear items like that back then? I know I did and loved the look. Fashion has certainly evolved. Just glad we are here to enjoy all the changes. 2017 will always be memorable for me. That was the year that my GI bleeds started and dr’s couldn’t find where I was bleeding from until November 2019 when I went to Vanderbilt to try and find answers.
Gosh, I remember that, I think! I didn’t realize it was so long ago. Glad you got it worked out.
I like this type of post. Definitely the flare jeans outfit looks better to me. I wore that same type outfit in 2017. I think women aren’t influenced by fashion like in the past. That’s why skinny jeans never went away. I’m glad there’s options for everyone. I’m sticking to what I like and flattering on me.
Hi Jo-Lynne,
Loved this post. Appreciate your analysis too! My own personal opinion is the 23″ sweater is much more flattering, encouraging a better proportional fit. Overall, I’m so happy to Say goodbye to the skinny jeans. The newer Silhouettes help my legs look longer, not a bad thing! 🙂
I agree with Annie who mentioned the skinny jeans look blue, not grey at all. But either way, the now is a great look. I didn’t like skinny jeans then and dislike them even more now. Wider leg jeans are so much more flattering on everyone. Skinny jeans worn under a tall boot is really the only way to wear them in my opinion. The burgundy sweater from Talbots is gorgeous, but ridiculously priced. I’m not very impressed with Talbots quality vs. the price. But burgundy and grey is a great combination.
Talbots has their cashmere on sale for 60% off starting today 1-13!!!
No way! I didn’t even check before publishing this a.m. I usually do. That is an AMAZING deal.
They were definitely grey, but those photos did make them look blue. I even mentioned it in that post. And that sweater was burgundy, not plum, as it appears in those pictures. My husband took those photos (that was before I had Alison!) And I remember trying to fix the white balance, but those colors never did look accurate. 🙂
Didn’t know that large cowl necks were out. I have a few in my closet, should I retire them?
Not if you enjoy wearing them! 🙂 It just depends on how important looking current matters to you. Also, I would say that in this case, the large cowl combined with the tunic really makes this particular item look dated, while a more traditional style top with a big cowl would be easier to style in a modern way (i.e. with more current pant and shoe styles). I hope that make sense.
While I’m sure that your 2017 look was on trend, I do like today’s outfit better. When I study the older outfit, I can see what you mean about the proportions. Everything changes and like this example, it’s for the better.
Great post as my favorite color is Burgundy or wine, specifically Cabernet Sauvignon. LOL! I love the breakdown and attention to detail you give on all of our posts. You do an incredible job and I should thank you more often.
Also, I love that you address world events with compassion and empathy. Other bloggers are not mentioning anything and we have enormous natural disasters all over the country. Buying premium denim and a $500 sweater is not a priority when others have literally lost everything they worked hard for. We should be acting like human beings and helping where we can. My son attends UCLA and even though the campus is not officially “closed or evacuated”, they sent the entire staff home, left 1 dining hall open and are encouraging everyone to leave. Luckily, we sent a car out there over the summer for my Celiac son to go grocery shopping when needed. The dining halls do not have GF meals 7 days a week. He is driving a few of his friends to San Diego and my brother-in-law is taking in these college kids until we figure out what is happening. Classes went remote last week and this week. You cannot go outside without a N95 mask because the air quality is so bad. Very few students have a car on campus and my heart goes out to the international students as they do not have options like other students.
I’m so sorry he is dealing with that, Melissa. The fallout from this is so wide-spread and it seems never-ending.
Love this kind of post and maybe along this line you can incorporate an item somewhat dated and update it to now to be current (for those people who may not get rid of items quite as often and how we can still wear in an updated way but show comparisons).
Love this post! Can you please do more of these as I struggle on how to update my styles.
Maybe show us how to update items we already may have in our closet.
I’d love for that to be a regular post for you (and us!)
I love the side by side comparison! I packed my skinny jeans away when the straight style was coming out and to be truthful when you try them back on they feel much more snug to the body then I remember and almost not comfortable or as flattering.. I guess I just got used to the looser fit of a Jean and it really is more flattering on..
I also feel that they are not as comfortable as I remember. It’s funny what you get used to, and then how it feels when it is not what you’re used to anymore.
I found this very interesting in trying to decide what to keep and what to get rid of in my wardrobe.
I say do more of these !!!!
I remember the before outfit and how those Rag and Bone booties with the notch were worn by celebrities everywhere. I could not afford but I definitely wanted them! I think your before outfit isn’t bad at all, we just have different eyes now and the after outfit looks more modern and fresh. I actually still have (and still love) the Rebecca Minkoff purse in the before outfit! I remember getting it for Christmas, not knowing you also had it, and later seeing it on you and thinking that I was so cool because I picked out something that you also liked, lol!
Yes, those boots and that bag were two of my favorite items for a few years running. The boots were a huge splurge, although I’m pretty sure I got them on sale. Even still, I loved them and didn’t imagine parting with them. I was still learning at that point how things tend to cycle in and out of style. And that bag… another longtime favorite. I am glad you still have yours. I only parted with mine because I like to keep a minimal closet and I prefer to have things I can link.
Loved this post comparing looks and how its updated for today!
I just love the updated grey denim and burgandy sweater!
It’s one of my favorite color combinations, too, along with burgundy and navy (or dark jeans). Pretty as always!
I really liked this Then and Now: Update with Gray and Burgundy. The differences were really interesting and I still like the color choices.
I would love to see more of these.
Thank You