Who remembers these waterfall cardigans and gingham shirts? After blogging for well over a decade, it’s always interesting to dig in the archives and see how much styles and preferences change. The outfit on the left was one of my most-Pinned posts ever circa 2014-2015, and although I wouldn’t reach for the exact combo today, it still serves as a solid starting point for an updated version!
See my video on updating this look (hit unmute for sound), and I’ve also listed my thoughts below.
The video also shows a final look with these Sézane flats instead – I absolutely love them in both leopard and black, but wear with heel lifts so they don’t rub the bottom of my ankles.
Updated Outfit Details
White tee (in video): Everlane XS. Nice cut & shorter length. I size up and have XS and S for a relaxed fit
Button-up shirt: Everlane silky cotton shirt xxs, great lightweight staple I own in several colors.
Jeans: Levi’s jeans 25 x 27 in “Indifferent Indigo.” Been sizing up lately since these fit slimmer.
Boots: Madewell boots 5.5 c/o, runs slightly narrow. J.Crew has similar.
Belt: Madewell triple metal belt xxs
Trench: Oak + Fort trench xxs. Oversized longer fit. Code JEANTRENCH for 20% off in April.
Bag: Etsy hobo bag in medium, corteccia color. Code JEANHOBOBAGS30 for a discount.
How I’d Update this Older Outfit
1. denim cut + rise
Denim trends are cyclical and skinny jeans can still look great on some, especially a solid dark blue wash. However for my proportions, low-rise bottoms make my torso appear longer and legs look shorter. And after 2 kids, I want more support at the tummy area.
I’ve shared about the Levi’s jeans on the 2025 side a lot, since they’re not skinny, not wide, and not particularly trendy. Just a classic 90s-inspired slim straight cut. The high rise elongates my leg line, and the length (hitting right below my ankle bone) works with many different shoes and flats. I own these same jeans in multiple colors from over the years, and also love “Fully Baked” for a lighter blue wash, and “In the Clouds” for white.
2. shoe + belt color
While I am a fan of sandwich style (color-matching a piece from the top of the outfit to a piece at the bottom), the 2015 contrast-colored belt and shoes further truncated my leg line at both the top and bottom. I think that one or the other could be fine, but wanted to illustrate the difference that similar-toned pants, belt and shoes can make.
3. Ankle boot styling
The bunching and cuffing where my 2015 jeans sit on top of the boot shaft doesn’t look streamlined. With ankle boots, even a slightly wider jean that fits over the top of the boot opening will instantly look more sleek.
After going through all the toe-shape phases over the years from round to pointy to square, my current favorite has been a rounded square toe. To transition this look for warmer spring weather, you can also do mary janes, ballet flats or loafers.
4. Shirt
Gingham always brings me back to the J.Crew 2000s era! I wore my share of this print, but a solid or striped button-down is more timeless and versatile.
5. layering piece
These waterfall cardigans had a chokehold on me 10 years ago and are still comfy to lounge in. But for a similar drape-front style that feels a little more sophisticated and less frilly, I’ve been loving a long cardigan (ie J.Crew Juliette cardigan) or trench coat.
6. accent piece
I used to love adding a pop of color to every outfit! A more subtle way of adding an element of interest can be via a patterned handbag, scarf, or shoe. I’ve always loved a leopard print shoe, but even more so in recent years now that I wear more neutrals and basics that benefit from a pop of something.
Do you agree with these updates?
I love this post! Could you share how you styled your hair? I’d love a how-to guide!
Would be fun to see what you’ll think about the 2025 version in 2035! Can’t wait lol
Unrelated, but a serious request… As someone blessed with a tiny flat butt, would love to have you review “butt enhancing” garments from skims etc…
Interesting analysis!
I like to leave my button downs untucked (bit of a tummy) but most of the ones I’ve seen, even in petite sizes, are longer than I like and shorten my leg line. Have you found petite sized button downs that shorten overall length, as well as arm length? If so, who makes them?
Thanks!
I’d try Banana or even Land’s End for petite button downs.
I love this, please do more!!
Thank you Sarah-Jayne! I would love to do more like this – it was fun to go down memory lane 🙂
I vividly remember the 2014 outfit and also had the waterfall cardigan (ordered from the US for delivery to the UK!) and a number of checked shirts! 🙂
I love how this post shows how a person’s style can shift and mature over time, while still having core elements. Thank you! xx
Hi Bethany! Those were some great closet staples at the time 🙂 Thank you so much for your kind note and for following along with me as my style has evolved xx
Hi Jean! Can’t believe I have been following you for 10 years plus! I had the same gingham shirt, cardigan, and the belt! Your kids are adorable! Why don’t you do an Hermes journey post one day? 🙂
Hi, thank you so much for following along for over a decade!! You’re so kind 🙂 And thank you for your post suggestion – I wish I had more of an Hermes journey to share! Haven’t had any luck at the H store on any of my Paris visits.
perfect updates!
Thank you!
I tried to use the coupon code for the Etsy hobo bag, but it didn’t work.
Hi Sri, I’m so sorry there was a typo in the code when I first published this blog post but it is fixed now! The correct code is JEANHOBOBAGS30
I enjoyed this. Please do more like this.
So glad you liked this!
I love this theme for a post! Super interesting and helpful to see how you updated the styles.
Thank you Laura, I had a lot of fun with this one!
You just keep getting more and more classy and beautiful!
You are too kind Sue, thank you, I hope you are well!
Well done update, really loved seeing this as it jars me to clear out a few items.
Thank you!
Can you share what size you chose in the Everlane shirt? I’m similar in size to you but haven’t purchased from this brand before. Thanks!
Hi Cynthia, I took an xxs in the Everlane shirt and found it to be very true to size. My usual size that I typically order in other brands fit perfectly relaxed, not too slim. I hope that helps!
Thanks; I’ll give this one a try! Love this post and hope you’ll do more in this vein :-).
Nice post
Thoughts on the H buckle belt, still timeless?
Honestly, I haven’t reached for mine in a while and prefer my belts without logo buckles now. But I never know – preferences might change again!
Such a cute idea for a post, especially for readers who’ve been along for the Extra Petite (and PAG) journey with you for years. Appreciating your longevity in this space!
Thank you so much Charissa, and I’m impressed you remember PAG! I’m so grateful for this community and readers like you who have been along for the ride all of these years xx