Updating an Old Outfit from 10+ years ago

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 Sezane 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

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 JEANHOBOBAGS 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?