Then & Now: How I’d Style These Outfits Today

Outfit #1: White Tee + Jeans

Let’s start with a combination that has probably appeared on this blog hundreds of times over the years: a white tee and jeans. It doesn’t get much more classic than that.

The first thing I noticed here was the rise of the jeans… ooof. What was that, like an 8-inch rise? Then there’s the skinny silhouette, the wide brown belt, and the cuffed hems.

The problem is that everything happening with those jeans works against the goal of creating a long leg line. The low rise shortens the leg line from the top, and the ankle-length inseam shortens it from the bottom. Then the wide belt and cuffed hems break up what little leg line is left. The end result is that my vertical proportions are cut right in half.

Now, that white tee? I would probably still wear it today. I actually like the v-neckline because it opens up the chest area and shows the collarbones, which is flattering. A more modern version might be a boxy crewneck tee like the MOTHER Little Goodie Goodie or a boxy v-neck like the Splendid Lila, but I don’t mind this one at all. It would probably just be a little too long for my higher-rise jeans today.

The jewelry, on the other hand, would definitely get an update. The long station necklace layered with the short coin pendant and that orange leather wrap bracelet all feel very of their era.

The one thing I would probably still wear today are those sandals. I actually don’t hate those. I think they were Vionics.

Okay, so here’s the modern update. I actually shared this outfit just last week, so you may remember it.

The 2026 Update

Splendid Lila V-Neck (also at Nordstrom) (M) // Madewell Jules Slim Straight Ankle Jeans (29) // Steve Madden Tracie Jelly (8) // Parissa Wang Gabrielle East-West Shoudler Bag // Madewell Semiprecious Paracord Charm Necklace (also at Nordstrom)

In the updated version, I kept the same basic formula—a white v-neck tee and blue jeans—but made a few key changes.

The higher rise of these jeans creates a longer leg line, and the slim straight silhouette feels much more current than the legging-tight skinny fit from 2016. There’s also no cuff or wide belt breaking up the line of the jeans. The lighter wash denim feels more modern as well, although the darker wash from the original outfit would work just fine today if you prefer a higher-contrast look.

The v-neck tee has a boxier shape and shorter length, and while I didn’t mind the sandals in the original outfit, these kitten-heel jelly thong sandals feel more polished and trend-forward.

I also traded the layered necklaces for a cord necklace with a fish charm that fills the neckline perfectly. And instead of the orange leather wrap bracelet, I’m wearing a mixed-stone stretch bracelet in neutral brown tones that coordinates with the rest of the outfit.

Finally, the handbag is larger and more proportional to my frame, and the east-west silhouette feels much more current than the smaller crossbody bag I carried in the original outfit. Even the sunglasses have a slightly more updated shape.

One quick note: I actually think this outfit would look great with a belt. Because the rise is higher and the jeans aren’t cuffed, a belt wouldn’t shorten the leg line nearly as much as it did in the original outfit. Instead, it would add a little definition and visual interest.

Outfit #2: Green Tee + White Jeans

What immediately jumps out at me here is that necklace—and the fact that I paired it with those long teardrop earrings. That’s a lot. Not only that, but it instantly dates an otherwise fairly classic outfit.

And I’m not sure what that green band is on my arm. Maybe a Fitbit? Whatever it is, it definitely needs to go.

The leopard wedge slide sandals also date this outfit, especially when paired with the white skinny jeans. If the jeans were a more relaxed fit, I don’t think the shoes would feel quite so out of place, but together they are very 2015.

The tee, on the other hand, is completely fine. In fact, I wish I still had it! I love the pretty jade green color, the scoop neckline, the way the sleeves skim the arms, and the slub texture of the fabric. Even the length works. I’d probably front-tuck it today depending on the rise of the jeans, but I think it still looks good worn untucked as shown here.

Unlike the first outfit, the proportions here actually hold up pretty well. The longer jeans and heeled sandals create a longer leg line, so the outfit doesn’t feel nearly as dated.

Okay, so here’s the modern update I chose.

The 2026 Update

Wit & Wisdom Crochet Cap Sleeve Tee (S) // KUT from the Kloth Kelsey High Waist Raw Hem Ankle Flare Leg Jeans (10) // Dolce Vita Laurie Wedge Sandal (8) // Clare V. Stripe Flat Clutch // Baublebar Maui Charm Necklace

For the updated version, I looked through my photos from this season and was surprised to find one that is actually very similar to the 2015 outfit. In fact, when I put these side by side, I realized this is clearly a formula I’ve loved for a long time.

The top is a different color, but it is otherwise remarkably similar. Instead of a jade green tee, I’m wearing a cobalt blue one, but both are simple slub-knit tees with a relaxed fit and abbreviated sleeves. I even wore this one untucked, just like the original. It also has some subtle crochet detailing, which is very much of-the-moment.

The biggest update is in the denim. The white jeans have a more relaxed ankle-flare silhouette, which feels much more current than the skinny jeans I was wearing with the green top.

I also thought it was interesting that I’m wearing platform wedge sandals in both outfits. Platform wedges aren’t exactly at the height of fashion right now, but the raffia texture and clean double-strap design make this pair feel much more current than the leopard-print version.

And while I’m still wearing a statement necklace, it’s a completely different kind of statement.

Instead of a large beaded multi-layered necklace and teardrop earrings competing for attention, this colorful beaded necklace with ocean-inspired charms feels more playful and modern. It’s also supported by simple gold hoops and a gold beaded bracelet, rather than more competing statement pieces.

The funniest coincidence might be the clutch. Somehow I’m carrying a flat clutch in both outfits, eleven years apart.

I rarely carry one, so that definitely wasn’t intentional. I already had this outfit photo and didn’t notice the similarity until I started putting this post together! That said, the blue-and-red striped canvas clutch feels much more current and casual than the black quilted version from 2015.

Outfit #3 Black Top + Olive Pants

Unlike the first two outfits, this one didn’t make me cringe when I found it in the archives. While there are definitely details that date it, overall I think it still works—and honestly, it’s pretty flattering. And not just because I was 20 pounds thinner! I think the proportions are actually pretty spot on.

And black and olive has always been one of my favorite color combinations. In fact, next to a white tee and blue jeans, it’s probably the outfit formula I’ve worn most often over the years.

Let’s start with the black top. I remember it fondly because I had it for years. It had such a flattering neckline and sleeve shape, and the subtle texture detail around the neckline elevated it just a bit.

The olive cargo pants hold up surprisingly well, too. Yes, they’re skinny pants, but they’re not quite as skin-tight as some of the styles we were wearing back then, and the longer ankle length still works today.

The gold espadrilles are a classic style. While I’ve passed most of mine on, I wouldn’t say they look dated as much as they feel a little less like my personal style these days. I tend to prefer footwear with a more modern feel.

As for the coral satchel, that silhouette is actually starting to come back around, and it’s still a beautiful bag, although I mostly carry neutrals these days.

Even some of the accessories hold up. I would probably swap the thin gold hoops for something slightly chunkier today, but I’d happily wear that black-and-ivory bangle again.

Now, for the update.

The 2026 Update

Free People Neria Rib Tank (L) // PAIGE Ari Wide Leg Pants (also at Nordstrom) (30) // Crocs Miami Toe Loop Sandal (8) // Clare V. Grande Fanny // YSL sunnies

When I went looking for a current version of the same idea, I landed on this black tank and olive wide-leg drawstring pants. The overall formula is remarkably similar, which just goes to show that some outfit combinations really do stand the test of time.

The wide-leg silhouette creates a very different effect than the skinny pants from the original outfit. It’s not as sleek or leg-lengthening, but this newer outfit feels more relaxed and current. And the fitted tank helps balance the volume of the pants, which keeps the overall silhouette from feeling overwhelming.

Like the original outfit, this outfit has a handbag serving as the statement piece, but this time it’s a modern woven leather belt bag in shades of brown, black, and ivory. Instead of making a statement with a bold pop of color, it stands out through texture and pattern, which feels more current.

And I still wore a neutral shoe, but a beige toe-loop sandal instead of the gold espadrilles. The overall look feels much more relaxed and casual.

So that’s all I’ve got for today! I found a bunch of other photos it would be fun to reinvent, but I felt like three was enough for one post.

If nothing else, this exercise was a good reminder that outfit formulas tend to stand the test of time. The biggest changes weren’t the color combinations or even the basic pieces—they were the silhouettes, shoes, accessories, and styling details.

And while I definitely prefer some of the updates, there are a few things in those old photos that I still like. Maybe that’s the real takeaway: style evolves, but not everything needs to be reinvented.

I’d love to know what you think. Which update was your favorite?