Dated vs. Modern Style: Restyling my Outfits from 2016
Every so often I look back at photos of myself from ten years ago and think, I loved that outfit. And I did! It was right for that moment. But if I put the exact same thing on today, something would feel a little off, and it usually has nothing to do with the clothes themselves.
Here's what I see all the time with clients who feel stuck: they assume the pieces are the problem. They pull out a top or a pair of pants, decide it's outdated, and start over. Most of the time, those pieces are perfectly fine. It's the proportions and the combinations that are making the outfit read dated.
Think about how this used to work. In our moms' and grandmothers' era, you could practically date an outfit by hemline. Skirts went short, then long, then short again, and that was the update. That's still a little bit true today, but now it works more like a domino effect.
Here's how the dominoes are falling right now. Pants went from skinny to wide. The rise went from low to high. So tops became a little shorter to work with that higher waist, and shoes got a little chunkier (hello, sneakers) to balance out the fullness in the leg. Change one element and everything around it has to shift too.
And this holds even if you're not wearing a true wide leg. A straight jean, a barrel, a trouser, the proportion play is the same. Once you understand how the balance works, you can rebalance what you already own instead of replacing it.
So I did something fun. I started with real photos of myself from 2016 and rebuilt those outfits for today, then recreated a handful of my other old looks in the studio. Same energy, updated proportions.
Let's take a look!
Part One: The Real Ones
These three are actual photos of me from 2016. Not recreations. Outfits I really wore, really loved, and really posted, rebuilt for right now.
Khaki Pants and a White Top
Khaki pants with a white top will always work, which is exactly why this one is such a good lesson. The formula is bulletproof and the styling still dates it.
In 2016 (left), the pant was a paper bag style with a sharp taper at the ankle. All that volume gathers at the waist and then narrows down to nothing, which turns the shoes into the focal point whether or not you meant them to be. I loved this outfit at the time and so did all of you. Looking back, I feel a little bit like a cupcake.
In 2026 (right), we're back to that one third, two thirds proportion. A shorter top, a longer and fuller leg, and an eye line that travels up rather than stopping at my ankles. Bonus, these pants have an elastic waist.
The shift: stop the taper, let the leg stay full to the floor.
Jeans and a Cardigan
In 2016 (left), the cardigan runs well past my hip and the mule cuts the leg partway down. That's two heavy visual stops in a row, and neither one is doing me a favor.
In 2026 (right), the topper comes up to the hip and the shoe gets sleeker. The volume moves into the jean instead of the layer. Everything is pulling the eye up rather than down.
The shift: shorter topper, lighter shoe, fuller leg.
Jeans and a White Top
This one shows the hip issue as clearly as anything in the post.
In 2016 (left), the top lands right at my hips, which is my widest point, partly because the pant was a mid to low rise and there was nowhere higher for it to sit. The shoes were the hero again. Your eye goes top, hips, feet, three stops on the way down.
In 2026 (right), the eye goes straight to the top, because the white shirt is the one third of the look. It doesn't need to be tucked. It has an elastic hem that lets it blouse and land right at the waistband. The other two thirds is a long, flowing jean.
The shift: give the top a waistband to land on.
Part Two: The Recreations
Now that you've seen the real ones, here are a few more of my old favorites, rebuilt side by side so you can see the swaps happen in real time.
Jean Shorts and a White Button Down
This was one of my absolute favorites back in the day, and I still love the spirit of it.
In 2016 (left), I went short and heavily distressed on the denim, tied the shirt at my waist, and finished it with a chunky gladiator sandal and a fine little necklace. Every one of those choices was correct for the moment. Together, they time stamp the outfit.
In 2026 (right), the short gets longer. Once the bottom half has more length, the top has to come up to meet it, so a cropped button down does the balancing. A belt at the waist keeps everything defined. The sandal still gives me an ankle strap and some height, and it does it without the weight.
If a longer short isn't for you, you don't have to go there. A cleaner, more tailored short in place of a heavily distressed one gets you most of the way.
The shift: length on the bottom, lift on the top.
A Black Skirt and a Tee
Note: the updated version is on the left in this one.
In 2016 (right), a skirt with a bootie and a slice of leg showing in between was the look. Today that reads choppy. Your eye stops at the hem, stops again at the boot, and the line never gets anywhere.
The graphic tee is doing something too. I used to wear one with almost anything. I'm more selective now, and I notice I'm not reaching for them with clients as often either. They're not out. I just wear them less. Keep the ones you truly love and let the rest go.
In 2026 (left), a longer skirt with a taller boot makes one uninterrupted line instead of three separate blocks. And the jacket is quietly doing a lot of work. A bomber sits higher than a traditional leather jacket, which puts the top at roughly one third of the look and the skirt at two thirds.
The shift: one third on top, two thirds on the bottom.
Stripes and Jeans
Updated version on the left again.
In 2016 (right), the jean was skinny and gripped tight at the ankle, with heavy fading through the thigh and knee. Add a chunky sneaker, a long cardigan, and a long fitted top underneath, and even tucked in it feels dated. The leg keeps narrowing while the layers stack up.
In 2026 (left), the jean is a touch darker with a much more even wash. The striped top is boxier through the body. The sneaker is low profile. Here's the part worth noticing: even without the sweater over my shoulders, that topper hits at the hip and still feels current. The cardigan was never the problem. The length was.
The shift: shorten the topper, widen the leg, calm the wash.
A White Tank and Jeans
Same three pieces on both sides. White tank, jeans, black heeled sandals.
In 2016 (left), a heavily faded light wash paired with a cropped kick flare ages the outfit faster than anything else in the frame. A fitted tank over a snug jean adds a lot of cling, and a chunky embellished platform was very much the shoe of that decade.
In 2026 (right), a cleaner mid blue in a full length wide leg does most of the updating on its own. I kept the top on the fitted side and let the eyelet texture and the wider leg handle the balance. A simple strappy sandal lets the whole thing relax.
The shift: if one piece is fitted, let the other one breathe.
White Jeans and a Tank
Updated version on the left.
In 2016 (right), the rise sat low and the top ran past my hip, which is the widest point on most of us. A chunky platform closed it out. Every element is quietly shortening the leg.
In 2026 (left), the rise comes up to my natural waist, which lengthens the leg and gives the top somewhere to land. The top ends at the waistband instead of covering my hip. A sleek sandal keeps the line going all the way to the floor.
I want to be clear that I'd still wear every piece on the 2016 side. They're styled a decade behind, and that's a very fixable problem.
One honest note while we're here. Those wide legs need a hem, half an inch at most, and I didn't get to it before we shot. A wide leg should skim the floor rather than sweep it, and tailoring is the cheapest styling upgrade there is.
The shift: raise the rise, stop the top at the waistband.
White Jeans and Wedges
Both sides follow the same recipe: navy top, white jeans, wedges. One reads 2015 and one reads 2026.
In 2016 (left), the top is fitted, the rise is lower, and the jean is stark white, which is a harder color to make feel soft.
In 2026 (right), the top loosens, the rise comes up, and the denim goes ecru instead of bright white. That color change alone does more than you'd expect. The wedge updates too, with a slimmer profile and a cleaner line through the ankle.
The shift: three small swaps, no new formula.
Same Dress, Two Different Wedges
I wanted to include this one because it isolates a single variable. Identical dress, identical sweater vest, and the only thing changing is the shoe.
On the left, a heavy gold platform espadrille. That thick sole and covered vamp stop the leg right at the ankle and pull all the attention to the floor.
On the right, a slimmer wedge in a natural finish, with straps that leave more of the foot showing. It still gives me height and it still gives me the stability that makes wedges worth wearing in the first place, but it keeps the leg line going instead of cutting it off.
That's really the whole story of how wedges have changed. They kept the comfort and lost the clunk. If you want the longer version, I broke down both styles of modern wedge in this post on what shoes to wear with summer dresses.
The shift: less shoe, more leg.
What I Want You to Take From This
Scroll back through all ten of these. In almost every case, I'd still wear the individual pieces on the 2016 side. Nothing there is ruined or unwearable. It's arranged in a way that belongs to a different decade.
That's the whole thing. Updating your proportions is what makes a closet feel current, and it costs you nothing.
This is what closet confidence actually looks like in real life. It's knowing the small shifts that move an outfit from dated to current, without overhauling everything you own.
So go pull out that thing you've written off. I'd bet the balance is the problem, not the piece.
xo, Hallie