The “Weird” But Forward Way Fashion People Are Styling Their Sweaters for Fall 2025

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It seems impossible, as of late, to scroll online without stumbling upon some debate, even about the more “superfluous” things happening in fashion. Admittedly, it’s what makes the internet, well, the internet. We’ve all come to relish live-tweeting our thoughts about what celebrities are donning on the red carpet, new creative director appointments, or the biggest trends of the season, all while sitting comfortably on our couch in sweatpants.

Love it or hate it, we’re living in one of the most polarizing periods in recent history; that’s no more apparent than with the reemergence of one specific styling trend: dresses over pants. Yes, really. While we might have thought that this controversial styling trend was a relic of the early aughts, collections from S/S 2024 through S/S 2026 have proven otherwise.

The “ugly” styling combo, which was first spotted at The Row, Ferragamo, Gucci, and a few other fashion houses, was one we all once swore off. But suddenly, it looked, dare we say, stylish—or at the very least interesting—again. While some might attribute this styling trend’s return to a heady dose of nostalgia (that almost teeters into Stockholm syndrome territory) or even to a growing disposition among the masses to use sartorial choices to stand out on social media, it was actually simple silhouette updates that made it stick. Skinny jeans were replaced with wide-leg pants, cotton dresses for lace slips, and even other pragmatic layers were added into the mix.

The result? A series of runway looks that gave a new generation a contemporary way to incorporate this formerly contentious outfit formula into their lives. And boy, have they done just that.

We’ve seen the style set quickly find new ways to wear dresses over pants, the latest version being to pair them with their trending sweaters, too. It’s a little peculiar, we know, but it’s quickly become so popular that it’s bound to become the way to wear sweaters for the rest of 2025. But if you’re unsure whether you’d want to wear this “weird” styling trend, let us share our case for you to test it out.

Ahead, we share eight fall outfit ideas, styling tips, and shopping recommendations that serve as a masterclass in how to wear sweaters over dresses and denim. If you don’t come to love this trend by the end of this story, at least you’ll be able to stand 10 toes down in your loathing.

How to Wear Sweaters Over Dresses and Denim

WEAR: Black sunglasses + gray oversize crewneck sweater + whi lace slip dress + black baggy jeans + two-tone flip-flops + black bowler bag

Styling Notes: At face value, the first benefit of testing out this styling trend is that you can get more wear out of your summer staples before winter. For example, you can wear your favorite lace slip dress on a crisp fall day if layered over a pair of baggy jeans and under a contrasting oversize crewneck sweater. Bonus points if you finish off your look with a pair of flip-flops to create an outfit from head to toe that challenges traditional notions of what one “should” wear in the fall.

Aritzia Plush Cashmere Oversized Crew Sweater

Not to be dramatic, but Aritzia’s cashmere is out of this world.

The Frankie Shop Elvina Lace Trim Slip Dress

You’ll wear this slip dress well into the spring.

Agolde ’90s Mid-Rise Straight-Leg Jeans

Every wardrobe needs a pair of black straight-leg jeans.

Ancient Greek Sandals Saionara Jelly Flip Flop

Yes, flip-flops can be worn in the fall!

Jacquemus Le Turismo Leather Bowling Bag

A girl can dream.

WEAR: Gray turtleneck + white slip dress + black wide-leg jeans + white pointed-toe pumps + black shoulder bag

Styling Notes: If you can’t fathom wearing flip-flops in the fall, much less styling a dress over denim, we recommend going back to the basics. The easiest way to make this trend feel more approachable for your everyday life is to turn to wardrobe essentials, such as a neutral turtleneck sweater, white slip dress, black wide-leg jeans, pointed pumps, and a minimal shoulder bag. Ultimately, by choosing to style your staples altogether in this way, you’ll take some of the “controversy” out of this trend (in a good way).

Massimo Dutti 100% Cashmere Knit Vest

So cozy.

Intimissimi Silk Slip With Lace Insert Detail

You can shop this slip dress in nine other colorways.

Everlane The Mid-Way Jean in Washed Black

Everlane’s denim is worth the investment.

Tony Bianco Cherry Pump

“She’s a lady, whoa, whoa, whoa.”

COACH Swing Zip Bag

Calling all ’90s minimalists: This Coach shoulder bag is made for you.

WEAR: White crewneck sweater + black lace slip dress + white baggy jeans + gold jewelry + black mesh flats

Styling Notes: If you were looking for further evidence that wearing dresses over denim, with the addition of knitwear, can be chic, look no further than the outfit above. You can make this traditionally over-the-top styling formula feel a bit more streamlined by opting for separates in shades of black and white. Pairing a white cashmere sweater with a black lace slip dress and white baggy jeans will make your look stand out without going over the top. Of course, if you feel it’s missing that something special, you can finish off the look with fun accessories, such as mesh flats and sculptural jewelry.

Gap Cashsoft Crewneck Sweater

You’ll wear this sweater all the time.

ZARA Asymmetric Lace Dress

The asymmetrical hemline on this dress makes it the perfect layering piece.

ALIGNE High Rise Straight Leg Jeans

Our editors love Aligne’s denim.

Le Monde Beryl Luna Leather-Trimmed Mesh Ballet Flats

We’re still into mesh flats over here!

Jenny Bird Sees Ring

If you were to look up the term “wearable art,” you’d find a photo of this ring.

WEAR: Two-tone aviator sunglasses + brown turtleneck + white lace slip dress + brown suede belt bag + black baggy jeans + suede sneakers

Styling Notes: While opting for black-and-white separates is the simplest way to ease into this styling trend, it’s not necessarily the most exciting. Enter the ensemble above as an alternative. You can still wear your fall staples while making a statement simply by embracing alternative neutral shades and different textures. Start by swapping your black or white sweater for a chocolate brown one. Next, add a slip dress with unique details (think embroidery, opacity, or color). Lastly, opt for other statement-making accessories such as suede sneakers, a belt bag, or oversize aviators. It’s a surefire way to make this styling formula stand out.

Nordstrom Wool & Cashmere Turtleneck Sweater

Espresso martinis have nothing on this decadent sweater.

Urban Outfitters Out From Under River Ruffle Lace Trim Slip Dress

The opacity of this slip will draw even more attention to your denim.

Citizens of Humanity Ayla Baggy Mid-Rise Jeans

Another great pair of jeans!

PUMA Speedcat OG Sneaker

All the fashion girls are obsessed with Speedcat sneakers right now.

Elisa Johnson Jane Mini Sunglasses

You’ll feel like a main character in these two-tone aviators.

WEAR: Black sunglasses + white blazer + white cashmere T-shirt + white slip dress + black wide-leg jeans + black pointed mules + black frame bag

Styling Notes: While embracing different colors, textures, and accessories is a surefire way to make this eye-catching styling combo stand out even further, there are moments when you might need your outfit to be on the chill side. Luckily for you, that’s where the formula outlined above comes in handy, as leaning into layering is the ultimate way to strike a delicate balance between an outfit that is understated but still unique. You can make your minimal separates stand out by styling them together—specifically by pairing a lightweight cashmere T-shirt with a matching blazer, a slip dress, and contrasting black denim. You’ll have an outfit that’s as eye-catching as it is elegant.

MANGO Double-Breasted Suit Blazer

Don’t be afraid to wear white well into the winter.

ZARA Combination Lingerie T-Shirt

The built-in lace detail means you don’t have to worry about layering.

AG Deven Ultra High Waist Wide Leg Jeans

The ultra-wide-leg flare on these jeans makes them look like trousers, so you can get away with wearing them to work.

Steve Madden Mod Pointed Toe Mule Pump

Minimal pointed mules will always be must-haves.

Freja New York Mercer Faux Leather Top Handle Bag

You can fit way more into this bag than you’d expect.

WEAR: Black sunglasses + navy turtleneck + white shoulder bag + white slip dress + white relaxed jeans + black ankle boots

Styling Notes: In addition to adding even more layers to the mix, another way to elevate this styling combo is to embrace color-blocking. And no, you don’t have to wear the rainbow! Start swapping out your classic black, white, or gray sweater with a knit in an alternative neutral, such as navy, to dial up the visual interest. Next, you can make your outfit even more polished by pairing your sweater with a pair of relaxed white jeans and a matching slip dress. Lastly, add a shoulder bag and ankle boots in matching colors to further emphasize the color-blocking in your look. By pairing dark and light tones together in this way, not only will you naturally draw onlookers’ eyes to your look, but you’ll also create an outfit that oozes effortless elegance.

Sézane Soren Jumper

Sézane’s knitwear is worth every cent.

Kat The Label Hayden Lace Trim Slip

Love, love, love.

Madewell Low-Slung Baggy Jeans

White denim will always scream “wealth” to us.

Vagabond Shoemakers Hedda Bootie

These boots were made for walking.

VERAFIED Clutch Shoulder Eclair Bag

Every editor wants this handbag right now.

WEAR: White polo knit shirt + white satin slip dress + red wide-leg pants + black jelly flip-flops + tan barrel bag

Styling Notes: Need a break from minimalism? We get it. If you want to take a risk, consider using the outfit above as your blueprint. Frankly, there’s no better way to make it abundantly clear that you’re wearing a dress over denim than by opting for jeans with a colorful wash. It will draw the eye naturally to the hemline of your dress, making the layering the focal point of the outfit. Of course, if you want to tame down your tinted denim a little, you can finish off the look with some basics, such as a beige polo sweater, flip-flops, and a barrel bag. It will let you indulge in maximalism without an entire wardrobe overhaul.

H&M Fine-Knit Collared Sweater

The perfect polo to layer with all your fall staples.

Reformation Cleodora Dress

The ruffle detailing on this dress will look so good under your sweater.

We The Free Deep Trance Dropped Boyfriend Jeans

Red hot.

Veronica Beard Clear Flip Flop

If you didn’t get a chance to buy into the jelly sandals trend, now’s your chance.

The Row ’90s Leather Tote

Santa, if you’re reading this story, you know what’s on our wish list.

WEAR: Tan trench coat + red V-neck sweater + white satin dress + black wide-leg jeans + white pumps + brown suede bowler bag

Styling Notes: Although we’ve seen the fashion crowd adopt more minimalist ways to pair dresses and denim work for everyday life, we’d argue it’s still not the best way to wear this “controversial” trend. You’re always free to make this trend align with your lifestyle or personal style, but if you really want to get why the fashion crowd loves this combo, you have to be willing to take a couple of risks. Rather than trying to make this styling trend something it’s not, embrace the fact that it’s supposed to be idiosyncratic. It’s your permission slip to get weird with it, so don’t be afraid to add a colorful sweater, an oversize trench coat, peep-toe pumps, a suede bowler bag, or anything else that feels excessively over-the-top to your outfit. It’s less about adhering to an idea of what you should wear and more about wearing what speaks to you (even if everyone will talk about it).