The 6 Shoe Trends Fashion People Will Wear With Leggings, Jeans, and Skirts in 2026

By wazup on December 31, 1969 Comments Closed / 1 views

It’s a tale as old as time: the clock strikes midnight, marking the start of a new year and the sudden, inescapable desire to overhaul your entire life. While the shift into a new year gives us all the best excuse to switch things up, that doesn’t mean choosing what to change is always easy. After all, where exactly does one start when trying to transform their life? Do you adopt a new wellness routine? Book a vacation? Reboot your capsule wardrobe? It’s not always easy to discern what resolutions to prioritize, but in those moments, it’s best to follow the old adage: start from the ground up.

One way you can do just that is by taking the advice literally through embracing a few new shoe trends in 2026. Admittedly, we know that sounds a little silly, but all resolutions are about making small steps, friends!

Whether you’re aiming to get a promotion, upgrade your style, or want to feel more self-assured, there’s no better way to start things off on the right foot than by reassessing your footwear. It’s not a massive life-altering change by any means, but you’ll be able to indicate you’ve stepped into a new era (at least visually).

Of course, we realize that trying to figure out which shoe trends to adopt, on top of coming up with footwear styling combos, can be just as time-consuming as choosing resolutions in the first place. Luckily for you, that’s where our expertise comes in handy.

We’ve used our research skills to identify how the style crowd will be wearing the biggest shoe trends for 2026 by looking through runway collections and recent outfit ideas. These shoe trends might not be life-changing, but these styling combos will surely add some pep to your step. Without further ado, here are 6 shoe trends to wear with leggings, jeans, skirts, dresses, and so much more…

1. High-Vamp Heels

Shoe trends to wear with leggings, jeans, and skirts are shown in a collage of runway and street style images. On the left, a small close-up photo of Chanel's spring 2026 collection shows a model wearing an orange fringe skirt with gold bangles and white and black high vamp pumps. On the right, a photo of a woman is standing in a stairwell wearing black sunglasses, a silver ear cuff, a gray coat styled as a dress worn with a black corset belt, black hobo bag, and black high vamp heels

Any true fashion buff can recall the famous quote from Victoria Beckham: “I can’t concentrate in flats.” While some might pass her words off as mere soundbites from a specific moment in pop culture, it seems creative directors took them as a call to action for their F/W 25 and S/S 26 collections. From Chanel to Toteme to Sportmax, fashion houses not only embraced high heels but also championed pairs with ’80s-inspired high-cut silhouettes.

The return of high-vamp heels might come as a surprise considering the trend comes right off the heels of years of ballet flats reigning supreme, but that’s what makes these shoes, well, worth our attention. Their return to the zeitgeist signifies the start of a new era, one that would surely get Posh Spice’s stamp of approval.

Shoe trends to wear with leggings, jeans, and skirts shown in a street style photo of a woman standing on a sidewalk in front of a concrete wall wearing black sunglasses, a white funnel neck bomber jacket, a black slip skirt with contrasting white lace trim, a black frame bag, a white resin rings, and black pointed high vamp pumps

Styling tips: If you really want to show off this shoe trend, consider pairing high-vamp pumps with pieces that will make them the focal point of your look. You can lean into the ’80s-inspired elements of the silhouette by pairing them with an oversized coat styled as a dress to give off “working girl” energy. Alternatively, if you want to make them feel less formal, consider styling them with a funnel-neck windbreaker jacket and lace slip skirt to dial up the visual contrast for everyday wear. Either way, you’ll find that this heel trend can elevate any outfit.

Tony Bianco

Cherry Pump

These high-vamp pumps want to make us break out in the chorus: “She’s a lady. Whoa, whoa, whoa.”

Reformation

Inez Pump

Calling all Upper East Siders!

Le Monde Beryl

Babouche Kitten Heel Pump

We’d style these pumps with a pair of black leggings to make them feel even fancier.

2. All Things Two-Toned

Shoe trends to wear with leggings, jeans, and skirts are shown in a collage of runway and street style images. On the left, a close-up photo from Ferragamo's spring runway show depicts a model's foot wearing two-tone pointed t-strap pumps with a gold chain layered on top. On the right, a woman is crouching on top of a concrete slab outside wearing black sunglasses, a gray blazer over a blue knit sweater dress styled with light blue tights, a bright blue clutch bag, and two-tone brown and white slingback heels.

If you’ve kept up with our reporting, you’re no stranger to the fact that a focus on shoe colors has been one of the most dominant footwear trends over the last few years—it’s a phenomenon that will continue well into 2026. While there are a few noteworthy color trends, the most significant development from S/S 26 runway shows wasn’t a single shade, but rather an embrace of all things two-toned.

From classic cap-toe slingback heels at Chanel to black loafers with a contrasting white vamp at Dior to pointed t-strap pumps at Ferragamo, no type of shoe was left untouched from getting the two-tone treatment. But the runways aren’t the only places the two-tone shoe trend has taken over; we’ve seen it quickly surface in paparazzi shots of stars like Bella Hadid and in social media posts from women around the world. It’s proof that the best things in life come in pairs, or rather, a pair of two-toned shoes.

Shoe trends to wear with leggings, jeans, and skirts are shown in a street style photo of a woman standing in an airport terminal next to luggage, wearing black sunglasses, a white turtleneck sweater, a black belt, white baggy trousers, and black and white two-tone ballet flats.

Styling tips: Lean into the signature element of the two-tone shoe trend by pairing this footwear with matching or contrasting shades. With the latter, you can really draw attention to a pair of two-tone slingback heels by styling them with separates in shades that contrast with those highlighted in the shoes—e.g., brown and white heels pop when paired with an oversized gray blazer and light blue sweater dress. If you prefer a muted color palette, you can try pairing neutral two-tone ballet flats with matching tailored separates to create a super-polished airport outfit.

Sam Edelman

Tarra Pump

These are so Chanel-coded.

Mansur Gavriel

Ballet Flat

You’ll wear these flats all the time.

JIL SANDER

Two-Tone Leather Slingback Sandals

We’re suckers for a two-tone strappy sandal.

3. Textured Kicks

Shoe trends to wear with leggings, jeans, and skirts are shown in a collage of runway and street style images. On the left, a close-up photo from Dries Van Noten's spring 2026 runway show depicts a model's foot wearing black leather sneakers. On the right, a woman stands outside in front of a concrete wall wearing brown sunglasses, a brown claw clip, a long brown maxi coat, a white t-shirt layered underneath a gray crewneck sweater styled with gray pinstripe trousers, a brown shoulder bag, and brown suede sneakers

Although there are plenty of trending sneaker styles to choose from in 2026, they can’t touch the rising popularity of textured kicks. Deviating from a focus on color, we first saw the beginning of this shoe trend in the F/W 25 collections of Miu Miu, Loewe, and even Adidas, which used texture (specifically suede sneakers) to give sneakers a contemporary spin.

Since then, we’ve seen footwear brands further lean into texture to add depth to flat shoes by using unexpected textiles; for example, models in Dries Van Noten‘s spring show sported sneakers made from saffron-red eel skin and shiny black leather. While at Prada and Puma, materials like pale pink satin and pony hair in animal prints were used to create sneakers that blended multiple trends. The result is a series of textured sneakers that everyone wants to get their hands on (literally).

Shoe trends to wear with leggings, jeans, and skirts in 2026 are shown in a street style photo of a woman standing on the sidewalk in front of a concrete wall wearing black sunglasses, a black funnel neck rain jacket, black trousers, a black baguette, and brown suede sneakers

Styling tips: Sneakers can be polished; the secret to making them look the part is by wearing textured-kicks with tailored separates. For example, you can elevate a pair of pony hair or suede sneakers by styling them with suiting staples, such as a long tailored coat, a crewneck sweater, and relaxed trousers. If you want to draw attention to your sneakers, consider matching them with your outerwear or styling them with an all-black outfit to make them really stand out. No matter how you choose to style your textured sneakers, you can trust that they’ll make you look sophisticated all year long.

Jeffrey Campbell

Aleta Sneakers

Suede sneakers are the fashion set’s kryptonite.

Larroudé

Stella Sneaker in Black Patent Leather

Another way to tap into this shoe trend is to opt for leather sneakers.

Miu Miu

Plume Satin Low Top Sneaker

Ballet flats to the back! Ballet-inspired sneakers to the front, please.

4. Posh Oxfords

Shoe trends to wear with leggings, jeans, and skirts are shown in a collage of runway and street style images. On the left, a close-up photo from Jil Sander's spring 2026 runway show depicts a model wearing a navy sweater, silver skirt, green bowler bag, and black Oxford shoes. On the right, a woman is walking on the sidewalk wearing black sunglasses, gold earrings, a brown fur coat, a black handbag, black trousers, and black derby shoes

For those who find sneakers (even suede and leather ones) far too casual for their taste, there’s another shoe trend that’s worth styling with your leggings, jeans, and skirts this year: oxfords. Given the continued popularity of loafers, it was only a matter of time before this preppy-coded shoe made a comeback, too.

That time has come, or that’s seemingly what the S/S 26 collections are trying to make happen this year. From Jil Sander to Ralph Lauren to Miu Miu, we saw multiple runway shows use variations of derby and oxford shoes to elevate everyday silhouettes, like navy blue hoodies and low-slung pencil skirts, poplin shirts and pleated shorts, and even embellished shift dresses. These runway looks served as a reminder that half the battle of creating a sophisticated outfit lies in picking the right pair of shoes—Oxfords are up for the job this season.

Shoe trends to wear with leggings, jeans, and skirts are shown in a street style photo of a woman standing on the sidewalk wearing silver earrings, a tan fuzzy crewneck sweater, a black shoulder bag, black bermuda shorts, white socks, and black oxford shoes

Styling tips: There’s no better way to embrace the return of Oxford shoes than by wearing this shoe trend with other “preppy” pieces. When you want to look like you come from old money, style a pair of derby-inspired flats with oversized golf earrings, a brown faux fur coat, a black crewneck sweater, black trousers, and a black handbag. When you’re feeling more inclined to look like one of the Oxford graduates from the series Industry rather than Succession characters, consider styling a brushed mohair sweater with relaxed pleated shorts, a shoulder bag, and prominent socks with your derby flats. It’s the perfect way to tap into the world of the wealthy, sans trust fund.

Dr. Martens

1461 Water-Repellent Leather Oxford

No, you don’t need to go to prep school in order to wear these shoes.

Camper

Myra Oxford

Beyond shorts, consider styling these oxfords with a pair of relaxed trousers to really lean into the polished feel of this shoe trend.

Kenneth Cole

Justice Square Toe Oxford

During the spring and summer, these shoes will go perfectly with denim shorts, mini skirts, and even linen dresses.

5. Peep-Toe Pumps

Shoe trends to wear with leggings, jeans, and skirts are shown in a collage of runway and street style images. On the left, a close-up photo from Tory Burch's fall 2025 runway show depicts a model wearing peep-toe t-strap pumps. On the right, a woman stands in front of an elevator bank wearing silver earrings, a black leather blazer layered over a white tank top, styled with a black handbag, a black and silver belt, black trousers, and white peep-toe pumps.

Don’t hate the messenger, but peep-toe pumps have officially popped out of hiding. The last time we saw this “controversial” heel silhouette trending was during the noughties; nowhere was safe from spotting strangers’ toes out in the wild. Peep-toe heels became so popular that they were the footwear of choice among every star during that time: Sarah Jessica Parker, Jennifer Lopez, and even Beyoncé. It’s no wonder then that after years of living in the limelight, they went into hiding—that is, until early last fall.

We first saw peep-toe heels emerge from hiding in the S/S 25 collections of Prada, Acne Studios, and Miu Miu. Since then, the signature shape has slowly reclaimed its spot in the limelight, thanks to the viral pairs from Tory Burch, Ferragamo, and Alaïa, which gave the risqué shoe an elegant update for a new era. With updates that include sleek square-toe beds, delicate t-straps, and sculptural wedges, it’s never been more risk-free to style this shoe trend with leggings, jeans, skirts, and really everything imaginable.

Shoe trends to wear with leggings, jeans, and skirts are shown in a street style photo of a woman standing in front of an elevator bank wearing a long black coat layered over a black blouse, black skinny belt, black mini skirt, and black sheer tights, styled with a red skinny clutch, and black patent leather peep-toe heels

Styling tips: The draw of peep-toe pumps has always been the semi-provocative element they offer through the silver of the exposed toe—rather than running away from that, embrace that with your styling. Nod to the “peek-a-boo” element of this particular shoe trend by pairing white pumps with a matching white tank top, a black boxy blazer, and baggy leather trousers (that slightly cover the shoes). The duality of the colors and drastic tailoring will draw attention to your peep-toe heels, perfectly. If that’s not spicy enough for your taste, you can make these shoes even hotter by styling them with a long tailored coat, semi-sheer blouse, a mini skirt, and sheer tights.

Tory Burch

Peep-Toe T-Strap Heeled Sandal

The season’s hottest shoes are still in stock (for now).

Arezzo

Olivia Slingback Peep Toe Pump

The hardware detail makes these peep-toe heels even more trend-forward.

FERRAGAMO

Arcadia Ankle Strap Wedge Pump

Ferragamo knows what the fashion girls want—ahem, patent leather peep-toe wedges in the perfect shade of merlot.

6. Luxe Slippers

Shoe trends to wear with leggings, jeans, and skirts are shown in a collage of runway and street style images. On the left, a close-up photo from Calvin Klein's fall 2025 runway show depicts a model wearing a silver sequin skirt, a brown suede flap bag, and sage green slippers. On the right, a woman is standing outside on the sidewalk in front of a building, wearing black oval sunglasses, a brown boxy blazer layered over a white t-shirt that's underneath a navy and white striped sweater that's styled with brown baggy pleated shorts, a black bowler bag, and black leather slippers

What’s the last shoe trend that you’re sure to spot everywhere in 2026? Drumroll, please… slippers. Yes, really. If your first thought to rationalize this shoe trend fell into the thinking that it could only be a thing because people would want to put on “casual” footwear after a crazy night out, you’ll want to think again—although for the record, we totally support that choice.

Slippers are no longer just for the house or even for going to the bodega in the morning; they are slowly on their way to becoming one of the year’s biggest shoe trends. We first saw slippers make a step in this direction with the debut of luxe leather, satin, and suede versions in the F/W 25 collections of Calvin Klein, Miu Miu, and The Row. Their debut in runway collections cemented them as a symbol of the quiet luxury aesthetic, quickly making them the shoe of choice among the style crowd for elevating everyday ensembles.

Shoe trends to wear with leggings, jeans, and skirts are shown in a photo of a woman standing inside her home in front of a door, wearing a long olive green maxi coat over a white maxi sweater dress styled with a yellow satin clutch bag and black slippers

Styling tips: While slippers might be the most “casual” shoe trend to surface for 2026, you better believe that you can make them feel fancy with some strategic styling. When you want to get away with wearing them to work, consider styling a pair of leather slippers with an oversized blazer, striped sweater, long pleated shorts, and a barrel bag—it’s a shoe styling formula that’s fit for a casual day at the office. When you’re unsure what to wear off the clock, look no further than a pair of slippers styled with a long, tailored coat, a maxi sweater dress, and a satin clutch bag. No matter if you’re running errands, achieving resolutions, or simply relishing in the new year, this shoe trend (and all the others listed before) will serve you well.