Always one styling step ahead, I just spotted Dua Lipa out and about in the autumn shoe trend that's set to dominate in just a few weeks' time. Stepping away from the flip-flops and barely-there sandals we've all been living in for the past few months, she instead reached for their antithesis: a pair of knee-high biker boots.

Poised to become one of autumn's biggest shoe trends, biker boots bring a slightly grungy edge to an outfit, which Dua put to work by pairing with a series of light, floaty dresses this week.

Spotted in the new-season pairing, not one, but twice, Dua first styled her Miu Miu Leather Biker Boots (£1890) with Marant Etoile's Preya Embroidered Cotton Minidress (£520), embracing the summer's white cotton minidress trend, all the while nodding to the autumn shoe trend that's yet to come. The chunky Miu Miu boots anchored the lightness of the dress, creating the transeasonal contrast that fashion people return to every year as the seasons begin to shift.

Later in the week, she returned to her Miu Miu boots, pairing them with a black lace-trim slip dress. Finished with a bandana tied over her hair and oversized bug-eye sunglasses, she created exactly the kind of transseasonal outfit I'll be recreating as soon as temperatures begin to dip.

As ever, Dua is a step ahead of the rest. If you're already planning your autumn wardrobe, scroll on to shop the best dresses and biker boots to recreate her looks below.

Shop Dresses and Biker Boots:

This might shock some of my fellow editors, but I don’t currently own a pair of high heels. For as long as I can remember, I’ve been averse to my feet hurting, especially living in New York, where I walk so much.

Ironically, I also don’t wear sneakers outside of the gym. Given this, I’ve spent a lot of time figuring out how to find shoes that feel chic and put-together but are still comfortable. Somewhere along the way, this turned into a “rule" I never consciously made but always follow: I check the heel height and make sure it’s two inches or under.

The obvious go-tos are ballet flats and kitten heels, which I feel most like myself in, but I also wear Mary Janes, knee-high boots, low-heel pumps, loafers, and the occasional flip-flop when it’s hot out.

Below, shop two-inch-and-under shoes from brands like Camper, Gimaguas, Margaux, Miu Miu, Prada, Repetto, Vagabond, and more.

Ballet Flats

For flats, I love my pairs from Camper and Margaux. So many people I know have been raving about E. Porselli ones, so those are next on my wish list, as well as the iconic French labels Carel and Repetto. I’ve also noticed neoprene flats trending lately, like Gimaguas’s Bailarina Neopreno or Zara’s Neoprene Effect Ballet Flats with Pull Tab.

Kitten-Heel Sandals

As for kitten heels, I have a pair from Studio Amelia on the way, and I love my Stuart Weitzman Minimalist Slide 50 Sandal. Of course, I can't forget Manolo Blahniks and archival pairs from Prada or Miu Miu as well.

Low-Heel Pumps

For a low-heel pump, Ferragamo's Vara Soft Pump has been one of my favorites for ages. High-vamp pumps have been everywhere lately as well, so they feel like the shoe of spring. Many of our editors either have or want the Reformation Inez Pumps, which are similar looking to the $990 Phoebe Philo Club Slippers.

Walkable Mary Janes

I like having a sneaker alternative for extra-long walking days, and I'm drawn to what I call the “walkable Mary Jane.” I’ve been eyeing Camper’s mesh Mary Janes, but for a non–Mary Jane option, I’ve saved the vintage Cole Haan x Nike Air collaboration, which you can usually find on eBay.

Knee-High Boots

For knee-high boots, I’m loyal to my Vagabond Blanca pair and the Frye Campus boots.

Loafers

Loafers are another reliable shoe, like the classic G.H.Bass ones. Tony Bianco's $190 Gatsby Loafer as an alternative to The Row's Soft Loafer too.

Flip-Flops

I also keep a pair of Havaianas Slim flip-flops on hand to throw on.

I never thought I'd see the day, but it's officially miniskirt season. I have a few miniskirts I kept tucked away during the winter, and I searched for cool spring shoe trends to style them with while I waited for the snow to thaw. Not much was inspiring me, but one recent outfit finally has. Alana Haim was just spotted wearing an edgy shoe trend with her miniskirt that's been living in my mind rent-free for the past few days: knee-high black leather boots.

Her outfit had cool model-off-duty vibes in spades, and her shoe choice had a lot to do with that. Black leather knee-high boots aren't always considered a spring shoe trend, but this outfit begs to differ. While we all think of boots for winter, I encourage you to consider styling them for spring like Haim did—with a skirt, simple tank top, and shoulder bag. (I would love to also carry a monogrammed Louis Vuitton east-west bag.) Her leather knee-high boots made the look so much cooler, adding a subtly edgy contrast to an otherwise basic look.

If you're into wearing knee-high boots for spring, keep scrolling to re-create this look and shop similar items.

On Alana Haim: Khaite Jett Leather Mini Skirt ($1680); Louis Vuitton bag

Get the Look

Shop More Knee-High Boots to Wear With Miniskirts

Gen Z It girls have patented the boots-with-skirts formula. The hallmarks of a well-done outfit lie in the balance between edgy and preppy. Exhibit A: A sheer lace skirt must be paired with a suede knee-high boot. Exhibit B: A pleated miniskirt should always be countered by a chunky moto boot. Follow this, and you'll find getting dressed this spring a breeze.

While the unexpected pairing might seem obvious to some, let me break it down. The boot is a remnant of chic winter outfits whose sole duty is to protect against elements, that is, the unpredictable spring forecast. One day it's in the mid-70s, and the next it's below freezing. The skirt: It's a signal to the fashion set that summer is just around the corner.

Keep scrolling to shop the cool-girl outfit formula and how the fashion set, from your favorite Gen Z celebs (hi, Iris Law) to IG's It girls are styling boots-with-skirts outfits this spring.

7 Chic Boots-with-Skirts Outfits for Spring 2026

1. Suede Midi Skirt + Kitten-Heel Boots

Style Notes: Midi skirts have my heart. One: They are the perfect-length skirt to wear with boots. Two: They are incredibly easy to style. I love this double-layered neckline.

2. Animal-Print Skirt + Knee-High Leather Boots

Style Notes: From leopard to Dalmatian, animal print is in. Complement the funky print with a graphic tee and a pair of skin-tight leather boots.

3. Slip Skirt + Suede Tall Boots

Style Notes: Break up an all-black outfit with texture focused accents like a utility belt, suede boots, or bangle stack.

4. Sheer Lace Skirt + Block-Heel Boots

Style Notes: NYC It girl Aïsha Farida styled her sheer lace skirt and suede knee-high boots with a Y2K-style hack (a long-sleeve under a crewneck tee).

5. Miniskirt + Chunky Boots

Style Note: The Iris Law is my go-to for cool Gen Z celeb outfits. The miniskirt-and-chunky-boot 'fit is next on my list to re-create. I love the use of texture, the ruffles on the skirt, the embroidered knee-high socks, and the cropped jacket over a soft knit.

6. Knee-Length Skirt + Campus Boots

Style Notes: Call it the CBK effect—knee-length skirts and knee-high boots are a spring 2026 outfit formula you can find on every It girl's IG feed. Bonus points if you style it with a fitted button-down.

7. Pleated Skirt + Moto Boots

Style Notes: East Coast prep meets grunge—the wonders a pair of moto boots and a pleated miniskirt and do. Pair with a striped rugby shirt for an added flair.

The feeling of spring is finally in the air, and for those of us in New York especially, the excitement is palpable. We're getting through the days by looking forward to shedding winter layers and swapping our favorite jeans or trousers for skirts. The pencil skirt, a fitted, knee-length silhouette that tapers from the waist to the hem, is the trend currently dominating our thoughts. Its clean, sophisticated aesthetic and runway endorsement—seen in the spring 2026 collections of brands like Khaite, Saint Laurent, and Tory Burch—have made it a favorite among fashion insiders. While versatile with a range of footwear, the current go-to pairing for the best dressed women is knee-high boots.

It girls like Bella Hadid and Hailey Bieber are championing the pencil-skirt-and-knee-high-boot combination. During Paris Fashion Week, Hadid was spotted in a vintage Fendi skirt and a white long-sleeve shirt, elevated with tan heeled knee-high boots and a suede Prada tote. Meanwhile, on her trip to Tokyo, Bieber wore a leather pencil skirt styled with a leather blazer, a V-neck sweater, and black sock-like knee-high boots.

In the past, the styling rule dictated that the skirt hem had to overlap the top of the boot to create a polished, streamlined look. However, in 2026, Hadid and Bieber are challenging this idea. They demonstrate that showing your kneecaps is now the chic way to go. Plus, it provides a welcome bit of breathability on warmer spring days.

If Hadid and Bieber have inspired you to embrace the pencil skirt trend and pair it with knee-high boots, keep scrolling because I've curated an edit of the best styles for both.

On Bella Hadid: Fendi skirt; Dôen Lidie Tee ($178); Saint Laurent Francoise Leather Knee-High Boots ($2150); Prada Bonnie Bag ($3650)

Shop Pencil Skirts and Knee-High Boots

I’m calling it: tights season is officially over, and bare legs and boots season has begun. That bridge between winter and spring—when it’s still too brisk for sandals but also too bright for heavy layers—has its own dress code. And the chicest way to navigate it? Hailey Bieber has just weighed in.

Styling up a pair of sleek, knee-grazing leather boots in an inky shade of black, Bieber made dressing for this transitional period seem easy. Forgoing tights, she styled her pointed-toe boots with a skin-skimming pencil skirt crafted from glossy leather, creating a streamlined silhouette that felt supremely sharp.

Up top, the model kept things simple, styling a fine V-neck knit in a soft mole shade with a structured leather blazer on top.

Whilst, in my opinion, it’s still a little too chilly to fully commit to sandals, it’s certainly too mild, and too sunny, to justify tights. As such, knee-high boots and knee-length skirts will be my go-to for the foreseeable. The perfect outfit formula for those early spring days, read on to shop the chicest knee-length skirts and knee-high boots to recreate the look yourself.

Shop Knee-Length Skirts and Knee-High Boots:

If you're looking for an excuse to go shoe shopping, I recommend Nordstrom's winter sale. If I could only buy one pair across all of the discounts, I'd choose the Stuart Weitzman Minimalist Slide 50 Sandals.

In the boot selection, there are highlights such as Vince's Harlan Knee-High Boots, Tony Bianco's Fantasy Knee-High Boots, and Frye's Kate Block Heel Boots.

There are plenty of standout heels too. Tory Burch has a leopard-printed colorway of the Double T Buckle Pointed-Toe Pumps. As I scrolled, it was my first time seeing heeled loafers from G.H.Bass, the Penny Loafer Pumps. Mansur Gavriel's Ballerina Kitten Heel Pumps are chic as well, and the espresso suede iteration is almost sold out.

For flats, you'll find styles from one of my all-time favorite brands, Camper, along with options from Mansur Gavriel, and the sneaker section has markdowns on popular brands such as Salomon, Nike, Adidas, and Keen.

Shop Nordstrom Boots

Shop Nordstrom Heels

Shop Nordstrom Flats

Shop Nordstrom Sneakers

When I set my sights on something, I'll stop at nothing to get it, and no, I'm not just talking about major life goals or achievements. Smaller things, like a specific skirt from 1998 or a sweater I saw once, left behind at an outlet mall, and never stopped thinking about, can likewise drive me up a wall. I'll spend as many hours as it takes to find it, scouring Google reverse image searches and resale websites until it's secured in my size and desired colour. And right now, the item I can't stop thinking about (and shopping for) is a pair of tan boots.

One look inside my closet will no doubt have you questioning why I could ever possibly need another pair of shoes, but wait! I own brown boots, black boots, burgundy boots, and grey boots, all of which I do love. (Why else would I waste precious New York City real estate housing them?) What I don't have in my possession are tan boots, which I personally believe are chicer than all of the above. Specifically, I either want The Row's Liv Boots that appear to be sold out everywhere—I'll hunt them down, don't worry—or a vintage pair of leather Chanel stiletto boots with a fitted calf and pointed toe.

While I go about my days thinking endlessly about these two things, I don't expect anyone else to follow suit. That's why I went ahead and rounded up the best tan boots on the market in 2026, from lighter suede pairs to darker leather alts, all of which feel elevated, elegant, and different from the shoes everyone else is wearing. Plus, they're just as versatile and easy to style as all the other neutral-coloured boot options, except that tan boots have a Carolyn Bessette-Kennedy vibe to them, which makes them that much more desirable.

Ahead, see how fashion people are styling tan boots in 2026 and shop the year's top pairs.

How to Style Tan Boots

Style Notes: The easiest way to style tan boots? Follow TikTok's sandwich rule and wear them with a matching tan faux-fur jacket and a pair of black jeans and a handbag.

Style Notes: This leather jacket and tan boots outfit is effortlessly chic.

Style Notes: Tan suede + tan boots = a match made in heaven.

Style Notes: Tan boots pair so well with darker neutrals like black or chocolate brown. Use them to brighten up an all-black outfit as shown above.

Style Notes: Lighter tans are perfect for spring. Wear them with matching jeans, a white tee and a striped button-up to freshen up this classic look.

Style Notes: There's something about tan boots that feel inherently western. Fully embrace the look with a suede fringe jacket and patterned scarf.

Shop Tan Boots

Jeans will always have a place in my daily wardrobe rotation, but as spring approaches and the temperatures begin their slow climb, I'm definitely craving something lighter. With a penchant for less-is-more silhouettes and a minimalist approach to getting dressed, I often gravitate towards sleek '90s silhouettes—and this week, I was reminded of one particularly cool outfit formula that feels perfectly primed for spring 2026.

Posing for a photo, Bella Hadid swapped long-line jeans for a chic knee-length skirt, anchoring the look with a pair of knee-high boots. Skimming the hem of the skirt, the pairing creates a streamlined, cohesive silhouette with a distinct ’90s energy.

Keeping things simple, Bella styled the look with a white tank and a black knitted cardigan, creating exactly the kind of fuss-free and elevated outfit formula that fashion people will undoubtedly return to all spring long.

With a soft spot for nostalgic styling—Bella is no stranger to Y2K and ’90s-inspired looks—this restrained take feels especially wearable. While her checked skirt leans fully into the era, the formula itself is incredibly versatile and would work just as well with a sleek monochrome design.

Gwyneth Paltrow wears a knee-length skirt with knee-high boots in 1999.

No, I’m not suggesting you abandon your jeans, but if you’re ready to embrace a lighter, more refined silhouette this season, this outfit formula is the perfect place to start. Read on to discover the knee-length skirts and knee-high boots I’m recommending below.

Shop Knee-Lengths Skirts + Knee-High Boots:

By now, we're well into boot season, and black, brown, and burgundy pairs continue to be the go-to choices for most people—emphasis on the word most. A select few with especially good taste are relying on another boot color trend to make their 2026 outfits feel elegant and fresh instead of predictable. From deeper cognac to softer sand, tan boots have been quietly taking over the new year, and Elsa Hosk is among those responsible for their rise. Shocker!

The model and Helsa founder has been donning tan boots for a while now, always dishing out styling inspiration for the neutral footwear on her Instagram. Her latest tan-boot outfit is, by far, her best yet. On Monday, Hosk posted a slideshow captioned, "Furs and joggers," tagging her brand. In the photos that followed, she can be seen wearing a butter-yellow oversize T-shirt with matching lounge pants. For contrast, she styled them alongside all-tan accessories, including a faux-fur scarf, a small Hermès Birkin bag, and a pair of knee-high, pointed-toe stiletto boots. One can rarely make a glorified sweatsuit appear elegant, but Hosk did just that, and her boots (and bag) are majorly responsible.

On Elsa Hosk: Helsa Double Sleeve Tee ($159), The Puff Pant ($219), and scarf; Hermès bag

What makes tan boots so desirable right now is that they're just as versatile and easy to style as any of the other popular neutral boot colors on the market. Still, they have a more vintage look that's appealing, especially pointed-toe stiletto boots in suede and smooth leather. For secondhand pairs, I suggest looking for a version from Chanel, Ralph Lauren, Jimmy Choo, or Manolo Blahnik. Jimmy Choo's modern versions and Staud's Wally Boots in the shade are equally buy-worthy. As they're dependable, unique, and beloved by fashion people with expensive taste who have a finger on the pulse of what's cool right now, it's no wonder tan boots are *the* buy of boot season.

Keep scrolling to mimic Hosk's tan-boot outfit and shop the best pairs on the market in 2026.

Get Elsa Hosk's Look

Shop Tan Boots

When I set my sights on something, I'll stop at nothing to get it, and no, I'm not just talking about major life goals or achievements. Smaller things, like a specific skirt from 1998 or a sweater I saw once, left behind at an outlet mall, and never stopped thinking about, can likewise drive me up a wall. I'll spend as many hours as it takes to find it, scouring Google reverse image searches and resale websites until it's secured in my size and desired color. And right now, the item I can't stop thinking about (and shopping for) is a pair of tan boots.

One look inside my closet will no doubt have you questioning why I could ever possibly need another pair of shoes, but wait! I own brown boots, black boots, burgundy boots, and gray boots, all of which I do love. (Why else would I waste precious New York City real estate housing them?) What I don't have in my possession are tan boots, which I personally believe are chicer than all of the above. Specifically, I either want The Row's Liv Boots that appear to be sold out everywhere—I'll hunt them down, don't worry—or a vintage pair of leather Chanel stiletto boots with a fitted calf and pointed toe.

While I go about my days thinking endlessly about these two things, I don't expect anyone else to follow suit. That's why I went ahead and rounded up the best tan boots on the market in 2026, from lighter suede pairs to darker leather alts, all of which feel elevated, elegant, and different from the shoes everyone else is wearing. Plus, they're just as versatile and easy to style as all the other neutral-colored boot options, except that tan boots have a Carolyn Bessette-Kennedy vibe to them, which makes them that much more desirable.

Ahead, see how fashion people are styling tan boots in 2026 and shop the year's top pairs.

How to Style Tan Boots

Get the look: Shearling midi coat + dark-wash jeans + tan shearling boots

Get the look: Leather jacket + V-neck sweater + leopard-print bag + jeans + tan boots

Get the look: Suede matching set + tan boots + silk scarf

Get the look: Long shearling coat + brown bag + pointed-toe tan boots

Get the look: Black shearling skirt + maxi skirt + tan boots

Get the look: Striped shirt + white T-shirt + tan jeans + tan boots

Get the look: Fringe jacket + silk scarf + dark-wash jeans + tan boots

Shop Tan Boots

Some say basics are "boring," but fashion people will call them "classics." I'll always say yes to a crisp button-down tucked into a pair of straight-leg jeans, or a black slip dress finished with a pair of flats, or a cashmere crewneck draped over a wide-leg pant. The key to beating the "boring" allegations? Shop elevated basics.

From now until January 17, score an extra 25% off on Shopbop sale finds with code EXTRA25. Shop affordable faux-fur, designer boutique steals (ahem, Tibi, Stella McCartney, and Veronica Beard are experiencing some major markdowns), and of course, the best elevated basics.

Lucky for you, I've compiled a list of 31 rich-looking everyday items perfect to wear now through spring. Think suede totes that whisper quiet luxury, cool jeans fashion people are wearing in 2026, sophisticated button-downs, calf-hair ballet flats, and more. Scroll on to see the makings of a chic capsule wardrobe.

Shop 31 Elevated and Rich-Looking Shopbop Sale Finds

In need of a 2026 closet upgrade? Then look no further. My sister's resolution was to update her wardrobe, so being the generous sister I am, I offered to help. She is a chic 32-year-old who appreciates a faux-fur moment, a quality cashmere sweater, and affordable luxury. So to honor her elevated style, I turned to one of my most-shopped retailers: Nordstrom. I can always trust I'll find a good deal or snag a Ref style all the It girls will be wearing in a few weeks. It's my go-to. Not to mention Nordstrom's in-house brands are next-level. Think fitted blazers that resemble a designer find or rich-looking moc-toe leather loafers. Come with me as I walk through the 11 chic Nordstrom buys I sent my sister that will make her closet feel more 2026.

Below, you'll find an on-sale Coach Empire 34, flirty lace-trim silk trousers (these would have done numbers during summer 2025), a high-V-neck sweater from COS, an affordable faux-fur coat, and more. Ring in 2026 with a chic Nordstrom closet upgrade.

11 Chic Nordstrom Buys to Upgrade Your Closet in 2026

1. Fitted Blazer

2. East-West Bag

3. High-V-Neck Sweater

4. Lace-Trim Silk Trousers

6. Cashmere Sweater

5. Pointed-Toe Knee-High Boots

7. Wool-Blend Coat

8. Leather Gloves

9. Straight-Leg Jeans

10. Faux-Fur Coat

11. Slim Loafer

Shop More Chic Nordstrom Buys

While fashion trends don't change as soon as the clock strikes midnight on December 31, the start of a new year is nonetheless a time of looking ahead at what's to come and shedding what no longer feels relevant from the year prior. As far as the style landscape goes, there's already one category that's shaping up to have a, well, reboot in 2026. The biggest boot trends for the year ahead? Think modern takes on cowboy styles, sleek kitten-heel silhouettes, and pops of animal print.

And since the arrival of a new batch of trends naturally indicates the decline of several others, I'm also outlining which boot trends are, for better or worse, beginning to hit their expiration dates. While these are merely my own observations, they're well-informed by what featured on the spring/summer 2026 runways and what fashion people are currently wearing (and not wearing).

From kitten heels to modern Western boots, ahead are the boot trends that will dominate in 2026 and, consequently, the styles that are on the decline this year. As the tarot-card readers in my TikTok feed would say, feel free to take what resonates and leave what doesn't.

Expiring: Block-Heel Boots

Trending: Kitten-Heel Boots

Over the past few years, we've seen a major shift happening in heel shapes, but specifically with boots. Chunky block-heel boots are all but disappearing, and in their place has arrived the new default heel shape for boots: kitten heels. Whether with denim, trousers, or a skirt, kitten-heel boots are the sleeker style that's in it for the long haul.

Expiring: Over-the-Knee Boots

Trending: Classic Riding Boots/Pull-On Boots

While I wouldn't say that riding boots have ever been "out," they're about to be more relevant than ever this year. Think super-sleek silhouettes with minimal hardware and logos that marry well with leggings and slim jeans.

Expiring: Platform Boots

Trending: Flat Sock Boots

Unlike the tall stiletto heels and logo branding that defined sock boots in the 2010s, the iterations arriving in 2026 are sleek flat-sole styles and largely come in leather finishes that give the boots a much more elegant feel for everyday. With jeans or long skirts, they're a fresher alt to classic ankle boots.

Expiring: Studded Boots

Trending: Calf-Hair Finishes

As far as finishes go, luxe calf hair texture is officially It right now. Coupled with animal prints like leopard, doe, and zebra, these are the statement boots of the moment, and while I'm sad to see them wane, studded boots are simply losing favor to these sumptuous finishes.

Expiring: Moto Boots

Trending: Western Boots

Western motifs come in and out of style like clockwork, and in 2026, modern cowboy boots are slated for a major return thanks to styles like the Khaite Clive Boots that feature quintessentially western details like a stacked heel and patinaed leather, but without the embroidery in more typical cowboy boots. Just as motorcycle boots were the trend-driven option of the past few seasons, I think we'll start to see these modern cowboy silhouettes take their place.

Expiring: Furry Boots

Trending: Modern Wellies

While they're "ugly" to some but functional to others, wellies are officially back on the menu. Burberry and TWP both highlighted rain-friendly boots on their spring 2026 runways, and with the aesthetic of country living with all its barn jackets and cable-knit sweaters coming into favor, prepare to see many more fashion-forward spins on wellies this year.

Expiring: Combat Boots

Trending: Slouchy Boots

I have always had a soft spot for combat boots, but while lug soles and chunky platforms have been in decline, so too have combat boots. Slouchy boots, however, are trending slightly differently but still give off the same lived-in vibe and can also be dressed up or down.

New year, new spending habits. That means no impulse purchases. In 2026, I'm considering all the variables: quality, versatility, practicality, and frugality. From socks to sweaters, no fashion purchase will be taken lightly. One place that hits all the marks: J.Crew. It's thoughtful, elegant, and sensible. Not to mention that it's known for its good sales. From now until January 4, shop 25% off select full-price items when you use code NEWYEAR at checkout. You'll find 2026 trends like faux-fur coats, barrel-leg jeans, cinched-waist cardigans, and more.

Staying true to my new resolutions, I dedicated two hours to browsing the J.Crew sale for stylish items that fit the bill. Below are 11 incredibly chic J.Crew sale finds that are first on my 2026 wishlist. From cobalt blue crewnecks and corduroy trousers to suede East-West bags and cable knit bomber jackets, save 25% on these 2026 must-haves. Discover standout knee-high boots, tailored denim, and affordable winter coats (ahem, this elegant scarf coat for $261) as you scroll.

Shop the 11 Incredibly Chic J.Crew Sale Finds

1. Cobalt Crewneck Sweater

2. Corduroy Pants

3. Suede East-West Bag

4. Leather Knee-High Boots

5. V-Neck Sweater

6. Wide-Leg Jeans

7. Sheer Tights

8. Collared Full-Zip Sweater

9. Scarf Coat

10. Polka-Dot Slip Skirt

11. Cable-Knit Bomber Jacket

Shop More Stylish J.Crew Sale Finds

Fashion people have long had a soft spot for the so-called "ugly" shoe. From sneakerinas to five-toe flats and wooden clogs, there’s something about a deliberately unsightly silhouette that adds edge. So when I heard whispers that wedge boots were shaping up to be next season’s most directional buy, I needed very little convincing.

At first glance, they resemble your classic heeled ankle or knee-high boots. But, instead of a traditional heel, this emerging style is anchored by a solid wedge that extends from sole to floor, creating a unified, sculptural silhouette with a satisfyingly weighty feel.

While wedge boots might not have the sleek sharpness of a stiletto or the daintiness of a kitten heel, that’s precisely their appeal. The architectural lines and chunkier profile give them a much more modern edge than your average heeled boot.

Poised to become one of the season’s defining footwear trends, high-street and designer labels are backing the silhouette right now. From Zara’s polished pairs to Paris Texas’s streamlined takes, scroll on to discover the chicest wedge boots to buy right now.

Shop Wedge Boots:

As it’s gotten colder in New York, boots have become essential. While I don’t love sacrificing style for warmth, black knee-high boots have quickly become my go-to when I want to look polished without freezing.

For a reliable outfit formula, I like layering them over thermal leggings or tights and pairing them with a midi or knee-length skirt and a cashmere sweater. It’s an easy combination that feels both warm and intentionally put together.

Two of my personal favorites are the Vagabond Blanca Tall Boots and the Frye Campus Knee High Boot. I reach for the Vagabond pair especially in the evenings because they’re a bit sleeker. They make me feel like I’m not compromising my outfit for the weather, and the low heel keeps them comfortable enough for when I'm out and about. They instantly elevate whatever I’m wearing.

Below, find a roundup of black knee-high boots worth wearing on repeat.

Shop Black Knee-High Boots

My New Year’s resolution is simple: In 2026, I will dress rich, elegant, and, above all, chic. I’m manifesting 365 days of effortlessly cool outfits, unforgettable coats, coveted kitten heels, and spectacular silhouettes. And to prove I’m not messing around, I’ve already begun preparations. For the past few weeks, I’ve scoured IG for chic winter outfits, consulted my fellow Who What Wear editors on the 2026 fashion must-haves, and observed the latest trends of the NYC style set. Spoiler: High V-neck sweaters, short faux-fur jackets, and elegant leather gloves will soon be gracing your feed, if they haven't already.

So, if your New Year’s resolution looks anything like mine, pay close attention. From London to Oslo, below are 10 chic winter outfits to wear in 2026. You'll find plenty of faux-fur trimmings, oversize totes (ahem, the Coach Soft Empire Carryall Bag 40), '90s-inspired straight-leg jeans, cool knee-high boots, and elegant winter coats. Let's make 2026 the most fashionable year yet.

1.

Get the Look: Oversize black leather jacket + wide-leg trousers + faux-fur scarf + flats + leather handbag

Shop the Look

2.

Get the Look: Black balloon pants + short-sleeve sweater + long leather gloves + woven tote + sunglasses

Shop the Look

3.

Get the Look: Fitted white turtleneck + suede trousers + tonal blazer + pointed-toe heels + ALO duffel + statement belt + sunglasses

Shop the Look

4.

Get the Look: Lace-trim camisole + black jeans + short faux-fur jacket + kitten heels + leather handbag

Shop the Look

5.

Get the Look: Basic white top + straight-leg jeans + long blazer coat + boots + skinny scarf + leather tote

Shop the Look

6.

Get the Look: Ribbed sweater + a second sweater tied around the shoulders + silver bangles + pleated shorts + suede knee-high boots + suede handbag

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7.

Get the Look: Oversize crewneck sweater + a second sweater tied at the waist + black overcoat + white denim jeans + leather handbag

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8.

Get the Look: Plain white long-sleeve + long leather skirt + black leather boots + double-breasted overcoat + oversize tote + sunglasses

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9.

Get the Look: Basic white crewneck + high-V-neck sweater + silk slip skirt + knee-high leather boots

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10.

Get the Look: Cape coat + straight-leg jeans + pointed-toe boots + leather handbag

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If you want to look rich and elegant in leggings next year, there’s one styling trick that instantly shifts them from “athleisure” to “effortlessly polished.” It’s all about treating leggings as a true wardrobe staple rather than a fallback piece—elevating them with luxe textures, intentional layers, and sharp silhouettes that read more 2026 street style than weekend errands. When done right, the combo feels impossibly sleek in that quiet luxury way that makes people assume you have impeccable taste (and a stylist on speed dial).

For 2026, the most elevated way to wear leggings is with tall or knee-high boots and a chic jacket—think refined outerwear, sculpted shoulders, buttery leather coats, cropped bouclé styles, or longline wool toppers. The contrast of the streamlined leggings with a structured boot instantly adds sophistication, while the jacket brings the whole look into “rich girl energy” territory. Instead of leaning sporty, the pieces work together to create a clean, elongated silhouette that feels luxurious yet completely wearable.

This is the kind of formula that looks considered without feeling fussy, which is exactly why fashion people are already adopting it for next year. Whether you choose all black leggings with pointed-toe boots or a stirrup pair tucked perfectly into a sleek riding boot, the styling reads intentional and elevated. Add polished accessories—oversize sunglasses, a minimalist shoulder bag, or a glossy belt—and you’ve officially cracked the code on making leggings look rich in 2026.

Get the look: Textured bucket hat + Midi coat + Leggings + Tall leather boots

Get the look: Faux fur coat + Leggings + Tall black boots

Get the look: Polished faux fur coat + Turtleneck + Leggings + Brown tall leather boots

Get the look: Leather coat + White top + Leggings + Tall leather boots

Get the look: Blazer + Black sweater + Leggings + Tall leather boots

Get the look: Long polished coat + Faux fur scarf + Leggings + Tall leather boots

Get the look: Puffer coat + Turtleneck + Leggings + Tall leather boots

Get the look: Faux fur coat + Turtleneck + Leggings + Tall leather boots

Get the look: Wool bucket hat + Oversized faux fur coat + Leggings + Tall leather boots

Get the look: Long coat + T-shirt + Sweater + Leggings + Tall leather boots

While I wouldn't say AI can replicate the intuitive aspect of shopping or the intrinsic elements of a human's identity, style, or fashion sense, I am intrigued by how new technologies focused on fashion can help curate results that inspire. Daydream, a chat-based AI-powered shopping platform, recently launched an iPhone app. Built to redefine online shopping, Daydream engages with users to provide a tailored shopping experience.

"We're building an intelligent layer of the world of fashion. One that understands taste, context, and individuality," said Daydream Founder and CEO Julie Bornstein in a press release. Users can search, converse, and shop via screenshots. The platform pulls products across a wide range of prices and categories from over 10,000 brands, such as Reformation, Revolve, Nordstrom, Saks Fifth Avenue, Madewell, J.Crew, to name a few.

With winter fashion in full effect, I couldn't think of a better way to try Daydream's capabilities than to find the best winter boots to pair with this season's top jean trends. As a shopping editor, I browse hundreds of product listings a day, and I know a standout fashion find when I see one, so I'm curious to see what Daydream will suggest.

Below, find my prompts followed by Daydream's responses. You'll notice the AI chat asks for help refining the search (e.g., color, price, fit). The goal here is to better the curation to your taste. One thing I appreciate about the open layout of the product recommendations is that ultimately, you get the last say. Scroll down to shop the best winter boots to pair with jeans, recommended by Daydream AI.

'90s Slim-Straight

My Prompt: I'd like to buy a new pair of straight-leg jeans. I usually shop at Banana Republic, Madewell, and J.Crew.

Response: These straight-leg jeans offer a clean, classic fit with a nod to vintage denim, which aligns well with your usual brands. Would you prefer a version with any special details, like raw hems or a particular wash, to refine the search?

I was intrigued by the many chic straight-leg jeans Daydream offered. My pick? The Banana Republic's High-Rise 90s Straight Jean ($120).

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Best Winter Boots to Wear With Straight-Leg Jeans

My Prompt: I'd like to wear straight-leg boots with a pair of boots in the winter. Could you recommend a few boots that would look cute? My budget is $150–$300.

Response: These options offer a sleek, neutral palette with practical details that suit winter styling and straight-leg fits. Would you prefer something with a chunkier sole for added edge or a more streamlined, classic silhouette?

My Prompt: I prefer a classic silhouette.

Response: These boots lean into classic shapes and quality materials, fitting well with your preference for a timeless silhouette. Would you want to focus on taller shafts for more coverage or something mid-calf that pairs easily with straight-leg pants?

I decided to clarify my prompt thanks to Daydream's follow-up questioning because the first round of products didn't precisely match my taste. Second time around, I was pleased with the winter boot options. Find my top three below.

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Trendy Barrel-Leg

My Prompt: I'm looking for a pair of new barrel-leg jeans. Could you suggest a few?

Response: These options capture the barrel-leg silhouette with a mix of cropped and full-length styles, plus variations in rise and detailing. Would you prefer to focus on a particular wash, fit, or length to narrow down the vibe?

I spent some time scrolling through the product suggestions, since many were already out of stock or soon to be. So, I recommend checking on stock before you go all in. These AG Hattie Barrel-Leg Denim Jeans, $265, were a standout, plus they are available in sizes 23 to 31.

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Best Winter Boots to Wear With Barrel-Leg Jeans

My Prompt: I'd also like to find a pair of boots. Can you recommend some boots to wear with barrel-leg jeans?

Response: These boot options offer a chic blend of modern style and practical design to perfectly complement barrel-leg jeans. What is your comfort zone price-wise for this search?

My Prompt: $150–$300.

Response: These boot selections offer a chic and polished aesthetic within your desired price range to beautifully complement barrel-leg jeans. What color would you like me to focus on?

Lots of chic boots to choose from, but ultimately, these three Daydream suggested were my top contenders. Scroll on to shop the best winter boots to wear with barrel-leg jeans.

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Luxe-Looking Leopard

My Prompt: Leopard-print jeans are so chic. Could you recommend a few pairs?

Response: These options possess the chic vibe you're going for, with versatile cuts that feel very now. How would you describe the formality of your event?

Animal-print jeans are a big hit with the fashion crowd lately. I suspect their popularity will only rise come 2026. The first pair Daydream recommended just so happened to be the exact pair I've had my eye on: the Charlee Low Rise Straight Leg Jeans from Reformation, $198. Curious about what winter boots look best with animal-print jeans? Don't worry—I've asked Daydream. Scroll on to see what it recommends.

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Best Winter Boots to Wear With Animal-Print Jeans

My Prompt: Could you share some cute boot options that would go with animal-print jeans?

Response: These boots seem like they would add a fantastic, playful touch to animal-print jeans. What is your comfort zone price-wise for this search?

No need to refine the search because I already spotted three of the chicest boots to wear with animal-print jeans. Including a Zebra option, burgundy hue, and matching leopard print heeled boots.

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Fitted Flare

My Prompt: I'm looking for a new pair of flare jeans. Could you please recommend a few in stock?

Response: These flare jeans offer a flattering, gradual widening from the knee with options in classic denim washes and a mix of mid to high rises. Would you prefer a more vintage-inspired look or something with a modern edge, like frayed hems or distressing?

After browsing Daydream's picks, these Citizens of Humanity Kimberly High-Rise Flared Jeans, $260, had my name written all over them. While they feel retro, the pleated denim blends modern and classic.

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Best Winter Boots to Wear With Flare Jeans

My Prompt: I'm looking for a new pair of boots to wear with my flare jeans. Can you please recommend some boots?

Response: These boots present a polished and sophisticated look well-suited to your flare jeans, with options in a few universally chic neutral tones. Let me know what you think of these options.

Keep scrolling to see which three boots Daydream suggested would look best with a pair of flare jeans, specifically the ones above.

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Relaxed Low-Rise

My Prompt: I'm looking for a new pair of low-rise loose jeans. Could you suggest a few? I've been looking at a few Reformation jeans online.

Response: These lean more toward a straight-leg fit rather than the loose, baggy silhouette you're after. Would you like me to widen the search to include more relaxed or oversize cuts beyond straight legs?

I found it helpful to clarify where you like to shop, so Daydream can better understand your preferences and taste and curate products to your liking.

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Best Winter Boots to Wear With Low-Rise Baggy Jeans

My Prompt: I'd like to buy a new pair of boots to go with the low-rise baggy jeans. Do you have a few you could suggest?

Response: These options offer a nice mix of relaxed, edgy, and slightly retro styles that could pair well with low-rise baggy jeans. Would you prefer something more rugged and chunky, or something with a bit of a softer, vintage vibe?

I appreciate the edgy boots paired with a relaxed pair of jeans. Truly matches the vibe. Check out these three cool boots, best worn with low-rise, baggy denim this winter.

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I've written before about my daily shopping-editor duty (i.e., browsing Nordstrom's new arrivals), but what I haven't shared is how much I genuinely enjoy it. So much so that I'll be on the train, and instead of scrolling IG and curating ultra-niche Spotify playlists, I'll scour Nordstrom's new arrivals. Seeing its chic latest additions is the motivation I need to start my day. Usually, I end up with a shopping cart full of winter closet must-haves, specifically this Boxy Faux Fur Coat, for a reasonable $149.

Below, check out my top 11 Nordstrom new arrivals that give cool girl. You'll find fashion person–approved sweater trends (ahem, argyle knits and striped preppy polos), Parisian-chic cold-weather essentials like burgundy scarves and leather gloves, knee-high boots, straight-leg jeans, faux-fur jackets, and the best ballet flats. Mix and match these chic Nordstrom picks for a winter-appropriate outfit that says "I know fashion." Scroll on to shop Nordstrom's latest cool-girl pieces.

Shop the Elegant Nordstrom New Arrivals

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For one day and one day only, shop 20% off winter 2025 essentials with Revolve. The sitewide sale includes elegant new arrivals from Agolde, SNDYS, Tony Bianco, Good American, and more. But if you're curious to know what an NYC shopping editor has their eyes on, scroll down to see my entire Revolve wishlist. Keep in mind, this sneaky Revolve sale ends tonight, so it's best not to wait.

Use promo code HAPPY20 at checkout to score 20% off these cool-girl winter 2025 picks. Ahead, you'll find chic scarf coats, cinched-waist cardigans, knee-high boots, short faux-fur jackets, animal-print handbags, and more. Thanks to all the holiday party invites in my inbox, I've made sure to include some festive dress options, flirty going-out tops, and fabulous shoes, ahem, these calf-hair knee-high boots are unforgettable.

Below, discover affordable winter coats, tailored blazers, dark-rinse jeans, and cow-print sneakers that deserve a spot in your winter shoe rotation.

Shop the Editor-Approved Revolve Sale Picks

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When you're tasked with buying a pair of boots, especially a pair that you intend to own and wear for years to come instead of just a few months, black or brown are usually the two color options that immediately come to mind. Classic, versatile, and widely available, the two neutrals are easily the most-purchased boot colors on the market. But what's the fun in buying what everyone else already has, especially when there is another option that's just as easy to style but tenfold more elegant? Burgundy boots make every outfit feel not only different from the masses but also far more elevated and intentional. Buying burgundy boots is the obvious choice, especially when you see the versions that are available going into 2026.

From Saint Laurent's already sold-out Françoise boots (as seen on Devon Lee Carlson) to Reformation's more attainable Claudette style, there's no shortage of chic burgundy boots to choose from this winter. Knee-high versions are definitely the favorite, especially when styled with soft, ethereal dresses à la Chloé and long column skirts and turtleneck knits for a more Carolyn Bessette-Kennedy–turned–office siren aesthetic. Black or brown boots would work in either of these occasions, sure, but opting for burgundy takes both ensembles up a notch without any added effort. Zara also has burgundy boot options at affordable prices, meaning you don't have to spend thousands or even hundreds of dollars to get a great pair.

Though knee-highs are showing the most promise at the moment, going with an ankle boot instead is never a bad idea. They're best styled with trousers or jeans, and go great with a chunky knit or suede jacket. If you're hunting for a more everyday choice, an ankle boot is the way to go. Guaranteed, they'll become your go-to for easy winter outfits that warrant compliments.

To help make the process of switching out your black and brown boots for a more enticing burgundy pair, I went ahead and curated a list of the 17 best pairs of ankle and knee-high boots that come in the rich shade below. Prices range from $90 to $2600 (Gucci Horsebit riding boots, anyone?), and styles include flat and heeled options, as well as rounded toe and flat versions. Basically, there's a pair for every interested shopper, and they're all just a scroll away.

The Best Burgundy Boots

I know I'm not the only one who loves winter fashion. The style set lives for the drama of layers, textures, and elegant winter coats. While some might think winter outfits, like simple jeans and boots, feel repetitive, the key to looking like a fashion person is all in upgrading your wardrobe. Zara's new arrivals and cool winter collection make it easy to stay up-to-date with the latest trends. Spoiler: Funnel-neck jackets are a top-ranking winter 2026 coat trend among NYC cool girls. Not to mention, Zara's affordable pricing is always a plus.

To inspire your next winter outfit, I've compiled a list of my top 13 Zara fashion finds that are at risk of selling out. So don't wait until the last minute or for the FOMO to set in. It's best to act ASAP. As you scroll, you'll find standout Zara winter essentials, including faux-leather jackets, argyle sweaters, cool ballet flats, scarf sweaters, and collarless blazers. Shop the chic, affordable winter finds below.

Shop the Standout Zara Winter Finds

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