Fall in New York City isn’t just a season—it’s a runway. The one where all crosswalks turn into catwalks and coffee-runs serve dual purpose of being fashion statements. But what does fall fashion look like in 2025? So what then characterizes cold weather street style layering when ‘comfy’ has collided with couture and street style casual is equally likely to include designer boots as it is oversized hoodies? We are going to do a guided tour of the inspirational avenues right off NYC sidewalks. These looks will shake up your wardrobe, even if you’re just layering up for a casual November dinner or planning the perfect night out fit.
Here is your inspiration of what to wear in NYC in the fall 2025 bbs get those pinterest boards ready.
Neon Vibes Meet Graphic Classics
Said who that fall dressing has to be muted and mellow? The aesthetic of this whole look is high-contrast clashing, juxtaposing an oversized black-and-white houndstooth coat with a flash of limelight green the bulky knit and the mini crossbody. With striped trousers that are sporty in nature and sharp green sunnies, this is a power outfit on the move. It screams streetwear 2025 insomuchas there is a bit of a 90s revival about it that is very on trend.
Houndstooth coat is an autumnal staple that can be worn big, so you can easily layer it with chunky knit tops and track-like pants, as it is the optimal attire to wear in street style cold weather layering. The neon sweater is the center of attention, which will get the most gloomy fall day brightened, and the lime mini bag is another addition to personality. The sporty pants help to unite the whole look, keeping it in the genre of street style casual without being downgraded in elegance.
Honestly, I’ve always been afraid of neon in fall—too loud, too summer? But this outfit made me rethink everything. A friend of mine has worn something like this the last October, and she was stopped twice in SoHo to be complimented. There’s something empowering about wearing bold colors when the air turns crisp.
I would pair chunky sneakers or even pointed-toe sock boots to tone down the vibe that is sporty. Oh and some greasy looking ponytail would cap this off with a zinger. You down for that energy?
Lavender Luxe With a Side of Edge
The idea of lavender during the fall is somewhat romantic and a bit secretive, as well, in the same way, ordering ros in November and having no regrets whatsoever. Combining the soft palette of pastels with the high-contrast of black, this appearance adds some drama into each step on a sidewalk. A lilac turtleneck is covered with a statement lavender plaid coat, the whole ensemble is deepened by a high-slit skirt, Sleek Gucci belt, and the aforementioned thigh-high boots that make jaws drop.
The texture here is everything. Wool, knit, leather—it’s like a playlist of fall favorites. The bucket hat makes it lighthearted and exceptionally trendy at the same time and the chain-strap crossbody makes it chic. If you’re looking for aesthetic going out ideas, this one works whether you’re a tourist in the city or a local with rooftop reservations.
I had a similar one on at the opening of a gallery in the Meatpacking District and I swear-I got three compliments before I even opened my coat. Are you one of the people who hesitates about lavender? Believe me, it is much more versatile than you might imagine.
To be frank, I would put on a pair of opaque tights or replace with a midi skirt when it is really cold. But overall? Chef’s kiss.
Checkmate: Cozy But Cool
Checks are back, and they’ve grown up. This checkerboard, boxy coating in cream is the epitome of comfy chic, wrapped up even further, with buttery off-white chunky boots and a dusty pink microbag. There is something casual about this appearance that remains so super confident yet it suits perfectly into the realm of the casual street style fall.
I adore that this coat can be flung over anything you like, even slouchy knits or a structured dress and still be pulled together. The stompers are an MVP, in this case: you can wear them in November, and they are leaving your street style 2025 images cool.
A beauty editor I follow said recently, “Coats should feel like a hug, but look like a statement,” and this one checks (literally) both boxes. It’s my go-to coat moodboard right now.
This outfit can be elevated completely by wearing cat-eye sunglasses or a giant knit scarf. Or change the mini bag to a beige slouchy hobo to have that Kendall on-the-go feeling.
Power Red: When Minimalism Meets Boldness
Not that grey has to be dull–at least when you pinch it and tie it and hang a fire-engine red scarf over it. The well-cut wool jacket is given a spurt of energy by the red tights and matching boots. It is a bold street style look with a minimalist touch and dramatic points.
The silhouette is simple, and accessories do all the talking. This combination is brilliant as a dinner date, a fashion event or even something to when you want to look polished, without feeling as though you have tried too hard.
My take? This is how you do red in fall. I would wear red during December holidays only, and layering it into outerwear has turned out to be a game-changer. Especially when paired with neutrals—it just pops.
It would be great to have a hook up with a statement lip, a groomed bun to enhance its edginess. But truly, this one’s nearly perfect as-is.
Elevated Athleisure in Cream and Black
This outfit helps demonstrate that, plus size girls and petite girls are equally capable of wearing athleisure in a large way. At the center rests a cream monochrome hoodie and jogger set which is paired with a longline black and white houndstooth coat. It pairs well with clean white socks, thick black sneakers, and a quilted tote, which is a lesson in layering that hits the spot when it comes to street style casual.
The neutral palette makes it endlessly remixable. You would be able to wear this set to a brunch, a tourist walk across the Central Park, or just put on an in-Your-Face-Lipstick and call it a day-to-night one. It’s that good.
Something eerily similar is what I sported in into NYC last November and it was literally like wearing a blanket but make it fashionable. A comfy win.
Next time? To give it some flair I could even add a gold hoop and baseball hat. Athleisure doesn’t mean skipping the glam, after all.
Red on Rose: City Sleek With a Twist
Color-blocking just got a romantic upgrade. Making sure that the look is not too highly tailored, this combo is sweetened by some red bottomed trousers, matched with a dusty rose coat and burgundy turtleneck. The triumvirate of red/white/pink sounds like a self-security jazz riff, though surprising in every way quite harmonious. It’s city-girl chic meets modern Valentine, and it’s serving serious street style with an elegant twist.
This long, softly floated type of coat gives it a soft flare and it is lovely to walk along with it swinging in the wind–just ideal to catch those November winds. The trousers are fitted, but idled right down to be able to display those white sneakers that are crispy and casual. Add a square ivory crossbody bag and oversized retro sunnies and you have a complete picture that will take you to both coffee date as well as dinner reservation.
Personally, I’ve always loved a high-contrast outfit. It gives me an instant feeling of being dressed up even when I am going out to run errands. As once stated by one of my favourite stylists, Shiona Turini,” playing with contrasting colors can help you liberate your wardrobe” -and there is not a better way to summarise this notion.
To give it a bit of an edge, I would add a matte red lip, or change the sneakers to ankle boots made of white leather. It’s all about keeping that energy balanced and strong.
Leopard and Sunshine: A Mood Booster
Now here’s a fit that radiates joy. The yellow leopard jacket, canary sneakers, and matching fringe earrings speak volumes as to the fact that fall does not need to equate to muted grays and browns. It is flippant, unafraid, and so adorable yet manages to pull things down to earth with a swishy black midi skirt and a simple white t-shirt. Refined and relaxed, it is perfect to go out on a weekend or sightseeing day when you want to shine but not to bother.
Every item in this ensemble is a stand out: the crop jacket with the puffy sleeve creates volume, the black skirt creates drama and the yellow sneakers provide the factor of youthful fun. The red round earrings also serve as a talking point. It is a sort of the look that makes people turn heads in the most appropriate way and appears extremely wearable on a sunny November day in New York City.
A friend of mine wore something similar to the Brooklyn Museum and ended up in three strangers’ Instagram Stories. Somehow there is something magnetic about this color combination too, it is bright and hopeful. When writer Tiffany Reid wrote in Allure that dopamine dressing is not only about fun, but also about control, she was referring to how it is possible to choose to be joyful, purposefully.
Personally, I would either put on top a cropped denim jacket under the leopard or add a fanny pack worn cross body, in case I was remixing this. Because sometimes, more is just right.
Mint Condition: Monochrome Reimagined
One thing about street style 2025? It loves monochrome done differently. This fresh mint vibe combines a green sweat suit with a white fitted jacket and complements them with high-platform white combat boots, which is basically a walking Pinterest board. The ensemble is that perfectly comfortable and daring, useful both on travel days, and on those when you do not need to think too much about the outfit.
The shape of the coat contrasted with the plushiness of the jogger set in my opinion makes the entire outfit possess a modern figure. The over-sized boots make it a bit rebellious, and clean lines of the Saint Laurent crossbody make the whole thing even better. It can only be described as street style cold weather layering at its best: functional and not boring!
Late last fall, I attempted to reproduce a more similar palette during a content shoot and was surprisingly powerful. The monochrome keeps everything streamlined, which I think makes you feel more put together—even if you’re wearing elastic waistbands. Beauty tip: Trendy tip: complete the entire minimalism look with a shiny clear lip and a straight middle part.
If I had to tweak it? Maybe a pop of color on the nails. A soft coral or unexpected navy would contrast beautifully.
Autumn Rebel in Leather and Plaid
Boots crunching through fall leaves, jacket warm leather on your bed, deep colors that remind you of the season- Enough said, this outfit is the purest of the street style autumn. A deep teal turtle neck under a burgundy plaid skirt, with a moto jacket on top of it and similarly colored burgundy ankle boots. It’s part prep, part rebel, and all-around iconic.
The micro plaid skirt here is the hero, it is flirty, but not too sweet. Combined with the sheer tights and heeled booties, it straddles the boundary between female and fierce. The burgundy bag on matching? Well, the leather jacket brings out the perfect amount of grit. Perfect punctuation.
This takes me back to my favourite coffee run outfit last year at Bryant park. Layered right, it’s warm enough for November, especially if you add a scarf. Caroline Maguire, a fashion editor, has once told us that leather is the shortcut to edge in the fall, and I adore this application, as it is not that extreme.
You might as well add gold hoops or felt fedora to make it look more downtown. Or get a smoky eye on special occasion that you are going out late.
Tailored Elegance at Home and Out
Sometimes street style starts right in your own mirror. This appearance passes as something that a fashion editor could actually wear on one of these WFH days which gets impulsively approved as an invite somewhere. The combination of wide navy trousers, a ribbed white top, and a dramatic floor-length burgundy coat creates a powerfully simple colour scheme that is classic and creative at the same time.
The outfit is extremely easy to recreate (the clean color-blocking), but the proportion is what makes it a song. The trousers have a high-waist, which lengthens the legs and the burgundy coat is important to structure and richness. This is ideal dining out wear that is more luxe than wearable.
This was my usual uniform for Zoom meeting to IRL meeting when I lived in the neighborhood around Union Square. It is elegant, cozy, and very flattering to various body shapes, even to plus size shapes, as high waist and the length of the coat help.
If I were to push this look a bit more, I’d add a statement necklace or maybe even bold loafers instead of heels. All in all, it is that vintage fall capsule that we all require.
Green Dream: Modern Monochrome With Edge
This outfit is unapologetically bold. The combination of greens, forest, kelly, and emerald as an inside coat can be scary to experiment with, but with this outfit, it is a fashionable idea. A structured and black leather-panelled coat that is lined with green shearling is important to the color story as it emits a complete street style cold weather-vibe. This monochrome moment paired with a matching green V-neck blouse and trousers is dramatic and not at all expected.
The shearling lining of the oversized tote reflects in the texture of the coat and gives the image its depth. The worn out beanie and chain necklace bring the casual touch to it, and the city cool nature of the black round sunglasses will help it fit in this setting. And we should not overlook the neutral platform sneakers-they make everything easy and walkable which is what one needs with street style in November.
I spotted a girl in Williamsburg last fall with a very similar palette and it totally changed my way of thinking about one tone dressing. She said, “It’s not about matching—it’s about echoing,” and that really stuck with me.
To mention one thing here, perhaps a dash of intense coral lipstick colour or a chunky gold bangle bracelet to contrast the saturation. But truly? It’s already a statement.
Minimalist Fog: Luxe in Ice Grey
The confidence in neutrals is a quiet one, and when combined methodically, it was a great part of the effect. This ensemble welcomes street style casual in a toned down light grey and creams color scheme, whereby an oversized coat was worn over a fitted grey turtleneck and cropped white pants. It is clean, sleek, and just right with NYC mornings that are a bit gray and the world is a bit cinematic.
White sneakers are a perfect decision as they not only keep the whole look down-to-earth and comfortable enough to walk around in, but also provide a dash of sportiness that stands out in other wise sophisticated silhouette. The small metal top-handle bag brings in a dash of glitz. I love how everything here feels both curated and cozy—basically the comfy minimalist’s fall uniform.
I poured on this to a brunch in SoHo last year and thought I might as well try to assimilate into a Pinterest board. It seems to be effortless in a way that not many girls and women can resist, especially during the 30s and 40s. You look like you’ve got it together—without really trying.
Would I switch anything out? Possibly only a tentative topper of silver rings or some fragile stack of earrings to augment a pinch of rocker status. This is a look that thrives on subtleties.
Downtown Grunge Goes Soft
Just because it is edgy does not necessarily mean it has to be uncomfortable and this fit disrups that notion. The black denim jacket (on top of cropped graphic tee), makes the outfit grunge-like, but the flowy wide-leg black pants balance the mass out. It is street style that girls who love the layered, matted look love to wear, but still wish to wear.
It is the chunky chain belt that is not immediately obvious and that provides shape and shine to an otherwise loose silhouette the MVP. Complemented by black-and-white platform sneakers and visible tattoos, the appearance seems completely purposeful. And yes, this is great when you are going out to watch some casual concert in the city at night.
The first I saw of this outfit, it brought me to think of post-punk on Tumblr but refined into 2025. There’s an authenticity here that makes it so magnetic. It’s not trying to impress—it’s just being.
To dress it up a notch, I would add a shiny black lips or even a beanie with torn edges. A super fall afternoons to cool November evenings shift.
Sporty Meets Street: Neon With Bite
Who knew that neon could look this sophisticated? This outfit is a combination of a lime high-waisted column skirt and a black sweatshirt paired with the statement sneakers and an eye-catching green crossbody bringing the fun graphic appeal. It is a bit sporty, urban, and totally in the present: it is surely one of the wow, NYC fall 2025 outfits.
It is a lime skirt, which is tight around the hips and flares a bit, so it has a touch of elegance that lifts the casuality of the sweatshirt. The contrast makes the outfit sing. The shoes are another good idea, plain black sneakers, but with a large white sole, so easy to walk in, as well as attention getting. It is extremely street style 2025 but with Gen Z twist.
I did this kind of thing actually when I saw a girl in the Oculus wearing a chartreuse dress and high-tops. I would never have considered the combination of sporty and sleek in this manner, yet it just flowed and I am now addicted.
Just to take this further, perhaps wear a sheer long-sleeved top under the sweatshirt or wear some silver hoops. It already is a look, but you can change it to be more your own.
Golden Hour Cozy: Fall Layers With Pop
It is a cozy as-heavy-as-it-wounds-me-up hug in a clothing form and I do mean that in the best sense. It is the classic base of leather-look leggings, black top, and a slouchy grey cardigan. But then, bam! Sunflower-yellow scarf, corresponding quilted bag, and pointy boots tie it all together. It is fun, it is something you can wear, it allows both plus size and petite people to go wild with color.
I love that this isn’t just cute—it’s practical. These boots are comfortable to walk in, the leggings are stretchy and the cardigan is cut to make you look good, so it does not engulf your figure. The bag and scarf make a sunshine contrast, that is ideal to wear to a November brunch, park walk and even dinner plans.
My first fall visit to Chelsea Market was done in a scarf of this yellow and I received comments on my appearance by a woman and a coffee making stranger. Did no more than make me feel awake–warm and sunny, when it was gray outside.
To go a step further I would add a beanie of the same shade of yellow or replace the cardigan with a longer one that had a belt making it feel more like a robe. Either way, it’s full of inspo.
Modern Prairie Meets City Cool
The combination of a cozy hoodie dress and a plaid longline shacket is a magic combination. There are some outer garments that are constructed and also comfortable in a manner that looks very natural, and this outfit does not appear to be uncomfortable in any shape or form. It is a particular flattering fit to plus size models since it has a loose structure yet it is still glamorous. With complete tan suede knee-high boots and a small form-fitting crossbody, it is an exemplary but still stylish autumn street style.
There is nothing wrong with the green hoodie dress as it is quite comfy but again, the damn interesting mixing up of that plaid coat with it comes into play. The jacket is the typical fall staple of NYC in this outfit as it looks casual, but it does have structure, also being referred to as a shacket. The boots dress up the outfit and make it a simple task to go out on errands during the day and dinner with no changes.
I tell everyone: plaid properly brought off is nostalgic and fresh at the same time. I actually wore something like this during a rainy day in November in Flatiron and didn t feel too casual or so stylish as I could use both words at the same time.
I would like to supplement the amount of thick above the ankle cable-knit socks that show out of the boots, or perhaps a lighter tan wool beret to soften that. But even without, this look speaks comfort and confidence.
Retro Flash Meets Checkmate Pants
One of these is to the girls who live in color but with that touch of anchorage in the form of classic prints. The outfit is matched with black and white checked cropped pants and tomato red oversized turtleneck, white crew socks and older versions of white sneakers. It is all about balance: loud on the top, pattern on the bottom and clean everywhere you look.
The pants are giving vintage prep while the sweater screams ‘cool-girl cozy.’ It is a kind of relaxed concept which seems extremely wearable I suppose, to go and have a coffee in Tribeca or go to a vintage market in Brooklyn. The sneakers with socks are all white, which is a slight reference to 90s skater trend with a younger twist.
One of my close friends has recently done a similar look during NYFW last year, and was photographed by a photographer in front of Spring Studios. It attests that simpler looks can become a personal style statement with the use of only one color that stands out.
Want to tweak it? Throw a trench coat in beige or black to give it another degree of refinement. But in real life, this one is already emanating the street-style star power.
Cocoa-Chic: Elevated Lounge
This collection is evidence that you do not have to leave your loungewear behind. The oversized chocolate-brown sweatshirt, a pair of fitted leggings, and a complex of potentiality are the early examples of what we would love wearing on the street in 2025. With orange-and-white Jordan and orange shoulder bag, which has quilting and gold hardware, this ensemble is as much about color story as it is about comfort.
The orange adornments are so magnificent due to the warmth of the brown base, and that bulkiness helps make the use of sneakers so appropriate. It is perfect to have it in the afternoon when it is time to go shopping, run errands, or even during airport travel days. And the orange bag? When combined with confidence and a top knot this renders it a going out outfit.
This makes me think of an outfit I would wear to get a matcha before a content shoot. Stylish but not overworked—my sweet spot. This is a fantastic example of what celebrity stylist Law Roach once said was the importance of fit, namely that, that color placement was just as important, as fit.
To make this much more significant, I would overload gold bracelets or layer thin gold chains. Now the rule of the luxuriously comfortable looks of great personality is to keep it minimal yet purposeful.
Grayscale Cool: Normcore Gets an Update
This fit has that “cool without trying” energy. Faded grey charcoal graphic sweatshirt, loose joggers and big grey sneakers give out a tone-on-tone effect, which is very contemporary and at ease. Lastly, a contrast and edgy undertone is provided by the visible white undershirt and platinum blonde shag hairstyle. It is a street style 2025 fashion that you may wear on Monday, on Tuesday, on your best mood or your worst mood.
This trend is heavy on the street style casual look yet there is reason as to why this trend still exists even in trendsetting NYC: proportions. The large unisex sweatshirt is not oversized to the point it swallows up the frame, the pants are narrow at the waist and wide at the calf and the sneakers add bulk to an area where it balances out the best. It’s a masterclass in minimal styling.
I spotted a person in Washington Square Park wearing almost the same combo a few weeks ago, and they looked like they have been shot in one of the KITH campaigns. It is still liked being comfortable, but in 2025, it has to be done purposefully.
To take this further? And a bitsy black-and-white ball cap, or bag, to complete that work look. But as is, it’s a full vibe.
Power Red: Statement Dress and Boots Combo
Let’s end this section on a high note—literally. This outfit is all legs, lines, and confidence. A shoulder knit dress cutout in firetruck red, the slit on the driving up to the thigh, and candy striped boots are very bold looks that can not be missed in the place. It is the best NYC fall outfits drama: unreserved, posed, and by all means a night-out outfits.
There’s so much happening here, but it’s all intentional. The cold shoulder cut gives it modernity, the slit is sexy and the boots? A walking work of art. You would see this fit strolling along Soho and it would squeeze out a second gaze-maybe even an interview on the pavement.
I would wear this to a cocktail event where there is an upscale casual atmosphere. It is something like wearing when you are aware what you are. As Chioma Nnadi, a former staff at Vogue once put it, a fashion confidence is when one dresses in a way one designed it to look on them not in the way people are going to comment.
You can even add a large cuff bracelet or showstopping hoops, depending on how maximal you want to be. But really, this outfit already speaks louder than words.
