NYC Fashion Trends: Street Style Fall Outfits 2025 for Women Who Want Cute, Comfy & Confident Looks

When the city switches to pumpkin lattes in September, something electric begins occurring on the streets of New York. You can smell it, the air gets cooler, the layers get heavier and the NYC fall outfits begin to blossom like fall leaves all over SoHo, Brooklyn and beyond. However, this winter it is not only about keeping warm, it is about the statement as well, even when your coffee is hot and your cheeks are flushed.

What makes street style autumn so fascinating in 2025? Are we leaning sporty or tailored? Minimal or maximal? Would a bright coat transform your entire mood of the season? And most importantly, how do we get fashion and real comfort in cold-weather months? Let’s find out together.

Color-Blocked & Cool: The Rise of the Urban Primary Palette

Cobalt knit turtleneck, bright red trousers, cherry sling bag, chunky black-and-white sneakers this combination is outrageously loud, but it is deeply modern. I just love the feeling of using loud primary colors together and being a little subversive to the season, as in, “It is fall, but I am still enjoying myself.” The layering is neat and precise, the white shirt tails have peeked through to disrupt the solid colors and to add that touch of surprise.

All of these work towards attaining that ideal street style casual look- one that is fun yet intelligent. The sneakers are comfy, the bag has the right amount of high-low contrast, and the blue-red color scheme is almost designed to stand out among a sea of beige. In case you have been feeling in a rut with neutrals in colder months, this is your cue to replace camel with color.

I have always considered that when the weather gets cold, the temptation to merge into the darkness of layers is high, however, items like this allow to resist easily. I tried this exact combo (with my own tweaks) running errands last November, and I swear I got three compliments before noon. There’s something confidence-boosting about color in cold weather. It’s like dressing for energy.

I would only append perhaps a soft beanie or a svelte belt bag to transform this into the ultimate tourist-friendly day outfit that becomes a casual dinner outing. It is not a shouty power outfit but it certainly hums.

Oversized and Unapologetic: The Power Coat Moment

An orange wool coat that nearly brushes the ground? Yes, please. Particularly when it is combined with the icy white sneakers, a monochrome dress under them, and the surprise of a street-style baseball cap. It is a tension look, masculine forms diffused in color, dramatic length coupled with off-duty cool. It’s like Carrie Bradshaw got lost in a skater store and loved it.

I would highly suggest keeping at least one oversized coat in your closet to wear during cold weather days in the street. It makes layering underneath a breeze (think chunky knits or hoodies), and there’s something cinematic about walking through the November chill wrapped in something so voluminous and bold. Pro tip: keep your proportions below clean, straight-leg jeans or skin-tight dresses are the best way to maintain the silhouette sleek.

I recall the first time I ever wore this coat shape, I was initially engulfed by it. But then, the mirror said fashion editor. There’s freedom in letting go of fitted shapes sometimes. According to stylist Maeve Reilly (who styles Megan Fox), a long structured coat “instantly makes any outfit look like a look.”

To elevate this even more? Change the sneakers to smooth heeled boots and this can be used as a night out or dinner outfit. Bonus: the warmth is unbeatable.

Faux Fur & Luxury Feels: Warmth Without the Weight

Faux fur oxblood jacket, ivory trousers and a sleek pair of sunglasses – this is luxury on the move. It feels expensive, without trying. The jacket is chic rather than costumey because of the slightly cropped hem and the voluminous sleeves. The color choice alone? A+ for fall.

If you’re looking for street style 2025 ideas that feel glamorous yet comfy, faux fur is your answer. It adds depth to any outfit, and in dark jewel colors such as burgundy, forest or navy, it is nearly a neutral. It is ideal in September layering when the cold sets in and the sun is still peeking out.

I personally turn to faux fur when I want to go high in 30 seconds flat. I had on something that looked like an opening in the Meatpacking District, and someone stopped me and asked me whether I was in the fashion business. (Nope. Just read a lot of Harper’s Bazaar and follow Bella Hadid on IG.)

The only thing I would change (just one little thing) here would be adding in some gold somewhere in the accessories to warm it up. A statement ring or a pair of sculptural earrings would give only a slight shine.

Retro Romance: Floral Meets Fierce

A flowy vintage floral mini dress gets paired with sleek, over the knee burgundy boots. The combo is ultra-feminine with an edge. It is this type of transitional style that is effective when the air has become crisp but not yet cold. It has motion, contrast, and a perfect amount of retro coolness.

This is a shout of the street style women not afraid of big prints or high boots. And those boots? A fall essential. They embrace the leg, lift up the silhouette and go equally well with skirts as they do with skinny jeans or sweater dresses. And the bell sleeves on the dress add a touch of that 70s dreamy aesthetic that is certainly returning in 2025.

I wore this outfit to a late lunch in Williamsburg and it was just right, not too casual, not too overdressed. The secret is to make the makeup softer and the hair looser in order to look not too perfect.

Would I change anything? Perhaps a small bag with an irreverent print to offset the floral, but really, it is going to be main character either way.

Fearless in Fuchsia: How to Clash Like a Queen

A pink leopard midi dress, fuzzy matching handbag, and risky cheetah print booties, this is what maximalism looks like. It’s vibrant, high-energy, and joyfully loud. An excellent fit to stomp the streets of Midtown or to have brunch downtown. It is brash yet not manic- the profile keeps it all in place.

It is one of these adorable, daring concepts that say, I am here and I am enjoying myself. Animal prints never go out of fashion, and wearing them in one ensemble is a real fashion statement. Add a fuzzy handbag to the mix? Suddenly it’s not just casual, it’s unforgettable. This would be so cute for a tourist day where you’re popping into galleries and snapping pics for Pinterest boards.

I never dared to go with mixed prints until I saw women in the NYC streets do it with such confidence. Stylist Shiona Turini once said, “Prints are personal. They’re power.” I totally get it now.

The only thing I would have wanted to change here perhaps a smart blazer flung over the shoulders to ton down the appearance. But honestly? This is street style happiness (or so I thought street style was all about).

Wild Chic: Leopard Print in the Fast Lane

Here is what happens when chic meets careless rebel: a leopard midi dress with an easy styling of chunky red sneakers, large hoop earrings, and rose-colored glasses. It is making NYC fall outfits real, like the kind that walks through Soho in October with a latte in hand and no time to elaborate. The heavy typeface and sensible shoes end up being balanced in a manner that is completely 2025.

It is airy but still has some structure: a slight cinch around the waist and flouncy sleeves adds the right amount of structure without making it too heavy. Add the comfy sneakers for all-day wear and a structured black handbag, and you’ve nailed the street style casual vibe that’s perfect for a tourist stroll or a quick errand with flair. Not too loud, but definitely not shy.

I styled a similar combination on a September shopping day in the West Village and was reminded just how right animal print is when you want one item to do all the talking. No layers, no overthinking — just one hero dress and you’re done. Pro tip from stylist Erin Walsh? The best statement looks are those that do not make you breathless.”

I would perhaps add a cropped jacket or an oversized cardigan in case of a windy day. Otherwise, this one’s got legs — literally and style-wise.

Mint Condition: Bold Dots & Brilliant Green

Black and white polka dots contrast with high-gloss mint green in this playful street style outfit that is both retro and completely modern. The jumpsuit has been waist-tied to give the old-Hollywood hourglass shape and then the sheer green trench makes the entire set-up futuristic. It is a mix that seems like Manhattan meets Milan, but it does.

This is what I would call a showstopper the green on green bag and glasses make the monochrome moment come to life and metallic pumps make it all grounded. It is ideal to wear it on a night out that is not too serious, or even a fashionable dinner. Also, who said polka dots had to stay sweet? The broad belt provides form and some sass.

Honestly, I’ve been obsessed with mint tones this year. It’s refreshing after years of beige and oatmeal. Soft green is even becoming the new neutral, especially in streetwear silhouettes, as even celebrity stylist Kate Young recently noted.

You may change the heels to kitten boots or spotless sneakers and go to brunch, however? Let this one live at full volume. Confidence required — and completely worth it.

Retro Polka Glam: Bringing Back Rainy Day Drama

This shiny red mini dress with black polka dots, shoulder detail, and a broad belt would be a movie still. It has a retro vibe to it something very Joan Crawford meets 2025 New York City. It contrasts brilliantly on a gray day with drizzling rain and hazy taxi lights. The power stance? Optional but recommended.

I adore the fact that it remains dressy due to the use of satin material, yet the polka dots make it fun. The cat-eye shades lean into the theatrical vibe — it’s like being in character, but still you. It is all night out fantasy and women who would like to stand out but still be covered in fall-appropriate layers.

The fact that it is the middle of a rainy November night and you are out in the city in such an outfit is just different. You are dressed up, not in the corporate sense. All you have to do is toss on a trench or long wool coat when the temperatures fall below 50. Glam with a plan.

It would be cool to wear it with patent pointed boots or even sheer tights and loafers, a fashion-editor touch.

Coffee Run Meets Cool Girl: Fall Layers That Work

The trench is rich cognac, the crewneck navy blue with a button down underneath, the jeans soft, and the boots tan: that is how to wear street style in the cold without freezing or blending in. The last wink is the baseball cap, casual, cool and so damn wearable.

I personally love such a look as it is comfy and yet has such city-girl chic. The layering feels intentional, not accidental. It is ideal to pick up a bagel, vintage shopping in the East Village, or even to enter a relaxed creative office. The aesthetic is classic tomboy with a luxury twist.

I’ve personally leaned on this style during November mornings when I just want to feel warm but still look like I tried. According to fashion consultant Chrissy Rutherford, there is no denying it: “Real style is when practicality and personality collide.” And this outfit? Totally gets that memo.

To add an extra touch I would probably add a plaid scarf or crossbody bag in a playful color. But honestly, it’s already everything.

Olive You More: Monochrome Cargo with Edge

The final word in power layering? This complete olive-colored ensemble, cargo pants, and slim-fitting turtleneck, belted coat, and those killer pointed-toe boots. It’s earthy, utilitarian, and ultra elevated. The crossbody structured bag makes it look like a streetwear piece, and the overall silhouette remains slim and muscular.

It is a masterclass in minimalism street style 2025: one tone, and no mistakes. It would suit all body images, particularly on the plus size appearances where the liquid flow and shape are the main consideration. It is a flattering counterbalance to the shape, with the cinched waist and the wide-leg pants.

I attempted something similar to Fashion Week and felt like a work of sculpture in motion. It seems something about going black and white makes people turn their heads, in a contemporary non-obvious manner. In Who What Wears trend forecast, utility forms are the most dominant in fall outfits, and the new black is olive.

Honestly, I wouldn’t change a thing here. It’s perfection. Add oversized gold hoops if you’re feeling flashy. Or a deep red lip if you want contrast. Otherwise, let the tone do the talking.

Emerald Edge: Sharp Silhouettes and High Shine

It is all about a structured leather appearance in deep emerald hues here, oversized blazer, wide-leg trousers, and chunky-soled boots make this one of the most dramatic street style autumn power plays I spotted this 2025 season. It’s moody, a little intimidating (in the best way), and screams “I know exactly what I’m doing.”

This ensemble shows that you do not need to use bright colors or crazy accessories to stand out, sometimes the shape and texture do all the talking. The delicate crop top underneath makes it edgy, and the patent-like finish gives the outfit a mirroring effect to the city lights like armor. Perfect street style cold weather, particularly, when it is layered with a thin thermal underneath.

This fall I have been experimenting with green on green and it is more versatile than I expected. Celebrity stylist Karla Welch just told Vogue that dark green is the new navy and I have to say that after looking at this, I agree.

I may add a shiny crossbody bag or add layers with rings. Still, it does not need it, and it is confident, curated, and fashion-forward, which are all my favorite elements of a cold-weather outfit.

Street Luxe Tracksuit: Glazed Green Comfort

Who says cozy can’t be couture? This glossy green forest tracksuit is a new definition of street style casual. Dressed in white sneakers, a loud baseball cap, and oversized sunglasses, it is the ideal comfortable flex that still makes heads turn, especially on a pleasant September day when you want to remain cool and stylish.

I adore how the fabric transforms the entire tracksuit brand, as well as loungewear to street royalty. The zip-up jacket and the loose-cut pants are practical, and still, that metallic finish adds a quick upgrade to everything. Paired with red lips? Game over. It’s smart, playful, and full of personality.

I styled something close to this recently at a casual brunch and felt that I could go street to studio without missing a beat. And bonus, it is plus-size friendly because of the forgiving shape and the draped silhouette. Refinery29 claims that metallic ensembles are the new power suits of casual glam. And I’m not arguing.

I would just perhaps add some gold hoops or chain necklace to cut the texture – but that is personal taste. The set alone holds it down.

Monochrome Minimalism: Earthy Texture & Tones

There is such a down-to-earth quality to this earthy-toned outfit, which comprises a chunky olive sweater, belted into slightly glossy cargo trousers, with a pair of luscious snake-printed boots. It’s elegant without trying. The knit texture makes it more three dimensional and the soft pants make it fluid. Cozy but elevated — and totally street style women.

This appearance is evidence that the aesthetic does not have to be loud to feel whole. The neutral color palette also makes it easy to layer or mix and match with other more bold items. The boots are worth a mention on their own, too: the pointed, textured pair is the perfect dose of drama.

It is the type of outfit I reach to on a Tuesday when I desire to look put together but not overdone. It’s practical for cooler mornings, and still breathable enough for a busy day. And those olive tones? They photograph beautifully in natural light.

It is a look that does not require a lot – perhaps a chunky watch or crossbody to give it some structure. But even alone, it tells a story.

Espresso Chic: A Study in Sophistication

This is an appearance that hangs out in a coffee shop and floats through boardrooms: dark chocolate trousers with a hint of leather luster, worn with a wide-belted sweater in the same warm hue. It’s polished, grounded, and all kinds of flattering. A proper full brown palette has something distinctly decadent about it.

I love the drama in those bell sleeves. They make the shape softer but the organized trousers and sharp heels maintain everything tidy. It would be ideal during a fancy dinner, gallery night or simply going to work and you want to feel like a CEO. And yes, brown officially passed as the new black, once more.

I have one in a similar silhouette that I wore last November and I was warm, luxurious, and dressed with ease all day. Fashion stylist Rachael Wang is a believer in monochrome dressing as a way of simplifying style, and I am right there with her, as it gives you the impression that your wardrobe is ten times larger.

This set wouldn’t need much else. Perhaps a low bun and a loud lip should you want to amp it up. Or an ice oat latte and a good tote.

Midnight Wild: Blue Leopard & Leather Power Mix

We can wrap it up with a bang: a silky blue leopard blouse fitted with pleated leather pants with gold hardware showing and that classic black pair of sunglasses. This is big energy. The shirt has color and pattern, the trousers have structure and the entire outfit shouts confidence. Street-style excellence, hands down.

The conflict between softness and sharpness is what I love here. Satin meets leather, cool tones meet warm metals. And that fit? Flattering to all figures, particularly when you are curvy or plus size, as the shirt is flowing, but the pants shape the waist.

I wore the silhouette on a spontaneous night in Tribeca and stayed out well past dinner time, it simply made me feel like I belonged in the room, wherever the room was. According to Elle magazine, which recently made the point, animal print is no longer a trend, but a wardrobe staple, particularly when done in unconventional tones.

Maybe swap the shades for statement earrings if you’re going indoors. Or wear them and take it on yourself, you own the moment.

Leopard Print & Luxe Confidence

Street style 2025 is serving unapologetic attitude as the air gets crisper and nothing is as bold as a head-to-toe leopard jumpsuit. The appearance is a combination of fierce and perfect with a silky touch that tones down the wildness of the print. It is a cut that is fitted but not too fitted to the point of being a constricting hug to the frame, hence it is perfect in that street style cold weather moment when you still want to slay but not too hard on the layers. The look is completed with an exaggerated pair of black sunglasses, gold accessories, and a structured leather clutch that gives this outfit a dose of alpha energy with a shot of espresso.

Let’s break this look down. The jumpsuit alone is a power piece, and it is easy, fuss-free and perfect during transitional weather. Leopard has been re-emerging season after season and in 2025 it is not as kitschy as it used to be but more editorial. This outfit is well balanced with chunky rings, layered chains and simple clutch to give a mix of edge and elegance. It shouts night out but is equally as good at an artsy dinner in Soho.

Honestly? Leopard never really left, but I love how it’s resurfacing as less trendy and more timeless. Law Roach, a celebrity stylist once said, Prints are the new neutrals when you wear them with intention and I could not agree more. I have taken such an outfit to a gallery event in Brooklyn, and it has not been too hard to attract attention.

And to take this up another notch in November, I would add a cropped leather moto jacket or even a faux fur bolero in chocolate brown. Just enough coverage, but still giving drama.

Monochrome Python, Reimagined

Some prints whisper. Others announce your arrival. This charcoal-and-ivory snakeskin blazer-and-shorts combination sits exactly in the middle- it demands attention but does not scream. It is new, fresh, and discreetly lavish, a new vision of street style that women in September can afford to display bare legs when they still make sense, and layers are accessories, not essential.

Time to dive in: the fitted cut of the jacket counters the lightheartedness of the shorts. The outfit is based on a nude bodysuit that allows the print to speak. Statement earrings elevate it without over-accessorizing. This outfit? It’s street style casual meets Wall Street editorial—something you could wear for a tourist-chic photo walk downtown or a fashion panel at The Standard.

This is one thing that I have learned watching several seasons of fall styling: subtle texture contrast like this feels expensive even when it is not. It is providing Gigi Hadid off-duty with a bit of aesthetic sophistication.

I’d add a sleek bun or hair pulled back with a silk scarf, and maybe sharp ankle boots in dove grey or white for colder days.

Power Pink & Cool Girl Denim

The new neutral is bold, and this bright pink coat is a great illustration of how the NYC fall outfits are not boring at all this year. This ensemble is flung over a pair of light-washed jeans, a chambray shirt, and a burgundy quilted shoulder bag, pairing contrast in a manner that is new but completely wearable. And don just sleep on the sneakers and matching socks, they are low key but genius.

Coats in 2025 aren’t just practical—they’re personality statements. Its laid back tailoring makes it super comfy, but the color is pure joy. With a denim-on-denim foundation and an iconic pair of New Balance sneakers, the entire outfit is fun but refined; it has the vibe of a tourist who is very certain of where she is going.

The last season when I had something like this on I was asked three times the same day where I bought my coat. My advice? Don’t be afraid of color. Fashion is subjective, and pink does not imply that you are too much, but it is an indication that you are present.

To make this more weatherproof for November, I’d layer with a chunky turtleneck under the shirt or swap the sneakers for heeled boots. But don’t lose the socks.

Wine & Chocolate Tones: Minimalist Chic

Plush, opulent, and irrefutably stylish, this combination of a burgundy turtleneck and dark brown leather trousers is fall at its most sophisticated. It’s simple, yes, but definitely not basic. The simplicity of the gold jewelry provides the right amount of shine and the sharp heels stretch the frame in a subtle strength. Think street style 2025 but elevated.

Leather pants possess this eerie quality of making relaxed fits as sharp as possible. I adore the fact that they have soft structure, not very stiff, which makes them perfect to wear in cold weather on the streets without compromising comfort. The ribbed knit fabric gives it some dimension and the tone on tone styling is perfection on a dinner date or gallery opening.

I love embracing this wine-and-chocolate color scheme in November. It feels cozy without looking cliché. As Who What Wear proposed this year, the use of color drenching in warm hues produces a luxurious look that is not costumey but curated.

The only thing I would adjust would be the coat: I would recommend it to have a mild camel undertone, just to contrast without clashing. Maybe even a structured trench in suede.

Red Hot Stripes & Attitude

Surprising, theatrical, and claiming the sidewalk like it was a runway, this red-hot skirt ensemble is one of those fall outfits in New York that turns heads in the most positive manner. The long red skirt is broken by the knotted pink striped shirt and fire is introduced by the deep red coat with animal print lining. It is the type of outfit that makes one look hot even when the cold wave is chilling.

This appearance is so layered in texture and color. Such a flowing but structured skirt is so versatile. And then there is the contrast of the striped shirt and you have visual intrigue. That coat, though—iconic. The not-so-obvious plus size friendliness of the fit, is inclusive and flattering, and it is the kind of thing a woman would want to wear to feel tall and proud when the temperatures are chilly.

Red has always been my power color. When I put it on I feel stronger–perhaps even invincible. And that is what this look is all about, stepping out, showing up, and not playing it safe.

To make it more dramatic, I would replace it with a tall heeled boot and possibly red gloves in case it gets cold. But even as is, this one’s a scene-stealer.

Sunset Knit & Downtown Energy

There is this golden hour light in New York in the fall that covers everything in a warm glow, and this gradient, cozy sweater captures that energy just right. The ombr effect of pink to red makes the image look soft visually, yet the shape remains crisp. Combined with charcoal denim and bright red pointed-toe shoes, this outfit is not striving to be anything, it simply is. Fall street style casual done right, whether you’re grabbing a latte in Soho or heading to a creative co-working space in Brooklyn.

The star of this outfit is this sweater, oversized, textured, and layering-friendly without any loss of shape. Its proportions are kept down by the wide-leg jeans, and the red leather boots are the punctuation marks. The side hair clip? The mini handbag is just edgy enough. Quietly intentional. This would be easy to re-design in plus size silhouettes or even completely different styles because it is so versatile.

I’m always drawn to anything gradient for fall. It shows the falling leaves and the changing light in the city. I recall pulling on a sweater of this ilk on a cold November walk and immediately being put together.

Throw in a trench in camel or oxblood when temps are colder. Bonus points if it’s belted and slouchy for contrast.

Striped Confidence with a Retro Kick

There’s something so confidently effortless about wide stripes. They add an immediate character to an outfit and look best with classic denim, and statement heels. This striped sweater in black, red and cream has a cozy-chic vibe that is not too cliched. It is the type of NYC fall outfit that I am obsessed with on transitional days when you are feeling snug and still put together.

The relaxed but balanced look is achieved with the slouchy sweater pulled in a bit into the high-waisted denim wide legs. There is enough drama with bright red pointed heels, and that is the secret sauce. I believe it is the type of appearance that you would see on an empowered street style women icon strolling through Williamsburg or even making a quick stop in the West Village bookstore.

I learned this fast trick in InStyle last fall: when you team wild stripes with heels you have transformed comfort into something authoritative. And trust me, those red pumps? They’ll get compliments all day.

To make it a bit easier, swap the shoes with a red lip to match or swap the heels with retro sneakers to have a tourist friendly outfit.

Golden Suit, Golden Hour

There is nothing that says NYC power woman more than a custom gold suit walking down Fifth Ave. This silky two-piece isn’t about blending in—it’s about radiating. This outfit smoulders with the deep V neckline, delicate layered necklaces, and cat-eye sunnies. It is flashy but not tacky, which is shockingly difficult to achieve in street style 2025.

The soft texture and drape of the suit provide it with dimension. The cloth takes on the right amount of light to move with you glamour without being stiff. This is the time to find night out ideas that do not involve sequins but are still high impact. Gold jewelry accents everything without overpowering the outfit.

I dressed up in a gold blazer and vintage denim to a rooftop party in Chelsea and I felt like a moving sunset. And apparently, designers are on board with this, too Tom Ford and Brandon Maxwell both sent golden hues down their respective runways in the past few months, opting for luster rather than sparkle.

You can definitely sub out the heels and replace them with mules or loafers and still be editorial. Or put on a red lip and make that your dinner uniform.

Earth Tones and Cropped Coziness

This look captures what I call “intentional layering.” A turtleneck in forest green, cropped, and a pair of caramel leather pants could be a simple combination, but combine them? They feel like fall incarnate. The neat pants and the cozy top are the opposites in the right ways. It is a serious fashion IQ minimalist cold weather street style energy.

Let’s talk about these pants—faux leather (or real, if you’re luxe) in a warm saddle shade is so 2025. They’re structured but relaxed at the hip, which makes them comfy but chic. The sweater runs to the right length to expose a waistline but not full crop-top. This is the balance, that is why I repeat again and again: good fall outfits are not necessarily layered, they are just smart.

I’ve styled this combo before with a long trench and white sneakers when I was out shopping in September, and it felt luxe without trying. Trust me, this is your casual but elevated moment.

A camel scarf or a suede jacket would fit in perfectly in case you wanted to turn up the cozy.

Spice Tones on the Subway Platform

It is daring, spicy and mature all at once. Burnt orange turtleneck under a high-waisted, satin olive skirt is an eye-catching combination that is completely season-appropriate. Throw in that large olive tote bag and you have a street style women moment on the move. The cut in the skirt creates the right amount of movement that keeps it playful yet poised.

Warm ochres, greens, and golds of this sort, are all over this fall 2025, and justly so. They compliment every skin color, and they look excellent in natural light. The black cat-eye sunglasses keep the look not too sweet and the belt detail tightens everything to make the silhouette flattering.

I’ve always loved pairing spice tones with unexpected fabric textures. this kind of a satin skirt reflects light and adds movement to it, yet it is easy to walk in it. Heading to your dinner date or getting on a train? This look brings it.

To winterize it? Throw on some tights and change the shirt to a form-fitting mock neck in cashmere or blend of wool. You’re golden—literally.

Minimal Layers & Major Cool

This look is the solution when fall reaches the sweet spot, when it is neither too warm nor too cold. A longline chocolate jacket with a white tank, neutral wide-leg pants, and a baseball cap mixes the street with the structured polish. It is quite upper west side meets downtown dog walk and yes, the dog is optional but welcome. A humble reference to street style cold weather that is both comfortable and ingenious.

The coat carries the entire outfit—it’s the anchor. And when it is styled over a plain tank, it becomes a statement. Trousers in neutral shades bring the palette down to earth and the black belt provides contrast and form. A leather crossbody balances the vibe in such a way that makes it casual but the cap makes it relatable, urban, and a little ironic. This outfit can be an off-duty model, as well as an elegant tourist who wishes to have a local look.

I’m a sucker for clean layers that don’t feel like effort. I had such a thing on one foggy morning in November, and it seemed as though I had made an outfit before I had coffee. Real talk? Neutrals need not be dull- they should be intelligent.

To finish it off, I’d add gold hoops or a bold lip if you’re feeling it. Or keep it as-is for maximum “cool girl” aesthetic.

Soft Power Dressing for Everyday

This outfit gives “I have errands but I still might run into my ex” energy—in the best way. An open button-down shirt over a cropped white tank, fluid tan trousers, and a navy baseball cap translate that free-spirited but considered layering that characterizes the street style women this fall. It’s cozy without being heavy, styled without being styled. A perfect September outfit for transition days.

The airiness is added with the light blue shirt, and the white crop top underneath makes it youthful. The loose fit of the tan pants allows one to breathe, just perfect in the city as one goes out or even have brunch with friends. The white handbag makes it elegant yet not pretentious and the simple layered necklaces are enough to give it the right amount of character.

This combination makes me think of all the cool girls I see in Nolita, who somehow manage to wake up like that. I even did a copy of a similar outfit to see a late matinee at Angelika and I felt like I could have walked off a Pinterest board. It’s those little choices—like the cap—that transform a basic fit into an aesthetic.

If it’s breezier? Put a cropped bomber or a lightweight trench on top of the shirt. Or trade the sneakers in favor of red ballet flats to make it all come together.