Officially summer is already drifting into memory, but the September style game? It’s just getting warmed up. It actually turns out that that transitional season feeling when both the weather begins to lose its summertime feeling and your perception is still appreciative of the sun process is the perfect time to play around with. So what do you wear when it’s not quite cold, not quite hot, and you’re stuck somewhere between iced lattes and pumpkin everything?
This guide includes 23 outfits ideas to help you to not think too much about it and still own the September aesthetic. Whether you’re planning to stroll through Copenhagen, heading to an Alaska cruise, or just need ideas to wear in New York, we’re breaking it all down here. Let’s find a look that makes you say: “Yes. This is so me.”
Oversized Wool Meets Parisian Drama
There is something very chic about the opposition of softness to structure and this appearance gets this very right. A thick mustard knit coat falls fluidly over wide leg trousers in slate and a fitted top in baby blue is ribbed and cinches at the waist through the help of a large belt. White sneakers help to keep the entire look all down-to-earth and a chocolate quilted tote adds a touch of depth and refinement.
This is a set that can only have the real Lake Como and Venice in September vibes. It’s relaxed, but put-together. The wool jacket is too large, actually, but purposeful; the extra-big pants are fresh–not sloppy. This would most certainly be my Day One fit in case I were to curate a capsule wardrobe to travel in the European cities. This cue is all about playing the texture: smooth, cushy and soft every inch.
I wore a variation of this once in Madrid and was three times (on the same day) halted by strangers admiring the coat. And if you’re worried about wide-leg pants being “too much” for your frame? Don’t be. Just counter it with something more appropriate on top and put some sneakers to make it casual. Hailey Bieber vouches on this balancing tip-and she is not mistaken.
I could also layer on a thin chain of gold to disrupt the knit or perhaps a less-is-more pair of studies with amber-coloured lenses as a pop. Otherwise? This is a 10/10 city stroll slay.
Soft Neutrals, Strong Silhouettes
There is an easy elegance about this appearance-think pistachio shades that are worn simply and efficiently. There is a beige coat that slithers over a ribbed taupe sweater and then loose trousers touch the ankle in a perfectly formulated way to emphasize tan sock boots. The pop of color from the slouchy orange clutch? A delicious surprise.
The following palette is what you would like to have on when in Seattle or Washington DC early fall. It means: I am not trying too hard, but I do care. I adore the way the collared shirt shows through the sweater-which gives definition, but in a without-shouting kind of a way. Everything about this is cozy, confident, and quietly cool.
To me, the boots make it. I just spotted one of those on a stylist in London wearing them to an all-ivory ensemble and added, soft boots ground soft outfits.” It stuck with me. It can be worn out to brunch and a museum trip can be sneaked.
I might swap the sweater for a mock neck if it’s cooler, but otherwise, this whole look travels effortlessly. Ideas women who want polish without the pressure? This one’s yours.
Urban Edge in Monochrome Black
All black, all attitude. This is one of those outfits that puts you straight in the posture. The next combination was a leather moto jacket over a black turtleneck sweater, smart sleek skinny jeans and sturdy lace-up combat boots. It’s clean, a little rebellious, and undeniably powerful.
Perfect to wear in New York, especially if your plans involve coffee, art galleries, or just looking like you know what you’re doing (even if you don’t). That is the type of style I resort to on those days- when I want to be part of the crowd yet make a cool statement. The leather adds warmth and weight for September’s mood swings.
Moto like this should be bought, in case you are developing a fall wardrobe. According to celebrity stylist Maeve Reilly as she puts it on InStyle, a leather jacket is the one item that does not disappoint. It doesn’t age; it levels up any outfit.” And I couldn’t agree more. With the change of jeans into joggers or even layering it over a midi dress- game changer.
Perhaps add a silver chain or hoops to give it some more of a punk attribute or leave it plain to adorn that allusion to minimalism. Either way, this outfit just works.
Denim with a Whisper of Softness
This look is a masterclass in proportion and tone. Casually oversized turtleneck comes in chunky dove grey floating above distressed skinny jeans. White sneakers make the things simple and practical- as though they were meant to explore alleys and gather stamps of espresso.
This provides me with the Ireland of the early fall or Copenhagen energy after rain. The looseness of the fold of the knit, those sleeves slipping over your hands–it has a comfort but yet is cool. There’s a calm confidence in not trying too hard.
I am used to wearing oversized knits with skinnies, and when I travel. The balance is achieved successfully and does not look excessive. As one of the stylists at Net-a-Porter has claimed, jeans should become the grounding piece; knits should be the softness. That combo? Always a win.
I would probably pair that with a navy trench to add some semblance of order or just have a claw clip on hand to flex the turtleneck. This outfit is your fast track when you desire to be yourself, but comfy.
Streetwear Gets a Soft Twist
It is a tribute to twisty sporty-casual. The outfit is anchored with a classic beige trench coat, which is over a white tee and black leggings. The bold and youthful energy is added by the green cap and crossbody bag; the sneakers of the dad are kept functional and entertaining.
This one screams Japan or South of France tourist-chic. I have a few similar days when I took a day trip to Munich and the look just made sense. It is easy to move in, nice and breezy, and yet somehow it all looks like it is all together enough to take selfies in museums or go to outdoor markets.
These caps, which are coming back into vogue through the quiet-luxury-meets-athleisure thing, are caps. And honestly? I’m not mad at it. One stylist (Who What Wear) once proclaimed the baseball cap the unsung hero of fall style, and after this outfit: I understand.
I would say this is lacking nothing but some little gold hoops. It lifts the casual, puts a touch of polish to it, and makes the entire outfit looks a little extra glamorous.
Fierce Meets Refined in Fall Neutrals
It is this type of outfit that sounds grace but manages to bite just a little. A black leather jacket is neatly cropped and makes the silhouette more defined though a leopard maxi skirt is airy and a tier skirt drifts down below. Pinned and stitched together, the entire look is paired with sharp black boots and a quilted chain bag, both, at once, femme and fierce.
Whether you are on your way to the South of France, Venice in September or even out to have a dressy dinner just to wear in New York, then this outfit delivers. It is beautiful because of the way it contrasts softness and strength, flowy fabric paired with structured and rigid leather. It is posh, wearable and even a tad dramatic and in the most fashionable manner.
Honestly, I’ve been keeping an animal print skirt like this on standby for years. It’s my wild card—instantly stylish, zero effort. As one fashion stylist once said, Rachel Zoe, who explained that style is a mean to express your personality without saying a word, we found out that there is indeed a very nice accent available to anyone who expresses it in this way.
Would I change anything? And perhaps red lipstick or a sleek low ponytail to finish the sleek look. But even without extras, this outfit is a showstopper.
Cozy Weekend Layers with a Touch of Wild
Its something so happy when something matches your personality and you feel so happy wearing it. This oversized beige tee in cozy sweater-like material and a black pair of leggings is about the softest base I could think of, but what makes this star is the leopard open cardigan which is a little bit of sass. It is held down by a tan baseball cap and lightened up by chunky white sneakers.
It is a perfect look to wear during the casual September days when you are in Cape Cod or Ireland or even on a casual afternoon in Seattle. Like you know there are days it is too cold to be extra styled up yet you want to be cute? This outfit is that mood in a nutshell.
As far as I am concerned I do this as a leopard neutral it has the characteristics of a neutral but is more of a personifier rather than overshadowing the other. One of my stylist friends always says, if your base is soft then you can afford to have your pattern loud. I had this vibe on another rainy Sunday coffee run last year, and yep, became addicted since.
Want to elevate it slightly? Add gold hoop earrings and a crossbody bag. Done and done.
Muted Blush and Black for Effortless Elegance
The moment I saw this outfit, I felt it. An oversized turtleneck in a dusty rose color combined with plain black leggings and corresponding blush knee-high boots, this was an outfit that looks elegant even when you are in a hurry. Include a blush tote to keep it all smooth and you just turned the softness up to a 10.
If you’re wandering boutique-lined streets in Switzerland or on a city break in Scotland, this look just makes sense. It’s warm but breathable. Structured but forgiving. Leggings makes it comfortable, the sweater is voluminous and the boots say, I meant to do this even when you did not.
Personally, this outfit makes me recall why I like September. It is the month you can still show off a bit of a leg–but wrapped in suede. I have teamed this look with a loose trench once in a cool spring morning in London and the compliments were unending.
Would I tweak it? Perhaps a broad headband or languid locks to repeat the fluidity of the outfit. But truthfully? This one’s a whole mood already.
Rich Chocolate Comfort for Crisp Mornings
Here’s your September athleisure dream. This appearance inclines to shades of black and white in a casual look with a warm cocoa hoodie and joggers outfit and completed with a down puffer jacket that appeared in a smoky chocolate shade. It is light with chunky white sneakers and sleek mini shades which add the edge without being too much.
I would love to take this out to a deck in Alaska on a cruise morning when it is early to get coffee and I am watching the fog move across. It’s also perfect for errands in Washington DC when the breeze gets a little nippy but you’re not ready for full winter wear. The tones do not sound laid-back, but refined such as a premium version of your well-loved hoodie.
So if you were pondering how to make sweats look intentional this is your answer. Stick to one color family, and vary the textures. I once read in Refinery29 that “monochrome isn’t boring when you layer smart,” and this outfit proves it.
To make a small change in the style, accessorise it with a beanie or use a long trench instead of the puffer when the weather is not that cold. But honestly? Don’t overthink it.
City Chic with Luxe Texture Play
Mixing it up like this makes the cry of ‘I have stuff to do, and make it trending. Black faux leather leggings against a background of a beige structured coat over a ribbed camel turtleneck offer wealth of contrast. Unexpected casuality comes in the crisp white sneakers but finishing it with a designer belt bag slung on the chest pulls it all together with a professional nonchalance.
It is one of those going that fits that trip to Japan, walk along Lake Como, any brunch in downtown to wear in New York. It is comfortable to wear traveling, fashionable to photograph and fitted to make you feel superior.
This outfit is one that I have re-created many times, when I am aiming to combine sporty and luxe. Faux leather leggings are my thing-stretchy, breathe-able and can be polished up with a good coat. Good layering is the secret sauce of seasonal style, as it was once phrased by stylist Monica Rose and this outfit does not lack in this area.
To tweak it? Perhaps a pair of big gold earrings or she can take off the sneakers to put on a pair of chunky loafers. It all depends on your mood- but in any case, this look should be taken into your September rotation.
Denim Layers for Crisp-Cool Days
The denim jacket in this outfit has a strong argument in claiming September as a staple as it comes with a sherpa lining. Combined with matte-black leggings, loosely fitting white tee and dirty-looking beige combat boots, this entire ensemble is completed with a vintage tan cap telling it a sporty twist. It’s casual, functional, and still totally cute.
It fits in Seattle, or the weekend trip to Copenhagen when you know you will be packing light. Denim never wears out and sherpa is the September surprise that keeps you warm without the bulk. The leggings are an asset to the boxy jacket and the neutral accessories make it earthy.
I adore the fact that this vibe is fresh, although it is constructed on the everyday basics. It looks like it is serving up an unbothered girl in the coffee shop, and to be quite frank, that aesthetic is one we all deserve this season. I have dressed up in something like this before in a road trip to Switzerland and all through it I was feeling very comfortable.
I might also throw in a little crossbody bag to make it a little more practical or to up the style a bit with some gold bangles on the event of knowing I was going to be out past nightfall.
Dusty Lilac and Winter Greys for a Regal Touch
This one’s for the days when you want to feel a little elegant, even if you’re just walking through crisp autumn air. It is a dusty mauve coat with huge buttons, a light grey sweater and a black mini-skirt sticking out at the bottom. What steals the show? Pairs suede thigh-high boots with a structured grey handbag creating the perfect balance to the color story.
This ensemble would be out of this world at Scotland, Ireland or Munich. It’s the kind of look you wear when you’re out museum hopping, then end up at a cozy restaurant with red wine and a view. It is warm and the color is rich and everything seems to flow in a muffled unity.
Honestly, I was not a boots over the knee girl over the years and it is only when I saw a similar combo in a French fashion blog that I changed my mind. When styled right—like this—it reads more graceful than daring. It is just a matter of matching it with soft lines and chaste covers.
What would I add? Perhaps a bit of polish in the form of a silk scarf tied to the handle of the bag.
Tailored Blazer Energy with a Weekend Twist
This ensemble teeters on the balance between formal and laid-back to a T. The plain white tee gets a step up with a navy blazer and the ole classic light-wash jeans lends a broken-in feel. She has leopard-print high-top sneakers and a black Prada mini tote, and it is a coffee meeting then errands kind of vibe.
That is one of the outfits I could attend in Washington DC or visiting the city Madrid. In this you could be sitting in a first row seat in a gallery, or you could be simply strolling through a farmer?s market. It’s casual, but make it cool—with a capital C. I adore the animal print on the sneakers that lends the wink of playfulness onto the otherwise classic combination.
It made me think of a comment stylist Allison Bornstein made: “When you are unsure how to put together an outfit, then use the three-word formula: classic, edgy and comfy.” This outfit nails it.
To make it pop even more? A red lip or stack of skinny bangles on an arm might add the finishing touch to an afternoon-to-evening look.
The Return of the Denim Maxi Skirt
And by the way, is your sign to invest in a denim maxi in case you haven hidden the fact that you have not done it this year. This outfit consists of a clean black-body tight-looking top, a fitted black cropped blazer and a high waistlight was denim skirt with a slit down the front creating a sneak peek. To class it up there is black ankle boots and a structured tote, over-sized sunglasses complete the look resting on the head.
So good to wear in New York, or anywhere really with a bit of a breeze and a whole lot of street style– Italy, Japan or even in Lake Como. It is so 2025 about the attitude with which denim has been redesigned this season. Not only jeans anymore but it is now structured, elegant and surprisingly versatile.
I’m obsessed with the proportions here. The length of blazer versus crop of the skirt? Perfect harmony. I shot in London last spring wearing this silhouette and could not believe how serene and statuesque it made me feel.
Only thing I’d swap depending on my plans? A more contrasting belt in gold hardware or perhaps a brightly colored clutch when there is a day outing involved.
Color Blocking Done Right
Talk about dopamine dressing. The bright color blocked sweatshirt in pink, red, orange and green is not overbearing. It is whimsical but entirely sophisticated when paired with a clean camel bag and high-waisted orange wide-leg trousers. There is a pair of minimalist gold earrings and thin sunglasses that complete the entire look.
This is so yes to those intending to go to Greece, Cape Cod, or even Venice in the late-summer later heat which extends until September. It’s sunshine in outfit form—bold, unapologetic, and fun. It is not only the feeling of being energetic that comes with this kind of color blocking.
I sported a de-moded version of this same outfit to a creative industry event and the amount of compliments I received? Wild. As Elle Magazine once put it, “Color is a confidence move” and this is a confident move.
Assuming I wanted something to offset it, a similarly playful pair of strappy heels or perhaps even a statement-ring in an an eye-catching shade to balance out the top.
Mocha on Mocha: The New Parisian Uniform
Nothing says “quiet luxury” like head-to-toe neutrals. This black-and-white aesthetic is a sense of playing with textures and colours: a camel knit dress with a soft flow and a caramel leather bomber. Sporty effect is added by matching brown Adidas sneakers, and a pop of red is only bold enough, provided by the structured handbag. It complete with a casual coolness of a soft gray beanie.
And this is one of these outfits to wear when having a weekend coffee stroll in London, one to the patisserie in Paris, and even a simple wine tasting in South of France. The color scheme fuses with urban streets and however, it does come out because of the silhouette and tasteful accessories.
I had spotted a similar appearance on a local in Madrid, who moved with that remained unaffected attitude we all desire. The part that hit me was the casual feeling of the outfit, i.e. there was no posing, vibe included. Vogue recently called mocha one of 2025’s “anchor colors,” and this is exactly why.
I might possibly substitute the sneakers with white platform boots, in case I had a more elevated finish in mind, but besides that, it is this combination that works.
Chilly Morning Uniform in Black and Ice
This outfit leans fully into comfy-cool territory. Soft black sweatshirt and matching leggings form the foundation with the extra large oversize light-wash sherpa denim jacket providing the street-ready edge. It is all fresh due to bright white sneakers, and the entire outfit is crowned with a black beanie and flashy sunglasses. The vibe? Urban athleisure with a shot of espresso.
This one has got the energetics of Washington DC, Switzerland, Alaska even Alaska cruise- where you need warmth and movement and a touch of mystery. You would be able to walk the streets at 8 in the morning with a cup of coffee in your hand and that look would last you till evening. It’s practical, but also really cute in that I-just-threw-this-on kind of way.
This is the formula on which I have depended to early autumn travel. With a large size denim jacket and black hoodie thrown over it, you get that feeling of being with-it in the world but you are also kept safe by a trendy piece of clothing. Insider tip? Take matte sunglasses and delogoize it to make it luxe.
Slip on a slim-line backpack or make use of Chelsea boots on any more rugged ground. Otherwise, the simplicity is what makes it shine.
Retro Prep with a Modern Mood
Businesslike, yet not too serious, the ensemble combines the black ribbed sweater with the grey plaid shorts and sheer black tights and is complemented by the ankle boots and the structured brown leather tote. It is bringing new prep school juice, but recast and remixed, brunch, but boutique shopping, or creative office environment.
This would completely kill in Scotland, Switzerland, or Munich at the end of September in cool weather. It is clean, edgy but with a touch of softness to not make things hard or too edgy. I like how the hot bag color does not make things too rigid-it brings life to it.
I would never wear shorts in the fall, but watching the street-style pros on Instagram, I have started doing it. It lies with tights, the dress needs something that makes it look glamorous- find some with a touch of sheen or sturdy pair of toes. This precise pairing would also look gorgeous out on a cobblestone path or on top of some fall colors.
If you’re unsure how to style the top half? Try layering a long camel coat over the shoulders. It adds dimension and an instant dose of cool.
Tailored Vintage Vibes in Check Print
A bold houndstooth print coat is placed on a simple black turtleneck and cropped jeans which are given balance with sleek heeled boots. The thing that makes it a deal though is the lipstick red lips she has, it has that old fashioned look, that dominating look, slightly old fashioned, but all modern at shape.
This is the one to consider in case you have been wondering what to wear in New York, Copenhagen, or Ireland this fall. It is the style that is attractive on the street at crossing point, and which flows perfectly in the middle of a museum lobby, or window seat at the bookstore.
I already had a similar coat handed down to me by my grandmother and I felt this generational type of power wearing it- there is something powerful about the things that can feel historical but designed in the present day. I know it was once said by Elle that a good coat does all the talking and I perfectly agree with it.
I would love to max out the drama and include a structured hat, which I would wear to add some change of silhouette another day I might wear some wide-leg jeans to shake it up a little.
Oversized Knits and Thigh-High Drama
This look takes cozy to a high-fashion level. An oversized, slouchy waffle-knit turtleneck sweater is worn as a dress and combined with thigh high boots in a sleek black color. It’s minimal, sure—but the impact is major. Soft and strong, oversized and tailored, relaxed and striking.
This would be absolutely suitable to a night out in Greece, Italy or in Downtown London. Its sexy even without trying the difference between the warm knit and bold stiff boot. And honestly? That is what so much of the best stuff on the go is about- and dressing with self confidence and not feeling guilty because you want to look good.
I actually wore it one time as a dare one cool September evening in Lake Como and I was invincible. There is just something about being warm yet still being able to show some skin that just makes you feel as though you are in control of the season.
What I would complete the look with, though, would be a couple pieces of minimalist jewelry a gold cuff or silver hoops. It doesn’t need much. The boots do all the talking.
Lime Layers and Loungewear Luxe
That is the technique of selecting bold color in a comfy profile. A bright lime green jacket that goes over a knit sweat suit of sage green tones is an impressive fashion statement. Throw in a structured mini bag with chain detail, the black ballet flats and a gray beanie and you have a composition of soft and edge that just pop.
It has all the major Japan and Greece fashion district senses where streetwear is not only comfortable, it is also planned. And in 2025, matching loungewear sets aren’t going anywhere. The approach is new: we are dressing them in drama-coats and accessories which have more of an art object feeling.
I have had on the somewhat resemblance of an outfit in a visit to Copenhagen, and the people did take notice. Secret is in tone-on-tones palette -it is a cozy piece but the color blocking makes it something more than sweats. Glamour UK recently pointed out this very trend as being the most chic way to keep warm yet not lose cool.
Unless you want to go this vibrant, use lime instead of emerald or cobalt blue, still strong, but a little more down to earth.
Parisian-Inspired Autumn Tailoring
Here, this is fall fashion in one garment. An ageless trench coat is worn on top of a white turtleneck and high-waisted plaid pants. Shiny ankle boots of brown leather provide the entire ensemble some form, and a glasslike beret of wine-red is a romantic, iconic touch. Soft waves and a red lip complete the story.
I envisage this appearance touring along cobblestone streets in Venice, visiting a bookstore in London or watching a canal in Amsterdam on a crisp Sunday afternoon. It is versatile, wearable, and easy to wear mix and match in to your European capsule wardrobe.
When I had this trench+trouser combination in Ireland a lady even asked me whether I was in Fashion School. I wasn’t—but that’s the power of good tailoring. Trench coats never go out of style and coupled with warm-plaids and boots? It’s impossible not to feel pulled-together.
To add another layer on top, put on a cashmere scarf or structured cross body. If you’re traveling light, this look covers both business lunch and sunset strolls.
Cool Slate Tones Meet Power Suiting
To conclude the last look, we are leaving on the neat modern note. Over a blue-gray knit bralette and wide-leg trousers is a slate blue-gray blazer that makes one look smart yet relaxed. Throw in a corresponding pair of baseball cap, crossbody bag, soft scarf and sleek sandals, and this ensemble makes it to the tone of laid back authority.
It would be a dream to wear to a New York meeting, in a cafe and take some city blog content. It would also be the very item I would pack to do a creative project in Madrid or the trendy ends of Cape Cod. It incorporates softness with structure and that subdued color palette makes it look sophisticated, wearable energy.
This takes me back to Marie Claire dubbing it the new monochrome; not only one colour, but layering tone and texture. The cap makes it sporty. The suit makes it powerful. The scarf softens it all. It’s a quiet standout.
I wouldn’t change a thing. Perhaps all we need is a powerful iced coffee and a couple of over-sized headphones in order to dwell in such an aesthetic.
So there you have it — 23 casual September outfits designed to meet you wherever you are in 2025: whether you’re sipping espresso in Italy, gallery hopping in Washington DC, or just layering up to walk the dog before your morning Zoom. These outfits are more than just clothes. They’re moods. They’re intention. And they are one of the evidences that being stylish can still be easy.
Which look are you planning to try first? Keep me posted–fall is coming and no one can wait around and show up half-dressed.
