Festive coats, wicker bags, cosy texture, booties, scarfs: is there anything more amazing than dressing the autumn wardrobe and seeing how fall gradually flows into winter and crisp wintry mornings start rolling. And this is the season when we dive into the style closet, retrieve the oversized sweaters and thigh-highs, and we even are looking forward to be dressed again.
But how do you dress for that in-between time? A day that is slightly too cool to be wearing complete puffers but altogether too breezy to wear skirts. What are you going to wear to avoid looking like an idiot (upstage that horrid thing between orange fall and tinsel glitter)?
This is what I have been questioning myself on every year. Thus, here is my guide that will help you plan your fall-winter transition in 2025 that is composed of outfits I have liked in real life set up. Whether you’re heading to University, layering for work office wear cold weather, dressing a plus size cold weather figure, or curating your own aesthetic, this list is filled with inspiration that feels grounded, wearable, and 100% current.
Let’s dive into the first looks.
Cozy Red with City Sparkle
Red in the winter months has certain unpardonably brash tone to it. It brightens everything up when it is grayscale in the streets and exudes this swaggerish carefree attitude that is magical in itself. In this glance, red knit mini dress is a perfect match to a thick matching sweater, a checker fringed scarf, and thigh-high black boots classic but the impact is dead serious.
I love how each element here pulls its weight. The velvet Gucci shoulder bag is a mini but posh embellishing the outfit with that finishing matte black color. The pom-pom beanie is not at all cutesy. And the scarf? A total layering essential. Each article of this ensemble is functional, so it will not make you freeze but will still bring that urban outlook. Going to work by train to York or NYC, this is the notice me outfit.
I had near exactly the same thing on when I walked in downtown last December, and I had three women stop me to ask me where I found my boots. It’s such an approachable way to do bold. Pair it with a bare leg if you’re brave or thermal tights when temps really drop.
What I’d add? A longline tailored jacket to wear when it is windy but still overcast, versus an entirely different style, camel or even plaid, would just fit in here.
Urban Plaid and Elevated Neutrals
Neutral layering is always (or at least should always be) timeless, but it helps to give it some form and structure, such as this one. Grey plaid coat with a belt and a buckle on a marshmallow soft beige tunic or mini-dress topped off with camel suede over-the-knee boots? This is quiet power that I may describe as quiet elegance. It is business casual dress code office business casual but make it fancier.
It is that broad plaid print that is so right now 2025 trends are moving towards larger checks again and they are long overdue. And I always tell people, when you go to invest into a long wool coat, you have to get one that does the talking. Belt it in addition to defining the waist; it also gives structure to bulkier layers. The sunglasses and mini crossbody pull it all together.
And you are midsize like me so you realize the struggle between the form and comfort. This type of form-play (long coat, thigh-high boot, fitted lining) is both warm and yet the structure. Also: the boots. Caramel or tan suede boots are the ones of those basic staples in closets which are a must.
If I could tweak anything? I would even consider changing the belt to a croc-like leather belt just to introduce some more textures in the scenario.
Laid-Back Texture with a Vintage Twist
Earth tones will always be fall classics, and this one is spot on in terms of a layering formula and casual at the same time. The huge size of a cable-knit sweater of shiny green, a huge loop scarf of cinnamon coloring, skinny jeans of dirty denim and the level of the riding boots made of leather? Cozy without trying too hard. This is peak university or 40 casual weekend material.
What I also really love about this outfit is how there is slouch utilized. The neckline almost gets sucked up in the scarf – and it does work. It is somehow comfortably romantic and it is good during the changing seasons. Paired with the knee-highs, it’s giving “apple-picking Sunday meets vintage bookstore girl” and I’m very here for it.
The oversized bag adds function and texture, perfect for colder months when you’re carrying gloves, lip balm, and everything else. Even as plus size cold weather inspo this would work as a charm, large sweaters with skinny jeans would create the illusion of the long silhouette.
Would I change anything? Perhaps add a felt hat or a row of rings to make the accessories even a bit more. Otherwise, perfection.
Scandi Sweater Dress Simplicity
Sweater dresses These dresses I could write love letters to every fall. This kind, in particular: sloppy, refined, with a large comfortable turtleneck and well-defined silhouette. The soft beige color in this case makes everything look controlled. Paired with opaque tights and knee-high suede boots? It’s understated elegance.
This appearance would confidently waltz into a work office room elegant environment or into a brunch date and no point would be missed. It is avoided by the black mini bag which is making it less monochrome, and the height of the boot balances everything. And this is one of those outfits you can wear every other day throughout this fall and still look cool.
If you’re on the hunt for elegant, low-effort dressing, this is it. Once a stylist at Nordstrom commented to me: The most spectacular looks are usually the quietest of all. This is what she meant.
Here I may include a polished low bun and gold hoops. Or in case of cold days, a cocoon wool coat of a complimentary hue.
Retro Autumn Revival
In the middle of 1960s-style Mod and Gen Z cool girl style, this one is it. A cropped orange sweater over a check mini skirt and pale suede boots and a knit beanie? Tell me that isn’t a total Pinterest mood board. And yes, it screams Y2k revival meets modern minimal.
This one’s fun because it’s youthful but polished. The top is fitted on the flared skirt and the neutral boots prevent the costumany. And it is the brunch on the West Village or a walk down Central Park with leaves the color of fire, in case you live in NYC.
I wore an outfit something like this last October and added a plaid blazer as it got windy. It was a one of those days when you were cute, and you knew it. Isn’t that half the joy of fashion?
Honestly? I’d wear this on Thanksgiving Day, indoors or out. It is playful, but classy enough.
Power Neutrals and Monochrome Grace
Nothing says I’m in control like an all-cream ensemble layered to perfection. It is the style I resort to when I want to feel or rather appear pulled-together but do not want to put a lot into thinking. A ribbed knit sweater tied into a corresponding midi skirt, covered by a loose-fitting structured overcoat, it is armor of the modern world in the most delicate and exquisite coloration.
The large sun glasses and the chocolate check Louis Vuitton hand bag is what gives the look that hint of luxury and yet it does not stand out. I love everything about how the whole outfit is lengthening the limbs – even more so with soft blush suede knee boots, which are much like the heart-timing warmest whisper on cold pavement. Beautiful work office wears that can be described as business casual or just for that extra oomph that makes you feel like you cannot be stopped upon entry into any room, then this is it.
Personally, I’ve learned that monochrome doesn’t mean boring. Fashion editors such as Elaine Welteroth have got it all right; the trick to getting neutrals right is to mix and match textures rather than colors. And this look proves it.
To give this look a little more, I would top off the charms with gold earrings and a clean low ponytail with a satin scrunchie to add some minor surprise, but still remain high-end.
Off-Duty Layers and Street Cool
There are days when you simply want to look good without making an effort, aren t there? This outfit gets that. An oversized shacket with a layering hoodie on top, black skinny jeans, and lace-up combat boots, all that check all the boxes. It is as elemental as can be without being a bad thing and is something that I have personally grown to appreciate with every cold season.
I always assumed that plaid outerwear can be of two kinds flannel-lazy or modern-cool. And this one is the latter. The soft taupe hoodie under the plaid is well balanced with the warm coloring of it, giving that vibe of being snug in your own world kind of feeling. The quilted crossbody bag adds just the right punch of texture — and the black Dr. Martens (or similar) are always a fall winter outfits staple. Rain, wind, errands? You’re covered.
As someone who’s 5’6″ and wears a midsize, this silhouette is one I revisit over and over. Its reason works because it is big on the top and small at the bottom, and the reason is always a success.
Would I add anything? A big knit hat and a touch of red lipstick. Sometimes all you need is that one unexpected element.
Soft Taupes and Morning Coffee Walks
Strolling with a bestie, with coffee mugs in their hands, and with buttery-soft neutrals? It is what I envisage in the dream when the first cold enters the air. Neither of these two outfits can be described as less than a fashion equivalent of oat milk lattes – cozy, comforting, yet somehow luxurious. Coordinated coats, cozy scarves, relaxed trousers, and tonal layering. It’s the aesthetic moment we all secretly crave.
The best part of this scene is that everything is so wearable. Just picture long camel and ivory coats, large-knit scarves with an image of kinds, wide-leg cream trousers, and effortless tan Chelsea boots. It would fit in the workplace or when you are working remotely in a cafe you like in Nyc or York it goes well in either place.
Something I admire here is the layering balance. Chunky scarves don’t overpower because everything else is streamlined. I have also used such a look on a Monday team meeting and though I did not speak a word, my attire spoke nonetheless. Trust me, these pieces speak volumes in silence.
If you’re curating a minimalist cold-weather capsule wardrobe, start here. Pair a ribbed knit beanie and a natural lip on your undercast mornings.
Cotton Candy Cozy with a Twist
Sweet, soft, and somewhat sporty, this pastel dream outfit shows that you do not really have to become dark to jump into the season. Shearling jacket in cropped blush pink looks paired with a matching fuzzy clutch and cap, ivory trousers and pink slip-ons? I would die over a surprise of soft in 2025 trends such as this.
Pink outerwear gives you that feeling, that it is rebellious to wear and like you are dressing up to have fun as opposed to dressing up based on the weather. It gives the impression that it is more stylized yet retains the fun with the tonality in the jacket, the fussy handbag and the structured hat. The plush against sleek is also something I adore: with the wooley jacket and the clean wide-leg pants, a combination that is very fresh.
Being always cold is a curse and I always need to feel warm but not puffy at the same time and this jacket can become my dream that comes true. I noticed the same expression on the face of Hailey Bieber in January, and it impressed me. It’s playful but very much grown-woman ready.
This would also pass as a pregnancy friendly appearance depending on which trousers you settle on, the stretchier ones. Earmuffs instead of hat and it is holiday market chic.
Statement Fur and After-Dark Energy
Some outfits just say “I’ve arrived.” This one? It practically roars. A blazing orange fake fur jacket on top of an all black fabric of skinny jeans and body suit with plunge front, that screams big city night party, eye popping boldness. The sparkle-toe stilettos don’t whisper, they shine.
It is the type of outfit that I will put on when I want to be bold not only how it is. The volume is more than compensated by the sleek silhouette of the cropped jacket and the furry texture poses the luxe contrast to the smoothness of the rest. That mini monogram handbag? Icon behavior.
It is for a night that you are going out, and your style needs to support you compared to you. According to fashion savants, such a type of fur pop can be seen as a power move in 2025 in citrus shades. It is also 100% plus size cold weather and 40 besides classy adaptable, the form suits all body shape when properly done.
What would I tweak? Perhaps add emphasis to the jeans with a gold chain belt. Otherwise, the drama is just right.
Classic Checks and City Sass
The thing is: a daring plaid coat, with a slim mini and boots above the knees is not only good-looking, but a symbol. The good old structure of the coat and the crisp white turtleneck, which is tucked into a deep wine hued skirt is classic in a sense but very in-fashion. This is the look I turn to when I have to wake up a weekday and take the energy.
It is the blend of textures and tones that make it sell: wool on wool with a rigid style of leather boot. You have a neutral base, white, burgundy, tan with the warm brown suede boots. The longline plaid coat takes up the volume and warms you up, so the look is ideal to wear to the office on cold days or in winter when you need to walk through the city in the morning.
I gave it an attempt last fall in London, and you know it just makes you feel like you own the street when you are rocking in your heeled boots against the pavement and your coat is flowing behind you making you feel like the proprietress of the street. It’s definitely a “main character” outfit.
In order to zhuzh this up even more, I would add a mini structured handbag to this effect. Maybe something boxy with gold hardware.
Playful Plaid and Retro Vibes
Now this look? It’s joy in outfit form. Plaid mustard, soft denim, a green turtleneck with, hm, notes of red, this is a look that could only be described as quirky retro with some cool-girl aspects. It is not only aesthetic, it is also energetic and I truthfully enjoy the way it expresses confidence without trying to be perfect.
So much to deconstruct: the fitted belted coat tucks in the waist creating a silhouette above the wide-leg crop jeans. The combination of coral and emerald is strong, unconventional – and it is so applied. The knit hat the red and Adidas sneakers take the outfit into fun street wear, the kind that can be worn by anyone who wants to be part of the Y2k renaissance but in a more down to earth manner.
I would wear it on a day when I have a sh*t-ton of errands to do, but I do not want to feel sh*tty. To be truthful, I believe it is one of those outfits that would be listed as a mood lifter one, you look in the mirror and smile because you are doing something that you normally never did.
Given the choice to restyle though, I would probably replace the bag with a crossbody in a lighter color or even canvas tote bag to make a more informal look.
Powder Blue and Winter Calm
Do you remember mornings when there is the snow in the air and everything seems to be quiet? This look captures that moment in clothing. A complete collection of pale blues and greys, with warm tan accessories and boots – it creates warmth in the coldest weather.
The intelligent, not heavy layers I most adore in the look: a knit turtleneck under a midweight coat made of wool, thin trousers that are tucked into some socks and ankle boots. The pom-pom hat alongside the mittens and the large clutch ensure that it will be soft and non-intimidating something that is ideal to wear to work during office days in rainy weather or brunchilarious weather would only be under 30 degrees Fahrenheit outdoors.
It is another of those plus size cold weather versatile (ever so important) looks I always suggest: a longline coat to make the body slim, comfy fabric on top, dark bottoms to anchor it. It’s beautifully balanced.
To add a bit of color I would include a soft rose lip and a wool scarf of the same color. But honestly? It is already so beautiful just the way it is, peaceful, wintry and so good-looking to wear.
Blush Elegance in a Snowy Frame
Others are made of softness, albeit luxe. This blush and ivory outfit is the style that looks like you walked out of a Christmas film. Grey on purpose, suit-like without being stuffy, light as it could nearly fade into the snow in the background.
The top underneath has moves freely which contrasts with the structure of the coat, and the high-waisted trousers appear to provide the apt polish. And the color palette is the real gem about this. When you are ready to taste something feminine and nonetheless classy, this is where you get your inspiration. The best suited choice on those days when you need to do your job remotely and would love a break in the fresh air, but look fancy doing so.
I had on about the same thing on a holiday dinner last year, and I was complimented pretty constantly. “You look like a Pinterest board” was my favorite.
If I had to recommend one addition? The perfect way to tie this all together would be a statement earring – perhaps a pair of gold hoops or just a plain pearl drop.
Château Chic with Vintage Flair
It is kind of romantic lost in the turtleneck inserted into high-waisted trousers, and this one captures the approach. A thick ivory cable-knit sweater, perfectly fitted pleated pants and warm brown accessories? It’s a walking dream. French countryside or not this outfit is 40 ladylike done correctly.
The collar-high look creates the focus on the top, which is ideal when you have something grander on your ears, or a sleek updo. The sweater is tucked in, and the trousers gracefully cascade onto heels boots. It is the type of an outfit that makes an ordinary day cinematic.
I’ve always found that mixing textures like this — soft cable knit and structured wool — creates such a harmonious outfit. It is also perfect in the category of work office outfits when you are not planning to look more empowered in dark colors.
What would I do differently? Perhaps something like a camel trench on top, when it is windy, and I have a soft scarf tied loosely so that it is layered on. Either way, it’s one of my forever favorites.
Checked Elegance with a Vintage Pulse
It is a way to look that seems like a contemporary interpretation of classicism that kind of outfit that does not shout but deserves all the looks. A neat houndstooth coat on top of a ribbed turtleneck, combined with high-waisted creamy pants? This is office attire classy dressing with a lot of finesse.
The shape in this piece is magical: wide-leg pants make the body elongated and the top is tucked inside to emphasize the waist. At the right touch of texture and depth are the hot chocolate handbag and the tortoiseshell sunglasses which are perfect with it. I would definitely suggest this combination on days in which you have absolutely no time to get ready even though you would like to feel dressed up.
The stylist once remarked, it seems that, tailoring is a shortcut to a polished appearance and the case is proved by this outfit. The cut is good and the fabric is quality, then you need not much.
If it were me? I would throw in a big lip or a fragrant perfume something sexy to punctuate the suave pitch.
Winter Club Meets Baby Blue Fantasy
Now this is a showstopper. An icy blue faux fur coat with a structured white corset bodysuit, and white knee-high boots with it, it is cool, it is daring, and it definitely belongs to 2025. It is street life combined with night life, and a hint of 90s club nostalgia.
I would not lie, this outfit is not everyone. It’s fierce, flirty, and unapologetically daring. The silhouette also focuses on the form of the corset and brings the focus on the waist, balancing against the plush coat. It is completed by boots with mod-glam spirit, ideal in anyone whose fashion motto is Y2k.
Would I wear this to a dinner party? No. However, when it comes to rooftop cocktails or a winter event, which requires a pinch of drama, then yes, definitely. Dress up in sheer tights or put some sparkly accessories in case of a drop in temperatures.
I’d add a clear clutch or metallic micro bag to finish. Maybe some frosted makeup for a dreamy, frozen vibe.
Café Cool with a Parisian Twist
It is that “rushed out to have a cup of latte, and yet has compliments” appearance. Thick grey turtleneck, traditional black leggings, white sneakers, and a smooth puffer vest it is perhaps the formula of chic and comfortable errands. Throw in a baseball cap and a cappuccino? Insta-worthy basic comfort.
This outfit is so much into that comfort zone in the middle: large top, small bottom, and plain shoes. The puffer vest is doing all the lifting in terms of warmness with none of the bulkiness on the arms thus it may be the ideal choice in cold weather even at the plus size too.
I have versions of this that I wear practically every week and when going on Saturday strolls. You can modify this look infinitely – replace the cap with a beanie, and add a trench or crossbody and it has turned into a completely different thing.
To be a little more detailed, I would wear hoop earrings and wear multi-strand necklaces to slightly upgrading the vibe and not losing the off duty thing.
Effortless Neutrals on Repeat
Whenever those oatmeal and sand tones are involved, it is somehow always classy. This look is soft, breathable, and totally seasonally flexible. An ever so tight knnit turtleneck under baggy tan leggings with sneakers? Yes, yes, and yes. Its fall winter outfits comfort can be described as the look that could have been taken out of a French lookbook.
I adore the balance here. The sweater keeps giving the cozy winter hug, yet the light tones make everything appear brightening even as days grow darker and darker. The practicality of the outfit is underpinned by some sneakers, as it can easily be worn at university, during the weekend or just enjoying the life stylishly.
Minimalism like this doesn’t have to be boring. Such an appearance is an empty palette that can be filled with accessories: the tortoiseshells tint, a chain of many gold necklaces, or a burn-orange crossbody might all different color it according to your mood.
When it comes to cooler weather, I would put a camel coat on top and that would be it.
Pumpkin Spice with Street Chic
This one feels like autumn itself. The oversized plaid shacket, warm shearling-lined booties, and the white beanie are simply amazing. Combined with skinny black pants and a caramel-colored Chanel cross body? It is made of such fall casual weekend style dreams.
The style is rather comfort-based and casual but also looks completely Instagram-worthy. The color palette (muted neutrals with pops of rust and tan) plays beautifully with the leaves — ideal for early November when everything outside looks like a vintage filter.
It is an oversized top layer for those ladies who desire to have the pregnancy-friendly or plus size cold weather style, as it is wide, warm, and uncomplicated. Honestly, it’s giving soft luxury without even trying.
A dog on a leash and warm latte in hand, and this outfit? Add-to-cart energy.
Sporty Luxe for City Errands
We end strong and on point with a real chic hybrid: laid back but sophisticated, active yet purposeful. The oversized teddy coat, a white sweatshirt, black skinny pants, chunky Chelsea boots, Yankees cap, and so forth, it is streetwear that has a reason.
This is not the case of the neutrals making this work, it is the silhouette. The baggy outer layer that combines with the skinny bottom part makes it mobile and at the same time very comfortable. The white Ladies crewneck one can see peeking under the coat, and the baseball cap makes it personal.
It is that sort of thing I put on when I am supposed to complete three errands and have no time to act overdressed but have to believe that I am cool. Particularly in work office attire during rainy mornings when you are not going to meetings anymore but you still need to present yourself with a purpose.
Assuming that I was going somewhere a little more social, I could replace my large leather tote with that or add a shiny lip. But really, this one’s ready as-is.
So, which one are you trying first? Whether you’re into soft layers, bold outerwear, or chic neutrals, these 21 looks are your 2025 trends toolkit. Browse having your guide to hand, bookmark it, pin your faves and seasonally update your closet. And bear in mind that it does not matter what you put on it is the way it makes you feel.
