With the fall right behind our backs, we have one of our most beloved fashion essentials back right along with it: boots. If you’re searching for Fall 2025 outfits to wear with boots, you’re in for a season filled with cozy textures, effortless layering, and chic silhouettes that suit every body and lifestyle. The combination of adorable ankle boots with ripped jeans to elegant skirt-and-boot sets offers a right mix of comfort and confidence this year.
Whether you’re building fall outfits with boots and leggings, styling cozy knits with brown booties, or finding fresh ways to wear your favorite dress, these outfit ideas were made to carry you from early September mornings to late November evenings. Consider relaxed, rural, plus size accommodating or stylish but demure-this guide has got it all.
Once the leaves have turned and the air has sharpened just how do we manage to make our fall wardrobe as crisp as the chill outdoors? Whether you’re heading to brunch, the office, or a cozy walk through the park, boots become the stylish anchor of any outfit. But what outfits really make those boots shine? Will one pair of leggings change to a skirt or even that of an early work look? In this article, these issues are addressed by using life examples of outfit inspirations which are appropriately layered, seasonal, and easy to wear.
Mint-Coated Edge With Ankle Boots
Here immediately attracted my attention the clash of soft and sharp. The tone is is established with a pastel mint tailored coat, finished in a polished and lightweight manner opposed with a bold Fair Isle knit, which is screaming nostagic fall warmth. Withered shoulder jeans are slack and sun-worn, and shiny white leather ankle boots provide a contrast of the futuristic, hitching the entire thing up into 2025. It’s playful but commanding. Certainly the sort of combo that attracts approval in the coffee shop.
Each item here plays its role well. Mint coat is probably the coat you need on your few fall days when you still feel like tipping hat to the spring color schemes without appearing out of fashion. That isle of fair sweater tricked out to go with any skirts, or over midi dresses. The stone-washed mom cut jeans make things casual, and the boots rolled well above the ankle? They’re a total game changer. They’re bold, crisp, and perfect with anything cropped or cuffed.
My favorite thing about this is this balance between sweet and strong. If you’re someone who usually leans romantic in your fashion but wants to explore a tougher fall edge, this look is that sweet spot. Think cozy, but a little daring too.
Personally, I’d throw in a chunky knit scarf or oversized tote in a neutral gray to ground the brightness of the coat, especially if you’re wearing this in the city. For a comfy but intentional look, don’t skip the boot socks peeking over the edge either.
Classy Neutrals for a Chic Day Out
An old-fashioned camel coat on top of striped top is one such ageless foundation. But what elevates this look into Fall 2025? The tailoring of the slim black trousers, the softness of the loafers, and a luxurious quilted bag that whispers “I’ve arrived.” This ensemble exudes the right gone-to-work-weekend look when you put it together without putting too much effort.
This isn’t about reinventing the wheel—it’s about refining it. A striped knit pattern will add just right amount of stripe to make the outfit not boring and the camel coat is a real seasonal hero. It’s structured, classy, and warm enough to carry through November. The cropped tailored pants highlight footwear, and while loafers are featured here, it’s a perfect setup for leather ankle boots in taupe or glossy brown.
I tend to lean on looks like this when I need to be “on” but still feel grounded. Whether you’re in your 20s or 50s, it’s one of those outfits that never misses. Coco Chanel told everyone, that simplicity is the mark of all true elegance. This proves that principle with every clean line.
To add a bit more trendy flair? Swap the loafers for boots with a block heel, add a bold burgundy lip, and suddenly you’re styled for a gallery opening or downtown dinner.
Ivory Layers for a Soft Statement
Monochrome has never looked so inviting. This outfit steps in zoned neutrals with a cream beige coat, a white turtleneck, a loose ivory jogger, and chunky boots with a barely there glow. It’s modern-day royalty energy—polished, cozy, and styled to look effortless. The tone-on-tone softness makes it feel high-end but approachable.
This ensemble suits one who does not want to fall in the trap of dark fall colors and end up drowning in it. The longline wool coat is work enough but soft enough to be comfortable. The turtleneck is a wardrobe essential, and those joggers? It shows how pants can be as comfy as pajamas, but with a little care they can be polished when worn. Combining the classic styles and giving it simply the right edge are the boots, chunky, white and practical in a stylish modern take of combat styles.
Having seen this, my instant thought was: this is what I would wear travelling in early fall. It was stylish enough to get to any airport in NYC or Paris and step off the plane to lunch meeting. Another thing that comes to mind is what Refinery29 has previously said once, and that is, power dressing is nothing other than the power of dressing. This outfit is a quiet power move.
What could round this out? Maybe a creamy beret or oversized square sunglasses. When the ground tones are as relaxing as these, there is no need to be cautious with going full monochrome.
Structured Urban Classic with Riding Boots
The silhouette is trim, with a little bit of boxiness in the top, trimmed at the legs, the latter which are perfect. A beige overcoat I cut was thrown on in striped knit and a chunky turtleneck. The outfit is held together by black leggings and completed with an optimal touch of the tradition by sleek riding boots. The universal street-plugger vibe can complement a museum visit or a power stroll in the park as well as it can complete a daydreaming-in-a-cafe ritual.
I adore how this and yet still, this outfit is very minimalistic. The color story, beige and black is never unflattering and the gold clasp bag gives it a vintage feel. The leggings are sleek, and perfect with a coat such as this one- you do not want bulk. And those boots? High, smooth, riding-style black leather which came just below the knee. A forever staple.
In all honesty, I will revert to this interpretation of this look throughout the season. And it is dependable, no-fuss, but yet, well-groomed to be self-respecting. So-called city-casual minimalism vogue fashion recently presented similar silhouettes as fitting well into that style of dressing, and they were not untruthful.
I would do some gold hoops or a silk scarf around the coat when I would be venturing out in this, a bit of feminity. It’s a look that’s built to adapt.
Snowy Stroll in Textures and Trousers
And there is hardly anything that is more comfy and cosy in the fall than cable knits and wide-leg trousers. In this case, a boxy white sweater with dramatic sleeves is a perfect contrast to pale gray pleated pants, whereas chocolate heeled boots somehow manage to appear out of it. The color scheme is of a light but rich seasonal color it is frosty and romantic simultaneously.
Every element here is deliberate. The oversized turtleneck adds both volume and warmth. The trousers are made of light wool and are very elegant and are perfect in combination with boots, which are tied. These chocolate heels not only complete the outfit in terms of styling, but also give it an elevated height literally. However, the heights are not over the top. A shoulder bag made of cream does not spoil the atmosphere of classiness and calmness.
This is what I’d call a “walk and wander” outfit. Think bookstore dates or coffee outside your favorite bistro. I have traveled to New England in such a look and I always feel comfortable and more or less elegant. The soft knit coupled with the strong tailoring is never failing in its flattery.
Throw on a tailored jacket (or even a belted trench) and you will be all set. Matching beanie or leather gloves are important items when the cold strikes.
Mustard Knit & Chunky Neutrals
There is something in this juxtaposition that reminds me about golden leaves drifting in the gentle wind. The most noticeable one is the knitted sweater: The mustard size oh-so-chunky knit- and positivistic and all-seasonal. It’s paired with cropped wide-leg pants in a soft beige tone and grounded by black moc-style shoes with platform soles. The proportion is played with in the most desirable manner by the ensemble, in between relaxed slouch and elegant lines. The organised LV mini bag gives the entire narrative a posh finish.
This type of appearance suits being transitional fall attires with boots and plus size as wellcompliments, but not too trendy. The cable knit provides bulk on the upper part and the wide-leg pants provide a lot of comfort and ease. White Hutton Chelsea booties that give me a little platform would be my choice to pair with the knit at the ankle. Add a neutral trench and you’re off to a cozy brunch in style.
I am more geared towards warm colors to alleviate a rainy day and this color does so without showing off. It is happy, yet down-to-earth with neutrals which are relaxing and elegant.
To harmonize with the warm shades, I could take this appearance to an even more pronounced level by adding a matte brick-red lipstick or gold noticeable earrings to coordinate with the color schemes.
Chartreuse Pop & Polished Bottoms
There’s something exciting about the unexpected. The outfit is focused on a bright chartreuse oversized, complex in its knitting, pattern, sweater, and straight-cut, cuffed trousers of beige. Black patent chunky loafers- that can be quickly changed to boots- form the grounding. The entire ensemble is juvenile, crisply cut and on the verge of action, hence the tucking of the top just a little. Extra style features namely the sparse makeup and the snappy bob, it adds to the vibrancy of the clothes.
It is an ideal choice of fall looks with boots lady who prefers a more intense color scheme. The trousers are also slim and cropped, so any ankle or heeled boot will do the job here. Looking to have the added fashion twist, go with a sock boot in ivory or a two tone pointed toe. It will be super fine when you are going shopping, visiting a museum, or even when you are planning to meet with acquaintances and you need to be seen.
It remains no secret that daring knitwear is one of the major trends of the season as Harper Bazaar even recognized one of the most needed shades of Fall 2025 as chartreuse. And I’m on board. When combined with beige it is wearable on any skin color.
To make this complete, a crossbody or color-blocked crossbody will complete the look. And if you’re color confident? Add cobalt blue nails. Trust me.
Coffee-Toned Utility Meets Street Softness
This is a quiet, yet rich outfit, which toys with warm brown shades in a sensitive manner. The foundation is a ribbed turtleneck in camel and is combined with cropped black pants layered over a draped wool shawl. The hero element? Aged, brown, lace-up boots, sturdy soled, sensible, old fashioned, terribly fierce. Workwear elegance is also achieved by using the large leather satchel bag.
And this is an ideal formula to country or coy fall outfits with boots: it takes that line quite perfectly. The shoes are easy to walk in but sturdy, and they are ideal when you are on the go, yet you do not want to lose your feeling of being carefully chosen. And the movement of the shawl gives that action and warmth we desire at early fall days.
Putting on a look as such makes me feel I can handle anything- errands, lunch even the client call that comes on a last-minute notice. The top softness contrasts with structure at the bottom and reacts as a very well-coordinated pair. Plus, neutrals like these never date.
All I’d add? Maybe a leather belt to cinch the waist if you’re after more definition. Or a few little hoops in delicate gold, to match the warm coloring.
Parisian Stripes and Denim Simplicity
There’s always room for a classic. The tuck of a striped white and black sweater into light-wash skinny jeans hits the ankle-length magic right between the perfect ankle boot and that of warm suede in a rust shade. The mix is casual and yet sophisticated and it is based on the classic French girl style. Some sunglasses and a structured brown bag are applied to make the look even better.
To create fall looks, the person who wondered how to wear jeans and boots with everything should be given this answer. These distressed jeans go particularly well with heeled ankle boots as they make legs seem longer and it makes them focus on the shoes. The sweater is not heavy and the light wight makes it comfortable, and ideal in combination with transitional weather.
I am somewhere attracted towards simple formula as this one because I can have space to experiment the accessories. It might be a trench coat on some days or a bright red lipstick or a scarf on another. It is a base appearance, which leaves space to be outgoing.
Instead, I would wear a relaxed-fit stripe knit and a cropped flare jean in a throwback, but even more fitted to plus-size figures.
Tailored Blazer and Knit Dress Combo
It does not say anything about the strength of a knitted dress and tall black boots in fall, because it is flattering, feminine and convenient. This outfit incorporates this combination and tops it with a camel blazer to make it look sharp. The dress is a high neck and ribbed sleeve dress that fits tightly but not clingingly, and the boots are shaped and slimmish and create a good contrast to the loose materials. There is a hint of the white handbag to brighten the whole look.
It is the perfect choice of fall clothes with boots and even fall clothes with boots black women provided you have style and preference of tone in lifestyle. The design fits on so many figurations, and the combination of structured and gentle fabrics comes off modest, yet is not a single bit dull. And it’s warm enough for early fall when you’re not quite ready for tights.
I own a variation of this and wore it to a family dinner last year and it was a success–comfortable, stylish and not try-hard. It is one of those looks when every item does its work and does not require many accessories.
To take this style to another level you could add an eye-catching coat over the top or replace the white handbag with a jewel tone handbag. Or even throw on a brooch—yes, they’re making a comeback!
Modern Minimalism with a Monochrome Punch
I love the quiet strength in this outfit. It combines an oversized black sweater that is vulnerably stylish on top of the oversized shirt that is ample-sized and decent over a long shirt in white color, combined with leggings in deep black color and topped off with a pair of knee-high boots that are very stylish and at the same time daring. This is a style that travels through the city like a whisper  nightmare, it is deliberate, sparse, dramatic in its sparseness. To maintain the architectural and forward fashion level, the pointed form of the hem of the check shirt sticking out under the bottom is helping.
This is a great outfit of fall boots and leggings and sends off a professional-but-cool vibe. The following layer of orderly refinement provided by the structured collar puts this above mere lounge wear and brings it to the pure street style. These platform boots are chunky, which is best–adding height and confidence, and comfort as well.
In cases where I am going out to coffee runs or informal meetings, I resort to variants of this ensemble. They are comfortable yet crisp and are versatile to be used in the errands and eat out lunch of your choice. It even goes really well with a coat thrown over the shoulders.
I would add silver as an accent: a crossbody bag or some striking red lipstick to bring this style more towards the “power casual” on the scale. Because sometimes all it takes is one extra detail.
Soft Layers and Street-Ready Leggings
There are some days when the comfort has its day, but that does not imply that style cannot be on the other side. Off-white oversized beige crewneck sweatshirt and classic black leggings with contrasting white sneakers will give you a dose of off-duty model effect. It is decked out with the white slouch socks, which lends the whole thing a nostalgic element, and which says, in one phrase, Yes, I dress for me.
This one does not come with boots, but by all means could be- particular ankle or lug sole ones to add a bit more country grit. Think about fall clothes with boots and leggings but sportier. The sweatshirt has the neutral color that you can combine with anything and plus size women can adjust to this layout by using proportion adjustments easily.
This is my preferred type of outfit on days when I am traveling, during early fall dog walks, or even during a grocery trip when I still feel like I would like to look presentable. It’s a safe zone between effortlessness and intentionality.
To adapt it further for a chilly day? Throw in a trench or a camel coat, a thick scarf and a pair of boots of the combat kind- you have an instant upgrade.
Preppy Skirt Layers With a Sporty Spin
This is what the uniform of the fashion-forward could have been like in the academia. A beige pleated skirt with neutral-colored sneakers, black tights, makes a prep outfit and yet casual. The classic button-down of the striped shirt beneath the oversized sweatshirt brings the outfit together with a hint of schoolhouse chic, and a cross-body in a deep brown brings solidity.
When you want to have fall clothes with the boots and skirt, then this is a good place to start. Trade the sneakers in favor of ankle and sock boots, and it suddenly becomes declassified from classroom cutie to urban-chic. The combination of the pleated skirt and the sweatshirt is both forgiving to different body types as well as youthful and trendy.
I adore the way in which this appearance is a combination of contrarieties, formal and just fun, and layered but light. On clear fall mornings, I would complete this with a trench or varsity coat and ankle boot to strike the comfortable balance of youthful and presentable.
To add a more editorial edge? Think about a plaid skirt, structured satchel and chunky heel boots in ivory or navy.
Edgy Academia with Leather and Checks
This is where it is cool and a little rebellious. A white turtleneck shirt gets combined with a pair of cropped black leather jacket, a tan plaid mini skirt, sheer tights and chunky ankle boots. It is traditional and modern at the same time, a kind of a trip through time since the outfit reminds of the nineties with a touch of the future 2025. The earth tones used are semi neutral and this makes it liquefy that one can accessorize it at will.
I think it is an excellent example of fall ensemble with boots and skirt- both tough and full of personality. The combat-style boots make the look down-to-earth, whereas, the short skirt and the tights emphasize the legs. It is an hourglass and petite silhouette, which fits petite and hourglass silhouette best.
I really love such combinations to attend concerts, go to the cafes, or go out and walk around, taking unexpected photos. There’s attitude here, but also softness. You don’t have to choose between the two.
Even more still, a bold lip or cat-eye liner. Or exchange a red beret with some Paris style. Either way, it’s fun and fierce.
Clean Lines in Soft Neutrals
Nothing is more relaxing than a color scheme that features shades of blue, cream and light white. This look builds on that peace. a white-tailored pair of pants, a thick-knit cardigan was draped on the shoulders and a long light-blue shirt was worn with a pair of ivory loafers. The large tote in beige and brown adds polish. It’s business-casual but Sunday brunch-ready at the same time.
This can look really nice with loafers but it would be just right with heeled boots sleek and maybe ivory or brown to keep the softness there. It is also a perfect fall outfit that can accompany you to a work environment with the boots where you do not want to look like you are trying hard to be dressed but you are not overdressed.
Personally, I feel calm just looking at this one. It is a type of a outfit that I will wear on the days that I desire to feel that everything is in check. And who doesn’t need that vibe now and then?
I would probably just add a tan wool coat and minor gold hoop earrings to complete the outfit. That’s all it really needs.
Modern Street Edge with Leather Contrast
When I jump into fall, I would like to have some flexibility but firmness in the pieces I wear, and this ensemble does hit the right mark. The long camel coat is paired with a stylish taupe sweater that provides the entire comfort of autumnal layers, and the sudden twist in the form of the leather shorts puts an edge to the ensemble immediately. The outfit is completed with the black lace-up combat boots, and it is simply eloquent in the urban language of style. It’s that kind of fall outfits with boots women vibe that walks confidently between coffee shop errands and spontaneous art openings.
I am fond of the huge coat that keeps the ensemble on the venal plane and with the more serious silhouette that contrasts with the jocular layering of the sweater. Its shorts in leather are style as well as functional as they can be layered over tights when it gets cold. And those black ankle boots? They are the foundation of the entire attire: hip, trusty and absolutely fashionable.
On a personal level, I resort to this kind of styling when I want to appear without trying too hard at being put together. It’s a confident, slightly rebellious take on cold-weather dressing, and something about the interplay of fabrics makes it unexpectedly cozy.
I’d probably add a crossbody in a rich brown or oxblood tone for a pop of fall color, maybe even a structured hat for that downtown-meets-uptown energy. What do you think—too much or just enough?
Soft Neutrals for Elegant Mornings
The clean air, the autumn leaves, and a warm cup of latte in the hand, this outfit seems to be an embodiment of the first days of autumn. An oversized plush turtleneck is covered in a soft mocha coat that makes this look very luxurious and relaxed. It looks cool combined with creamy pants and sleek black booties as one of the chic fall outfits which can be worn to meetings and is cozy enough to enjoy a leisure stroll under the trees covered with gold leaves.
Take the textures in this outfit that truly enhance the overall appearance: the fluffy knit turtleneck serves as a contrast to the structure of a wide-leg pair of trousers in cream and balances out the figure instead of making it bulkier. The ankle black suede boots complete the perfect creation in a very elegant way, that is, combining softness with structure.
I have taken outfits like that to work and weekend brunches and every time I get compliments on how it looks chic and comfortable. Fashion editors at Harper s Bazaar usually stress on the strength of head-to-toe neutrals in transitional seasons, and as far as this ensemble is concerned, it is true.
If I were to tweak it, I’d maybe add a minimal gold chain or hoop earrings for just a touch of shimmer, and a brown leather tote bag to pull it all together.
Knit Dress Chic for a Cozy City Walk
There is hardly anything less like bright pink and sheer than a knitted sweater dress and tall suede boots. That seasonal coziness is easily captured with this look, which features snug textures but still looks city-ready in a more sophisticated sense. The oversized chunky chunky scarf is gorgeous with the beige ribbed sweater dress worn over a light camel coat and the brown suede knee length boots. It is simple and all-cute display of fall outfits with boots and dress properly tackled.
The bulky scarf is not merely functional, it is also fashionable in the fall and it adds more volume and texture on the top, which can be contrasted with the skinny fabric of the dress. Its boots are both seasonal and structural, a perfect combination of comfort and country-style good looks, suitable to wear on a city sidewalk and a weekend vacation alike.
It is my kind of outfit, which I prefer wearing when I desire something tidy and casual. It is particularly excellent when you need variety on days early in the fall where the days are changeable in temperature. Also, it is a forgiving and flattering sweater dress, which is a great outfit that you can wear well layered with tights underneath or even go over the leggings when it is cool.
I would not feel offended to complement it with a tote of a deep cognac leather or even a fedora and add a hint of a Parisian to this appearance. Even consider changing the scarf with a more patterned one should you feel adventurous?
Warm Tones in a Playful Silhouette
There is nothing more playful and liberating than matching leggings in creamy white with an oversized sweater, it is exactly the background you have been waiting to adorn yourself with this season. This ensemble plays into softness, including a wide-knit, taupe-colored pullover and skinny-fitting ankle boots that blend with the light colors with an ease. This is designed to make you more stylish when you are having a lazy morning, celebrating with some festive decorations and everything in the middle, it is fall fun in a relaxed and casual look.
I believe that the contrast is the best part of it: slim leggings stretch the legs, and the oversized sweater makes the figure more voluminous, and this way, you get that ideal cozy look. The ankle boots anchor the rest of the outfit without breaking its line. This is one of those fall outfits with boots and leggings that works whether you’re curled up on the couch or heading to a local café.
I dress it up in this way for casual weekends and during the holidays. It is also a terrific canvas to dress up should you feel like it, simply add a plaid scarf or a wool coat and voila, you are dressed up.
Perhaps I would include a slouchy tote or crossback to maintain the cute style with the functionality. And, to be frank, who does not like an outfit, which hugs them?
Refined Heritage Meets Mini Skirt Energy
This one is a fusion of a classic and a bold one- a vintage trench coat and a plain white button up, with a high-waist houndstooth skirt and capped off with knee high brown boots. It is preppy, precise and the perfect mix of prim at the top and naughty at the bottom. Fall fall outfits with boots and skirt is just that: a good mix of smart and cute.
Every element here adds to the strong silhouette. The skirt is a welcome hit of pattern and energy and the double-breasted coat is a clean, tailored polish. The crispy white shirt makes the appearance even more colorful and out in that classy, structured world. The brown boots? They make the legs longer and deepen the fall warmer colors.
I have taken this kind to work and relaxed dinners and I always feel sharp and stylish. It is inspired by a fall dressing of the East Coast, where traditional prints and equestrian both never seem to be out-of-fashion.
I would certainly wear tights on colder days or wear a scarf of camel under the blue and add texture. This is an outfit that may easily carry you through the day to night- all it has to do is sip on a clutch and a fat lipstick.
Effortless Cool with a Minimalist Touch
Since I have days when I want to be on the ground but without so much effort, this look provides the level of comfort that does not make me feel at all disheveled. It has a custom-made beige coat on top of a soft sweater and cut jeans, which is only the perfect degree of casual. This is provided by the black leather ankle boots which give it that unobtrusive framework, a sturdy, trouble-free appeal with a muffled confidence that is also full of pure comfort in casual elegance. It is a refined version of an autumn look with boots and jeans, and one that already repeated in me more than once.
The denim in this case is cut just right- the right length to reveal the boots and not distract the flow of the ensemble. I never stop wearing two pairs of these medium-wash cut jeans during the fall. They’re versatile and adapt beautifully to almost any outerwear. The minimal lightly colored coat is sophisticated without being conservative, and the black and white boots have that classic appeal.
This reminds me of a Saturday morning outfit when you’re sipping coffee outdoors, maybe waiting for your friend to join you for a walk. It’s not about dressing to impress—it’s about wearing pieces that feel like you. In my opinion, it is one of these outfits that makes a subtle statement, which is, “I am what I like, and I like how I wear it.”
To fully round off the look, I would add a knife tie or perhaps some fine cashmere scarf hidden within the lapel as an added texture. A brash watch or metallic hoop earrings may add an extra dimension and leave the entire atmosphere cool.
Coffee Date Sharp with Tailored Cool
The power of a grey coat over an all-black background is very definite. It is clean, crisp, and is just what you need on a sunny Autumn morning, when the wind is in the right direction. In this ensemble, torn jeans are put over a black top and a tailored longline grey coat, with sleek black ankle boots and dark sunglasses, completing the look to a perfect shiny finish. The atmosphere here is literally shouting fall looks with footwear, and yet classy enough with a proper dose of comfortable wear, which fits in every-day life.
The reason why this look commands authority is the structure of the coat that seems to move with each stride and keeps its form like a pro. The jeans are slacking but not too much, as to attract attention to the boots, which are thin and sophisticated, and can be worn with both fancy and casual styles. The coat and the rest of the outfit contrast in color and thus, serves as a winner as an everyday work or a weekend thing.
I love how this ensemble works whether you’re grabbing your morning flat white or popping into a bookstore. It’s one of those trendy looks that doesn’t age because it never tries too hard. I have worn variations of this personally when I need to immediately look hybrid jane birkin in an instant when I only a five minutes of time to get ready.
I would have to accessorize this to the work meeting level e.g. add a belt or a leather tote. Otherwise, it’s one of those looks that needs very little help—it’s already spot on.
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