24 Transitional Summer to Fall Outfits 2025 That Are Chic, Comfy, and Ready for Every Occasion

When the sun starts getting softer and a breath of fresh air is slipping into the evenings, our wardrobes go through that seasonal dilemma: What am I going to wear when it is still somehow warm, but not really? I’ve been thinking about this a lot lately. Anyway, because it is in the middle of September, and to be honest, it is not starting to feel like pumpkin spice yet, but I would like to look fashionable when drinking it. Anyways, I have collected 24 ensembles that are just right in this in-between season what we are going to be calling transitional summer to fall outfit 2025.

Whether you’re heading to work, out with the girls, doing school drop-off, or strolling through Nyc, these pieces layer effortlessly and lean into everything we’re craving this season: casual chic, pops of unexpected color, flowy silhouettes, and a little denim magic. And best part? You probably already own some of these.

Let’s get into the looks…

Boho Bloom with a Denim Edge

The guru word is the best to describe those days in late August. The dark berry-red background with accents of inky black-colored flowers have here a rich depth, but are not heavy. The fall touch is the denim jacket thrown on the shoulders, and it is perfect since every day is hot at some point, and we have the cool breeze that follows. Add a wide-brim hat and sunnies and you’ve got the ultimate casual 2025 vibe that easily moves from a downtown farmer’s market to a laid-back dinner with friends.

The red maxi is classic – it is wearable yet romantic. The denim jacket? This is your secret fashion move to any transitional summer to fall wardrobe 2025. The addition of suede, preferably camel or tobacco, ankle boots casts earthy foundation under the ensemble that is just so appropriate in September.

Honestly, I’ve worn variations of this outfit on repeat. The denim layer is an adequate cover during the mornings of cold weather and the afternoons when the day gets sweaty. It feels comfy, feminine, and still pulled-together. Fashion stylist Allison Bornstein, known for her capsule method, often talks about the “hero piece” — and this dress is exactly that.

It would even be possible to replace it with a cream knit or longline cardigan in temperatures that are lower. I’d just add a chunky gold necklace or hoops to polish it off.

Power Denim Meets Bold Boots

The Denim skirts are making a comeback officially and with the slit? That is not only dramatic but that is practical when it comes to striding forward willingly. This outfit is timeless, yet edgy with a button-down shirt and fuchsia knee boots on the side of being outrageous. Ideal work office style: I have style and spreadsheets under control. It’s also ideal for those casual women who like their fashion sharp with a touch of flair.

I enjoyed the fact that the shirt is fuss-free in that you can half-tuck it or tie it at the waist at will. The pink boots are a mood on their own. Big boots are as massive as the non-formal wardrobe update in 2025, and they are inexpressibly multipurpose.

This combination is one that I have tried the last September to take a day trip to Nyc. I received compliments at a brunch and at the showroom visited by me. Vogue’s accessories editor once said bold boots are the easiest way to “add intentionality” to an otherwise neutral outfit — and she’s right.

It would be so simple to replace the blouse with a graphic shirt and jacket of leather to edge that piece up, or leave it sharp and go to a slightly work casual office. Either way, the boots are doing the talking.

Dark Romance on the Waterfront

Now this is a doubling that fits in the capsule wardrobe sweet spot. The must make emerald green stretched green skirt, obligatory swishiness, classic white tee and tailored black leather jacket. It is dark, crisp and simply refined to the extent of being adult. Wear black accessories and you will be delivering low-key casual chic with attitude. The style has enormous potential of a plus size variant as well since the volume and construct suits any type of body.

This is the example of the leather jacket being one of the most important layers when making transition outfits in summer to fall 2025 because it is warmer but not too hot, and it gives an immediate shine. The shape of this skirt is incredibly elegant and the deep green is just so refreshing as far as the autumn shades are concerned.

I’ve worn something similar for early evening drinks by the water — wind in your hair, a chilled glass of white, and that perfect jacket hug when the temperature drops. You know what I mean?

I’d maybe switch the tee for a knit tank or swap the skirt for tailored culottes depending on how much you’re moving around that day. Either way, this one’s timeless.

Weekend-Ready Stripes and Olive Green Cool

This fashion strikes that non-chalant polished mark that many of us strive to achieve. There is that end-of-summer looseness of a striped mini-dress but it is grounded, in no uncertain terms, by an army-green jacket that lands the whole ensemble into fall-forward territory. Delightfully snarkish, it was made to run your errands, socialize with friends, or, yes, even a mom on the go, this is what casual in the year 2025 with the touch of practical and cute to it.

Every element here is so wearable. Stripe dress is one of those magic items, which can look dressed up and down. The olive jacket? It is a couple of years old trend and it is still on-going in 2025 – the military shape is soft and goes well with all types of outfits.

I’ve thrown this on for school runs, coffee dates, even casual church mornings. It’s one of those looks that works when you don’t have time to think but still want to look intentional.

Round out with sneakers and have a sporty effect or ankle boots to slide into fall. Bonus: it would be a cute going-out look as a replacement of the heels and gold hoops.

Blush on Blush Street Chic

Soft blush tones, flowing pleats, and a cozy hoodie? I could even say that this could be my dream casual attire that has remained stylish. The cropped sweatshirt helps to make it down-to-earth and younger, whereas the movement and grace are added with the help of pale lilac-pink skirt. It’s giving balletcore — but elevated. It is ideal on lazy Sunday or in between errands or even a brunch under gentle sunlight.

It is the best casual chic trick: long skirt + crop+ sneaker = instant look. And it’s completely cute without trying too hard.

I had a similar one which I wore at the time when traveling cross-country years ago, it was the best match as far as softness and warmth in the over-air-conditioned airports were concerned. Fashion designers such as Sandy Liang are experimenting with this sweet tough game, and it is just perfect to fit the transitional summer fall outfits 2025 aesthetic.

To make it even higher, you may replace the hoodie with a croop blazer or a leather jacket. Add a clutch or statement bag, and you’re golden.

Little Black Romper with a Denim Twist

One can never think of something as timeless as a black romper as it is flirty and easy and never overdressed. Yet to finish the outfit, pair it with a light-wash denim jacket on top, and you have got yourself a superhero piece during winter transition summer to fall looks in 2025. This look is simple, elegant, and walkable. It’s something I’d wear on a hot day in early September when you still want your arms out by noon but need a layer for those 8 PM patio drinks.

Even the romper (itself) is clean and basic – that allows it plenty of versatility. You may wear sneakers with it or use pointy flats or block heels. The denim jacket makes it structured and provides some casual vibes that we all seek in a good outfit of the solid casual type of 2025.

This is one of those formulas that I tend to use whenever I am lacking time to think. Black foundation + denim jacket + little shoulder bag = one that can not be missed. According to fashion writer Kristen Nichols at Who What Wear, the denim layer is the ideal transitional MVP this year and I could not get into agreement with this statement.

Want to style it up further? Attach a silk scarf at the handle of the bag or put on a red red lipstick. It turns heads without trying too hard.

Edgy Blazer & Mini Skirt Mix

This outfit has attitude and I’m here for it. A full size blazer worn with a torn denim mini skirt, sheer tights, combat boots and a fitting top in white summons serious street style power. It is great when you have some urban days and you want to look presentable without being dressy. Unapologetic yet tasteful, aggressive yet adorable it was, and extremely applicable in the case of the ordinary female who is trying to construct a statement-related capsule collection.

The ripped mini and the sharp blazer is what makes this pop. It is the example of the high-low mixing that editors talk about. And those black tights? They extend the usage of summer items far into autumn. A total going out win.

I recall doing a rooftop bar night last fall and The Docs performed admirably all the way to the end of the night. My hint: the blazer should fit excellently on shoulders, it cannot look overturned and give an impression that you borrowed it to your father.

To give the appearance a reverse, swap the boots for heeled ankle booties and make the hit out monochrome with black or navy blazer. Still edgy, still current.

Rust Cardigan & Denim: Fall’s Coziest Power Couple

Practically nothing shouts autumn as much as rust-colored, cable-knit duster cardigan. It’s a hug in outfit form. It is crafted in a material that is suitable enough to wear on top of a fitted tank and high-waisted casual jeans as its simple uniform in coffee dates and during relaxed work-from-home days. It is one of such plus size friendly formulas that suit every body to a T. It’s cozy, long, elongating, and totally timeless.

This cardigan gives serious structure while staying relaxed. The denim is washed lightly, and it makes it look contemporary, and the woven tote adds this texture to it, which is a bit unexpected but lifts the whole look.

This is the type of clothing I put on when I am in the mood to be put together and at the same time blanket blanketed. There has been one more popular fashion item, however, the unsung heroes, of the back-to-office hybrid fashion worlds, which is longline cardigans, according to the style team of Refinery29.

To make this sharp quickly, I would add sharpened flats or mules and a smooth low bun in case I wanted to make my quick work office atmosphere sharper. And some chunky gold earrings never hurt.

Soft Neutrals with Downtown Cool

This one gives modern city romance. A beige slip dress, tight waist, decorated with light azure jacket and white boots covered with imitation of a snake skin? Chic meets chill in the best way. Add a formal wide-brim hat on the head and, voila, you are in fall in Nyc, even though you are only strolling through your own farmer market. It’s subtle luxury that doesn’t try too hard.

Slip dress is a sure hit, no matter how light and warm the temperature might be, it gets shape easily. It has a shape of denim and is sharpened with white boots. When you are building a capsule wardrobe with a look of casual chic, such items are the ones that work in their favour.

I did a variation of this to go to lunch with a client and then to the galleries. I felt that I fit in everywhere I moved. The neutrals done well are just quiet confident.

Could you switch the jacket for a leather blazer? Absolutely. The hat for gold hoops? Done. It adapts to your energy without losing its base.

Earthy Florals & Structured Layers

This is transitional layering done right. Maxi floral dresses with a dark green tone and a spacious slit on the top and suede or leather moto jacket with a touch of softness but stability characteristic of 2025. Throw in a pair of neutral booties and the felt hat and you are in the mood board of transitional summer to fall 2025 collections. I think there is something very adorable in the huge contrast of the floaty hem and the hard jacket.

This ensemble actually exists in the intersections point of casual, romantic and weather wise. The booties solidify the outfit and the jackets add form in the case that you happen to be blowing in and out of chilly buildings.

The formula can work in church mornings, casual work meetings or lunches with in-laws among other events. I have a friend who says that a dress and a jacket is her answer when she wants to impress but she has no idea what to wear, and does not have time to care.

This is an effective combination in case you are creating a capsule wardrobe. You have the freedom to remix it anytime you want, you can ditch the boots and replace them with sneakers, you can also switch a hat to a big lip or full-on chains.

Florals with a Leather Twist

Here’s proof that florals don’t have to be soft. This long maxi floral dress with a leather black moto vest falls somewhere in the middle of tender and brave. It has a feminine touch but it is also solid and it is one of those fall summer outfits 2025 pieces that will actually take you through. The bolder is contrasting, the leather is lending an outline, and that Gucci belt is just the extra dose of the bossiness. I adore the fact that this can be taken to a gallery opening or a casual church fare without appearing overdressed and safe.

The black leather vest is a genius layer that is going to be applied in 2025. It does not hide the sleeves like a jacket does thus giving it full effect of the floral print. And, of course, leather is never a wrong texture to introduce when it is needed to complement romance and roughness. It is lightweight enough to wear during warm afternoons but the volume remains intact even in a windy day.

On personal level, mixing soft and rough items is one of my favorite things to do, because it does not make me look try-hard. Micaela Erlanger, a fashion stylist, has once stated that a good layer of leather has a capability to instantly make a flowy silhouette look smarter, and she is right. It is sort of bringing out eyeliner on the fresh face, but the same face nonetheless, but it has punch.

Instead of the feel of slouchy knit cardigan you can substitute this with a zippier cardigan and in case you want to add an extra edge then you can substitute the cardigan with heels. The structure is already doing the heavy lifting.

The New Work Uniform: Wide-Leg Trousers & Blazer

This is pure power dressing, only the softness is easy and relaxing, just fitting in this modern day casual attitude in the workplace. Beige blazer on top of nude square-neck top and high-waist wide-leg tavern pant is all that a contemporary office attire deserves to be clean yet comfortable and quietly classy. It’s no longer about stiff suiting — it’s about smart layering and knowing when to go wide with your silhouette.

These waffle-cotton trousers belong to the wide-leg category which suits all body types and swish just right. The blazer makes it more defined and the tied in top makes it less masculine. It may be perfect on the plus size especially when a neutral belt is used to stress the waistline.

I have also put on such outfits to do interviews and Zoom calls of various forms even when it was only the top half that was visible to the camera. It’s all about how the outfit makes you feel. and this is: self-assured, not over-doing anything, totally in control. Recently, InStyle has recommended this silhouette as one of the leading trends of 2025, and frankly speaking, it is not so bad that women want to be comfortable yet still look elegant.

As a way to mix it up, just interchange the blazer with a knit camel or replace with a belt that is wide and flashy one to give it some taste.

Prep Meets Punk with a Plaid Mini

Plaid and boots are pretty much the staple of fall, but this outfit? This one introduces a cool-girl aura that is already prepared to go to Nyc streets and museum weekend outings. A baggy blue sweater on top of a skirt with plaid patterns, adorned with polished combat boots and cross body bag. It is all about proportions, namely oversized on the upper part and with a narrow-enough place to make you feel like wearing shorts on the bottom and with the correct degree of efffaceness. Ideal to wear to cooler hot days which lead to a comfortable evening.

The boots make it serious the sweater makes it friendly and the mini keeps it light hearted. The style of this outfit is so casually fun with an air of smartness. Another way of taking the first steps out of the neutrals zone is when you are the person who tends to choose the neutral color gamut when it comes to choosing something rather bold like plaid with a classic color scheme.

I would say so, and the fact is that it makes me think of what I wore during my first trip to NYC during fall several years ago, and this outfit has remained just as topical as it can be. Dark red lipstick and other details most certainly came out in this mood, as Taylor Swift has often been spotted in this vibe, and stylists have defined it as refined prep 2.0, where the matching sets cease to be the main point but it is about combination of shapes and assertiveness.

This can be extended to colder days by wearing tights or a trench can be worn. It’s got flexibility built in.

Mad for Plaid: Structured Coat with Over-the-Knee Boots

This one’s a true cold-weather slayer. Tall brown suede boots, mini burgundy skirt with cream turtleneck and a coat of plaid with long length. It is posh, cozy and has a sort of retro and somewhat cultured touch. The gear falls into the category of outerwear that is a hero in transitional summer to fall clothes 2025 when it comes to all of us who live in regions where fall comes like a bandit. It looks trendy to have brunch in the uptown but formal to wear to work.

The colour scheme is high autumn in this – rich burgundy, cream and deep chestnut. The skirt length keeps it playful, and those high boots are both warming and leg-lengthening (a total win). This is definitely cute, but still grown-up.

I adore to wear them during my days of working on cities. It can stand the test of long walks, meetings and at random lunch places. A plaid coat is also surprisingly versatile. To be honest, I have had them over jeans and a hoodie, over slip dresses, and even with joggers. Not only has fashion stylist Tan France stated that a bold coat is enough to make an outfit but this one actually proves that.

Having a variety of textures is a good idea and all you have to do is to add a leather crossbody or a scarf, and you are good to go.

Burgundy & Grey with a Pop of Plaid

Here is the lay your finishing masterpiece that would make a killer Instagram sidewalk shot: a slim fit grey pullover under a high wasted burgundy mini, a soft grey plaid oversized scarf that was wrapped over the neck and multi-used as a head scarf with grey suede over-the-knee boots. The colour saturation is just perfect: not too loud, yet not too cool. It is like one of those casual chic attires that appear to have taken 45 minutes to put up, but in reality it became just 10.

It is hard work that scarf is doing- providing pattern, color, warmth and texture. The mini skirt is subtly ribbed, which adds dimension. This type of combo is ultra 2025- it is not only that things match it is that things have layers in the form of personality. It would be sweet as a going out lunch or a casual meeting but not that casual that it will still require some effort to go.

I wore a version of this last fall to meet friends for apple cider donuts (yes, very specific, but it’s the vibe). I received such compliments: it is not only friendly and stylish but also interesting due to textures.

Add a wool coat to top it off or switch the scarf and replace it with chains and it can get easily turned into a dinner outfit.

Soft Neutrals, Maximum Impact

This look is the ultimate quiet luxury moment. A ribbed knit dress in the lightest of beige and a chunky cable-knit duster over it and sleek ankle boots in the same beige, that is minimal, but not at all boring. This is that outfit that works whether you’re grabbing matcha or heading to a gallery opening. It is one of the best transitional summer to fall outfits 2025 and flatters, layers and gives you the feeling of being transported in a luxury because it works on so many levels.

So, what about the silhouette: it fits without being tight, and not strictly constraining. The cardigan makes everything more soft and smooth to neutralise the tight-fitting dress. The boots add sheen and order to the outfit – no bulky accessories and contrast, nothing but precise lines and over-all comfort.

There is almost something like I wore last October and received compliments everywhere. Tonal layering was recently dubbed the minimalist dressing of the future by Harper Bazaar and it does work. It is also a dream to wear plus size spin, you could loop on a belt to emphasise your waist, or you could alternate by using a looser midi.

To switch it up? To dress up cardigan, knee boots or a long trench over cardigan will look fancy and editorial.

Boho Meets Cozy on the Porch

This ensemble is delivering cabin-core with an edging of sultry. An oversized wavy cardigan, worn over the black lace camisole, a distressed skinny jeans and a felt hat. This contains every drop of all the slow coffee, warm sunlight, stay-a-little-longer atmosphere of early fall. Put yourself behind the thought of mornings being soft, cinnamon in the latte and long-lasting talk away on the porch swing.

The hat and lace cami transform this to the state of styled cozy, not the out of bed cozy. The skinny jeans provide the balance of the overlaying structure of the oversized knit. It is one of these everyday 2025 necessities casual elements that help you around in the weekend plans.

I have done this myself on my lazy Saturdays, and it makes me feel like I am nobody who has edited his life, but the number of outfits. It’s Pinterest but wearable.

You would completely change the tone by wearing wide-leg jeans, or leggings or even just wearing this over a slip dress. The cardigan holds the energy.

Parisian Fall Girl Fantasy

The French-girl fall style is the one that is worth considering now. This outfit does not disappoint: a very clear blouse in puff sleeves that is tucked in a check mini skirt with a buckle at the waist, combined with knee-high black boots, a classic hat. It’s playful, polished, and just a little flirtatious. They are ideal to go shopping in the city, or to drink espresso on a terrace. It’s giving casual chic, with some editorial flair.

The blouse itself looks fancy in its structure and the mini skirt makes it light and young. Those boots? They mean business. Throw in the quilted Chanel-style bag and it is balanced – classic and up-to-date.

I had this look on when we went on a date night during fall, and I was proud to wear it. Even such fashion gurus as Brittany Xavier have labeled this look combination as iconic as it relates to transitional dressing. And well, she is not wrong, and it feels appropriate with the season, but at the same time, it is a very airy and breathable thing.

Could you wear tights with this? Absolutely. Substitute red lip and you get even more impressive.

Floral Mini & Cozy Texture Combo

It is so easy-going, comfortable, daily clothes that still seem to belong in Pinterest. A floral mini ruffle hem skirt with a cream textured model of sweater and completed with a pair of tan knee high boots. It’s a combo that works on literally everyone. It is highly mom-friendly with a case of yes, I did give thought to this.

The mini skirt in this case is a coy soft one and the sweater balances it by being practical. The boots add the shape to the ensemble and that change of texture and tone of season. It is the final quick and casual wear when you cannot decide what to wear and yet want to look cute.

I have an alternative of this to events like early school pick ups and informal days of brain storming at work. The combination simply looks great that is, even in 2025 where the combination of mixed lengths and feminine tones are going strong.

Change to sneakers should you prefer to remain sporty or put on a denim jacket to have extra layers. You’ll wear each piece again and again.

Power Pink for a Mood Boost

This look brings the dopamine. A light pink jacket, which has two inverted flaps, dark pink shirt, timeless jeans and pink block heels. It is vibrant, assertive, and it makes itself felt with a ton of energy, so it is the type of attire that would make every gray Monday a full-blown main character experience. It is ideal to work office or going out occasion when you fancy standing out in the better way possible.

The color pop does not seem to be overwhelming because of the structure of the blazer. It all becomes mellow with the femininity of the blouse but still with the footing of the jeans. The monochrome pink heels are just chef’s kiss.

This is one of the main reasons why I now include some bold blazers in my capsule wardrobe they make any getup look complete and they only make you feel happier. To be honest, Law Roach (a stylist) admitted that color is a visual attitude. That applies here more than ever.

Remix: one of the ways to remix is to layer the blazer over a tee and trousers or even a slip dress at a weekend brunch.

Rainy Day Sporty Chic

Everybody is familiar with the fact that transition seasons are not only characterized by chilling winds but also rain water. This ensemble is a dream outfit when it rains or shady days: a cropped hoodie in soft blue color, covered by a structured midi skirt in the shade of beige, white chunky shoes, a cap, and a handy backpack are an ensemble to dream about. It’s the kind of casual 2025 look that doesn’t scream “trying” but still feels completely intentional.

The cropped hoodie with sneakers outfit makes it lightweight and comfortable to go around the puddles. This is more than a hoodie because of the A-line shape of the skirt, which looks more formal. And the beigeness of the color scale makes it plain enough to be used in any capsular collection.

I have been downtown in this specific mood on a rainy day (smells of rain in the air, my earbuds on, and hands in my pockets) and I have never felt more suited to the occasion. This is an evidence that comfortable does not have to be dull and weather-friendly does not have to be frumpy.

Add a trench or utility raincoat to cover more, and you will end up having a complete fall formula.

English Countryside Minimalism

This outfit is almost in quiet elegance, taupe sweater, in a refreshing white midi, with a girly scarf, herringbone newsboy cap, and pointed heels, black. It’s giving “soft academia” meets Jane Birkin. A more formal, mature version of the casual chic, which can be used when going to the office and can be used in case a person needs to dress up.

The flattering pleated skirt works with the loosely fitted knit, which makes it look not too stiff. What makes it special is the accessories: the scarf provides the face with a soft frame and the cap does its retroistic impression. This is the kind of layering we are plunging into in 2025, care-free, nostalgic, and very intimate.

This would go with a relaxing office lunch or even a book date. It lasts throughout the day without making even a single adjustment.

To move the energy, replace the heels with loafers or boots – it stands its ground in any of the forms.

Warm Neutrals with a Side of Spice

Something is crisply and fall ideal about this combination of warm camel tones. Caramel leather mini-dress covered with a brown over-sized sweater, a white pair of sneakers and a wide-brim hat to complete the look. The crossbody bag makes it weekend-ready. This is a style that appeals to someone in 2025 (I notice these boots are worn casually, but they are extremely reasonable, as well as currently fashionable, so beautiful and comfortable, and above all, it is also perfect to walk in a pumpkin run).

The knit helps to tone down the edge of leather, the hat is dramatic, but not over-striving. You can completely change this up to plus size by replacing it with a faux leather midi or belted tunic one, it all comes down to balance of shape and gentleness.

I have, in my own person, twisted forms of this on misty mornings in early fall, with a cup of coffee in my arms, and when the leaves are yet green, but the light already beginning to turn. It’s the perfect “between seasons” energy.

Want to shift it toward going out? Add a pair of heeled boots, tuck in the sweater and aim at gold accessories.

Street Blazer Energy with a Crop

This ensemble is on the verge of sharp and cool, i.e. an all-time camel blazer on a black cropped top and a pair of distressed casual jeans and coupled with the neutral pair of heels and black sunglasses. It’s bold, minimal, and very editorial. It is ideal where you really do not need anything in-between the weather. Probably one of the best transitional summer to fall looks 2025 I have ever seen, and the grandmothers are not going to leave anyone indifferent.

Distressed jeans make it more down to earth, the crop will keep it in time and the structured blazer will put the finishing touch. I adore it in work casual environments when creativity is a uniform requirement, such as in the fashion, media or even a chic tech occupation.

I have been also resting on crops and blazers, I think it is a bit controversial, however, never out of fashion. It is the cut of the blazer that makes all the deal. You want it tailored but not tight.

Wear a longer blouse or change it into loafers in case you prefer it to be more conservatory.

Thus, this is where we are -24 looks on and the only thing to inspire us at the moment is putting something heavy on in case the weather seems to be shifting five degrees in one direction in the near future. This is what makes transitional summer to fall outfits 2025 so beautiful: they are fluid, easy-to-wear and have much character. So knits, oversized blazers, ominous flowers, or casual skirts with shorts with boots, they are the items, which will make your wardrobe a story- chapter by chapter.

The best part? These aren’t one-time outfits. These are mixable, repeatable, adaptable looks that work whether you’re a downtown Nyc girl, a cozy-at-home mom, or heading to work feeling polished and powerful.

Just open that wardrobe, explore these fabrics and do not be afraid trying something new. Transitional dressing isn’t about rules — it’s about flow. It’s that perfect mix of the old and the fresh, the warm and the cool, the layered and the stripped-down. And it’s yours to play with.