Fall 2025 is on the doorstep, not the crunchy leaves and pumpkin-spice-everything fall, though. It is still warm, sticky during the afternoons, and breezy during the evenings, that awkward time of the year when you wonder to yourself: Do I need a jacket? Can I still wear sandals? Is this too summery for September?
In this post, I am getting into the versatile early fall outfits, which not only hit the nail on the head of transitional dressing but also give you an idea of how to style what you already have in a new way. Each look you’ll see below (with links!) will speak to different moods — from late summer casual strolls through Paris to work business casual mornings in Italy. Whether you’re heading to dinner, commuting to the office, or curating your own late summer aesthetic, there’s a look for you — and yes, even women over 50 will find inspo here.
So… are you ready to turn a corner into September like it is a personal runway?
Retro Film Noir with a Modern Twist
An all-black sharp silhouette is never out of place, particularly during early fall when the weather is crisp and not cold. This style is a combination of sultry chic and daring accessories: the long-sleeved, tight black dress with a cut-out in the middle of the stomach makes the traditional LBD a bit more urban, and the leopard silk scarf evokes the retro atmosphere of Rome or Milan in the 60s. The sharp loafers, adorned with crystal buckles, are a wink to the old school glamour, however, with the comfort we all are seeking nowadays.
The bright yellow bag is a statement; and a clever one. It disrupts the monochrome, but does not overpower it, as a slice of lemon in a perfectly balanced spritz. The headscarf isn’t just pretty; it’s practical on windy late summer going days, and elevates any outfit into chic, European territory. This would be gorgeous for a warm weather dinner, or even as a dramatic late summer aesthetic office day where you’re feeling bold.
I also wore something close to this during aperitivo in Florence last year and let me tell you, I did not have to stop and ask people how I looked, they stopped and told me. I will never forget such looks as being Italian, smooth, self-assured, classic. When each of the pieces has a role to play, you do not have to think too hard about an outfit.
What’s missing here? Perhaps only a red lip or a dramatic flick of eyeliner to give the vintage moment full commitment, otherwise, perfection. Better still when you have dramatic staircases such as these in your day.
Power Pink That Plays and Works
This fall early outfit is saying: I am the boss of the meeting, then I am the boss of the street. You cannot miss the fuchsia tailoring that is so bright. And this is the idea. The longline coat and high-waisted trousers make it dramatic, and the bandeau top underneath balances it out in the right amount to make it a hot weather or late summer work office look. The patterned silk scarf gives a slick European feel and mellows the effect with the perfect contrast.
All of this screams work business casual, with a good dose of fashion-week fabulous. This is the type of set that I will grab when I need to take control of the room without uttering a single word. I adore the fact that you can add layers or remove them according to the temperature change, you are basically ready to go straight into a rooftop dinner in late summer.
Celebrity stylist Micaela Erlanger says that bold monochrome makes any person look instantly pulled together, even when the color is loud. Pair that with classic tailoring and voilà: wearable armor. And trust me, pink isn’t just for spring anymore.
If I were adding anything to this look, it might be a sleek nude heel or white mule to break up the color block — but honestly, if you’re going for boss Barbie vibes, more pink is always welcome.
Minimalist with a Hint of Sporty Luxe
This is what casual and tailored come together in the most Pinterest-worthy manner. The blush blazer is over-sized: boxy, clean-lined, and cool as it gets. This outfit is worn with a black crop top, a baseball cap and sleek riding boots and creates the downtown Paris meets fall-ready late summer casual chic. It is quiet luxury with a street-style twist, which is ideal to run errands in the city, last-minute dinner, or a day in a creative studio that ends in happy hour.
I have discovered that a large neutral blazer is the best trick of warm weather, it fits over everything, does not make you feel hot and always looks purposeful. And the boots? Perfect on those late summer going days when your sandals are giving up and you are not yet ready to wear tights.
My one girlfriend can not live without this look, and she claims that thin gold hoops and a bold brow are the best match to it. It is the way she makes it seem special, even when she is simply taking an iced latte. When your style is saying, I am cool but it also speaks money, you are in the right place.
A crossbody bag would be perfect to this, anything, that is, quilted or structured to contrast the softness of the jacket.
Barbiecore, but Make It Fall
This ensemble is a complete dive into the late summer vibe, which is pretty and playful at the same time. It is casual enough to wear on a weekend errand but the pink blazer with its sharp shoulders and those matching pointed heels makes the entire outfit more than casual. Throw on a mini chain bag and a baseball cap and suddenly it has off-duty model vibes to it – even when you are just on your way to brunch or to a late movie.
It is all about the balance, late summer casual jeans at the bottom and business on the top. I like that this is not overdone and is young and fresh. And it is also very versatile among women of different ages. Women of 50 and over can completely make this their own with a darker wash denim and a deeper rose colored blazer, still on trend, but more mature.
One of my fashion rules? If your shoes and jacket match, you’re golden. It completes any appearance, even when everything is basic. It is a casual uniform to wear in late summer, easy, breezy, and it would be acceptable in Europe, on Milan sidewalks, and NYC crosswalks.
What would I tweak? Maybe a chunky gold necklace or a high ponytail. Otherwise, it is just what early September dressing must be: fun, easy, powerful.
Gilded Evening for Golden Hour
Okay, this one’s for when fall flirts with drama. This bronze satin slinky gown fits the body like a second skin, and the corseted bodice gives old Hollywood meets new femme fatale. It is topped with a fur dusty rose jacket that is plush and a textural dream and the Gucci shoulder bag is the finishing touch that makes the entire look scream luxury. The dressing is like it is pulled out of a castle terrace or a Parisian gala.
This would be a deadly early fall wardrobe choice to wear to a formal dinner, wedding or fancy cocktail party in Italy or Europe. It is that type of dress that does not only make you look beautiful but it makes you feel beautiful. The structure, the sheen, the confidence it gives… everything.
My take? It is the type of article that does not require a lot of accessories, only glowing skin and silent confidence. Metallics are the new black InStyle recently declared metallics the new black when it comes to eveningwear and I am here for it.
In case I needed to dress this up to wear during cooler nights, I would wear a sheer black tight and perhaps a closed-toe mule. However, the look is already fall glam-ready, no need to make any changes.
Monochrome Layers for the Academic Muse
Rich fall tones are so down to earth and intellectual, and this styling is just so good. The combination of a sleeveless cream suit vest and trousers on top of a burgundy turtleneck is immediately museum date or coffee by the colonnade very late summer work office chic. The clean tailoring is relaxed with the help of warm accessories: square glasses, cognac ankle boots, and a black trapezoid top-handle bag which shouts curated minimalism.
I would suggest that you always invest in structured, ivory or cream trousers particularly during the transitional months. They brighten up business casual work attires, particularly when they are combined with darker fall tops. One of my favorite trends this season is the vest-as-topper; it is a polishing trend that is not bulky. And yes, I would recommend this appearance to women older than 50 as fast as I would to a woman in her twenties, it is all about being confident and not age.
The burgundy is so rich that it reminds me of new notebooks and the early sunsets. A tip from stylist Tan France? When going tonal, always combine textures, it makes it interesting and deep. In this case, the turtleneck made of soft wool contrasts with the more formal tailoring in a manner that is simply… clever.
What I’d add? Perhaps a gold pin or brooch on the vest, just to introduce a bit of glitter when you are going to a dinner after hours.
Soft Volume and Sharp Structure
This silhouette is balanced to perfection shape-wise: puffed sleeves and slouchy turtleneck on top, sharp and tailored trousers on the bottom. The breezy, oversized knit is contrasted to the sleek pointed heels so that things do not become too casual. Throw in the cinnamon brown handbag and matching pants and now you are wearing the shades of early fall outfits without having to wear a jacket.
It is an ideal outfit of late summer casual women dressing that can work in so many cities, I mean Europe, in a waterfront in Istanbul or Lisbon. The pants are silky and the structured bag keeps it on a higher level. It is ideal to have a day time office meet or to pick up a wine glass when the sun is down.
I adore a big loose sweater with extra long sleeves, it is so decadent and yet still polished when you tuck only the front. I used that trick all the time last fall and it gives any warm outfit a shape without effort. Also? This color scheme is literally flattering to everyone, warm neutrals are a sure thing.
In case you were looking to take this a step further, I would introduce a stacked earring or a statement lip, something to balance out the femininity with a touch of an edge.
Forest Green Femme Fatale
This outfit feels like stepping into a Vogue editorial. The green blazer is double-breasted, the pants are made of leather, the over-the-knee boots are croc-embossed, and all of it is a perfect combination of chic, commanding, and work business casual. The large tweed coat provides texture and seriousness, and the tan clutch makes the cool tones so warm.
Let’s talk about color. The deep green color is not the most obvious option when it comes to early fall outfits, but it definitely should be. It is deep, bold and less predictable than camel or navy. This ensemble is made for a big-city street, probably Paris or New York, where you’re heading into a high-stakes meeting and then straight to a rooftop dinner.
I have seen an increasing number of editors gravitating toward long coats and tall boots in September, when it is still hot but the chill is setting in, and they do not want to go all the way into full layering. And when the coat matches your boots like this? Chef’s kiss.
To finish off this real life look I would perhaps wear a soft ivory or camel blouse underneath, something silky to bring a contrast. And yes, this silhouette could be easily recreated by women over 50 with some slight adjustments in mind, i.e. longer blazer and less shine, but same effect.
Preppy Mod in Emerald Green
This is the way to turn a skirt into a late summer casual without losing polish. A well-ordered green mini, with a houndstooth zip-up jacket and matching satin boots strike the right balance between retro and runway. The oversized coat thrown over the shoulders adds a lot of energy to this look, but it is fall prep with a Gen-Z twist, which, in fact, makes it much more wearable by all ages.
The most outstanding here is the way it is coordinated but at the same time it is easy. Black and white dressing does not have to be dull especially when you experiment with fabrics and mini dresses. I would wear this running through Europe or even to an early fall party when you want to be remembered.
The best thing is that it is not overdoing it. The esthetic is clean, sharp, and completely in line with 2025 returning to polished femininity. According to fashion stylist Allison Bornstein, the big trend in dressing now is called uniform dressing and this? It’s a perfect example of having a statement uniform.
When you are thinking, could I do this, the answer is yes. The other thing is just to make sure that your boots are in the right place on your calves that is the true secret to this look singing.
Color-Blocked Confidence
When in doubt, go bold. This electric sky blue leather and neon fuchsia boots combination is not sorry to be strong. The coordinating pair of shorts and crop top is futuristic and new-feeling, very late summer going, perhaps a fashion show or rooftop gallery in Italy or Miami. The color story is also connected in a completely deliberate manner as the pink mini bag reflects the boots.
I believe that this is the happiest expression of the set, to be honest. The playfulness is here, which reminds me of the time when fashion was all about experimenting, no rules, just vibes. The long sleeves are the perfect match to the mini shorts in hot weather, and the leather makes it feel fancy even when it is bare legs.
I get that energy in a stylist I follow on TikTok who swears by the two statement colors and letting them fight it out. It functions since it does not play it safe, there are no neutrals, no distractions, just color blocking at its finest.
Would I wear this to the office? No. Would I put it on an impromptu occasion when I need to make people stare and feel like a protagonist? Absolutely.
Sequins at Sunset
It is all fantasy-meets-function late summer going. The turquoise sequined shift captures all the golden hour light, and the blush feather trim at the hem creates that surreal couture effect. Combined with shiny pink stiletto heels, it is reminding of rooftop party in New York or Paris, no coat required. It is daring, yet the silhouette remains uncluttered, that is why it looks cool.
This made me change my mind as I always swore that sequins were meant in December. It has a breezy irreverence to it to wear sparkle in warm weather. This is effective because it is not tight or overdesigned, it is one strong piece and that is it. The feather trim could be so easy to be dramatic, but here it only speaks glam.
I did something like this once to an evening event at a gallery in Milan and I felt like a walking disco ball – but in a good way. Such sort of glances is flattery, but also changes the way you feel, making you feel lighter, more playful, less serious. I say lean in.
I would also put on magenta lipstick and a high bun. The dress will do most of the work, so the beauty should be minimal, but fierce.
Barbie Goes Boardroom
This power suit is so pink and I am loving it. The custom-made blazer with flared pants and a double-breasted design is soft in its construction and is feminine and aggressive at the same time. Combined with a black mini top-handle bag and classic heels, this outfit will take you through an afternoon strategy meeting to dinner on the terrace and not break a sweat.
This is what I call “pink with purpose.” It’s not childish, not ironic — just flat-out chic. I have also observed women above 50 years adopting this look to perfection, with a slightly paler pink or raspberry lipstick to add a tinge of sophistication. The clean cut and the color confidence are what makes it so versatile.
According to fashion psychologist Shakaila Forbes-Bell, the bright color such as pink can make you feel energized and positive, so yes, that energy is also contagious.
I would not change much here, but in case you would like to make it more casual late summer, replace the heels with white sneakers and the top with a cotton tank. Still fabulous, just a little more relaxed.
Red, Floral, and Ready
This one is when your late summer style wants to make people stare without uttering a single word. A cropped jacket in red leather on top of a glossy floral mini-dress, daring, but classy. The red strappy sandals and a quilted crossbody finish off the look and there is something about the texture play here that seems very editorial.
This screams dinner with a skyline view. It is flirty and down-to-earth, and it is a good example of the combination of romantic patterns and tougher outerwear, which the French can easily do. I would wear this in Italy, as well, somewhere on the coast, where the jacket is more about the style than about keeping warm.
And, in case you have never tried a combination of leather and florals, this is your push. It’s unexpected, but it makes the whole thing feel modern. I adore the fact that the dress itself is cut simply, which is a good lesson that bold does not have to be complex.
Honestly? I’d only add a glossy red lip. This look deserves that final touch.
Playful Retro Riviera
This appearance is making me think of a last minute get away to the French coast. The red-and-white striped cardigan with a flared mini skirt and the red accessories are a complete late summer casual chic vibe. The cat-eye shades and the traditional gold bangles provide the right amount of glam to the light-hearted foundation.
You are aware that I am a sucker for a theme and this one is nautical without being costume. The material is thin enough to wear in hot weather, and you would not have a problem replacing the top with a tank in case you are going out in the middle of the day. I had a similar outfit as I strolled on the Amalfi coast and actually did not want to change when the sun went down.
Here the trick is to be consistent: accessories of the same color family should be used to simplify the striking colors. The women who are over 50 may experiment with a longer skirt and the red color that is softer, but still, it is fun, only a bit more sophisticated.
The only thing I would add here is a straw hat or a large tote bag – it is more convenient, but also to be in the complete fantasy.
Varsity Vogue Vibes
This is your preppy-gone-global moment. A long white shirt-dress under a lime gingham vest, knee-high boots and a mini bag, all the details stand out. The sporty edge is added by the green baseball cap, however, the proportions and the fabric make it sophisticated. This is pre-fall clothing that can be applied to all ages, geographical locations and styles.
I love this silhouette as it is contrasting: large upper part, fitted accessories, sharp lines. This might be strolling through a museum in Europe, jumping on a scooter in Italy or taking a brunch table in L.A. It is the type of ensemble that makes you feel put together even when it took you 5 minutes to put together.
When you are styling something similar, ensure that the shirt-dress is not light, crisp cotton or poplin will be the best so that it does not crumple under the vest. And yes, it is perfectly possible to wear a cap with boots. It’s 2025, no one’s gatekeeping anymore.
If I were adding anything? Perhaps a large pair of headphones and a latte, just so that the cool girl moment could be complete.
Parisian Stripes Meet Denim Cool
This combination is magnetic in some way, the stripes in red and white are so bold and the blue wrap denim mini is classic. It is that late summer casual chic that we are looking forward to when September is playing with the heat of summer but promises cool air in the future. The red sunglasses and that famous quilted bag scream European, possibly even Paris, without even trying so hard. This is not a costume, this is a state of mind, happy, sexy, and well-groomed. It is perfect for ladies who desire to look fancy without losing comfort even during a coffee run.
The mini skirt is breezy in hot weather yet it has a structured wrap cut making it polished. The knit has long sleeves, which balances the proportions and fits right into that late summer look, i.e., golden hour in Italy or a visit to a flower market in Europe. The quilted bag? Timeless. That kind of red doesn’t whisper; it winks.
To me, this look is perfect for those late summer going days when you’re not sure if you’re headed for brunch, a stroll, or an impromptu photo shoot. It is also timeless – yes, even women past 50 can make this their staple with a longer version of the skirt or opaque tights as the weather turns colder. Do not like red? Change the color, but not the concept: classic lines and one bright accent.
Understated Luxe in Black and Blue
What would I say about this look in three words? Sleek, grounded, refined. A fitted black knit top with exaggerated bell sleeves and vintage-cut jeans is like a daydream of a late summer working day in the office. This style is fit on a European terrace as well as it is fit in a Soho creative studio. It is not shouting out to be heard, it is demanding attention gracefully.
The sleeve detail of the top makes it stylish, even when the baggy jeans are the most casual. It is a combination that is good to wear in warm weather but can easily be taken into early fall, all you need to do is add a cropped trench or leather jacket. The loafers balance the look out with some structure, and that quiet power you desire in your business casual rotation of work.
I attempted the same style last September during a client pitch and I felt like I had finally figured it out: how to be late summer casual without being boring. One of the tips I learned by celebrity stylist Karla Welch? Always have at least one unexpected element. Here, it’s the sleeves — dramatic but wearable.
The only thing that I would have adjusted is perhaps skinny leather belt or minimal gold jewelry. This uniform does not require a lot of things, its strength lies in the accuracy.
New York Attitude, Italian Ease
It is that in-between of carefree and put-together: a neat button-down shirt, a light-wash wide-leg jean and a baseball cap that brings it all right back to the ground. It is ideal to be worn by late summer casual women who do not want to make an effort to look stylish. And yes, this is definitely late summer casual jeans that do not feel like fashion.
The secret here is in the tailoring. That shirt is big in a good way, not baggy, and it is tucked in just so that a waistline can be seen. The pants? This ankle-soft pool is giving a lot 2025. And the cap, you see, a sort of mutiny of silence, which says, Yes, I can dress up. I just don’t feel like it today.”
I always use this formula when I have coffee meetings or downtown days. If you’re heading to Italy or Europe in late August or early fall, this is what you’ll want to pack. It is effortless to assemble but makes you feel like you are expensive. Throw in mules or a smooth bag to go with dinner, it is that versatile.
Denim Jumpsuit with Main Character Energy
Now, let us discuss power dressing with a twist, a full denim jumpsuit that fits like a glove, tucks you in at the waist and makes you feel like the heroine in your own movie. It is chic, it is office and it is very much a 2025 update of 1970s glam. The type of outfit that can take you through a late summer work day in the office to the drinks in one swift change of lipstick.
The secret is that the light wash makes it breathable in the warm weather, but the long sleeves and flared leg make it seasonal. I am particularly fond of the structured belt – that metal ring buckle is one of those tiny details that makes it utility to runway.
It is one of those songs that you either memorize or leave. For me? Total commitment. I had something like it last fall to a gallery opening and received more compliments than I ever received on any fancy dress. If you’re women over 50 looking to turn heads while keeping it modern, swap heels for stacked loafers and you’re golden.
I would add something, perhaps a bold lip or large tortoiseshell sunnies to make it extra. Otherwise? Perfection.
Western Light with Euro Softness
You remember how late summer gets to that point when it is cool in the morning and hot in the afternoon? This is what you wear. A light denim jacket of oversized fit, wide-leg pants of the same color, a white tank, and accessories in camel tones. It is a late summer casual comfort with an evident reference to the European silhouettes.
Talking of layers: the jacket is perfect during hot days that change rapidly. I love the earthy tan belt bag — it’s practical but not frumpy. The hat? A moment. It is such an Italy in September, such a burnt-orange sky over a cobblestone piazza. And those suede boots? The ideal way to anchor the appearance as we enter the early fall.
I find this to be the final late summer aesthetic inspo. It is the type of outfit that goes, I am cool but I am so sure of what I am doing. You can wear this to an outdoor market, wine tasting or even a work business casual Friday in case your office is more on the creative side.
What might I add? A long silk scarf to the bag or around the neck. And only a bit more softness to reinforce the entire atmosphere.
Modern Equestrian Meets Urban Autumn
Olive green is the quiet hero of fall. It fits perfectly into the early fall wardrobe, particularly in combination with the soft materials, such as faux leather and cotton. This black and white outfit is brought to a new level with a rustic tone-on-tone color scheme, with the edge provided by the sleek knee-high brown boots and a wide-brim woven hat that is a wink at the late summer going countryside moment we all desire before the true fall arrives. It is posh, but still wearable, a real harmony of comfort and sharp cut.
The secret behind this outfit is the flow: the lightweight trench, cropped pants that are fitted and the boots that are cut just below the knee, they all blend. And that scarf? It brings some softness and warmth but is not stuffy. This is ideal work business casual if you’re in fashion or creative fields, or the perfect look for a crisp late summer casual chic day in Europe.
For me, this whole look whispers confidence. I had something similar in Milan years ago and I have been trying to find the silhouette ever since. One pro tip? Swap the scarf for a bold gold pendant if you’re indoors — keep the texture rotation going.
Botanical Brunch Energy
There’s an ease to this ensemble that’s undeniably fresh. The pleated khaki pants are soft, and the oversized leaf-print shirt adds the vacation vibe to the look that makes you wish you were in Italy in September. This look is finished off with a large brim hat and a soft caramel bag, which screams, let us have brunch or going to a gallery with my girls. And it’s age-inclusive — women over 50 could pull this off just as easily by leaning into that generous silhouette.
I adore the combination of high and low: shiny trousers, fun top and accessories that make it down to earth. The hat is particularly a late summer essential, perfect on the days when it is hot but you do not want to feel overheated. And the leafy pattern? So 2025. The current trend is green, both in New York and Paris, and it means that people are falling in love with organic beauty once again.
This would be a beautiful appearance on a tour of the wine roads in Tuscany or even a cup of espresso in a Manhattan courtyard. If I were to style it further? Perhaps one sculptural earring or a linen blazer that is lightweight and thrown over the shoulder.
Sunset Pop: Citrus and Candy Vibes
Bold and beautiful — that’s the theme here. Red tailored shorts and a pink-and-white stripe blouse with balloon sleeves that are exaggerated? Hello late summer aesthetic. The fabrics are airy, the atmosphere is carefree, and this whole image was created to enjoy warm sunset and laugh on the roof. The yellow bag with sunny yellow color gives that happy touch that makes everything pop without being too much.
What I like about this is that it is balanced, statement sleeves and sleek, high rise shorts. The blouse is made of soft cotton that keeps you cool and yet it is structured enough to make you feel dressed. This can be worn in hot weather and can be easily transformed into a September picnic or an al fresco dinner date style.
I personally think these tones are so flattering on all skin tones, red and pink are such a shocker in that they go with everything when done in this manner. One of the Vogue editors has recently advised to treat bold colors as neutrals in case you wear them with confidence. This tip opened up a world of freedom to me and I began to color-block without any second thoughts.
I would probably include an open-toe block heel or even espadrilles to finish the mood. But it is the smile that clinches the appearance joy is the accessory.
Playful Meets Polished: Skirt Edition
Those combinations that are like the joy of summer into early fall, you know? This is it. Orange smiley tee and silky red skirt which flows with each step is the best late summer casual combination of fun and fashion. It’s youthful, yes, but don’t let that fool you. This outfit is stylishly versatile, particularly to the type of woman more than 50 years old who adores free-flowing style and natural comfort.
The tee makes it earthy, a bit big and vibrant. The satin skirt is elegant due to the flowing texture and jewel color. Leopard slides? Genius. They violate the red-orange story only to make it interesting. The woven bag is simply the icing on the cake – ideal to take on a laid back day out or on a work-from-wherever occasion.
It is a type of appearance that will earn you compliments by strangers. I had something similar in a solo trip to southern Italy and I was asked more than once where I got the skirt. It makes me remember that fashion is not obliged to be serious to be effective.
If I wanted to tweak this? During October, when it is colder in the morning, I would wear a blazer or a cropped denim jacket with a structured form. However, to be fair to this one, this one is rather close to perfection.
Soft Neutrals, Big Impact
This is what I would call the quiet luxury of early fall outfits, soft camel and creamy whites coupled with minor details that make a world of difference. The loosely-buttoned shirt, the bound scarf, the eye-catching gold-ring belt, are united in a studied still life. This is late summer casual chic at its peak. It is ideal on hot days when you do not want to feel undressed but at the same time you need to feel confident.
The palette is work business casual, but can be used on the road as well, I can see myself wearing this walking through a museum in Paris or sipping cappuccino in a small alley in Rome. The white trousers with pleats are particularly flattering, lengthening the leg and providing a background to the warmer-coloured top.
For me, this look feels like a reset. When I have to clean my mind and re-balance my energy, I turn to such tones. It’s light, but not basic. Breezy, but grounded. Once, stylist Micaela Erlanger stated that neutrals must never be dull, they must speak something about the owner. This outfit gets that exactly right.
If I were to enhance it slightly? Maybe add an ankle-length trench or fine-knit cardigan. Or better still- just leave it as it is and make the fabric speak.
Monochrome Drama in Chocolate Tones
This look is pure power. A rich chocolate color that runs through the shirt to the gloves to a structured bag makes a statement without uttering a word. Tonal dressing at its best, this is the kind of tonal dressing that works in work business casual environments where quiet luxury is the order of the day. The rolled sleeves, the broad collar, and the powerful shoulder line provide this outfit with the bold architectural power. And those gloves? Surprising genius – ideal for a late summer going out night or a high-flying office occasion.
When you go all black and white, then the secret is to experiment with textures. The cotton suit matte, the buttery leather of the gloves, the slight shine of the handbag, all of them make a visual depth without a single color clash. This is perfect on warm weather days in between when you are still required to polish up. Brown tones also: they are especially beautiful on darker skin and extremely flattering on women who are past 50.
This brings to mind one of my styling tips that I read in Harper Bazaar last fall, which was, rich colors make rich characters. When you dress brown-on-brown this way you exude earthy chic. I have done a similar look to an early fall downtown dinner and felt like a 1970s Parisian art dealer, in the best way possible.
The only thing I might add? Drama on the lip, perhaps burgundy, or a small gold brooch to signify the individual.
Retro Knit Meets Soft Tailoring
There’s something so reassuring about an oversized argyle sweater. It makes you feel warm and never unstylish, particularly with casual tan pants and strappy sandals. The style is a comfortable wink to back-to-school style but made over in the modern woman way, i.e. late summer office in Europe where smart layering is the order of the day.
The pattern of the cardigan is big and the colors are earthy, so it is very 2025, but graphic and down to earth. The wide-leg pants are cropped to make it breathable in hot weather, and the low-heeled sandals are easy and elegant at the same time. It is one of those late summer casual outfits that can be easily worn in the morning or during cool evenings.
I am personally a fan of oversized knits such as this one when September comes around. I put them over slip dresses, jeans or in this case, light tailoring. This look is a sweet spot in the case of women who are over 50 and like structure with softness. You can even change the sandals with loafers or sneakers and still maintain the energy.
The only thing I would have tried is a beret or a crossbody bag in ivory, just a little contrast to work with the warm colors. However, to be serious, this costume already resembles a hug in a dress.
