Fall Old Money Outfits Ideas 2025 to Look Classy, Cozy, and Chic This Season
Is it not something that cannot be resisted about the fall old money outfits aesthetic? That effortless grace. That whisper of tradition. That delicious tug between casual elegance and aristocratic polish. When you have ever found yourself in the middle of scrolling and wondered how can I make myself look like I just stepped out of a modern-day Nancy Meyers film, then this is the one. No matter what kind of fall you have to dress up, whether it is crisp early morning walks with a coffee cup in your hand, a family photos shoot, or a serious main-character energy when going to work, fall is your runway.
And no, you don’t need an Ivy League lineage. Only a bit of inspiration, considered layering, and a wardrobe edit that is like your personal version of the good life. Let’s dive in.
Timeless Comfort in Powder Blue
Soft tailoring combined with oversized knits is something luxurious in its own way. This outfit captures that exact vibe — relaxed, but so polished it whispers “heritage wardrobe.” The oversized, powder blue turtleneck is not only warm, but it is also tastefully accessorized by a thick gold chain. The front is tucked-in to make it easy, and the pleated beige trousers bring the outfit down to a solid confidence. It’s the type of fall old money outfit that feels both familiar and freshly inspired — the kind of style you reach for when you want to look like you’re not trying too hard, but still turning heads at brunch.
I adore the fact that each and every item in this outfit can be worn separately, a women fall essential wardrobe on the move. A well-made turtleneck in a saturated pastel (yes, even in fall!) feels modern and a little unexpected. And the high-waisted pleated trousers? Classic. They are hard workers: to work, weekend walks, even family photography, in case you add a belt and heeled boot. And those white flats add a finishing editorial touch to the look but do not make it look fussy.
This season I have been noticing more and more editors styling soft knits with menswear-inspired trousers, a styling tip which is lifted directly out of Paris street style. Here is one of the tips I got by stylist Allison Bornstein: balance volume and structure. So, oversized top? You’ll want a trouser that’s tailored but not tight. It’s a little formula I keep coming back to.
To complete this look to go out on fall errands or to have a coffee date, I would add a camel coat on top of it and possibly change to Blundstone boots to make it a little more casual yet still elegant. Effortless layers, thoughtful details — that’s the energy.
City Sophisticate with a Camel Twist
The first time I ever saw this look, I thought: that is the coat you give your daughter one day. A camel coat that covers an entire body over a monochrome base is the epitome of old money style and it is royal, sure, but it is also highly wearable. It is the most chic fall fashion: a fitted tan turtleneck, dark-wash denim, leather boots with a perfect structure, and oversized sunglasses that add a bit of mystery.
The secret here is in the color story. Warm neutrals are always rich in tonal dressing. The jeans make it casual, the turtleneck makes it clear that I did think this through and the long coat ties it all together like a fashionable exclamation point. These high boots made of caramel leather have a bit of Western reference without pushing the outfit into costume mode.
This style seems perfect to those women who are over 30 and need something dressy and down-to-earth. I had the same outfit on a client meeting last October and I received more compliments on the coat than the actual proposal I was presenting. Funny how fashion can do that. Fashion psychologist Shakaila Forbes-Bell says neutrals make us feel more “anchored and secure” — I believe it. This kind of look wraps you in confidence.
All that’s missing? Perhaps a silk scarf to the bag as a touch of something. Because we are going timeless does not mean we should not flirt with detail.
Crisp Layers for Golden Hour
This one has a clean, college-like vibe to it, like fall leaves, a good cup of coffee, and an 11 AM meeting that has just become your runway. The ensemble is supported by a cable-knit vest on top of a classic white shirt, which is worn in a carefree way with creamy pleated trousers. It’s clean, it’s cool, it’s quiet confidence in motion. The whole silhouette is a reference to fall old money clothes it is almost cinematic, as you are leaving a 90s Ralph Lauren ad campaign.
Every item in this outfit is classic: the fitted white shirt, the knitted fabric in a neutral color, and those fitted trousers that are sophisticated and relaxed at the same time. And, yes, every woman in the world needs to have something like this in her wardrobe, it is a perfect piece to wear to work, or even such an event as a fall photoshoot.
I personally wore this combo last Thanksgiving weekend. Surprisingly, it was warm, and I did not wear a coat, put on a red lip, and received so many DMs with the question of where to buy the vest. The best part? This outfit transitions easily with a coat or trench, or even an oversized blazer if you’re chasing that layered early fall feel.
The only thing I would change is to add a mini-structured bag or even change the sneakers to Sambas adidas to make it a bit sporty and elegant at the same time since we all love contrast.
Tweed Revival in the City
There is no jacket that says, I have a trust fund and a French bulldog more than the cropped tweed blazer. This outfit is the best combination of old and new when worn with light denim and block heels. It is feminine, it is sharp and it is 100 percent old money core. The thing is that you do not have to inherit it to wear it, you only need a good tailoring and a strong sense of self.
The neat lapels, the gold buttons, the fact that the light-wash jeans makes things a bit playful, it is a fun combination. I always say: tweed doesn’t have to be stiff. You can match it with jeans, leather or even a sweet skirt. I believe that this style is particularly clever among women aged over 50 who desire chic with a twist.
A Vogue stylist once said, that it is not what you wear but how you mix it. And this combo proves it. The classy bag adds order to it and the heels make it ladylike without being overdone. I’ve worn a similar outfit for a gallery opening and a casual work lunch — it works both ways.
Would I add anything? Perhaps, only a deep berry lip and a pair of structured gold earrings to embrace the feminine touch.
Clean Lines, Cool Mood
This look? It is mumbling old school prep but with a quite current twist. The casual pinstripe shirt with the wide-leg white trousers is a minimalism at its best. Throw in the hint of brown belt, a leather bucket bag and pointed shoes and it is downtown girl with uptown instincts. It is one of those fall old money outfits that will look good regardless of your age, it is classy and timeless.
The shirt is light and breathable and this makes it an excellent early fall shirt. The suit is made of tailored trousers, and the accessories (such as the sleek bag and headband) are very much of the quiet luxury. It is the kind of attire that I would use during a photoshoot, a creative working day, or when I am just strolling around a museum with a friend.
This is the one that makes me think of the now-legendary style of Sofia Richie: gentle neutrals, minimal lines, and nothing extra. It’s proof that you can create impact without over-accessorizing. I feel motivated to raid my personal closet and dig out those basics that I have been neglecting. There are occasions when you just need a belt and a tucked shirt.
The only thing that is lacking is a transitional jacket, perhaps a cream trench or a wool shacket. But really? It’s already perfect as is.
Château Elegance in Earth Tones
Strolling over groomed lawns in a fitted check trouser and a fresh white shirt- it does not get more classy than this. This ensemble is a compromise between the aristocratic tradition and the contemporary femininity. The autumn old money outfit energy is casual, subtle and discreetly strong. It is the type of outfit you put on when you have a breakfast date at a small hotel and a visit to a bookstore with a mahogany and history aura.
What makes this style shine is the impeccable fit. The houndstooth or micro-check trousers are a bit high-waisted and narrow legged, but not tight, polished. The white shirt is semi-transparent and loose with rolled-up sleeves, which suggests the confidence without the bling. I adore the classic brown leather handbag, which is a discreet reference to heritage brands, but not so many logos.
This style is ideal either to women over 50 who are not ready to give up on playing with chic tailoring, or to younger women who are in need of timelessness. It’s age-fluid, setting-free. Stylist Micaela Erlanger has long championed “pared-down pieces with maximal impact,” and this is it. I had something like a countryside birthday weekend on and it took me through lunch to wine tasting without a change at all.
Should you be styling this, then you might as well add a pair of brown Blundstone Chelsea boots on colder days, which is unexpected, yet grounding.
Plum Tones and Power Layers
This appearance is irresistible – daring, urban and yummy-trendy. The large charcoal blazer, which is tightened at the waist with a shiny plum belt, is matched with a dressy twist through patterned tights and patent leather heels. It’s that sweet spot between fashion-forward and luxe. I would be honest and say I would expect this on a person entering a late night art opening or sneaking into a cocktail bar through a back door.
These knit tights in deep berry take the look to a new level in a second – they are the perfect amount of fall pop without being too obnoxious. And the matching structured handbag gives power woman energy. I adore the way the turtleneck makes everything down-to-earth, but the playful legwear makes it not that serious. This kind of look is awesome when you are taking family pictures and you need a bit of extra style but you want to remain classic.
Sometimes people assume old money has to mean beige-on-beige. However, this shows that luxury dwells in deliberateness- not colorlessness. I think of this as a “city heiress” moment. It also addresses plus size girls as well: blazers and belts can make the silhouette fit you.
I would also include a brooch or a bright lip to create even more contrast, but to be honest, it is already giving.
Parisian Prep with Ice Cream Chic
Oh, I do love style not taking itself too seriously. This ensemble is playful in timeless clothes. A knit beige vest over a white shirt and with loose pleated trousers? Classic. Throw in an ice cream cone, and it becomes the sort of style that has been lived in, that is spontaneous, a bit Audrey Hepburn in attitude.
What is good here is the balance of each item with the other. The ivory shirt is built and the sweater vest makes it soft. High-waisted pleated pants, yes, again, because they are the anchor of most fall old money outfits. And that crossbody bag worn up high? It is irreverent, surprising, and seems to be appropriate on early fall weekends when you want to walk or watch people in a cafe.
Honestly, I was almost wearing this same outfit in family photos last September and the response was incredible, someone told me, I looked like a French editor. I’ll take it.
In case of restyling this, I would replace the bag with a mini vintage satchel and give it a skirt alternative to make a playful switch. It works in so many ways.
Effortlessly Refined Stripes
In the event there is a uniform of ladies who bring home baguette in a woven tote bag, this is it. A plain white tank top hidden in fitted pants, over which a striped cardigan was thrown casually over the shoulders. Minimal effort, maximum elegance. It is one of those fall old money outfits that you can wear over and over again and still receive compliments.
The palette is neutral but warm. The cut cream pants and the thin flats with black capped toes are a reference to the classic French fashion. The entire ensemble is as though it was stolen out of the wardrobe of some casually beautiful grandmother… and updated.
Women of all ages can wear this look. It is particularly beautiful to work in, or even as the outfit of a photoshoot in case you need a sophisticated, editorial style that does not make you stand out.
On breezier days I would add a light trench over it. And, by the way, exchange the coffee cup with a bouquet of dahlias, just out of the beauty of it. But in truth you could go into a gallery or a second-date lunch and feel that you belonged in it with this.
Playful Academia in Monochrome
Those are the feelings you have when you walk on crunchy leaves in knee-high boots and you feel powerful. That’s this outfit. A turtleneck made of chunky charcoal, pleated mini skirt, and sleek platform boots make a combination of structure and softness. It’s youthful, yes, but it doesn’t lose sophistication. The best thing about this is that it is ideal during those in-between weeks of fall when you need warmth but do not want to compromise your style.
The gray on gray color scheme is invigorating, surprising yet somehow unified. It reads cozy but crisp. The fun element in the outfit is that mini crossbody bag with the strong red accent. The oversized sweater is a great idea when it comes to women over 30 who need something cute and casual yet not childish.
I have observed this fashion on college campuses and street-style roundups and both of them carry it off. My friend Jenna has done something like that in a fall photoshoot, and the photos turned out cloudy, cinematic, and fit her Pinterest.
If you prefer to make it more casual, wear Swap in Sambas adidas to go on errands during the day. Or wear the boots and wear a trench over it. Either way, it’s full-on inspo.
Power Café Dressing in Espresso Layers
A customized rust colored overcoat, in an open style to show off a crisp white shirt over a black turtleneck, now this is how you make neutrals dramatic. It’s structured, it’s sharp, and it’s very much giving “Paris in November, espresso in hand, and a full calendar.” This outfit reeks of fall old money outfits, not loud, not flashy but commanding. Put on some tall black boots and buttery leather gloves and there is a whole story in a sidewalk cafe.
This kind of ensemble is built around layering essentials. The black turtleneck is form-fitting and functional (the best kind), while the white button-down brings brightness. The coat is the star, it makes silhouette, it makes mood, and quite frankly anything under it looks more expensive. This outfit is both polished and practical in the case of women who are above 30 or even above 50.
I have personally tried this combination on cold mornings and felt so put-together. Gloves are an energy thing, it is so uncommon to wear them nowadays, and that is precisely why it is special. Karla Welch, a celebrity stylist once remarked that, accessories should not simply be used to complete the outfit, but they should also be used to advance the conversation. Agreed.
Only thing missing here might be a sleek umbrella. But honestly? I’m into the mystery.
Red Accents and Parisian Attitude
Let’s talk about the power of red. This is a confident look that is not ashamed to repeat itself, beginning with cherry red beret and continuing on gloves, purse, and lipstick. The contrast is strong yet equalized with the ivory coat and gray turtleneck. It is the type of ensemble that makes you walk a bit taller and perhaps, start learning French just because it is fun. It is an entry into the fall old money outfits hall of fame because of heritage styling with a little bit of theatrical touch.
The best part about it is that the silhouette is classic despite the color play. Longline coat, clean tailoring, minimal jewelry. It is providing retro cinema, yet with a 2025 perspective. And yes, ladies who are not usually into brights this one is yours. A single daring colour can transform a whole outfit into an eye-catching one.
Once a fashion editor wrote that old money style is not about excess, it is about precision. This is precisely what is going on here, all the details are intentional, yet it does not seem excessive.
Want an instant mood boost and you are in the process of creating your wardrobe? Get red gloves. Trust me.
Cable Knits by the Lake
It is a soft neutral and casual chic kind of look, ideal in a warm early fall day. It designs the polish but breathable look with the cream cable-knit sweater on top of the structured collared shirt, tucked into the tailored shorts. It is easily comfortable, and it is perfect to anyone who wants their fall old money clothes with a pinch of lakeside nostalgia.
This ensemble shows that you do not have to compromise structure over softness. The tailored shorts keep things refined (and very much not “just summer leftovers”), while the knit sweater adds that coveted “borrowed from grandpa” texture. With a pair of leather accessories and a bare minimum of makeup, it has that casual elegance that would be suitable to a day out, a museum tour or a family photo shoot.
I had this very outfit on a Vermont weekend with high socks and Blundstone boots, and it was all Pinterest.
If you’re curating a capsule wardrobe, don’t skip neutral shorts — they layer beautifully, and surprise, they photograph like a dream.
Monochrome Glamour in Ivory
A full monochrome outfit is something magnetic, and creamy ivory is the most appealing. This is a show-stopper: a fitted high-waisted pair of pants, a blouse with a slightly cropped top and puffed sleeves, and a statement necklace that could have been inherited by three generations. It’s elevated minimalism with a twist — classic enough for women over 50, sleek enough for downtown evenings. Certainly a more formal outfit in this fall old money outfits roundup.
All of these are layering or stand alone pieces. The material appears to be structured yet light so that you will not feel hot inside. I consider this the work dinner of all work dinners, or the type of outfit that you put on when you want to feel like a Vogue editor who bakes her own sourdough in secret.
It is also a very versatile look that can be applied to plus size fashion as well- belts, tailoring and high-end jewelry can accentuate the shape without compromising comfort.
I would complete it with a dark clutch and perhaps a strong lip. But honestly, it’s already ticking every box.
Coffee Break Elegance
At a sunny table in a cafe, in a complete ivory suit, with a cappuccino in his hand – this is an atmosphere, a style of life, a style. The patterned blazer on top of a ribbed knit top, high-waisted trousers, and simple gold jewelry make a perfect combination of elegant and casual. It is minimal, sure, but with a lot of texture and detailing in it, which is very much in line with the most effortless fall old money looks I have seen this year.
This style is applicable in any age, body shapes and environments. Its polish will be welcome by women in the workplace, and its versatility will be adored by creatives and travellers. The brown leather belt provides a sufficient amount of definition and the gold hoops are interesting but not noisy.
Personally, this is the type of an outfit that does not require much thinking, as long as you have the items, you are ready to go in five minutes. It is clever to have these tones in your rotation, as they never look accidental.
Would I add a trench or a bold bag? Yes, but it is just as powerful as it is.
Crimson Power with a Pinstripe Attitude
The combination of structured striped blouse and tailored red trousers is something unapologetically chic, especially when both items are fluent in the language of quiet luxury. This is a power suit with the exactness of a power suit but relaxed with pearls and shiny waves and graceful restraint. It is where Paris and prep school get together and it says: I am sophisticated, but I do not shout.
This blouse? A timeless women fall staple. That old-money academia vibe is provided by the narrow collar, a bit loose fit, and thin vertical stripes. The crimson wide-leg trousers take the show with color authority, but not costume. Black leather accessories, a shoulder clutch, and square sunglasses are saying, in a low tone, that this is a wealthy woman with her own time. And we must not overlook the pearl drop earrings,–modern nobility in the shape of an ornament.
I once wore something like a lunch meeting and before the bread basket arrived I had received three compliments. It is the sort of a look that makes you feel both down-to-earth and majestic. That is what fall style is all about, you put your attitude into the silhouette.
To elevate this look further? Perhaps a coat of camel wool or a light beige trench would be heavenly against a pre-winter chill. Or even Sambas adidas in white to go a little more casual and still have that highbrow touch.
Minimalist Neutrals, Maximal Impact
This particular combination of cream, tan and warm brown is what I think of when I think of timeless style. It all reminds me of a homage to old Ralph Lauren campaigns – the blazers are longline, the leather is buttery, and women are cool without even trying. An ideal transition-to-fall outfit that will be equally good over 30 as it will be over 50.
Here’s the breakdown: a tailored taupe blazer (sleeves pushed up for flair), crisp white tee (crew neck, no logos — this is important), and wide-leg cream trousers. Cognac-colored belted with a statement buckle is a detail that in itself refers to Western heritage with a sophisticated touch. Throw in a curvy leather bag and shiny pointed-toe shoes and it is an Ivy League fantasy.
I once styled my aunt (she’s 57) in something just like this for a family photoshoot, and the compliments? Endless. It is universally flattering and whisper level trendy, which is why it takes the top position in any fall old money outfits guide.
You may replace the tee with a turtleneck in case of cold weather or add a silk scarf under the blazer to get an additional dose of sophistication. But honestly? It’s pretty flawless as-is.
Preppy in Paris, With a Twist
There is a little bit of romanticism in the French-girl style mixed with preppy country-side, and this outfit embodies it all. The mini skirt suit with textured surface, the warm beret, and those boots inspired by the West unite the traditions that seem to be both modern and nostalgic. The dreamy, polished look that fall fashion is so cozy? It lives here.
Let’s talk wardrobe pieces. A cropped houndstooth blazer with wide lapels? Perfection. The high-waisted skirt with curved pocket details is a matching item that adds the school-girl-meets-socialite feel. Put on the beret and a structured black mini bag and you are ready to go out of an editorial. And then – the surprise: high brown boots, with large gold buckles, and cream knee-socks showing. Cute with just the right dose of retro rebellion.
I would wear this same outfit to a photoshoot day where I visit an old museum or a brunch with my girlfriends when I want to feel a bit more styled than normal. It is sexy, fancy, and shamelessly fashionable, but traditional.
Want to modernize this? Throw in Blundstone Chelsea boots to make it practical or replace the beret with a velvet hair bow. Fall’s all about charming contradictions.
Equestrian Roots, Urban Polish
This is the appearance that should be on the pages of Tatler and Vogue simultaneously. Checkered blazer, pearl necklace, cinched belt it is all Old Money Weekend in Paris, but make it suitable to wear to a fancy business lunch or a clean stroll through the museum. And, if you love fall old money looks that tip the scale toward the equestrian end of prep, you are going to love this.
Check pattern in this case is deep and rich with warm undertones a typical fall women wear. It goes so well with jet black trousers and warm brown leather riding boots. It is all the right shaping that is done by that bold black belt with gold buckle at the waist. And the pearls? A tip of the hat to the past that is still so so now.
In one of her interviews, stylist Allison Bornstein said, If you are going to invest in a fall blazer, then make it long, tailored, and in a masculine cut, it will never date. This look proves her point. I also love the minimal makeup here. It lets the tailoring do the talking.
You may include a structured clutch or a velvet headband to introduce more photos appeal. Or change to plus size trousers with a broad waistband so that it fits well and reflects the vibe.
Timeless Walks & Office Drama
Now this is a fall ensemble with action – physical and emotional. That long black coat sweeping behind? It adds heavy drama to the simplest of pieces below. However, they are not what they seem to be, this is how old money women dress to work: restrained, traditional, and reserved. A wardrobe moment when you feel like saying it all without uttering a single word.
The base of this look is so clean: a crisp white button-up (slightly unbuttoned for ease), warm-toned houndstooth pants, and almond-toe heels. But the black full-length coat ties it all together. It moves with the breeze and adds instant authority. Add to that a brown leather shoulder bag and a voluminous fall hair and you are good to go.
I have borrowed a variation of this ensemble to a work dinner before and I swear I felt like I owned the room. It’s confident, modest, and a bit mysterious. That is why I love these kinds of fall old money outfits, they are stories.
If I were adding to this? Perhaps a silk handkerchief, or tortoiseshell spectacles, to be bookish. You might also put a warm fine-knit vest underneath the coat to add more texture and warmth.
Checkmate in Heritage Tones
If you’re into sharp lines and even sharper presence, this one’s for you. A blazer in a deep neutral color palette over everything in black? Instant power combo. It’s clean, composed, and looks straight out of an autumn fashion editorial that celebrates women who command every room they walk into.
The black wide-leg trousers puddle at the right length to the shoes and give the authority. The knit mock-neck underneath is classy, sophisticated and so layering friendly, especially during those in-between days when you want to be warm. The classic check blazer? It’s all about that British prep lineage. The purse and GG belt and chain strap can be used with gold accents, but do not appear overly luxe.
As an individual, I never hesitate to use such outfits when I need to impress without uttering a single word. It is popular at work events, gallery openings or even in over 50 fashion moments that do not compromise on edge.
You may definitely combine this with elegant Blundstone Chelsea boots to make it more toned down. Or just add on statement earrings in case you need a bit more light around your face. Either way, it’s fashion with a legacy.
Glossed Bordeaux Drama
A patent leather pencil skirt in burgundy is not subtle at all, but that is what makes this particular look so outstanding. When combined with ribbed black turtleneck and tonal heels, it is sexy, sleek, and very Upper East Side in a rainy day. Think women fall fashion with bite.
This entire outfit plays with shine and structure. The wine color of the skirt is screaming expensive and the texture is so lovely against the matte ribbed knit. The silhouette is elongated with pointed heels in the same color so that the legs appear to be a mile long. It is black and white, yet not dull, an ideal fancy occasion to wear to a night out in the city or a fancy date.
I have something like this as a fashion dinner last fall and I combined it with a camel coat. Necks craned–not because it was a showy thing, but because it was so assuredly done.
Wish to wear it down during casual Fridays or even family pictures? Trade the heels in with black tights and patent Mary Janes or flat loafers. Still elevated, still stunning.
Coastal Cool Meets City Classic
Certain appearances are so casually stylish that they seem like a vacation and a fashion week in one. This is the one that toys with adorable French-girl allure and angular lines – the daringness of black and white stripes is offset by a Western-inspired mini skirt and high leather boots.
This is the type of ensemble that begins with a striped knit sweater, a little bit oversized and always in fashion, and works around it. The mini is made of leather, and it is sharp and surprising, and the tall black boots make the entire outfit seasonally prepared without being overthought. The crossbody is tan, and it is a break in the palette that is enough to make it warm.
I was wearing something similar on a girls trip to San Francisco, I recall the compliments as we were getting coffee around the ferry building. It is simply one of those ensembles that are energetic and fashionable, yet they are based on old money basics.
Throw in a trench or a wool blazer to take it into early fall when the wind is nippy. Or layer in tights if you’re styling it over 30 and prefer a little more coverage.
The Uniform of a Chic Librarian Heiress
We are obsessed with a twist on a uniform- especially when it comes to a bell-sleeve white blouse, houndstooth mini and leather boots. It’s giving library in Florence meets modern-day Blair Waldorf. That is where fall old money outfits tip into feminine tailoring and academia as play.
The statement sleeves immediately draw the eye — wide, dramatic, and whispering “couture.” The mini skirt is custom-made yet tender and has boxy pockets and small check design. Black tights and patent boots make everything smooth and earthly. And the hair? Voluminous, unapologetic, and made for photos.
This reminds me of something I’d wear to a photoshoot in a historic home or chic afternoon tea in the city. It is not juvenile, not too serious, but girly and refined at the same time.
To make this plus size friendly, select another silhouette that is a bit longer and softer bell sleeve that does not overwhelm the frame. It’s all about proportion play.
Deep Reds and Quiet Confidence
Sometimes, you wear red. And there are times when you are wearing red, and it is the best thing in the world. This ensemble covers fall old money ensembles with warmth, depth and black and white wealth. It is the type of style that does not attempt to be trendy, and it simply never fails.
A casual V-neck knit and a high-waist leather pencil skirt in a rich maroon color make a sophisticated yet friendly outfit. The belt is too big but it is tied at the right spot to make the body look good and the quilted chain bag gives that vintage look. It is all completed with a delicate cross necklace with a touch of spirituality.
What I love here is how ageless it feels. This can be worn over 30, over 50, to work, to dinner, and still look like your most fashionable self. It is also very comfortable, even though it is made of leather, since that sweater introduces all the softness.
To make this a perfect transition look I would style it with a beige wool coat and gold hoops. Add Blundstone boots to make it more down to earth or ankle boots that are pointed to make it edgy.