Fall old money outfits – here. Pov, somewhere on Brunette from Wall Street. Truth be told, the real old money dresses whatever. If you want to see what the real old money wear in fall you will have to browse through all fall outfit edits published on Brunette from Wall Street. But wait, the title was not a clickbait. You were looking for classy fall outfits – and here they are – mixed with outfits my family wears. Scroll down to see classy fall outfits and indulge the internet fall old money aesthetic – do it for the plot.

OGLAS I get a commission for purchases or clicks made through links in this post.

Old money fall outfits 2025 for those captivated by classic wealthy vibes or seeking to perfect the old money fashion trend this season or just want to dress to impress for the plot. Also, sophisticated fall attire for the real old money and those who don’t take fashion trends too seriously, simply aspiring to exude admirable style during luncheons at the country club or casual dinners at home.

Now here is something you don’t know about me yet. Unless I need to wear something fashionable and eclectic, I dress classy. My personal style is elegant feminine chic – it’s a mix of old money central European style with a dash of French influence from my mother. And today, I am sharing my favourite classy feminine outfits for fall 2025 to inspire all of you want to make your grandmother proud of you. POV Our mothers don’t care much about old money standards, do they? But grandmothers and mothers-in-law do.

Also, the old money trend is on the rise again (more on Brunette from Wall Street Substack – subscribe now). Some draw the connection to the upcoming recession. But, I looked into the data (I checked the sales of “internet old money clothes” – midi skirts, blouses, dress shoes, top handle bags, tweed jackets, candy pants, mid-heel shoes – prior and in the time of recessions from 1950 to 2023 and there is not enough data that would prove the correlation between the amount of “classy clothes” sold and the recession. We would more likely be able to prove the statement that people tend to dress more classy in times of recession if we looked into the balance sheet of second-hand stores and flea markets. Still, we don’t have data for these businesses – some were not registered and didn’t report their financial statements. Also, girlies got their clothes from their older relatives. Like me, the blue pleated midi skirt.

THE BEST CLASSY FALL OUTFITS 2025

While you will not be able to buy my midi blue pleated skirt – the exact blue midi skirt I’m wearing in the first collage because I got it from my mother, I made sure to find a similar skirt. And linked it.

All the collages and product galleries with my classy fall outfits are hyperlinked and shoppable. I made sure you can shop all of my classy fall outfits 2025 immediately.

Click on the garment or accessory you need to copy my classy fall outfit and you will be pointed to the online store where you can shop for the same or close to the same item. POV If not taken from my mother, I bought my clothes on Farfetch, 24s, Net-a-porter, Luisaviaroma, Harrods or Mytheresa. But to reduce your shipping costs, I linked some of the garments to Nordstrom and Saks Fifth Avenue as well.

CLASSY FALL OUTFITS WITH A SWEATER FOR WORK AND BEYOND

Classy but cosy, invest in fundamental building blocks for your everyday fall wardrobe. Cable knitted sweaters are work-friendly items that pair easily with pleated midi skirts and camel trench coats as we transition deep into autumn.

1 CABLE KNIT CAMEL SWEATER WITH PLEATED MIDI SKIRT AND PUMPS

For moments when attitude remains essential but you want to reach for comfort, look to a camel sweater and midi skirt.

From elegant midi pleated skirt to a comforting cable knit sweater, this classy fall outfit will have you looking refined for daytime while retaining the feminine appeal.

EASY FALL CLASSY OUTFITS FOR EVERY DAY

Elegant and assured, simple and effortless, these are the classy fall looks that will be your wardrobe favourites for years to come.

Simple lines and intricate fabrics make these fall classy outfits the go-to option for a variety of occasions. From pretty knitwear to soft tailoring, these classy fall options will help you tackle your busy schedule looking effortlessly graceful.

POV This is what I wear at home in autumn.

2 BLACK TURTLENECK TOP WITH HOUNDSTOOTH PANTS AND FLATS

Throw the old rulebook out the window, and don’t be afraid of bringing a black turtleneck sweater into the mix. Powerfully simple, everyday outfits have never felt this elated.

OLD MONEY CLASSY FALL OUTFITS WITH A SILK BLOUSE

Looking elegant is not easy if you were not born with grace. But a comforting red silk blouse brightens up the darkest of autumn days. POV Don’t look to discrete details like precious buttons or ruffle collars that elevate beyond the basics. You want to look basic and poised at the art gallery.

3 BERRY RED SILK BLOUSE WITH TWEED SHORTS AND POINTY BALLET FLATS

Imagine this: The crisp fall air nips at your cheeks as you step into the art gallery, your heart pounding with a mix ofexcitement and anticipation.

You’re dressed in a vibrant red silk blouse, the ruffles cascading down like delicate petals. The tweed shorts add a touch of playful sophistication, while the pointed ballet flats lend a timeless elegance. And let’s not forget the small black top handle bag, the one that you always wear (from now on at least).

As you wander through the gallery, the artwork seems to come alive around you. The colors on the canvas blend seamlessly with the hues of your outfit, creating a harmonious symphony of sight and sound (you hear the piano from the grand hall).

As you admire a particularly captivating piece, you catch a glimpse of yourself in a nearby mirror. The image that stares back at you is one of refined elegance, a girlie who exudes grace and charm.

You spot him across the room, a handsome figure standing before a particularly striking piece of art. His eyes meet yours, and a warm smile spreads across his face. As you approach, he compliments your outfit, his voice soft and sincere.

You blush slightly, feeling a flutter in your chest.

He takes your hand and takes you to his favourite painting. You know the painting well – this art gallery is your second home. But you let him talk about the painting as you didn’t know the attributes and the plot. It’s a test – you want to see if he is the salon guy.

When it’s time to leave, he offers to walk you to your car. As you stroll down the street, the autumn leaves crunches beneath your feet.

CLASSY FALL OUTFITS WITH A CARDIGAN

As the weather cools down and the search begins for elegant items to keep you warm, look no further than this edit of elegant seasonal staples with a cardigan.

4 STRIPED CARDIGAN WITH STRIPED SHIRT AND WIDE-LEG PANTS WITH BALLET FLATS

Look casual for work or slip into the soft embrace of cardigan and wool wide-leg pants, and you will be out of the door in no time paired with golden ballet flats.

Pretty and sophisticated, indulge in a heady mix of old money fabrics with a poplin shirt, wool cardigan and pants. Whether you are going to the country club or getting ready for a day with your mother in law.

POV Leave a pearl necklace at home if you are an old money. Remember, this is not a cosplay for you. You are just finally dressing up to your family’s standards to make your grandma proud at the club.

CLASSY FALL OUTFITS FOR BRUNCH

You are invited to brunch! What next? Brunch dates come with their own set of rules. You have read the brunch dress etiquette guide, right?

POV We usually have lunch at home, and I only go to brunch occasionally – three times a month with my mother or sister, when we have nothing better to do or just want to have champagne with no excuse.

Even so, when we go to brunch, we don’t make a fuss about it and prefer to wear something nice. But nothing that would show we made any effort. Rember dressing like this is not cosplay for me.

Discover my favourite brunch outfits with a poised elegance just ready and waiting for the social season ahead. Finding your next brunch outfit has never been easier.

5 CARDIGAN AND TAILORED SHORTS WITH MARY JANE PUMPS

Ladylike options for fall brunch abound in delectable outfits presented in classic knits and pretty cardigans. We are obsessed with a red cardigan sweater this fall.

Dress to match for brunch or ritzy afternoon tea at your favourite dining spot. You will look positively charming in a cable knit cardigan and midi skirt paired with heels.

Not just for brunch, tailored shorts make a striped cardigan an enticing option for lunch and afternoon tea, too. Go for short lengths that will pair beautifully with Mary Janes and trench coat.

CASUAL CLASSY FALL OUTFITS WITH JEANS

As said, my personal style is elegant feminine preppy chic, and the chic comes from my infinite love for denim jeans. I got that from my half French mom. She lives in denim jeans and mid heel pumps. By the way, I just bought her these pumps.

There is a certain thrill that only denim can bring. We reach for denim jeans on a daily.

6 BURGUNDY RED SILK BLOUSE WITH DARK WASH JEANS AND POINTY FLAT MULES

For a casual day, feel extra special the moment you slip into your jeans paired with a silk blouse and pointy flats.

Endlessly pragmatic, shape your classy wardrobe around dark denim jeans and silk shirts and silk blouses. A burgundy red silk shirt gives a modern update to any classy fall outfit. Paired with designer flats and a headband (if you don’t have the best hair day), it will take you straight from breakfast meetings to after-work drinks.

7 CREW NECK SWEATER WITH DARK SKINNY JEANS AND LOAFERS WITH A HAIR BOW

For the ultimate old money aesthetic fit, pair your dark wash jeans with loafers and a hair bow.

CLASSY FALL OUTFITS FOR GRAND OUTDOORS

Times will change, but you know some looks will forever play a part in your life. A black riding outfit will be your number one choice for the grand outdoors if you are an equestrian.

8 BARBOUR QUILTED BARN JACKET WITH BLACK TURTLENECK SWEATER AND BLACK LEGGINGS WITH RIDING BOOTS AND A HEADBAND

Match your black breeches and black riding boots with a quilted jacket as you saddle your horse to explore your estate.

9 BARBOUR QUILTED BARN JACKET WITH CREW NECK KNIT SWEATER AND LEGGINGS WITH HUNTER BOOTS AND HEADBAND

Or maybe you are pregnant and prefer to walk to your orchard to get an apple. Be careful! There is mud! You will need a pair of Hunter boots and a barn jacket.

10 TWEED JACKET WITH RUFFLED BLOUSE AND LEGGINGS WITH HUNTER BOOTS

Or revel in the luxurious feel of a tweed jacket as you join the grape harvest.

Picture the moment just before the sun gently rises over the vineyard. The warm golden hue spreads across the rows of vines, though the air is still cold with dawn lingering in the sky.

With a red plastic harvest bin in one hand and a new pair of thinning shears in the other, you run downhill to the first row.The vines stretch out before you, heavy with plump, ripe clusters of grapes ready to be harvested. The air is fragrant with the earthy aroma of the vineyard, and the gentle rustle of leaves and distant hum of birdsong (and that annoying sound meant to scare the birds away) provide the soundtrack to this idyllic morning.

As you reach the first row, you carefully scan the clusters, selecting the one that looks the ripest. You snip the stem with the thinning shears and pick a berry from the cluster to savor its sweet, sun-kissed flavor.

11 TWEED JACKET WITH RUFFLED BLOUSE AND BLACK LEGGINGS WITH RIDING BOOTS

Or mix and match the tweed jacket and riding boots for your next wine tasting tour.

CLASSY FALL OUTFITS FOR DINNER PARTY

As the social whirl of the holiday season begins, you need a classy wardrobe at the ready.

From family gatherings to work parties, there is endless occasions you will be dressing up for.

12 BLACK BLOUSE WITH FULL SKIRT AND HEELS

For charity fundraising dinners, a thoughtfully chosen outfit can make a significant impact. A standout piece, this full skirt – it’s only $53.

Pov, wearing an excessively expensive attire for a fundraising event just doesn’t feel right. The skirt’s modest price tag aligns well with the charitable nature of the occasion, while its design and quality (my dress is well made – my seamstress couldn’t believe the price tag – btw for the size and fit info, subscribe to Brunette from Wall Street Substack – I share size/fit info with free subscribers too) ensure you look polished and appropriate. 

With this budget-conscious pieces, you can demonstrate that true elegance stems from thoughtful consideration rather than extravagance, which resonates with the event’s philanthropic goals.

With no one noticing the blouse, you can go for a more precious piece to wear with the skirt.

13 LITTLE BLACK DRESS WITH HEELS

For times when dressing up needs to be poised, look to a little black dress. A little black dress will take you easily from day to night with a black blazer and will suit any number of occasions.

14 BLACK TIE DRESS WITH PUMPS

And when you are expected to go all out, it’s time to step out with your best foot forward.

Put on a glistering gown that will have you set for a big affair. Btw this is my favourite opera outfit – I wear it every time I go to a new opera house.

FAQ FALL CLASSY STYLE

If you are feeling overwhelmed by choice and deliberating which direction to turn when you want to impress, go through FAQ – it will help, for sure.

POV I am guilty of having fun with tweed sets as well. But you can break the rules if you don’t have to pretend to be old money or sophisticated. Also, I wear tweed instead of bounclé.

MORE ELEGANT OUTFITS FOR FALL

Wearing classy clothes is not the only way to look elegant. Elegant style can be classy or formal, fashion forward or basic. Explore my favourite elegant fall outfits to dress more elegant, but never look like a TikTok fool with pink cheeks, fake pearls and Bounclé sets. Up next: formal fall outfits and classy fall outfits for church.