Cosplay? No! This Is What the Old Money Really Wears in Winter
Classy winter outfits 2023 for all who are fascinated by the old money style or trying to nail the old money fashion trend this winter. But also winter classy outfits for the real old money and all who don’t take fashion trends too seriously and merely want to dress admirably in winter but somehow ran out of style ideas for the luncheon at the country club or casual dinners at home. Point of view, I put together these winter outfits for the second group as I disapprove of cosplay. Last but not least, these winter outfits are true to this author’s personal style. So scroll down to see what I wear on a daily – when I’m not working for Brunette from Wall Street and don’t need to dress fashionably.
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Not one, and not only two, but a number too significant I couldn’t leave in doubt, has asked me to reveal my true personal style this winter since you figured out I might be wearing something else IRL. And indeed, you were right.
I dress more classy (boring) when I don’t need to take photos and videos of fashionable outfits for Brunette from Wall Street. My unique personal style is elegant feminine chic. We could say it’s a mix of old money central European style influenced by my grandmothers and French style influenced by my half-French mother.
Admittedly, my grandmothers prefer the classy winter outfits presented in this article more than my mother. My mother doesn’t really care much about old money standards. I guess yours doesn’t either. But our grandmothers and mothers-in-law do.
So if you want to leave a good impression on your mother-in-law or to make your grandparents proud, better save/shop for these outfits.
THE BEST CLASSY WINTER OUTFITS 2023
All the collages and product galleries with my classy winter outfits presented in this article are hyperlinked and shoppable. I made sure you can shop all of my classy winter outfits 2023 with just a few clicks.
Click on the garment or accessory you need to copy my classy winter outfit, and you will be pointed to the online store where you can shop for the same item – or a very similar item if my item is already sold out. Point of view, this might happen in many cases. All in all, I shop for quality pieces that last me seasons and don’t need to shop for a new coat, or a new sweater every winter. Many of the clothes presented in this article are not from the latest collection. But they look as if they were brand new.
SIMPLE CLASSY WINTER OUTFITS FOR BRUNCH
We all feel the need to wear something new for brunch. All in all, dressing up for brunch comes with its own set of rules.
But to be entirely honest with you, I don’t make a fuss about it. I just grab the first dress, or bring some dark denim into the mix.
Discover my favourite winter brunch outfits with a poised elegance just ready and waiting for champagne and a French omelette. Finding your next brunch outfit has never been easier.
1 CAMEL COAT WITH DARK DENIM JEANS AND ANKLE BOOTS
A camel wrap coat is an investment piece that will stand the test of time and successfully bring some dark denim into the edit.
2 STRIPED BUTTON DOWN SHIRT WITH TWEED SKIRT AND CASHMERE TIGHTS
Be the talk of the country club in a striped button down and a short tweed skirt, or draw all eyes to you with a tweed jacket and cashmere tights.
Admittedly, this winter outfit presents a vision of winter classy that is more exceptional (read a bit too much of everything) than others. But if you are legit old money, you are entitled to have fun. It’s not cosplay for you.
EASY WINTER CLASSY OUTFITS FOR EVERYDAY
Simple and effortless, elegant and assured, these are the classy winter outfits that will be your winter wardrobe favourites for years to come.
Simple silhouettes and warm fabrics make these classy winter outfits the put-on-and-go option for a number of occasions. From fetching knitwear to soft tailoring, these classy winter looks will help you go through your busy schedule looking sophisticated with no effort at all.
3 CASHMERE TURTLENECK SWEATER WITH WOOL PANTS AND POINTY FLATS
You might be staying at home, but there is no room for sweatpants in this winter edit.
No matter what you are doing or where you might go, we all need that ultimate one-and-done outfit conventionally waiting in the drawer, ready to be picked up on a daily.
4 CARDIGAN SWEATER WITH BLACK WOOL SKINNY PANTS AND BALLET FLATS
Soft knits in pink set a cosy scene as we transition out of winter. Keep things classy with a pair of black wool skinny pants and precious slippers.
5 HOUNDSTOOTH WOOL BLAZER WITH DARK JEANS AND ANKLE BOOTS
We love winter for the layers. Enjoy the freedom of personalising your look with an expanded offering of separates.
Put on a chic black turtleneck top and dark denim jeans, style with a wool blazer and layer on a double-breasted coat.
Old money preppy looks are our preferred classy winter looks as we step forward into the future.
FORMAL CLASSY WINTER OUTFITS FOR DINNER
There are definitive occasions where you need to dress up for impact. From ball to dinner at home, each scenario calls for a formal classy winter outfit that looks sophisticated with just the right amount of effort implied.
6 A GOWN WITH OPERA GLOVES AND HEELS
From ballet to opera or ball, this winter is full of grand affairs to show off a proper gown. Stand out in deep hues paired with crisp white opera gloves for timeless elegance that whispers.
7 LONG SLEEVE PLEATED DRESS WITH PUMPS
Ready to dazzle, even the simplest of looks can be party ready for a casual old fashioned family dinner at home with the addition of a bow or pleats.
The vintage appeal of the bow tie and pleats are the perfect accompaniment for more formal events at home, whilst green hues are designed for a good night out.
CLASSY WINTER DATE NIGHT OUTFITS
Take the most effortless approach to winter date nights with a classy winter date night outfit that never disappoints.
Even though dressing up came back in full force for winter 2023, you might don’t want to embrace everything all at once.
From dinners at the restaurant to a night at the theatre, a little black dress is the best offering to match the mood and blend in with refined surroundings.
8 CAPE AND A LITTLE BLACK DRESS WITH HEELS
With a nod to vintage glamour, try an A-style little black dress. Layer with a black cape for a classy approach to dressing up.
QUIET LUXURY CLASSY WINTER OUTFITS FOR GRAND OUTDOORS
Times change, but if you know, you know. Some winter outdoor looks never feel old.
9 BARBOUR JACKET WITH SKINNY PANTS AND TALL BOOTS
Equestrians will always wear a simple black riding outfit with a Barbour jacket and tall boots for the grand outdoors.
Point of view, many times with skinny wool pants instead of breeches and casual brown tall leather boots. But you might want to shop for a black winter riding outfit first.
Browse through the widget below to shop for my Barbour jacket, black riding boots (similar to mine, but not real equestrian winter boots – you can’t walk in real equestrian boots – I added black riding style boots you will actually be able to walk in), and black skinny pants (IMAO you don’t need breeches if you are not equestrian).
10 CAPE WITH TURTLENECK TOP AND TWEED SHORTS
Go for a more fashion-forward option instead of the duffle jacket and leggings for ice skating. Tweed shorts have a vintage charm that lasts throughout the season paired with a cape and a cable knit turtleneck sweater. Plus, you can do jumps in tweed shorts and a cape more effortlessly.
By the way, I have a black cape and black ice skates, but white are more old fashioned.
FAQ WINTER CLASSY STYLE 2023
If you are feeling overwhelmed by choice and deliberating which direction to turn when you want to impress, go through the FAQ for classy winter style 2023 – it will help, for sure.
Not really. Classy winter outfits refer to the old money style, while elegant winter outfits can be classy, formal or fashion forward.
No! Winter classy is not the same as fancy winter style. Classy style is simple and refined, while fancy is cute but kitschy. POV Fancy is in style for winter 2023 – check fashionable winter outfits if you are looking for fancy winter outfits.
Rarely. At least not in Europe. Excluding the United Kingdom, of course. UK old money can often be everything but sophisticated and modest.
You can, but why would you want to pretend? You will only make a fool out of yourself. Instead, opt for quality pieces and simple silhouettes.
Elegance never goes out of style, not even when it’s cold.
Partly. You need to differentiate between the old money as a fashion trend of 2023/24 and the old money as what the old money actually wears. IRL, the old money doesn’t dress like from the Ralph Lauren catalogue for winter. All the contrary, the old money as a fashion trend of 2023/24 is inspired by Ralph Lauren, whereas the old money society wears whatever they have in their capsule winter wardrobe. POV Quality winter clothes and winter shoes that could resist the edge of time but are nonetheless contemporary.
First, invest in quality pieces that fit you well and are not too loose or too tight. Point of view, a good fit is key to looking polished and put together. Make sure you build a classy winter capsule wardrobe that applies to your lifestyle and has all the key winter pieces. Once you have your capsule wardrobe, copy the classy winter outfits presented in this article.
If you want to build a classy winter capsule wardrobe to look more elegant, you might want to get a Max Mara double breasted coat, Max Mara camel wrap coat, cape, duffle coat, duffle jacket, Barbour quilted jacket, cashmere shawl, a tweed jacket, wool blazer, striped button down shirt, ruffled silk blouse, neck tie blouse, cable knit crewneck sweater, cashmere turtleneck sweater, a pretty cardigan sweater, black skinny wool pants, midi pleated skirt, tweed skirt, midi A-style wool skirt, wool wide-leg pants, black jeans, knee high boots, mid heel leather ankle boots, riding boots, a top handle bag, leather gloves, wide brim felt hat, and a little black dress.
The easiest way to look classy in winter is to look for styles that are well-made and versatile, simple and sophisticated, preferably in neutral colors. Check classy winter outfits in this article for inspiration. Remember, it’s essential to keep your outfit understated and simple in order to achieve a classic, timeless look. Stick to solid colors and neutral patterns, and avoid anything too bold or flashy.
Sophisticated midi wedding guest dresses. Check winter wedding guest outfits to see the best classy wedding guest dresses for winter.
A little black dress, and a dress with long sleeves, a lapel collar and pleats that add elegance and sophistication to your outfits.
Bounclé jackets and bounclé skirts – Blair style bounclé set and bounclé sets you see on tiktok labelled as old money – is not old money. Little less classy. Tiktok “old money” and Blair’s style are kitschy and tacky. Do yourself a favour and wear something less tacky instead.
Point of view, I am guilty of having fun with tweed sets as well. Especially this season, when short tweed sets are in fashion. But you can disobey the rules if you don’t have to pretend to be old money or sophisticated. Also, I wear tweed instead of bounclé.
SEVEN MORE ELEGANT OUTFITS FOR WINTER
Wearing classy winter clothes is not the only way to look elegant in winter. Elegant winter style can be classy or formal, fashion forward or simple. Explore my favourite elegant winter outfits to dress more elegantly, but never look like a TikTok jester with pink cheeks, fake pearls, cropped Bounclé sets and riding boots. Up next: formal winter outfits.