As someone who values timeless style, I’m always on the lookout for outfit inspiration that evokes refinement, sophistication, and just a touch of luxury. Lately, I’ve been obsessed with the old money aesthetic—think Blair Waldorf from Gossip Girl or the Hamptons socialite. It’s a look that manages to be both elegant and effortlessly chic.
This trend harkens back to a bygone era of refined taste and sophisticated dressing, embodying the essence of classic American and European upper-class style. If you’re looking to infuse your wardrobe with some old money vibes, you’ve come to the right place. I’ve curated a comprehensive list of 40 old money aesthetic outfits that will help you achieve that coveted look of effortless chic.
Old money style is all about quality over quantity, favoring well-tailored pieces in neutral colors and classic patterns. Think preppy meets vintage with a touch of modern flair. These outfits aren’t just about looking wealthy; they’re about cultivating an air of timeless sophistication that never goes out of style.
Whether you’re heading to a country club brunch, a day at the office, or a casual weekend outing, these old money outfits will ensure you look polished and put-together.
So, if you also love the Blair Waldorf style and want to channel the refined prep of old money fashion, keep reading for chic inspiration on how to nail the aesthetic from head to toe!
1. Slip Dress with a Tweed Blazer
Nothing says old money quite like the combination of a sleek slip dress and a structured tweed blazer. This outfit seamlessly blends feminine charm with masculine tailoring, creating a look that’s both sophisticated and effortlessly chic.
I recommend opting for a silk slip dress in a neutral tone like champagne or ivory, paired with a tweed blazer in a complementary hue.
The key to nailing this old money outfit is in the accessories. Add a pair of pearl earrings and a delicate gold necklace to enhance the elegant vibe. Finish the look with a pair of pointed-toe kitten heels or classic pumps. This ensemble is perfect for a gallery opening or a fancy lunch date.
2. White Skirt Suit
Channel your inner Jackie Kennedy with a crisp white skirt suit. This timeless ensemble screams old money fashion and exudes an air of refined elegance. Choose a well-tailored blazer with a nipped-in waist and pair it with a knee-length pencil skirt for a classic silhouette.
To truly embody the old money aesthetic, keep accessories minimal but impactful. A strand of pearls or a vintage brooch adds just the right touch of sophistication.
I always advise wearing nude or white pumps or knee-high boots to elongate the legs and maintain the clean, monochromatic look. This outfit is ideal for business meetings or upscale daytime events.
3. Linen Shirt, Pleated Shorts, and Cozy Sweater
For a more casual take on old money style, try pairing a crisp linen shirt with pleated shorts and a cozy sweater draped over your shoulders. This outfit is perfect for a day of sailing or a leisurely brunch at the country club. I love how this combination balances comfort with polish, embodying the effortless chic that’s so central to old money fashion.
Choose high-quality fabrics in neutral tones like white, beige, or navy to keep the look authentic. Add a pair of leather loafers or boat shoes to complete the preppy vibe.
Don’t forget to accessorize with a classic watch and maybe a pair of tortoiseshell sunglasses for that extra touch of old money elegance.
4. Cable Knit V-Neck Sweaters with Khaki Pants
Nothing says old money quite like a cable knit sweater paired with well-fitted khaki pants. This classic combination is a staple of preppy, old money style. Opt for a V-neck sweater in a rich, neutral color like cream, navy, or forest green. The texture of the cable knit adds visual interest while maintaining that air of understated luxury.
I recommend choosing khaki pants with a straight or slightly tapered leg for a timeless silhouette. Roll the cuffs slightly to show off a pair of leather loafers or boat shoes.
This outfit is perfect for a casual day out or a weekend at the family estate. Add a leather belt and a simple watch to complete the look.
5. Ribbed Dress with Sweater
For a feminine take on old money fashion, try a ribbed dress layered with a sweater. This combination is both comfortable and elegant, perfect for transitional weather or air-conditioned interiors.
Complete the look with a pair of ballet flats or low-heeled pumps. This ensemble is ideal for a day of shopping or afternoon tea with friends.
6. High-Neck Top with Crop Blazer and Jeans Combo
This outfit perfectly blends classic old money style with a modern twist. Start with a high-neck top in a luxurious fabric like silk or fine cotton. Layer it with a cropped blazer – I recommend opting for a tailored piece in a neutral color like navy or camel. The cropped length adds a contemporary touch to the traditional blazer silhouette.
Pair this top half with well-fitted, straight-leg jeans in a light wash. The key to making jeans work in an old money outfit is choosing a pair with a clean, classic cut and no distressing.
Finish the look with pointed-toe flats or low heels. This ensemble is perfect for casual Fridays at the office or a weekend lunch date.
7. White Cardigan with Flowing White Long Skirt
Nothing says old money quite like an all-white ensemble. A soft, white cardigan paired with a flowing white long skirt creates a look of effortless elegance. I love how this combination exudes a sense of purity and sophistication that’s quintessentially old money.
Choose a cardigan in a fine knit and a skirt in a lightweight fabric like linen or cotton for the perfect summer outfit. Add a delicate gold necklace and some simple sandals to complete the look. This outfit is ideal for a garden party or a seaside stroll.
8. Black Ruffle Top with White Linen Trousers
For a chic monochrome look with old money vibes, pair a black ruffle top with crisp white linen trousers. The contrast between the black and white creates a striking visual, while the ruffle detail adds a touch of femininity to the ensemble.
I recommend choosing a ruffle top with subtle details – think small ruffles along the neckline or sleeves rather than overly dramatic ones.
9. Floral Dress with White Tall Boots
While old money style often leans towards solid colors, a tasteful floral print can add a touch of whimsy to your outfit. Pair this dress with white tall boots for an unexpected twist that still feels classic.
I always advise opting for boots with a low to medium heel to maintain that effortless old money vibe. This combination works wonderfully for transitional seasons and can take you from day to night with ease.
10. Turtleneck Sweater with Mini Skirt and Long Blazer
This outfit combines several old money staples into one chic ensemble. Start with a fitted turtleneck sweater – cashmere if you really want to lean into the luxury. Pair it with a mini skirt in a complementary color or pattern (think plaid or houndstooth for true old money vibes).
Layer a long blazer over the top to add sophistication and balance out the shorter skirt. I recommend choosing a blazer in a neutral tone like camel or navy. Finish the look with loafers or ankle boots. This outfit is perfect for a day at the office or a dinner date.
11. Tweed Blazer with Matching Pants
Nothing says old money quite like a tweed suit. This classic fabric has been a staple of upper-class wardrobes for generations, and for good reason. It’s durable, stylish, and exudes an air of refined taste. Choose a well-tailored blazer and pair it with matching pants for a cohesive look.
Pair your tweed suit with a simple white blouse and classic pumps. Add a strand of pearls for that extra touch of old money elegance. This outfit is perfect for business meetings or upscale daytime events.
12. Classy Black Top with Blue Jeans
While jeans might not be the first thing that comes to mind when you think of old money style, a well-chosen pair can work beautifully in a sophisticated outfit. The key is to choose a pair of light wash, straight-leg jeans with no distressing. Pair these with a classy black top – think a silk blouse or a fine-knit sweater.
I recommend adding some old money touches to elevate this casual combo. A string of pearls, a classic watch, or a pair of diamond stud earrings can transform this look from everyday to elegant. This outfit is perfect for casual Fridays or weekend brunches.
13. Long Wool Coat with White Trousers
A long wool coat is a staple of old money winter wardrobes. Choose a coat in a classic color like camel, navy, or black. The key is to ensure it’s well-tailored and made from high-quality wool. Pair this statement piece with crisp white trousers for a striking contrast.
Keep the rest of the outfit simple when wearing such a strong combination. A simple sweater or blouse underneath will suffice. This outfit is perfect for chilly days and will have you looking effortlessly chic as you stroll through the city.
14. Beige Turtleneck Knit Sweater with Beige Pants
Monochromatic outfits are a hallmark of old money style, and this all-beige ensemble is no exception. Start with a luxurious beige turtleneck sweater – cashmere if you want to fully embrace the old money aesthetic. Pair this with beige trousers in a slightly different shade for some subtle contrast.
The key to pulling off this look is in the fit and quality of the pieces. Both the sweater and pants should be well-tailored to your body. I recommend adding some texture with accessories – perhaps a crocodile-embossed belt or a pair of suede loafers. This outfit is perfect for a day at the office or a casual dinner out.
15. Blue Ruffle Blouse with White Jeans
For a fresh take on old money style, try pairing a blue ruffle blouse with crisp white jeans. The ruffle detail adds a touch of femininity and whimsy to the outfit, while still maintaining that air of sophistication. Choose a blouse in a light, airy fabric like silk or chiffon for the best effect.
I always advise keeping the ruffles subtle – think a small ruffle along the neckline or sleeves rather than an overly fussy design. Pair this with straight-leg or slightly bootcut white jeans. Finish the look with strappy heels and delicate gold jewelry. This outfit is perfect for a summer garden party or a casual day out.
16. Crewneck Striped T-Shirt with Shorts
Channel preppy old money vibes with a classic crewneck striped t-shirt paired with tailored shorts. This combination is perfect for casual summer days while still maintaining that air of effortless elegance. This ensemble is ideal for a day of sailing or a casual lunch at the country club.
17. Gray Vest with Jeans
For a more casual take on old money style, try pairing a tailored gray vest with well-fitted jeans. This combination strikes the perfect balance between formal and relaxed, embodying the effortless chic that’s so central to old money fashion.
This ensemble is perfect for casual Fridays at the office or weekend outings.
18. White Vest with Black Shorts
This black and white combination is a fresh take on old money style, perfect for warmer weather. Start with a crisp white vest – choose one that’s well-tailored and made from a high-quality fabric like linen or a cotton blend. Pair this with black tailored shorts for a striking contrast.
Complete the outfit with black or white loafers and minimal gold jewelry. This ensemble is ideal for a summer lunch date or a day at the yacht club.
19. Front-Open Cardigan Sweaters with Black Top and Shorts Combo
Layering is key in old money fashion, and this outfit perfectly demonstrates how to do it with style. Start with a simple black top – a silk camisole or a fitted t-shirt works well. Pair this with tailored shorts for a sleek base.
I always advise choosing a cardigan in a neutral color like beige, gray, or cream for versatility. The cardigan should be lightweight and drape nicely for that effortless old money vibe. This outfit is perfect for a casual day out or a relaxed dinner with friends.
20. Blue Striped Shirt with Navy Blue Pants
This classic combination is a staple of old money wardrobes. Start with a crisp blue and white striped button-down shirt. The stripes should be thin and even for that timeless look. Pair this with well-tailored navy blue pants – choose a straight leg or slightly tapered cut for the most flattering silhouette.
I recommend tucking in the shirt and adding a leather belt for a polished finish. Complete the look with brown leather loafers and a matching watch. This outfit is versatile enough for the office, a lunch meeting, or even a casual dinner out.
21. Pink Button-Up Shirt with White Dress Pants
For a fresh take on old money style, try pairing a soft pink button-up shirt with crisp white dress pants. This combination is perfect for spring and summer, offering a light and elegant look that’s still firmly rooted in classic style. Choose a shirt in a high-quality cotton or linen for the best effect.
Complete the look with brown ballet flats and delicate gold jewelry. This outfit is ideal for a summer wedding or an upscale daytime event.
22. Long Gray Coat with Jeans
A long gray coat is a versatile piece that can instantly elevate any outfit to old money status. Pair it with well-fitted jeans for a look that’s both sophisticated and relaxed. Choose a coat in a luxurious wool or cashmere blend for the ultimate in old money style.
I recommend opting for dark wash, straight-leg jeans to keep the look polished. Layer a simple sweater or blouse underneath the coat. This ensemble is perfect for running errands in style or a casual day out in the city.
23. Vest Top with Slim Pants
For a sleek and modern take on old money style, try pairing a tailored vest top with slim pants. This combination offers a sophisticated silhouette that’s both timeless and contemporary. Choose a vest in a luxurious fabric like silk or a fine wool blend, and pair it with well-fitted slim pants in a complementary color.
Add a crisp white shirt underneath the vest for a more formal touch, or wear it alone for a sleeker look. Complete the outfit with ballet flats and minimal jewelry. This ensemble is perfect for a business meeting or an upscale dinner event.
24. Blue Button-Up Shirt with Beige Shorts
This classic combination is a staple of preppy old money style, perfect for warm weather. Start with a crisp blue button-up shirt in a high-quality cotton. Choose a light to medium blue for a fresh, summery look. Pair this with well-tailored beige shorts that hit just above the knee.
I recommend rolling up the sleeves of the shirt for a more relaxed vibe. Add a braided leather belt and boat shoes or ballet flats to complete the look. This outfit is ideal for a casual day out, a weekend brunch, or even a relaxed business casual setting in warmer months.
25. Quarter Zip with White Jeans
A quarter zip sweater paired with white jeans is a classic old money look that’s perfect for transitional weather. Choose a quarter zip in a luxurious fabric like cashmere or a fine wool blend. Navy, forest green, or burgundy are all great color choices that embody that old money aesthetic.
Complete the look with leather loafers and a simple watch. This outfit works well for casual Fridays at the office or weekend outings.
26. Ribbed Top with Tennis Skirt and Pullover Ensemble
Channel your inner country club chic with this sporty yet sophisticated ensemble. Start with a fitted ribbed top in a neutral color like white or cream. Pair this with a pleated tennis skirt – white is classic, but navy or forest green can also work well.
Layer a V-neck pullover sweater over your shoulders for that quintessential old money look. I recommend choosing a sweater in a complementary color to your skirt. Finish the outfit with knee high boots. This look is perfect for a day at the country club or a casual weekend outing.
27. Long Light Blue Dress
A long, flowing dress in light blue is the epitome of old money summer style. Choose a dress in a lightweight fabric like cotton or linen, with a simple, elegant cut. The length should be midi to maxi for that classic old money look.
I always advise keeping accessories minimal with this type of dress – a pair of pearl earrings and a delicate bracelet are all you need. Add a pair of neutral sandals or pumps to complete the look. This outfit is perfect for a summer garden party, a day at the races, or an outdoor wedding.
28. Trench Coat with White Pants
A classic trench coat paired with crisp white pants is a timeless old money combination that works for various occasions. Choose a high-quality trench in a neutral color like beige or khaki. The coat should be well-fitted and hit just above the knee for the most flattering silhouette.
I recommend pairing this with straight-leg or slightly wide-leg white pants for a clean, sophisticated look. Add a simple blouse or sweater underneath the coat. This ensemble is perfect for transitional weather and can take you from the office to dinner with ease.
29. Fuzzy Cardigan with White Pants
For a cozy yet elegant look, try pairing a fuzzy cardigan with white pants. Choose a cardigan in a luxurious fabric like mohair or a soft wool blend. Neutral colors like cream, beige, or light gray work best for that old money aesthetic.
Pair this combination with a simple silk camisole or light sweater underneath. Complete the look with loafers or ballet flats and delicate gold jewelry. This outfit is perfect for a casual day out or a cozy dinner at home.
30. Black Long Fitted Dress with Neck Scarf
A black long fitted dress is a timeless piece that exudes old money elegance. Choose a dress in a luxurious fabric like silk or a high-quality jersey, with a simple, classic cut. The length should be midi to maxi for that sophisticated look.
Add a silk neck scarf to elevate this outfit and give it that quintessential old money touch. Choose a scarf with a subtle pattern in complementary colors. Finish the look with pointed-toe pumps and minimal jewelry. This ensemble is perfect for an evening event, a formal dinner, or any occasion where you want to look effortlessly chic.
31. Black Top with Brown Trousers
For a sophisticated and versatile old money look, pair a simple black top with brown trousers. Opt for brown trousers in a rich, warm tone like chestnut or chocolate. The pants should be well-tailored with a straight or slightly wide leg.
Add a pair of black or brown leather pumps and a black belt to complete the look. This outfit is perfect for the office, a business lunch, or an art gallery opening.
32. Black Off-the-Shoulder Top with Grey Pants
An off-the-shoulder top adds a touch of elegance and femininity to any outfit. Pair this with well-tailored grey pants for a sophisticated monochrome look.
Complete the look with black pumps and statement earrings. This ensemble is perfect for a dinner date, a cocktail party, or any event where you want to look effortlessly chic.
33. Cropped Jacket with Jeans
A cropped jacket paired with jeans is a classic old money look that balances casual and refined. Finish the look with loafers or ankle boots and a structured handbag. This outfit is perfect for a casual day out, shopping, or a lunch date.
34. Brown Long Skirt with White Shirt
A brown long skirt paired with a white shirt is a timeless combination that exudes old money elegance. Choose a flowing skirt in a rich brown tone, ideally in a luxurious fabric like silk or fine wool. Pair this with a crisp white button-down shirt for a classic look.
I recommend tucking in the shirt and adding a slim belt for definition. Complete the outfit with pointed-toe flats or low heels in a complementary color. This ensemble is perfect for a variety of occasions, from the office to an art gallery opening to a dinner out.
35. All White Set with Brown Belt
An all-white outfit is a hallmark of old money summer style. Choose a matching set in a high-quality fabric like linen or cotton – think wide-leg pants with a matching blazer or a tailored shirt and trouser combination.
I always advise adding a brown leather belt to break up the monochrome and add a touch of contrast. Finish the look with brown leather sandals or pointed toe flats and minimal gold jewelry. This outfit is perfect for a summer garden party, a day at the races, or any upscale daytime event.
36. Contrast Knit Dress
A contrast knit dress is a versatile piece that can easily fit into an old money wardrobe. Look for a dress with a classic silhouette – perhaps an A-line or sheath style – in a fine knit material. The contrast could come in the form of color blocking or textural differences in the knit pattern.
I recommend keeping accessories minimal with this type of dress – a simple pair of earrings and a watch should suffice. Add a pair of pointed-toe pumps or strappy heels to complete the look. This outfit is ideal for a day at the office, a lunch meeting, or even a casual dinner out.
37. Black Tank Top with Pants and Striped Sweater
This layered look is perfect for transitional weather and embodies the preppy side of old money style. This outfit is versatile enough for a day of shopping, a casual lunch, or even a relaxed office environment.
38. White Shirt with Khaki Pants and Sweater
This classic combination is a staple of old money casual wear. Start with a crisp white button-down shirt and well-fitted khaki pants. Layer a sweater over your shoulders for that preppy touch – choose a color that complements the khaki, like navy, forest green, or burgundy.
I recommend completing the look with leather loafers and a matching belt. Add a simple watch for that final old money touch. This outfit is versatile enough for a day at the office, a weekend outing, or a casual dinner with friends.
39. Button-Down Long Sleeve Knit Cardigans with Black Jeans
For a cozy yet elegant look, pair a button-down, long sleeve knit cardigan with black jeans. Choose a cardigan in a luxurious fabric like cashmere or merino wool, in a neutral color like beige, gray, or cream.
I always advise opting for high-quality, well-fitted black jeans without any distressing for that polished old money look. Complete the outfit with ankle boots or loafers and minimal jewelry. This ensemble is perfect for a casual day out, running errands in style, or a relaxed dinner with friends.
40. Hair Bow with Black Blazer
While not an outfit per se, adding a hair bow to your look is a classic old money touch that can elevate any ensemble. Pair a simple black velvet or grosgrain ribbon bow with a tailored black blazer for a sophisticated and feminine look.
I recommend keeping the rest of the outfit simple – perhaps a white blouse and well-fitted trousers or a pencil skirt. The key is to let the hair bow and blazer be the focal points. This look works well for the office, a formal lunch, or any event where you want to add a touch of old money elegance to your outfit.
