Fashion trends come and go, but some styles never go out of fashion. The old money aesthetic is one of them. It’s all about looking classy, elegant, and timeless without trying too hard.
Think tailored blazers, soft neutral colors, and simple yet luxurious details. This style isn’t about flashy logos or bold statements—it’s about quiet confidence and understated charm.
In this blog post, we’ve put together 30 outfit ideas that capture the essence of old money elegance. Whether you’re dressing up for a special event or keeping it casual, these looks are perfect for anyone who loves classic, sophisticated fashion.
Get ready to discover how to create a wardrobe that’s both timeless and effortlessly chic. Let’s dive in!
1. Brown Blazer and Mini Pencil Skirt
Pair a tailored brown blazer with a mini pencil skirt for a look that’s both professional and chic.
Add black sheer tights and black pointed-toe heels to elongate your legs, and finish with a black quilted shoulder bag for a touch of understated luxury.
2. White Striped Button-Up Cardigan
A white striped button-up cardigan paired with a white pencil skirt creates a monochromatic look that’s clean and sophisticated.
Accessorize with a black shoulder bag to keep the outfit balanced and timeless.
3. White Shirt and Beige High-Waisted Shorts
For a casual yet polished look, tuck a crisp white button-up shirt into beige high-waisted shorts.
Add a brown leather belt to define your waist and complete the outfit with classic loafers.
4. White Tweed Jacket and Mini Skirt
Nothing says old money quite like tweed. A white tweed jacket paired with a matching mini skirt creates a cohesive and sophisticated look.
The black quilted handbag adds a classic touch, while two-tone ballet flats bring a playful yet elegant element to the outfit. This ensemble is perfect for afternoon tea or a day at the races.
5. White Off-Shoulder Shirt and Button-Fly Jeans
Embrace feminine charm with this outfit. An off-shoulder white button-up shirt paired with button-fly jeans creates a perfect balance between casual and chic.
This look is ideal for weekend outings or casual dinner dates, offering a fresh take on the classic white shirt.
6. Black Button-Up Vest and Beige Wide-Leg Trousers
For a more androgynous old money look, try this combination. A black button-up vest paired with beige wide-leg trousers creates a sleek, sophisticated silhouette.
The thin belt adds definition to the waist, enhancing the overall polished appearance.
7. Light Blue Shirt and Dark Pinstriped Maxi Skirt
This outfit brings a sporty twist to the old money aesthetic. A light blue button-up shirt tucked into a dark pinstriped maxi skirt creates an interesting contrast.
The white baseball cap adds a casual, preppy touch. This ensemble is perfect for a day at the country club or a casual lunch with friends.
8. Black Strapless Corset Top and White High-Waisted Shorts
For a more daring take on the old money look, try this combination.
A black strapless corset top paired with white high-waisted shorts creates a striking contrast. The black belt adds definition and ties the look together.
9. White Button-Up Shirt and Black Cropped Blazer
This outfit exudes power and elegance. A white button-up shirt layered under a black cropped blazer creates a sharp, professional look.
The black mini skirt with a slit adds a touch of allure while maintaining sophistication. This ensemble is perfect for important business meetings or high-end dinner events.
10. White Button-Up Shirt and Beige Tailored Shorts
For a relaxed yet polished look, try this combination. A white button-up shirt tucked into beige tailored shorts creates a fresh, summery vibe.
The brown leather belt adds structure, while the beige knit sweater tied around the shoulders is the quintessential old money accessory.
11. White Button-Up Shirt and Beige Wide-Leg Trousers
This outfit is a classic old money staple. A crisp white button-up shirt paired with beige wide-leg trousers creates a timeless silhouette.
The black thin belt adds definition, while the black handbag completes the look with a touch of sophistication.
12. Black Turtleneck Top and Houndstooth Skirt
Embrace classic patterns with this outfit. A black turtleneck top paired with a black and white houndstooth skirt creates a sophisticated look that’s straight out of a vintage fashion magazine.
The black handbag adds the finishing touch to this timeless ensemble, perfect for afternoon tea or a day at the museum.
13. Black Sleeveless Turtleneck Top and Wide-Leg Trousers
This all-black outfit is the epitome of understated elegance. A black sleeveless turtleneck top paired with black wide-leg trousers creates a sleek, elongated silhouette.
The black belt adds definition to the waist, enhancing the overall polished appearance.
14. Blue Striped Cropped Shirt and White Wide-Leg Trousers
Channel coastal chic with this outfit. A blue striped cropped button-up shirt paired with white wide-leg trousers creates a fresh, nautical-inspired look.
The brown leather crossbody bag adds a touch of warmth to the ensemble. This outfit is perfect for seaside lunches or yacht club events.
15. Blue Striped Shirt and Navy Wide-Leg Trousers
This outfit combines multiple old money staples. A blue striped button-up shirt paired with navy wide-leg trousers creates a cohesive base.
The cream sweater tied over the shoulders adds a preppy touch, while the two-tone ballet flats complete the look with classic elegance.
16. Black Turtleneck Top and Beige Trench Coat
This outfit is perfect for transitional weather. A black turtleneck top layered under a beige trench coat creates a sophisticated base.
Black shorts paired with sheer black tights add a touch of allure, while black pointed-toe heels elongate the legs. This ensemble is ideal for autumn gallery openings or upscale evening events.
17. Black Halter Neck Top and White Pencil Skirt
This outfit is a study in elegant contrasts. A black halter neck top paired with a white pencil skirt creates a striking yet sophisticated look.
Black pointed-toe heels and a black handbag complete the ensemble with classic accessories. This look is perfect for cocktail parties or evening events.
18. White Striped Sweater and Wide-Leg Trousers
This outfit combines comfort with style. A white striped sweater paired with white wide-leg trousers creates a cohesive, monochromatic base.
The black leather jacket adds an edge, while the black belt defines the waist. This ensemble is perfect for casual outings or weekend brunches.
19. White Strapless Mermaid Gown
Channel your inner Hollywood starlet with this glamorous outfit. A white strapless mermaid gown paired with white pointed-toe shoes creates a stunning, elegant silhouette.
This ensemble is perfect for formal events or black-tie galas, guaranteed to turn heads.
20. Red Strapless Midi Dress
Make a statement with this bold yet sophisticated outfit. A red strapless midi dress with a full skirt exudes confidence and elegance.
Paired with nude ankle-strap sandals, this ensemble is perfect for summer weddings or upscale garden parties.
21. White Sleeveless Mini Dress
Embrace simplicity with this sleek outfit. A white sleeveless mini dress with an A-line silhouette paired with white pointed-toe heels creates a fresh, modern look. This ensemble is perfect for summer events or cocktail parties.
22. Camel Long Coat and Black Turtleneck Top
This outfit is perfect for cooler weather. A camel long coat layered over a black turtleneck top creates a sophisticated silhouette.
The black quilted handbag adds a touch of luxury. This ensemble is ideal for autumn strolls in the park or upscale shopping trips.
23. White Cropped Cardigan and Wide-Leg Trousers
This monochromatic outfit exudes elegance. A white cropped cardigan paired with white wide-leg trousers creates a cohesive, sophisticated look.
Black pointed-toe shoes add a contrasting touch. This ensemble is perfect for summer events or upscale luncheons.
24. White Oversized Blazer and Wide-Leg Trousers
This outfit is a classic old money staple. A white oversized blazer paired with white wide-leg trousers creates a sleek, monochromatic look. The pearl necklace adds a touch of timeless elegance.
25. Black Baseball Cap and Oversized Blazer
This outfit combines casual elements with old money sophistication. A black baseball cap paired with a black oversized blazer and white t-shirt creates an interesting contrast.
White wide-leg trousers complete the look. This ensemble is perfect for casual outings or weekend brunches.
26. Cream Long Coat and Beige Wide-Leg Trousers
This outfit is a study in sophisticated neutrals. A cream long coat layered over a white top and beige wide-leg trousers creates a cohesive, elegant look.
This ensemble is perfect for autumn events or upscale shopping trips.
27. White Button-Up Mini Dress
Embrace feminine charm with this outfit. A white button-up mini dress with short sleeves creates a fresh, summery look.
The brown crossbody bag adds a touch of warmth. This ensemble is perfect for weekend outings or casual lunch dates.
28. Black Oversized Blazer and Turtleneck Sweater
This outfit combines multiple old money staples. A black oversized blazer layered over a white turtleneck sweater creates a sophisticated base.
Sheer black tights paired with white ribbed socks and black loafers add interesting texture. This ensemble is perfect for autumn gallery openings or casual dinner parties.
29. Black Off-Shoulder Mini Dress
This outfit is perfect for evening events. A black off-shoulder mini dress with long sleeves creates a sleek, sophisticated silhouette.
Black knee-high boots add a touch of drama. This ensemble is ideal for cocktail parties or upscale dinner dates.
30. Shirt Dress and Loafers
A shirt dress with a notched lapel collar is perfect for a casual yet polished look. Pair it with loafers for a touch of old-money charm.
