Introduction
Old Money fashion is all about timeless elegance, understated luxury, and refined taste. Inspired by icons like Carolyn Bessette-Kennedy and Grace Kelly, this style focuses on quality fabrics, classic cuts, and neutral tones. It’s less about trends and more about pieces that last a lifetime—think crisp white shirts, tailored trousers, and cashmere knits. In this guide, we’ll explore 25 Old Money Outfit Ideas to help you build a wardrobe rooted in grace, heritage, and quiet sophistication.
1. Crisp White Button-Up + Pleated Trousers for a Quietly Powerful Look
Channel timeless elegance with a crisp white button-up shirt paired with high-waisted pleated trousers. Opt for natural fabrics like cotton or linen in shades like cream or navy. Finish the look with leather loafers, a sleek bun, and a minimal gold necklace—perfect for a museum stroll or brunch at a private club.
2. Silk Scarf + Cashmere Sweater Draped Over Shoulders
Embrace European flair with a neutral cashmere sweater casually draped over your shoulders and a silk scarf tied at the neck. Style it over a fitted white tee and tailored pants. Add ballet flats, tortoiseshell sunglasses, and a structured handbag for a Riviera-inspired ensemble.
3. Tweed Skirt Suit + Classic Loafers for a Museum Date
Nothing says old money like a Chanel-style tweed skirt suit. Choose soft pastel or neutral tones and pair it with penny loafers or low kitten heels. Add pearl earrings, a leather strap watch, and a vintage clutch—ideal for gallery openings or afternoon teas.
4. Tennis Skirt + Cable-Knit Vest for a Preppy Edge
Tap into prep-school vibes with a crisp tennis skirt and a cable-knit vest layered over a button-down. Stick with whites, navies, or light grays. Complete the look with white sneakers, calf socks, and a canvas tote for a collegiate yet elevated day outfit.
5. Camel Trench Coat + Slacks for Transitional Seasons
A camel trench coat is a must-have in any old money wardrobe. Layer it over a black turtleneck and tailored slacks. Add leather loafers or heeled boots, a silk scarf around your neck, and minimal makeup for a rainy-day city walk or travel day.
6. Navy Blazer + Straight-Leg Jeans for Smart Casual
Pair a structured navy blazer with straight-leg jeans for a polished casual look. Underneath, wear a crisp white tee or blouse. Accessorize with a leather belt, loafers or ankle boots, and a top-handle bag. Perfect for casual lunches or semi-formal gatherings.
7. White Linen Dress + Straw Hat for a Garden Party
Lightweight and breathable, a white linen dress paired with a wide-brimmed straw hat is the epitome of summer elegance. Add tan leather sandals, pearl studs, and a woven clutch. Ideal for garden parties or country estate visits.
8. Black Turtleneck + Beige Trousers for a Minimalist Look
Go for a clean silhouette with a fitted black turtleneck tucked into beige or cream trousers. Add sleek loafers, a leather watch, and your hair slicked back in a bun or ponytail. A look that’s equal parts serious and chic.
9. Striped Button-Down + Khakis for a Weekend Retreat
A blue-striped button-down shirt and khaki trousers are classics that never fail. Keep it untucked for a more relaxed vibe and roll up the sleeves. Wear with driving shoes, a canvas tote, and sunglasses for a coastal or countryside weekend getaway.
10. Cream Cable-Knit Sweater + Midi Skirt for Cozy Elegance
Pair a thick cream cable-knit sweater with a pleated midi skirt in soft tones. Add riding boots or ballet flats, gold hoops, and a topcoat if needed. A great look for cooler months and leisurely outings.
11. White Polo + Tailored Shorts for Yacht Days
Wear a fitted white polo shirt with high-waisted tailored shorts in navy or tan. Add espadrilles or boat shoes, a woven bag, and aviator sunglasses. This outfit is ideal for boat days, lunches at the marina, or coastal vacations.
12. Silk Blouse + High-Waisted Trousers for Dinner Parties
A silk blouse in champagne or ivory tones pairs perfectly with high-waisted trousers and heels. Style your hair in soft waves and accessorize with pearls or gold drop earrings. Elegant and appropriate for formal dinners or social clubs.
13. Pastel Sweater Set + Ballet Flats for a Feminine Look
Match a pastel cardigan with a knit tank or bralette and a matching skirt. Stick to shades like dusty pink or lavender. Ballet flats, delicate necklaces, and natural makeup will complete this sweet and feminine old money look.
14. Oxford Shirt + Crewneck Sweater for Preppy Simplicity
Layer a crewneck sweater over an Oxford shirt for a true prep-school vibe. Pair with pressed chinos or slacks and loafers. Ideal for school campus strolls, coffee dates, or low-key errands.
15. Long Wool Coat + Leather Gloves for Winter Sophistication
During colder months, nothing says wealth like a tailored long wool coat in camel, black, or navy. Pair with leather gloves, a cashmere scarf, and riding boots. A sophisticated look that speaks volumes with minimal effort.
16. Linen Blazer + White Slacks for a Summer Soirée
Combine a lightweight linen blazer with white slacks and a pastel blouse underneath. Style with heeled sandals, dainty jewelry, and a straw clutch for summer dinners or outdoor weddings.
17. Silk Slip Dress + Cardigan for Evening Grace
A silk slip dress in a muted tone (champagne, navy, or black) worn with a soft cardigan over the shoulders is perfect for elegant evenings. Finish the look with strappy sandals, pearl earrings, and a vintage handbag.
18. Boatneck Top + Cropped Trousers for French Elegance
A striped or solid boatneck top paired with cropped trousers delivers Parisian chic. Add slingback heels, red lips, and a leather crossbody bag. Understated and effortlessly elegant.
19. White Jeans + Cashmere Tee for Luxe Casual
Style a neutral cashmere tee with white jeans and tan loafers. Add a silk hair scarf and structured handbag for a rich casual aesthetic that works well for city strolls or brunch.
20. Checked Blazer + Black Slacks for a Heritage Touch
A checked blazer adds a vintage, aristocratic flair to any outfit. Wear with black tailored slacks, a turtleneck, and ankle boots. Finish with gold studs and a minimalist bag for a classic, heritage-inspired look.
21. Maxi Skirt + Button-Up for Effortless Grace
Tuck a soft cotton or silk button-up into a high-waisted maxi skirt. Pair with sandals, a leather belt, and gold accessories for a feminine and fluid silhouette that’s perfect for weekends or vacations.
22. Monochrome Neutrals + Loafers for Everyday Chic
Style yourself in head-to-toe beige, ivory, or gray. Mix tones and textures to add interest. Add classic loafers, a belt, and a long coat for an everyday old money ensemble.
23. A-Line Dress + Pearls for a Classic Brunch Look
An A-line dress in a solid or small-print pattern paired with pearl accessories is timeless. Add kitten heels and a dainty purse for a polished outfit that works for church, brunch, or family events.
24. Beige Blouse + Pencil Skirt for Office Refinement
Choose a structured blouse in beige or ivory tucked into a tailored pencil skirt. Add low heels, a leather tote, and delicate jewelry for a look that transitions from office to dinner with ease.
25. Pleated Maxi Dress + Vintage Accessories for Formal Events
For fancier occasions, go for a pleated maxi dress in navy, emerald, or burgundy. Accessorize with vintage brooches, evening gloves, and satin heels. A show-stopping look that maintains quiet luxury roots.
Conclusion
The Old Money aesthetic is about investing in timeless, versatile pieces that exude quiet confidence. By choosing quality over quantity, and embracing classic silhouettes and neutral palettes, you can embody this iconic style daily. Whether you’re dressing for brunch, a yacht day, or simply want to refine your look, these 25 outfit ideas offer endless inspiration. Mix and match, stay elegant, and don’t forget—true style whispers. Save this post and share your favorite outfit below!
