The “old money” aesthetic has made a powerful return in modern fashion, yet it never truly went out of style. Quiet luxury, classic tailoring, and effortless elegance define this timeless trend. Unlike flashy fashion statements or fast-changing streetwear, old money casual outfits focus on quality over quantity, heritage over hype, and subtle sophistication over loud logos.
Whether you’re strolling through the French Riviera, enjoying a garden brunch in the Hamptons, or simply embodying an elegant yet relaxed vibe in your everyday life, the right wardrobe makes all the difference. In this article, we’ll break down 16 old money casual outfits that perfectly balance understated elegance with practical comfort.
What Is the “Old Money” Style?
Before diving into the outfits, it’s important to understand the ethos of old money style. It’s not about price tags—it’s about timeless taste. Inspired by generations of family wealth, prep school uniforms, country club leisure, and European vacations, the old money aesthetic reflects:
- Neutral colors
- Quality natural fabrics (linen, wool, cotton, cashmere)
- Classic silhouettes
- Minimal or no logos
- Polished but never showy accessories
Now, let’s explore 16 old money casual outfits that speak volumes without ever shouting.
1. Crisp White Button-Down & Khaki Trousers
This timeless pairing is the foundation of old money style. A well-fitted cotton or linen button-down shirt tucked into high-waisted khaki or beige trousers gives off an Ivy League charm. Add loafers or leather sandals and a leather belt to complete the look.
Style Tip: Roll the sleeves casually for a relaxed, “off-duty yacht club” vibe.
2. Cable-Knit Sweater Over Shoulders + Tennis Skirt
Popularized by prep schools and tennis clubs, this outfit screams vintage wealth. Tie a cable-knit sweater over your shoulders and pair it with a white pleated tennis skirt and simple sneakers or ballet flats.
Colors to Try: Navy, cream, soft pastels.
3. Tailored Blazer with White Jeans and Loafers
Blending business casual with weekend chic, a tailored navy or houndstooth blazer worn over a tucked-in t-shirt or blouse, paired with white denim, is a fail-proof old money casual look.
Footwear: Opt for suede loafers or low-heeled mules.
4. Polo Shirt & Pleated Trousers
The classic polo—especially in muted shades like forest green, navy, or soft pink—pairs beautifully with pleated trousers. This look is unisex and can be worn with subtle jewelry and leather belts for added polish.
Optional Accessories: Pearl studs or a leather-strap watch.
5. Linen Dress with Espadrilles
Light, breathable, and always classy, linen dresses in neutral or pastel tones are a warm-weather essential. Choose midi or knee-length styles for refined charm.
Perfect For: Garden parties, beach walks, or Sunday brunch.
6. Cashmere Sweater + Wool Skirt
Cashmere is the ultimate old money fabric. A camel or oatmeal-colored cashmere crewneck paired with a plaid or solid wool skirt is both cozy and chic.
Finish the Look: With Mary Janes or heeled ankle boots.
7. Oxford Shirt & High-Waisted Shorts
For a youthful but sophisticated summer look, pair a crisp Oxford shirt with tailored shorts in beige, navy, or white. Leather sandals and a straw hat add a European vacation feel.
Bonus Points: French tuck the shirt and accessorize with a silk scarf.
8. Silk Blouse & Wide-Leg Pants
Channel your inner aristocrat with a silk or satin blouse tucked into wide-leg trousers. Ideal for relaxed dinners or gallery visits, this outfit glides between casual and refined with ease.
Palette Tip: Soft ivory, olive green, or deep navy work beautifully.
9. Striped Breton Shirt & Cream Trousers
French-inspired and effortlessly chic, the Breton stripe top has long been associated with inherited wealth and sailing holidays. Pair with cream or beige trousers and simple loafers.
Keep It Classy: Avoid over-accessorizing—let the stripes speak.
10. Cardigan Set with Midi Skirt
Two-piece cardigan sets (especially in cashmere or fine wool) paired with midi skirts offer a nostalgic, ’50s socialite vibe. Look for pearl buttons or cable-knit patterns.
Style Trick: Button only the top or middle button for a laid-back charm.
11. Double-Breasted Blazer over Casual Dress
Throwing a well-structured blazer over a casual knit or cotton dress immediately elevates the look. Opt for tweed, plaid, or solid neutral tones.
Shoes: Loafers, brogues, or low block heels.
12. Turtleneck & High-Waisted Denim
A fitted turtleneck in a solid color (cream, navy, black) with high-waisted, straight-leg denim is a minimal, smart outfit. Think Jackie Kennedy on a chilly weekend getaway.
Add: A leather shoulder bag and oversized sunglasses.
13. Boat Neck Sweater & Slim Trousers
Boat neck sweaters reveal just a hint of collarbone while maintaining modesty. Pair with cigarette or slim-cut trousers and ballet flats.
Style Heritage: Inspired by old European seaside estates.
14. Quilted Vest with Riding Pants
For a countryside or autumn aesthetic, wear a quilted vest (Barbour style) over a long-sleeve shirt with riding pants or dark leggings.
Ideal For: Outdoor walks, country clubs, or morning markets.
15. Monochrome Beige or Cream Outfit
Wearing a single color—especially in rich neutral tones like beige or off-white—makes even the simplest outfit feel luxurious. A cashmere sweater and trousers or skirt in similar tones = quiet power.
Optional: Gold accessories, a silk headscarf, or a classic tote.
16. Denim Shirt with Cream Slacks
Yes, denim can be old money—if styled right. A soft chambray or light denim shirt, slightly oversized, tucked into cream slacks creates an easygoing yet tasteful outfit.
Look Complete: Finish with brown loafers and tortoiseshell sunglasses.
Old Money Brands to Explore
To truly embody the old money casual aesthetic, look for brands that prioritize heritage, tailoring, and craftsmanship. Here are a few labels often associated with the style:
- Ralph Lauren
- Brooks Brothers
- J.Crew (vintage line)
- Loro Piana
- Brunello Cucinelli
- Barbour
- GANT
- Max Mara
- Everlane (minimalist twist)
You don’t always need to buy from luxury brands—just opt for high-quality fabrics, tailored fits, and timeless cuts.
Final Thoughts
The beauty of the old money casual style lies in its restraint. It doesn’t beg for attention—it earns admiration quietly. By focusing on timeless pieces, natural fabrics, and refined silhouettes, you can build a wardrobe that doesn’t just follow trends but defies time itself.
Whether you’re assembling an outfit for a Sunday brunch, a museum outing, or a casual stroll through town, these 16 old money casual outfits will help you dress with elegance, confidence, and grace.