This post will inspire you with 24 chic wardrobe ideas to achieve the old money aesthetic.
When it comes to fashion, nothing says sophistication quite like the old money aesthetic.
Think chic, timeless looks, and your go-to response being “Oh, this? I’ve had it forever.”
If you’re ready to channel your inner “socialite”, these 24 wardrobe essentials will help you master old money outfits.
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The Timeless Basics
1. White Button-Down Shirt
Every old money wardrobe starts here. Crisp, tailored, and versatile, it’s the epitome of effortless elegance. Pair it with tailored trousers or tuck it into your favorite pleated skirt.
2. Classic Trench Coat
Perfect for rainy strolls on cobblestone streets or simply looking polished on a blustery day. Bonus points if it’s in a versatile, neutral color (like beige/tan).
Add a silk scarf for that extra dose of sophistication, and you’re ready to conquer the day (or at least look gorgeous trying).
3. Tailored Blazer
A structured blazer instantly elevates any look. Stick to neutral tones and wear it over a button-down or draped over your shoulders.
4. Wool Coat
A long, tailored wool coat screams sophistication, especially in camel, navy, or black.
It’s like a hug from your rich aunt who summers in the Hamptons — warm, reassuring, and oh-so-stylish.
5. Neutral Sweaters
Cashmere, merino, or a soft knit — layer them for that cozy, rich look.
Go for muted tones like cream, taupe, or grey. Bonus points for pairing it with pearls and a warm cup of tea in hand.
Preppy Must-Haves
6. Pleated Skirts
Channel your inner Ivy Leaguer with a structured pleated skirt, paired with a sweater or blazer.
Choose classic patterns like plaid or keep it simple with solid tones.
7. Polo Shirts
Understated and oh-so-preppy, polos are perfect for that “sailing on the weekend” aesthetic. Pair them with high-waisted shorts or linen trousers for that effortless, nautical look.
8. Cardigans
Buttoned up or draped over your shoulders, a cardigan adds a touch of vintage charm.
Go for soft pastels, neutrals, or even a bold red, and don’t be afraid to play with textures like cable knit or cashmere.
9. Loafers
The footwear equivalent of “I brunch at the country club.”
Leather or suede in neutral shades will be your best bet if you want to get a quality pair that is versatile. Add a tassel detail for that extra touch of preppy pizzazz.
10. Argyle Sweaters
A preppy staple that pairs beautifully with pleated skirts or tailored trousers.
Luxury Staples
11. Silk Scarves
Wear it around your neck, in your hair, or tied to your bag for a touch of Parisian chic.
Pro tip: Look for vintage designer ones — they’re instant conversation starter.
12. Pearl Jewelry
Classic, understated, and forever elegant — pearls are non-negotiable for old money outfits. Whether it’s a strand necklace or delicate earrings, pearls are your new best friend.
13. Leather Tote Bag
No logos, just buttery leather in a timeless design that whispers wealth instead of shouting it. It should be roomy enough for a hardcover novel and your monogrammed planner.
I love this simple but chic tote bag by Quince – it has an Italian leather exterior with an easy to clean lining and a center zipper divider roomy enough for a 13-inch laptop + 3 slip pockets.
14. Gold Hoop Earrings
Small, minimalist hoops are a subtle nod to old-school glamour. They pair perfectly with an updo or a slick ponytail.
15. Monogrammed Handkerchiefs
Because nothing says “luxury” quite like personalized accessories. Keep one tucked in your bag for those moments you need to dab your face.
Sophisticated Eveningwear
16. Little Black Dress
Coco Chanel got it right — every wardrobe needs a timeless LBD.
Think Audrey Hepburn in Breakfast at Tiffany’s. Add a string of pearls, and voilà, you’re ready for anything from cocktails to galas.
17. Floor-Length Gown
For those black-tie events (or just dressing up for fun), a sophisticated gown is essential.
Look for classic cuts in rich fabrics like silk or velvet.
18. Satin Midi Skirt
Chic, versatile, and perfect for pairing with a cashmere sweater or fitted top.
A satin midi skirt is the perfect option for those semi-formal evenings when you want to look polished but not overdone.
19. Pointed-Toe Heels
Elegant and elongating, a classic pair of pointed-toe heels is a must-have. Go for neutral tones or rich jewel colors like emerald or navy for versatile outfits.
Weekend Casual
20. Straight-Leg Jeans
Dark wash, no distressing. Pair with loafers, ballet flats, or heels for a polished off-duty look.
Add a trench coat and a Breton stripe top for a casual chic look.
21. Breton Stripe Top
Nothing says “old money” quite like navy-and-white stripes.
Pair it with linen trousers or denim for that carefree coastal vibe.
22. Ballet Flats
Comfortable yet chic, these are perfect for leisurely coffee dates or museum visits.
Choose pairs with subtle details like a bow or metallic trim for a hint of personality.
23. Linen Trousers
Breezy, sophisticated, and ideal for warmer weather. Pair with a solid top or button-down for a versatile, chic look.
24. Panama Hat
For sunny days, this stylish accessory adds a touch of flair to any outfit. Think “ladies who lunch” meets Riviera chic.
Achieving the old money aesthetic isn’t just about what you wear — it’s how you wear it.
Confidence, poise, and a no-fuss attitude are key. With these 24 chic wardrobe staples, you’re well on your way to curating the perfect “Pinterest-inspired” old money outfits.
Xoxo,
Diana Colibri
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