Let’s be clear right out the gate: I don’t own a yacht. My kid thinks “budget” means “we still get snacks.” And my idea of financial planning is a coupon code and store credit. But I do know how to dress like someone who casually summers in the Hamptons and winters in Lake Como—even if I’m actually just walking to Target with an overpriced latte.
Old money style is not about splashing logos or bragging with labels. It’s about elegance that doesn’t need validation. Quiet luxury. Intentional layering. Looking like your clothes were inherited, not bought during a 40% off flash sale (even if they totally were).
So let’s dig into 17 old money-inspired outfits that are trending right now—and that you can build with the wardrobe you probably already have, or a well-timed thrift store run. Because style? That’s forever. And rich energy? That’s free.
1. Crisp White Shirt + Camel Trousers + Loafers
This is the holy grail of old money vibes. The shirt should be oversized—think “borrowed from my investment banker dad.” Tuck it loosely into camel trousers and finish with leather loafers. You’ll look like you brunch in French cafés and complain about poor wine lists.
Style tip: Cuff the sleeves, tuck only the front hem, and add a delicate gold chain. Power casual.
2. Cream Sweater + White Jeans + Ballet Flats
A monochrome moment that reads pure sophistication. The cream tones make you look expensive, like you have a skincare fridge and speak three languages. Opt for a knit sweater with texture—cable, waffle, or ribbed.
Pro move: Throw a cardigan over your shoulders like a scarf. Call it your “reading sweater.” Even if you’re just scrolling Instagram.
3. Navy Blazer + Striped Tee + Pleated Trousers
It’s Ivy League without the tuition. The navy blazer is your anchor piece. Add a striped boatneck tee and pleated trousers in beige, cream, or navy. Bonus if the trousers are high-waisted and well-structured.
Footwear? Leather slides or minimal loafers. Add tortoiseshell sunglasses and pretend you just got off a yacht.
4. Slip Dress + Chunky Knit + Mule Slides
Understated elegance. Your slip dress should skim the body, not cling. Add an oversized knit or cashmere sweater on top. It should look like you threw it on effortlessly while sipping morning espresso on a stone terrace.
Shoes? Sleek mules or pointed flats. Jewelry? One dainty ring and a whisper-thin bracelet.
5. Linen Button-Up + Wide-Leg White Pants + Vintage Belt
There’s something about linen that screams old family vineyard. Pair a breezy button-up (half-tucked, always) with white wide-leg pants. Add a leather belt with subtle gold hardware and minimalist sandals.
Sunglasses tip: Think oversized Jackie O, not TikTok influencer.
6. Silk Scarf + Trench Coat + Dark Wash Jeans
Trench coats are the outerwear of the elite. Add a silk scarf tied at your neck or in your hair, and suddenly you’re someone who’s on their way to the opera (or Trader Joe’s). Keep your jeans high-rise and straight-leg.
Color palette: Neutrals only—beige, cream, navy. Avoid neon like your reputation depends on it.
7. Cashmere Cardigan + Midi Skirt + Slingback Heels
Timeless and ladylike. Button your cashmere cardigan up like a top (or wear it backwards for bonus points). Your skirt should hit mid-calf and move like it has opinions. Pair with slingbacks for that retro elegance.
Where to wear it? Anywhere. You’ll feel like the star of a 90s Chanel ad—on a budget.
8. Sweater Vest + Button-Up + Tailored Shorts
Think boarding school meets Milan street style. A knit vest layered over a crisp white shirt, paired with structured shorts (linen or cotton, please). Add loafers with socks for full academic-chic.
Optional flex: A brooch or enamel pin. Trust me.
9. Black Turtleneck + Camel Coat + Leather Pants
Power. Mystery. A touch of arrogance. This outfit says “I read The New Yorker” and “I don’t answer DMs.” The turtleneck grounds you. The camel coat elevates you. And the pants—well, they whisper scandal in the classiest way.
Finish the look with sleek ankle boots and a clean center part.
10. Monochrome Beige Layers
Old money loves a tonal moment. Beige, cream, sand—stack ‘em like pancakes. Try a beige knit tank, oat-colored trousers, and a light trench or longline cardigan.
Textures matter: Mix knits, cottons, and wool for dimension. Add nude heels or white sneakers for modern contrast.
11. Button-Up Shirt Dress + Minimal Sandals
Shirt dresses are your rich-aunt uniform. They’re timeless, breezy, and structured in all the right ways. Choose one in a neutral color (olive, ivory, slate) and add a skinny belt if needed.
Sandals: Think Hermès vibes on a Marshalls budget. Clean lines, soft leather, no sparkle.
12. Silk Blouse + High-Waisted Trousers + Block Heels
This is CEO energy. Soft silk on top, structure on the bottom. Tuck in the blouse, add a subtle belt, and keep colors neutral. You’ll look like you run a luxury skincare line—even if you’re just running late to school pickup.
Bag suggestion: A croc-embossed satchel or vintage leather crossbody.
13. Tennis Skirt + Cable Knit Sweater + White Sneakers
Preppy with a punch. This one leans young, yes, but it’s got serious old money energy—especially if your sweater is Ralph, your skirt is pleated, and your sneakers are pristine.
Warning: Will make you want to drink matcha and read gossip columns.
14. Wool Midi Skirt + Turtleneck + Riding Boots
The equestrian core of quiet luxury. Look like you just left the stables, but in a polished, editorial kind of way. Stick to browns, olives, and creams.
Pro styling: Tuck the turtleneck in, add a leather belt, and finish with gold studs.
15. Silk Cami + Linen Blazer + Tailored Trousers
Dinner date? Work thing? Feeling dramatic on a Tuesday? This outfit covers it all. The cami brings softness, the blazer brings sharpness, and the trousers are the classy glue.
Bonus points for a soft bun, statement earrings, and walking like you own a villa.
16. Polo Sweater + Dark Jeans + Loafers
Polo knits are everywhere this season—and they’re giving serious “legacy student” energy. Pair with dark denim and glossy loafers. Keep your hair neat and your tote structured.
Make it yours: Choose earth tones—olive, taupe, chocolate—for a modern take on tradition.
17. Vintage Tee + High-Waisted Trousers + Oversized Blazer
Old money…but make it Gen Z. This one’s for when you want your outfit to say “I collect vinyl” and “my grandmother left me an estate” simultaneously. The tee should look lived-in, the trousers well-fitted, and the blazer like it has stories.
Complete the vibe with ballet flats or square-toe boots. No sneakers allowed.
What’s the Real Secret to Nailing Old Money Style?
It’s not just the outfits—it’s the energy. Here’s your cheat sheet:
- Stick to neutrals: No flashy colors, no loud prints. Think ivory, tan, navy, black, sage.
- Fit is everything: Tailor it or thrift smarter. Even $10 pants can look like $200 if they fit right.
- Fabrics matter: Cotton, wool, silk, linen. Avoid shiny synthetics unless they look luxe.
- Less is more: No chunky logo belts. Keep accessories minimal—gold hoops, leather bags, simple watches.
- Posture and presence: Quiet luxury isn’t loud. It walks tall, speaks low, and sips slowly.
Before You Go…
Here’s the truth: you don’t need new clothes. You need new perspective. The most “wealthy” thing you can wear is confidence. It’s the way you style your thrifted blazer. The way you layer that cardigan. The fact that your $30 dress makes you feel like a million.
So go ahead. Wear that linen like you inherited it. Rock that silk like you iron it with champagne steam. Because you don’t need money to dress like old money—you just need taste.
