Let’s Be Real—Old Money Style Isn’t Just a Trend, It’s a Lifestyle
You know that person who always looks effortlessly elegant, even if they just threw something on? Yeah, that’s old money energy. No loud logos, no neon trends—just timeless, quiet luxury that says, “I know who I am, and no, I don’t need to prove it.”
So if you’re here looking to channel that “I spend my summers in the South of France” vibe—without, you know, actually needing to be a Rothschild—welcome to the club. I’ve pulled together 20 summer outfit ideas that never go out of style. Not in 1965, not in 2025, and definitely not when you rock them next weekend.
These aren’t Pinterest board dreams—they’re practical, elevated looks you can pull off right now with a few key pieces. Ready? Let’s get classy.
1. The Crisp White Button-Down + Tailored Shorts Combo
The outfit that says, “I’m polished, but I could also sail a yacht.”
There’s just something about a white button-down that screams “old money.” It’s fresh, clean, and completely unbothered by trends.
Why it works:
- It’s structured but not stiff.
- Looks expensive even when it’s not.
- Works tucked or untucked—depending on your mood (and the brunch location).
Pro tip: Pair it with high-waisted khaki or linen shorts, brown leather sandals, and tortoiseshell sunglasses. Boom—instant Euro heiress energy.
2. A-Line Midi Dress in a Neutral Shade
Not all dresses have to scream “look at me.” Some just whisper, “I belong at this vineyard.”
The A-line midi dress is quiet luxury in garment form. Go for shades like ivory, navy, sage, or dusty rose. No wild prints. No sequins. Just clean lines and subtle elegance.
Style tips:
- Add a leather belt to define the waist.
- Wear with pointed flats or low espadrilles.
- A silk scarf around your neck or in your hair takes it to the next level.
Trust me, I wore this combo on a day trip to Lake Como (humble brag), and I’ve never felt more like a real-life Vogue cover story.
3. Linen Trousers + Sleeveless Knit Top
Chic enough for lunch on a terrace, breezy enough for ice cream runs.
Linen trousers are the ultimate “I have money but I don’t flaunt it” piece. They wrinkle a little—but in a charming, European kind of way.
Why I love this outfit:
- The sleeveless knit adds just enough structure.
- You can wear it with leather sandals, ballet flats, or even low-top sneakers.
- It looks 10x more expensive than it is—especially if you keep the palette neutral.
Rhetorical question time: Who needs logos when your outfit says “I’ve had a private stylist since birth”?
4. Monochrome Set in Beige or Cream
Because matching sets are the cheat code to looking expensive AF.
Nothing says “old money summer” quite like a well-tailored two-piece. And no, I don’t mean a suit (unless you’re planning to litigate someone into giving you their villa).
I’m talking:
- Beige or cream short-sleeve blouse
- Matching high-waisted shorts or flowy midi skirt
Throw in some gold jewelry (minimal, please), sunglasses, and a woven bag, and people will assume you just flew in from Saint-Tropez.
FYI, this also photographs ridiculously well—just in case you’re planning a casual Instagram soft launch of your summer aesthetic.
5. White Tennis Skirt + Oversized Cable-Knit Vest
Peak “trust fund baby on summer break” energy.
This one’s sporty, preppy, and weirdly powerful. Like you could take a tennis lesson, then fire your financial advisor for underperforming in the same afternoon.
Pair it with:
- A cable-knit sweater vest (bonus points for vintage Ralph Lauren)
- White low-profile sneakers or loafers
- A structured mini tote and slick ponytail
IMO, this is one of those looks that’s secretly comfy but still makes people think you have a house in Nantucket. Not a bad illusion to maintain. 😉
6. Chambray Shirt Dress + Leather Sandals
Effortless. Breezy. Like you just stepped out of a Nancy Meyers movie.
Chambray is the linen of the denim world—lighter, softer, and infinitely more “old money.” A well-fitted shirt dress in this fabric is a total summer staple.
What makes it great:
- It’s one-and-done (bless).
- Looks great belted or loose.
- You can dress it up with a statement bag or down with a straw hat.
I wore this exact outfit during a wine tasting tour last summer and had three people ask me where I bought it. I just smiled and said, “Oh, it’s vintage.” (It wasn’t. I got it on sale at Mango.)
7. Navy Blazer Over a White Sundress
When you want to say, “Yes, I brunch—but I also close real estate deals.”
A structured navy blazer is the unsung hero of old money fashion. Toss it over a simple white sundress, and suddenly you look like you summer in the Hamptons—even if you’re actually just heading to your local café.
Style it with:
- Brown leather loafers or kitten heels
- Pearl earrings (or faux, we won’t tell)
- A sleek top-handle bag
Pro tip: Go for a lightweight linen or cotton blazer to avoid turning into a walking sauna.
8. Silk Slip Skirt + Cashmere Tee
Yes, you can look expensive and still feel like you're wearing pajamas.
This combo is so effortless it’s almost rude. The contrast between a flowy silk skirt and a soft cashmere tee gives quiet luxury in all the right ways.
Why it slaps (IMO):
- The textures = chef’s kiss.
- It flatters just about every body type.
- It transitions from day to night with zero stress.
Add strappy sandals and a pair of vintage sunnies, and you’ve got a look that could pass at a private garden party or a museum date. Just, you know, don’t spill anything.
9. High-Waisted Pleated Shorts + Breton Stripe Tee
The Parisian cousin of the East Coast prepster. Très chic.
This outfit lives somewhere between “weekend at the country house” and “spontaneous trip to the Riviera.” The pleated shorts bring structure, and the Breton stripes bring Je ne sais quoi.
To get it right:
- Stick with navy and white (old money hates neon, remember?)
- Tuck in the tee for that polished look
- Finish with espadrilles and a woven tote
Ever wonder how some people make casual outfits look luxe? This is how.
10. Seersucker Dress + White Sneakers
Southern belle meets cool girl with a trust fund.
Seersucker is that charming, puckered fabric that basically screams, “I own a horse or two.” But don’t worry—you don’t need equestrian experience to wear it.
Why I swear by this dress:
- It’s breathable AF.
- The texture hides wrinkles (thank the fashion gods).
- It gives off those Southern charm + Upper East Side vibes.
I like pairing mine with minimalist white sneakers and a canvas crossbody bag for that modern, wearable balance.
11. Cream-Colored Romper + Loafers
Playful, polished, and possibly plotting a trust fund escape.
Not all rompers are created equal. A well-tailored, cream romper with structured shoulders and clean lines? Now that’s old money approved.
Make it pop with:
- A thin leather belt
- Gold chain jewelry (dainty, not chunky)
- And yes—actual loafers
This is one of those outfits that makes people think you’re effortlessly stylish… even if it took 45 minutes and two wardrobe meltdowns to decide on it. 😅
12. Button-Front Skirt + Collared Sleeveless Blouse
Basically the uniform of a girl who summers in Tuscany and reads first editions.
The button-front skirt (especially in linen or cotton twill) feels feminine without trying too hard. Paired with a collared sleeveless blouse, you’ve got instant vintage academia meets garden party vibes.
Wear it with:
- Wicker sandals or ballet flats
- A silk hair tie
- And, if you’re extra like me, a basket-style handbag
Rhetorical question incoming: Is it really summer if you don’t look like a Jane Austen character who modernized her closet?
13. White Linen Jumpsuit + Leather Sandals
Minimal effort, maximum “I summer in Capri” energy.
A white linen jumpsuit is the kind of piece that looks like you have a yacht even if you’re catching the bus. It’s clean, classic, and ridiculously breathable.
Pair it with:
- Brown leather slides or sandals
- A straw fedora (for that Euro-rich vibe)
- Gold hoop earrings (small and subtle, of course)
FYI: Stick to structured styles. No drawstring waists or spaghetti straps—this isn’t Coachella.
14. Light Blue Oxford Shirt + White Trousers
It's giving: vintage Ralph Lauren ad from the ‘90s.
There’s something about a blue oxford shirt—bonus points if you “borrowed” it from your dad or significant other. Tuck it into crisp white wide-leg trousers, and suddenly you’re that girl at the marina.
To finish the look:
- Espadrilles or canvas sneakers
- A brown leather belt
- Optional: Pop the collar if you're feeling cheeky 😏
Ever wondered how old money looks laid-back and put-together? This outfit right here.
15. Belted Shirt Dress + Straw Accessories
“I woke up like this,” but make it $300 brunch reservations.
A belted shirt dress walks that perfect line between comfy and tailored. The built-in waist shape says, “I tried,” while the relaxed silhouette says, “but not too hard.”
Wear it with:
- Straw bucket hat
- A raffia clutch or woven tote
- Sunglasses that are more attitude than function
Trust me, this is a go-to for those I-have-no-idea-what-to-wear-but-I-want-to-look-rich days.
16. Cropped Cardigan + High-Waisted Linen Pants
Slightly preppy. Totally posh.
If your wardrobe doesn’t already include a cropped, short-sleeve cardigan, please fix that immediately. Pair it with high-waisted linen pants, and voilà—you look like you just stepped off someone’s private jet.
Style tips:
- Keep the color palette muted (ivory, taupe, soft sage)
- Tuck in or crop the cardigan so it hits at the waistband
- Finish with leather sandals or ballet flats
This one’s especially great for those cooler summer nights where you still want to flex style points.
17. Monochrome All-Neutrals Ensemble
Because old money LOVES looking “simple”—just never cheap simple.
You really can’t go wrong with a head-to-toe neutral look. Think cream trousers, a beige tank, and a taupe jacket tied around your shoulders (because, obviously, you’re not cold, just fabulous).
Key rules here:
- Mix textures to avoid looking flat (e.g., silk top + cotton pants)
- Keep accessories understated but intentional
- Confidence is required—monochrome isn’t for the shy 😉
Also, fun fact: Neutrals photograph beautifully. Just saying.
18. Tennis Skirt + Cable Knit Vest
Even if you’ve never held a racket, you can still serve looks.
Channel your inner Serena-meets-Sloane with a white tennis skirt and a light cable-knit vest (bonus if it has that old-school V neckline). This look screams prep school alumni with a six-figure trust fund.
Pair with:
- Sneakers (not the gym kind)
- White ankle socks
- A low bun and minimalist studs
Don’t play tennis? Neither do I. Doesn’t matter—this outfit scores every time.
19. Floral Maxi Dress + Barely-There Sandals
Long, flowy, floral—like if your grandma had style and a Chanel account.
A floral maxi dress in soft, vintage-inspired prints is the unsung hero of old money summer wardrobes. Make sure the cut is classic—no cutouts, high slits, or loud neon.
For an ultra-chic finish:
- Choose delicate straps or a square neckline
- Add barely-there leather sandals
- Carry a structured mini bag (not your beach tote, babe)
Bonus points if you casually wear this to a winery or bookshop and act like it’s no big deal.
20. Silk Scarf Top + Tailored Shorts
It’s giving yacht party, but tasteful.
A silk scarf worn as a top (secured, don’t worry—this isn’t college) paired with high-waisted, tailored shorts is how you do summer glam without being flashy.
To avoid looking like you’re going clubbing:
- Keep shorts knee-length or mid-thigh
- Add pointed-toe flats or luxe slides
- Throw on a linen blazer if you want to up the sophistication
You’ll look like you came from sailing lessons—and somehow didn’t spill rosé on yourself. Magic.
🎯 Final Thoughts: Keep It Timeless, Keep It Luxe
And there you have it—20 old money summer outfit ideas that never go out of style. The real secret? It’s not about labels or trends. It’s about choosing pieces that whisper quality, embracing a neutral color palette, and giving just enough effort that it looks effortless.
So next time you're sweating over what to wear, just ask yourself: Would a woman named Margaux with an inheritance wear this?
If yes—go forth and slay, subtly.