Let’s be real — some trends scream louder than a tourist at the Eiffel Tower. But old money style? Oh, honey… it whispers. And that’s exactly why it never goes out of fashion.
If you’ve ever looked at someone and thought, “She looks like she summers in the Hamptons and owns at least one yacht,” chances are, she’s rocking that quiet luxury aesthetic. The old-money look isn’t about screaming labels — it’s about looking effortlessly expensive. And yes, you can nail that vibe without maxing out your Amex (thankfully).
FYI, I’ve been living for this aesthetic lately. It’s like dressing for a Nancy Meyers movie… but make it 2025. So if you’re ready to serve understated elegance all summer long, I’ve rounded up 15 timeless outfit ideas that’ll have you oozing class — without looking like you tried too hard. Ready to look like your closet has a trust fund?
Let’s go, duchess 💅
1. White Linen Everything
You can’t talk about old money summer without mentioning white linen. It’s practically a uniform.
Why it works:
Breathable (aka sweat-proof-ish)
Always crisp and clean
Screams “I own a villa in Tuscany”
Style tip: Pair a white linen button-down with matching wide-leg trousers. Add gold hoops, leather sandals, and a low bun. Done. You look like you summer in Sicily.
Pro move: Drape a sweater over your shoulders. Because rich people are always prepared for a breeze.
2. The Tailored Shorts + Blazer Combo
You know what says, “I play tennis at the club and drink iced matcha”? A tailored short suit.
Go for:
A structured blazer in cream, beige, or muted pastels
High-waisted tailored shorts
A crisp white tee or silk cami underneath
Why it slays: It’s put-together but not stiff. Plus, it transitions from lunch to cocktails like a pro.
Add: Loafers or classic ballet flats (please, no flip-flops. We’re classy now.)
3. Nautical Stripes but Make It Luxe
Not the cheesy red-white-and-blue version. Think more French Riviera, less 4th of July BBQ.
What to wear:
Navy and white striped knit top
White A-line skirt or cropped trousers
Woven straw tote (bonus points for a vintage Hermès scarf tied to the handle)
Why it’s timeless: It’s Audrey Hepburn meets Sofia Richie.

4. Slip Dresses + Cardigans = Summer Romance
There’s something insanely elegant about a bias-cut silk slip dress with a soft cashmere cardigan casually tossed over the shoulders.
Why we love it:
It’s feminine without being fussy
Transitions easily from day to night
It whispers “old money” and flirts with “it girl”
Pro tip: Stick to muted tones like champagne, sage, or dusty rose. No neon. Ever. Like, ever ever.

5. Monochrome Neutrals (AKA the Secret Sauce)
Wearing all beige might sound boring… until you realize you look like you just stepped out of a Celine ad.
How to pull it off:
Choose shades that are just slightly off from each other (think oatmeal + camel)
Mix textures: linen, cotton, silk
Keep accessories minimal and luxe
You’ll look like you’re on your way to a silent auction, and honestly? We love that for you.
6. Pleated Tennis Skirts & Polos (Preppy Chic)
I know, I know — tennis core is having a thing right now, but old money girls have worn this for, like, ever.
What to wear:
Crisp white or pastel polo
High-waisted pleated mini or midi skirt
Pullover sweater tied around the neck (classic move)
Finish the look: Loafers, low ponytail, vintage watch. You’re officially main character at the country club.
7. The White Shirt Dress (A Must-Have)
Simple, elegant, endlessly wearable.
Why it’s old money approved:
Clean lines = timeless
Works with sandals, espadrilles, or heels
Easy to dress up or down
Add a belt if you want shape. Or leave it loose and breezy for that, “Oh, I just threw this on” vibe.
8. Cashmere + Shorts = Elite Casual
I swear this combo shouldn’t work — but it does.
Here’s the formula:
Lightweight cashmere sweater in ivory or powder blue
Tailored cotton shorts
Loafers or leather sandals
Add oversized sunnies and a leather crossbody, and you’ll look like you’re heading to a brunch that costs more than my weekly grocery bill.
9. Midi Skirts with Structure
Soft, swishy, and stunning.
Think:
A-line or pleated midi skirt
Sleeveless knit top
Minimalist leather sandals
Throw on a headband or a classic barrette and channel that 1950s understated glam.
10. Chic Jumpsuits That Mean Business
The right neutral-toned jumpsuit will have you looking very pulled together.
Why we love it:
It’s comfy but structured
One-and-done outfit (lazy girl win)
Feels modern but totally timeless
Belt it, add some gold jewelry, and voilà — instant elegance.
11. Button-Downs Tucked into High-Waisted Jeans
Yes, jeans can be old money… but only if they’re the right kind.
Golden rules:
Go for straight-leg, rigid denim
No rips, no distressing (we’re not influencers at Coachella)
Pair with a cotton or silk button-down
Tuck it in, throw on some loafers, and top with a straw hat. Boom — classy but casual.
12. Espadrilles + Flowy Dresses = Peak Summer Rich Girl
There’s something so coastal grandma about this pairing… and that’s not an insult. At all.
What works:
Flowy floral or eyelet midi/maxi dresses
Neutral espadrilles
Light cardigan or shawl for breezy nights
Add pearls if you’re feeling extra. Or don’t. You already look like a walking lifestyle Pinterest board.
13. Blazer Over a Mini Dress? Yes, Please.
It’s a bit “cool aunt with connections” — and I’m here for it.
Style formula:
Mini shift or slip dress
Oversized linen or cotton blazer
Pointed-toe flats or mules
Top it off with an Hermès-style scarf in your hair. Bonus if it flutters in the breeze like you’re in a perfume ad.
14. The Silk Scarf Moment
Okay, this isn’t an “outfit” per se, but it makes the outfit.
How to style it:
Tie around your neck like a Parisian
Use it as a headband or ponytail wrap
Add to your bag strap for instant luxe vibes
It’s a tiny detail that makes a massive impact. Trust.
15. All-White Ensemble = Instant Elegance
Monochrome white is risky if you’re clumsy (me 🙋♀️), but the reward is unmatched.
Why it works:
Makes you look taller, richer, and possibly unbothered
Feels luxe in literally any setting
Works with minimal effort
Just maybe don’t eat spaghetti in it. Unless you live dangerously. 😉
Final Thoughts: Be That Girl, Just Quieter
Old money style in summer is less about showing off and more about showing up — with confidence, grace, and a little glint of “I know something you don’t.” You don’t need a trust fund or a yacht (though, hey, if you have one, can I come?) — just great tailoring, quality fabrics, and an eye for timeless pieces.
So which of these outfits are you dying to try this summer? Are you more of a linen girl or a tennis-core queen? Whatever your vibe, lean in, stay classy, and let them wonder where your inheritance came from 😉
And hey — if you found this helpful, share it with your fashion bestie. Let’s keep the chic secrets between us… or not 😏