Because You Deserve to Look Like You Vacation in Monaco (Even If You’re Just Hitting Trader Joe’s)
Alright, let’s be honest — summer fashion can get... messy. Between the neon trends, see-through mesh disasters, and random fringe that somehow keeps coming back (why though?), it’s easy to forget one thing: class never goes out of style.
That’s where old money summer style struts in — calm, collected, and utterly timeless. Think barefoot at the country club energy. Minimal effort, max impact. I’ve personally leaned into this aesthetic over the past few summers, and not to be dramatic, but it’s changed my entire wardrobe mindset. Fewer pieces, better quality, and a whole lot of “Oh this? I’ve had it forever.”
Ready to channel that understated elegance? Let’s kick off with 6 old money-inspired outfits that’ll have you exuding quiet luxury all season long.
1. Crisp White Linen Set
The “I Have a Summer Home, Don’t Ask Where” Look
There’s just something magical about an all-white linen outfit — like it whispers trust fund with every sway in the breeze.
What you need:
- Linen button-down shirt (slightly oversized, always unwrinkled — or artfully wrinkled, if you know what I mean)
- Matching white linen shorts or wide-leg pants
- Neutral slides or espadrilles
This look is breezy, effortless, and somehow makes iced coffee taste better. Pair with oversized sunglasses and a smug sense of calm. It’s giving Amal Clooney on holiday, minus the paparazzi.
2. Pleated Tennis Skirt + Sleeveless Knit Polo
For When You Want to Look Athletic... But Don’t Do Sports 😅
You don’t need to swing a racket to rock tenniscore. This combo screams private school alumni brunch without looking like you’re trying too hard.
Try this:
- White pleated skirt or skort (bonus if it has a built-in short)
- Fine-knit sleeveless polo in cream, navy, or dusty blue
- White sneakers (leather, never mesh)
Add a gold bracelet or two, slick your hair into a low bun, and you’re basically ready to inherit a vineyard. IMO, this outfit works for both errands and accidental yacht invites.
3. Silk Slip Dress + Loafers
The Lazy Girl’s Secret Weapon (That Looks Like a Power Move)
Not gonna lie — this one’s my go-to when I have 10 minutes to get ready but still want to look like I read the Financial Times.
Your toolkit:
- Bias-cut silk or satin slip dress in a muted shade (champagne, forest green, or black)
- Leather loafers or classic ballet flats
- Optional: drape a cashmere sweater over your shoulders if you’re feeling extra prep
There’s nothing flashier than subtlety, and this combo nails it. It’s sexy without trying, elegant without effort, and shockingly comfy. Ever walked into a room and felt like old money? This does that.
4. Wide-Leg Trousers + Striped Button-Down
A Coastal Classic That Never Misses
Picture this: the wind off the Amalfi coast, a chilled glass of white wine, and your shirt gently billowing like you’re in a slow-motion movie scene. That’s the energy here.
The formula:
- High-waisted, wide-leg trousers (linen or lightweight wool)
- Light blue or pastel striped button-down (tucked in or tied at the waist)
- Brown leather belt + simple sandals
This look works for literally anything — lunch with the girls, strolling through an art gallery, or pretending you totally read all those books on your shelf.
5. Structured Sundress + Minimalist Accessories
Old Money Barbie, but Make It Subtle
You know those dresses that just fit right? Like they were made for sipping rosé on a shaded terrace? That’s what we’re after here.
Go for:
- A-line or belted midi sundress in soft cotton or linen
- Muted tones: sage green, blush, navy, or cream
- Keep accessories classic — gold hoops, dainty pendant, leather sandals
Avoid ruffles, glitter, or anything that screams “I bought this for Coachella.” Instead, aim for clean lines and quality fabric. Add a straw tote and boom — peak quiet luxury.
6. Cable-Knit Sweater Over the Shoulders (aka Rich Girl Layering)
Yes, It’s a Cliché. Yes, It Still Slaps.
The sweater-over-the-shoulders move is peak “my dad owns a country club” energy — and I love it. It’s not about the sweater itself. It’s the gesture.
Here’s how to wear it:
- Pair with a tank dress, skirt set, or button-down outfit
- Pick a lightweight knit in beige, ivory, or soft pastel
- Drape, tie, and walk around like you’re late for your tennis lesson
You won’t believe how this tiny styling trick elevates literally any outfit. I once wore it over a $15 dress and got asked if I was “in fashion.” Go figure.
7. Khaki Shorts + Cashmere Tee Combo
Minimalism, But With a Trust Fund
You know what never gets old? A well-fitting pair of khaki shorts paired with a buttery-soft tee. Add a little luxury with the fabric — think lightweight cashmere or a silk-cotton blend. And yes, even in summer. It’s all about the elevated basics here.
Here’s how to rock it:
- Tailored khaki or beige shorts (mid-thigh to knee length, no frays)
- Fitted cashmere or high-end cotton tee
- Leather slides or loafers
- A structured tote bag and timeless sunglasses (Ray-Ban Clubmasters, anyone?)
It’s chill. It’s classy. It makes it look like you “just threw something on” — except that something happens to be quiet-luxury perfection.
8. The White Eyelet Dress
Cottagecore, but She Went to Boarding School
Okay, hear me out — a white eyelet dress isn’t just for tea parties or family photos at the vineyard. It’s a summer staple that hits that perfect sweet spot between sweet and sophisticated.
Look for:
- Midi or maxi length (avoid anything too mini — we’re going for grace, not Gossip Girl reboot)
- Eyelet or broderie anglaise detailing
- Puff sleeves or a square neckline for a vintage nod
Pair it with tan sandals, a woven clutch, and simple pearl studs. FYI: this dress is also ideal for pretending you read Jane Austen by candlelight.
9. Navy Blazer + White Tee + High-Waisted Shorts
The “I Summer in the Hamptons” Starter Pack
There’s something incredibly powerful about mixing formal with chill — and this combo is a masterclass. It’s the “smart casual” of the old money universe.
Style it like this:
- Crisp white tee (or ribbed tank, if you’re feeling cheeky)
- Tailored high-waisted shorts — in white, tan, or muted plaid
- Navy blazer (unstructured or double-breasted = chef’s kiss)
- Loafers or leather sandals
Roll up the blazer sleeves, tuck in the tee, and maybe throw on a vintage gold chain. You’ll look like you walked straight off a Ralph Lauren ad, and TBH? We love that for you.
10. Silk Scarf as a Top (Yes, Really)
Flirty Meets Classy — The Summer Edition
Now, this one requires a bit of finesse — and fashion tape. But when done right? A silk scarf top oozes effortless summer glam. Old money girls love a good creative layering moment that still keeps things elegant.
Here’s the move:
- Pick a silk scarf in classic patterns (chains, paisleys, crests — think vintage Versace vibes)
- Fold and tie as a halter or bandeau
- Pair with linen trousers or a high-waisted midi skirt
- Add strappy flats and minimal gold jewelry
Just avoid neon or loud prints — we want to say “vintage Monaco,” not “TikTok try-on haul.” 😉
11. Monochrome Beige Ensemble
Because Looking Expensive Is a Color Palette
If beige were a personality, it’d definitely own multiple homes, play tennis on Wednesdays, and collect old books just because. A monochrome beige or cream outfit gives instant class — no logos needed, just clean lines and rich textures.
Try this combo:
- Beige high-waisted trousers or culottes
- Matching silk or linen tank
- Optional: Oversized blazer or trench for layering
- Finish with tan slides and a soft leather bag
Bonus: This look photographs insanely well. I wore something similar to a wine tasting last summer and got asked if I was an interior designer. (Reader, I am not.)
12. Seersucker Co-Ord Set
For When You Want to Channel “New England Summer Royalty”
Seersucker is like the unofficial fabric of old money summers. It’s breezy, it’s crisp, and it has that "I’ve been attending regattas since I was 7" vibe.
The set you need:
- Button-up seersucker shirt + matching high-waisted shorts or skirt
- Choose classic blue-and-white, or pastel yellow if you're feeling bold
- Boat shoes, leather sandals, or low espadrilles to complete the look
Wear it tucked or half-tucked, add a woven hat, and you’ve got the ideal outfit for summer brunches, art fairs, or pretending you’ve read The Economist front to back. 😉
🌞 Midway Style Tips: How to Keep It Looking Old Money, Not New Flashy
Before we move into the final part (yes, I’m saving the absolute best looks for last 👀), let’s lock in some key details. It’s not just what you wear — it’s how you wear it.
👗 Texture Over Trend
Stick with fabrics that feel elevated: linen, cotton poplin, silk, wool blends. Leave the polyester blends for the fast fashion crowd.
💄 Subtle > Flashy
Old money style isn’t about attention-seeking. It’s about confidence. Think natural makeup, classic hairdos (hello, bun or soft waves), and accessories that whisper, not scream.
🧺 Wrinkles? No Thanks.
Iron your linen. Steam your silk. Trust me, no outfit screams “wannabe” louder than crumpled pants. Ironically, effortless style actually takes effort.
13. White Linen Suit
Yes, You Can Wear a Suit in Summer — and Look Like a Fortune Heir
Let’s talk power. Not the loud, brash kind — the kind that strolls through a garden party in a white linen suit and makes people ask, “Wait, are they famous?”
Here’s how to work it:
- Crisp white or ivory linen blazer + matching trousers or skirt
- Keep it simple underneath: a silk cami or fitted tank
- Add loafers or low-heeled sandals
- Pearl studs, a structured handbag, and maybe a silk scarf for flair
Bonus points if you wear this to a gallery opening or wine tasting and pretend you own the vineyard. 😉
14. Cable Knit Sweater + Pleated Tennis Skirt
Ivy League Girl Summer — No Legacy Letter Required
This combo is so classically old money it might as well come with a monogrammed family crest. It's flirty, it's polished, and yes — it's comfy enough for both brunch and badminton.
To nail the look:
- Soft cable knit sweater (off-white or navy is ideal)
- High-waisted pleated skirt — aim for cream, beige, or pastel
- Sneakers, espadrilles, or ballet flats
- Throw on a pearl necklace or barrette if you’re going full prep
This is my go-to for coastal weekends. It says “I could have gone to Yale,” even if I barely passed geometry.
15. Cream Shirt Dress + Leather Belt
“I Woke Up at the Villa and Had to Dress in 5 Minutes”
Want the easiest way to look expensive with zero effort? Enter the shirt dress. Cream or ivory, in linen or cotton poplin, cinched with a sleek belt — it's practically the Swiss Army knife of the old money wardrobe.
Key details:
- Look for a structured collar and button-down front
- Cinch at the waist with a leather belt (brown, tan, or navy)
- Pair with loafers, simple sandals, or low wedges
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Add a straw hat and you’re good for the vineyard, museum, or casual yacht trip (because those are normal things, right?)
16. Boatneck Knit Top + Cropped Trousers
French Riviera, but Make It East Coast
There’s something ridiculously elegant about a boatneck knit top — it’s giving Grace Kelly without trying too hard. Pair it with tailored cropped trousers, and boom: effortless European chic with old-money attitude.
Your outfit checklist:
- Boatneck or bateau neckline top (navy, cream, or striped)
- High-waisted, cropped trousers — preferably in beige or white
- Leather slingbacks or pointy flats
- Add a watch and structured bag to elevate the whole vibe
Seriously, you’ll feel like you should be sipping an Aperol spritz somewhere with a view of yachts you pretend aren’t yours. 😉
17. Gingham Midi Dress
If “Picnic, But Wealthy” Were an Outfit
Ah, gingham — it walks the perfect line between girl-next-door and “my family owns an estate in Provence.” A midi gingham dress gives breezy charm with just the right amount of old-money whimsy.
Tips to wear it right:
- Stick with blue, green, or soft red checks
- Opt for flowy fabrics like cotton or linen blends
- Pair with low sandals, espadrilles, or kitten heels
- Accessorize with a straw bag and oversized sunnies
I wore one to a garden party last year and was literally handed a glass of rosé before I said a word. Coincidence? I think not. 😏
18. Silk Slip Dress + Oversized Shirt
Glamour, But on Vacation
Sometimes you want to be comfy, but still look like you might randomly run into your ex (and their new partner). That’s where this pairing shines.
Here’s how to slay it:
- Silk or satin slip dress in a neutral tone (champagne, navy, ivory)
- Throw on an oversized button-up shirt (linen or poplin)
- Leave it open or tie it at the waist
- Keep accessories understated — dainty jewelry, a clutch, and strappy sandals
The key? Let the fabrics do the talking. Silk screams luxury — even if your bank account's whispering something else. 🙃
19. Crisp Polo Shirt + Paperbag Shorts
Casual, but Still Inherited a Trust
A polo shirt is old money DNA. Tuck it into some tailored, high-waisted paperbag shorts, and you've got a modern twist on country club style.
Style this for summer:
- Polo in white, navy, or pastel
- Shorts in linen or cotton, tied at the waist
- Add loafers or low-profile sneakers
- Finish with a simple leather watch or canvas tote
This is what you wear when you’re pretending to “pop by” the market but secretly hoping someone notices your outfit. 😎
20. Flowy Culottes + Striped Button-Up
Boardroom Meets Beach House
Culottes are so underrated. They're breezy like a skirt but sharp like trousers. Pair them with a striped button-up (half-tucked, of course), and you’ve got the perfect balance between elegant and cool.
What you’ll need:
- Wide-legged culottes in cream or soft brown
- Vertical striped button-up (blue-and-white works every time)
- Finish with leather sandals or lace-up flats
- Optional oversized tote and sunnies for full “weekend away” energy
I wear this combo when I want to look important but also like I might spontaneously decide to hop on a sailboat.
21. Trench Coat Over Anything
The Quiet Luxury Final Boss
Okay — technically not a full “summer outfit,” but hear me out: a lightweight trench coat thrown over literally anything makes you look like you’re stepping off a private jet in the South of France.
Look for:
- Light cotton or silk-blend trench in camel or off-white
- Keep it classic: epaulettes, belt, clean lines
- Toss it over a slip dress, shorts-and-tee, or a linen set
- Finish with loafers or mules
Wear it draped over the shoulders if you’re feeling extra dramatic. IMO, this is the single most powerful piece in an old money closet. 💼
🧳 Final Takeaways: How to Nail Old Money Summer Vibes Year-Round
Before you run off to curate your wardrobe (or, you know, browse online while eating chips — no judgment), here’s a quick cheat sheet to keep you on the right track:
- Neutrals win. Stick with whites, creams, navies, soft blues, and beiges.
- Tailoring is everything. Even a basic tee looks luxe if it fits like a glove.
- Quality over quantity. One perfect blazer > ten trendy crop tops.
- Confidence sells the look. Walk like you belong in every room — or on every yacht.
☕ Final Thoughts
So, whether you’re strolling through your favorite seaside town or just trying to fake your way through a family reunion at the lake house, these 21+ old money summer outfits will have you radiating timeless elegance with zero effort (or at least make it look that way 😉).
Have a favorite look from the list? Planning to recreate one this weekend? Let me know — and FYI, you can absolutely wear linen three days in a row. I won’t tell. 💁♀️