The Secret to Looking Expensive? It’s Not What You Think
You don’t need a billionaire boyfriend or a last name that sounds like a trust fund to channel that old money summer vibe. What you really need? Effortless style, timeless pieces, and the confidence of someone who’s been drinking Pellegrino since birth.
I’ve been mildly obsessed with the old money aesthetic ever since I watched a certain tennis-themed perfume ad and thought, “Wait, I need that life.” So after several Pinterest boards, hours stalking Celine runway looks, and way too much time mentally moving into a Hamptons beach house I don’t own, I’ve figured out how to recreate that look without a black Amex.
Ready to look like you summer in Saint-Tropez, even if you’re just sweating through iced lattes downtown? Let’s go.
1. White Linen Trousers + Button-Down = Instant Heiress
Why it works:
- Linen screams luxury—wrinkles included.
- A button-down keeps it crisp and classic.
Pair soft, wide-leg white trousers with a slightly oversized cotton or linen shirt, half-tucked in. Bonus points if the shirt’s striped or monogrammed. Add espadrilles or loafers, throw on some tortoiseshell sunnies, and act like you forgot what TikTok is.
Pro tip: Stick to whites, creams, or pale blues. Old money doesn’t do neon.
2. Sleeveless Knit Top + Tailored Shorts
The look:
Think tennis club meets Roman holiday.
This one’s about keeping it structured up top and chill below. I love pairing a sleeveless cable-knit sweater (yes, even in summer—it’s breathable, I swear) with high-waisted, tailored shorts in neutral tones.
- Keep it monochromatic or go two-tone with beige and ivory.
- Footwear? Go for leather sandals or white sneakers if you’re feeling casual.
- Top it off with a silk scarf in your hair or tied to your bag handle. Just trust me.
Ever wondered why old money style always looks so put together? Tailoring. Every. Time.
3. The Midi Shirt Dress That Says, “My Dad Owns a Vineyard”
Why you need this in your closet:
- It’s one-piece and effortless—no overthinking required.
- Looks good with sandals, sneakers, or espadrilles.
Choose a button-down midi dress in white, navy, or a subtle print (stripes, maybe a quiet floral if you’re feeling whimsical). Cinch the waist with a leather belt if you want more shape. Toss on a pair of retro cat-eye sunglasses, and suddenly, you're Grace Kelly picking up rosé.\
IMO: Shirt dresses are the silent luxury MVP of summer wardrobes.
4. The White Tennis Skirt + Sweater Combo
Yep, we’re going preppy on purpose.
A pleated white tennis skirt paired with a fine-knit pullover or crewneck sweater casually thrown over your shoulders? That’s how you signal “old money” without saying a word. (And no, you don’t actually have to play tennis.)
Here’s how to style it:
- Tuck in a collared shirt or fitted tank.
- Drape a cashmere sweater over your shoulders like you’re auditioning for Gossip Girl: Country Club Edition.
- Finish with white sneakers or loafers, depending on the vibe.
Warning: You will be tempted to say “darling” unironically.
5. Silk Camisole + High-Waisted Trousers
Easy, breezy, and unbelievably chic.
This combo brings the old-money after-hours energy—think Amalfi Coast dinners or sipping cocktails on a rooftop terrace (or pretending you are).
Go for:
- A silk or satin camisole in ivory, champagne, or navy.
- High-waisted trousers in linen or crepe—nothing too tight, you want that floaty movement.
- Layer a lightweight cardigan or linen blazer if you’re stepping out in the evening.
Accessorize with dainty gold jewelry and leather sandals, and boom—you’re giving quiet luxury with just a touch of seduction.
6. The Breton Stripe Tee + White Jeans Combo
Because sometimes, the basics do it best.
You can’t talk old money without talking about Breton stripes. It’s the French Navy’s gift to fashion, and yes, it still slaps.
- Tuck a striped tee into high-rise white jeans.
- Roll the cuffs. Keep it relaxed.
- Add tan sandals, a basket bag, and pretend you’re off to a farmer’s market in Provence.
FYI: This outfit works just as well at a beach picnic or running errands in style. I wear mine at least once a week during summer—and the compliments don’t stop.
7. The Classic Navy Blazer Over Anything (Yes, Even Shorts)
When in doubt, throw on a blazer. Seriously.
The old money elite swear by the structured navy blazer, and honestly? So do I. It takes almost any outfit from basic to bougie in seconds.
Here’s how I style mine in summer:
- Over a white tank and tailored beige shorts.
- With a striped tee and crisp white jeans.
- Layered on top of a simple cotton sundress for cooler evenings.
Hot tip: Roll the sleeves up just a touch. It adds a relaxed, I-woke-up-rich kind of feel.
And yes, you can absolutely steal one from your dad’s or boyfriend’s closet. No judgment here.
8. A Simple Slip Dress + Flat Sandals = Quiet Luxury Perfection
Minimal effort, maximum effect.
A bias-cut slip dress in a neutral or jewel tone gives you that effortlessly luxe vibe. Think: 1990s Carolyn Bessette-Kennedy meets European summer goddess.
Why I love this combo:
- It’s light, breathable, and insanely flattering.
- You only need minimal accessories—a sleek bun, dainty gold hoops, and flat leather sandals are enough.
- It transitions beautifully from beach walk to rooftop aperitifs.
Ever tried one with a cardigan draped over your shoulders? Chef’s kiss.
9. Monochrome Beige with Linen Everything
No logos. No chaos. Just pure, buttery beige elegance.
Want to look like you own a Tuscan villa and a quiet art collection? Wear head-to-toe beige or tan in varied textures.
Go for:
- A linen button-down tucked into tailored beige trousers.
- Add a suede belt, woven tote, and strappy sandals.
- Throw on oversized sunnies and practice your best polite half-smile.
It’s giving old-money diplomat’s daughter, and I live for it.
IMO: Beige doesn’t have to be boring—it’s just bougie when styled right.
10. Crisp Poplin Dress + Basket Bag
You’re about to look like you picked flowers in Provence—even if you just got groceries.
There’s something about a structured cotton poplin dress that screams money (in a whispery, soft-spoken way, of course).
Here’s the breakdown:
- Choose midi-length for that grown-up energy.
- Look for puffed sleeves or subtle pleating for shape.
- Pair with a basket bag (hello, Jane Birkin energy) and leather sandals.
I wore this look to a casual brunch last summer and had a stranger ask if I was “from out of town”—code for you look suspiciously elegant to be here. 😏
11. Silk Blouse + Bermuda Shorts (Trust Me)
This one feels weird... until you wear it and get compliments from strangers.
Bermuda shorts, when tailored and worn right, are seriously underrated. And when you pair them with a fluid silk blouse? That’s quiet luxury 101.
What to look for:
- Bermudas in linen, twill, or cotton blends.
- A slightly oversized silk shirt tucked or tied at the waist.
- Minimal, clean sandals and maybe a woven clutch.
Add a low bun and a subtle red lip and pretend you just wrapped up an art auction.
.webp)
FYI: This is also a killer “I don’t sweat, I shimmer” look on hot days.
12. Boatneck Top + Wide-Leg Cropped Pants
If Jackie O and Audrey Hepburn had a fashion baby...
The boatneck silhouette gives total Riviera energy. I usually go for a knit version in navy or cream, and pair it with wide-leg cropped pants in a neutral.
Why it works:
- The neckline feels instantly refined.
- The wide-leg pants keep the outfit breathable and breezy.
- Add a leather belt, simple loafers, and you’re channeling Monaco royalty before noon.
Ever worn this with a silk scarf in your ponytail? Game-changer.
13. White Tennis Skirt + Cable-Knit Vest
Sporty... but make it heirloom-worthy.
Ever seen someone look like they don’t need to play tennis but could totally crush you at it anyway? That’s this look.
- White pleated tennis skirt (bonus points if it’s vintage Ralph Lauren).
- Sleeveless knit vest or sweater tied around the shoulders.
- Finish with white sneakers or loafers and a clean ponytail.
You’ll look like you summer in the Hamptons, even if you’re just at the neighborhood Starbucks.
14. Eyelet Dress + Espadrilles
Practically screams “old estate garden party.”
There’s something eternally elegant about white eyelet. It's one of those fabrics that makes you feel like you’ve inherited something—even if it’s just good taste.
What I love about this combo:
- Breathable, romantic, and very flattering.
- Espadrilles add height without the “look at me” vibes.
- You can dress it up with pearls or keep it casual with a straw tote.
Pro tip: A soft updo and vintage sunglasses take this from cute to capital-E Elegant.
15. Breton Striped Tee + Khaki Trousers
A French-inspired essential that old money types swear by.
This look’s been around since Coco Chanel said, “I don’t do basic,” and it’s stayed chic ever since.
- Opt for a fitted or boxy navy striped tee.
- Pair with high-waisted khaki pants or cropped chinos.
- Add a classic watch, minimal gold hoops, and leather loafers.
It’s comfy, unfussy, and says, “I inherited taste—not just cash.” 😉
16. Seersucker Dress + Panama Hat
Lightweight, breathable, and practically designed for yacht brunches.
Seersucker screams summer, and in a subtle pastel or navy stripe, it screams quiet luxury. I wore one of these to a lake house BBQ and looked far more put together than I had any right to.
Go for:
- Sleeveless or puff-sleeved seersucker dress.
- A structured Panama hat (not floppy, we’re not at Coachella).
- Optional: woven flats or low espadrilles.
Ever noticed how rich people’s summer outfits are always creased in the right places? Seersucker gives you that by default.
17. Silk Camisole + Pleated Trousers
It’s like wearing luxury pajamas... but you could run into your ex and still look 10/10.
This one is sleek, simple, and—honestly—pretty dang powerful.
- Pick a neutral silk cami (cream, blush, black).
- Pair with high-waisted, pleated trousers (think ‘90s Armani).
- Finish with strappy sandals or leather slides.
Add a tan leather clutch and a “just did my skincare” glow. You’ll thank me later.
18. Shirt Dress + Leather Belt
The ultimate “rich mom at brunch” look.
A button-down shirt dress cinched at the waist just works—every time. Choose one in white, olive, or chambray for max versatility.
Here’s how I rock it:
- Add a medium-width leather belt (brown or tan = extra preppy).
- Pair with pointed flats or minimalist sandals.
- Toss on a pair of cat-eye sunglasses and give “ladies who lunch” energy.
And if anyone asks, yes—it’s vintage. Always. 😌
19. Pale Yellow Knit + White Jeans
Underrated color combo that feels super elevated.
Pale yellow and white = sunshine on a trust fund. This combo is one of those things that shouldn’t work—but absolutely does.
Style it like this:
- Soft knit sweater or cardigan in buttery yellow.
- Pair with white denim (cuffed for a relaxed fit).
- Gold accents, brown loafers, and a vintage handbag to seal the deal.
IMO, this is one of the coziest ways to still look luxe on a breezy summer day.
20. Linen Jumpsuit + Gold Accessories
One-piece wonder that says, “I just got back from Capri.”
A linen jumpsuit can go from earthy to elite with the right tailoring and accessories.
Go for:
- A natural beige or olive tone.
- Defined waistline or belted versions for shape.
- Add gold hoops, leather sandals, and a structured tote.
You’ll look like you summer somewhere coastal, even if the closest water is your neighbor’s inflatable pool.
21. Scarf-Tied Hair + Oversized Button-Down
Casual glam with a side of espresso and luxury lineage.
This look is a whole vibe. I wear it when I want to look chic but don’t want to try too hard (which, ironically, takes some trying).
- Oversized white button-down (men’s section = treasure trove).
- Tuck into linen shorts or cigarette pants.
- Tie a silk scarf in your hair and let it flow.
Add a small leather shoulder bag, and boom—you’re Sofia Coppola-ing your way through summer.
22. Minimalist Tank Dress + Statement Sunnies
Effortless = expensive.
Tank dresses are the holy grail of low effort, high return.
- Choose a solid neutral like black, beige, or olive.
- Make sure it fits like it was tailored just for you (even if it wasn’t).
- Add structured sunnies, chunky slides, and a single gold bangle.
Minimalist never looked so extra in the best way.
23. Pastel Blouse + White Culottes
It’s giving “garden luncheon, but understated.”
Soft pastels + white equals “yes, I grew up going to boarding school in Switzerland.”
Try this:
- A pastel blouse (think powder blue, lavender, or blush).
- Tuck into white culottes or wide-leg trousers.
- Finish with simple slingbacks and pearl studs.
I wore this to a baby shower last summer and got more compliments than the actual baby. No regrets.
24. Neutral Maxi Skirt + Fitted Tee
Comfy and chic—a rare combo.
A flowy maxi skirt in beige, taupe, or olive gives you old-money mobility. Add a fitted ribbed tee and you’re golden.
Why it works:
- Comfortable enough for errands.
- Polished enough for impromptu lunch dates.
- Style with flat sandals, dainty necklace, and a low bun.
Add a woven or leather crossbody bag, and it’s giving “main character in a French indie film.”
25. Silk Scarf Top + High-Waisted Trousers
Last but definitely not least—vintage glam meets modern day yachtwear.
I saved this one for those ready to channel their inner Slim Aarons muse.
- Tie a silk scarf as a halter or bandeau top.
- Match with structured high-waisted trousers.
- Add wedges or kitten heels, big sunglasses, and maybe a glass of rosé.
Caution: You will turn heads.
💬 Final Thoughts: You Don’t Need a Trust Fund, Just Taste
And there you have it—25 old money-inspired summer outfits to help you channel timeless elegance without flashing a single logo.
Remember: it’s all about quality over quantity, tailoring over trends, and attitude over access. Confidence (and maybe a crisp collar) is your best accessory.
Which look are you trying first? Or better yet, got a favorite luxe summer staple I didn’t mention? Let’s chat about it 🧺✨