Here’s the thing nobody tells you about old money summer style: it’s not actually about money. It’s about looking like you stepped out of a coastal family portrait where everyone vacations in the same place every year and argues about sailboats over lunch. And honestly? I love that for us.
I started leaning into old money summer outfits the moment I realized I could look polished without trying to decode whatever chaotic trend TikTok was pushing that month. Because who has the energy to wonder if we’re still wearing micro shorts or if the girls have moved on to “coastal cowgirl but make it futuristic”? No thank you.
Old money summer outfits feel calm. They feel intentional. They feel like you but the elevated version who orders sparkling water instead of cola and somehow never sweats through linen (still working on that one, TBH). And if you’ve ever wanted to walk into a room and give off that this list will be your new style bible.
Ready? Grab your iced latte, because we’re going all in.
1. The White Linen Button-Down + Tailored Shorts Combo
Okay, you knew this one was coming. If Old Money Summer had a mascot, it would be a crisp white linen shirt. I swear, I wear this combination three days a week, and nobody has caught on yet (I think).
This outfit works because it looks:
- intentional
- breathable
- expensive (even when it’s not)
Style it with:
- Gold studs
- Leather sandals
- A woven tote bag
And ask yourself: Is any outfit more “I summer in the Hamptons” than this?
2. A Navy Knit Polo + High-Waisted Trousers
Navy instantly whispers wealth. I don’t make the rules; I just follow them.
A fitted knit polo tucked into cream trousers gives that “I golf recreationally but also for networking” vibe. IMO, this outfit works everywhere — from a seaside café to a Tuesday afternoon pretending you’re productive.
Pro tip: Choose a polo with a soft collar so it lays flat and looks polished rather than preppy.
3. The Striped Breton Tee + White Pants
Ever wondered how French women always look effortlessly put together? It’s not magic — it’s the Breton tee. Old money summer girls love stripes because they make even the simplest outfit look nautical without screaming I own a yacht.
Pair with:
- Straight-leg white jeans
- Brown leather loafers
- A navy cardigan draped over your shoulders (yes, we’re doing this now)
Trust me, this is the quiet-luxury starter pack.
4. The Flowy Midi Dress (Preferably Linen, Always Linen)
Some days I wake up and think, “I cannot be bothered.” That’s when the linen midi dress steps in like a dependable best friend.
Look for:
- Neutral tones
- A-line or tailored waist
- Soft, minimal detailing
Why does this work so well? Because linen naturally wrinkles — which sounds chaotic, but in old money fashion, it screams authenticity. Yes, you meant to look like that. Obviously.
5. Pleated Skirt + Cable Knit Shell Top
I used to think pleated skirts belonged only in tennis clubs and posh private schools, but I take it all back. A crisp pleated skirt with a cable knit shell top is such a power combo — elegant without trying too hard.
This outfit gives “classic boarding school alumna catching up with friends during summer break.” You know exactly the vibe I’m talking about.
Add subtle pearls, and boom: you’re basically royalty.
6. Linen Trousers + Silk Camisole + Oversized Shirt
This is one of those OOTDs that make people assume you read financial newspapers voluntarily.
The formula:
- Linen trousers
- Silk cami
- Oversized shirt as a light jacket
It’s breezy, feminine, and structured. And perfect for heat waves when you still want to look like you have your life together (even if you don’t — no judgment).
7. The Classic Tennis Dress (Athletic Old Money Is Still Old Money)
Old money aesthetic loves tennis, even if you’ve never picked up a racket in your life (hi, it’s me). A structured tennis dress in white or cream looks clean, polished, and surprisingly chic for errands or weekend brunch.
Choose one with:
- A tailored waist
- A-line skirt
- Minimal branding
Wear it with white sneakers and a messy bun that somehow looks intentional.
8. The Chic Monochrome Neutrals Look
Let’s talk monochrome — the secret weapon of people who always look expensive. Beige on beige? Cream on cream? Camel on white? Yes, yes, and yes.
Keep the tones similar, but mix:
- Textures
- Silhouettes
- Fabric weights
Ever wondered why celebrities look so put together on “casual stroll” paparazzi walks? It’s because monochrome outfits trick the eye into seeing polish.
Old money loves uniformity, and this is the easiest way to achieve it.
9. The Easy Linen Romper for Casual Days
Rompers get a bad rep, but hear me out: a linen romper in cream or oat tones absolutely fits into the old money summer universe — if it’s tailored correctly.
Look for:
- Structured waist
- Button-down front
- Longer inseam
I wore one of these to a weekend picnic last summer, and three people asked where I got it. That’s when I knew the romper agenda needed to be pushed.
10. The Satin Slip Dress With a Cashmere Wrap
Slip dresses aren’t just for date nights, especially when styled the right way. A neutral satin slip paired with a cashmere wrap feels refined rather than sultry.
Add:
- Thin strappy sandals
- A delicate necklace
- A small clutch
Tell me this outfit doesn’t scream “I drink sparkling water exclusively.”
11. The White Eyelet Sundress
Eyelet fabric instantly gives “European summer, but quietly.” The embroidery feels soft and feminine, but not overly romantic.
Choose:
- Midi length
- Square or sweetheart neckline
- Minimal frill
Wear it for seaside dinners or evenings on the balcony pretending you’re in Lake Como. (We’ve all done it.)
12. Wide-Leg Pants + Ribbed Tank + Belted Blazer
If you want a summer outfit that transitions from daytime errands to rooftop dinner, this combo wins every time.
The structure comes from:
- A sharp blazer
- A clean belt
- A long flowy pant
The softness comes from:
- The ribbed tank underneath
This contrast feels very old money because it suggests you understand tailoring — even if you actually got the blazer on sale for $39 (FYI, I support bargain brilliance).
13. Paperbag Shorts + Breton Sweater Draped Over Shoulders
I know what you’re thinking: paperbag shorts? Old money? Yes — when you wear them in neutral linen.
This outfit includes:
- Paperbag shorts
- Fitted basic tee
- Striped sweater draped casually across your shoulders
It gives that “I’m heading to the marina but also might take a nap later” confidence.
Bonus points if you accessorize with understated brown leather slides.
14. The Linen Vest + Matching Trousers Look (Quiet Money in Clothing Form)
The vest trend isn’t just a trend — it’s old money coded when executed properly. A buttoned linen vest with matching trousers looks tailored, timeless, and extremely elegant.
Keep it simple:
- Wear minimal jewelry
- Stick to muted tones
- Pair with leather flats or strappy sandals
Every time I wear this outfit, someone compliments it — and for a hot second, I feel like I inherited a vineyard.
How to Nail Old Money Summer Style (Without Overthinking It)
Let’s pull everything together, because old money style isn’t about buying expensive things — it’s about buying things that look expensive and wearing them with confidence.
Here are the essentials:
Stick to a Neutral Color Palette
Creams, oats, navies, whites, and tans always look refined. Ever wondered why bright colors can feel chaotic? It’s because they’re loud — and old money prefers whispers over speeches.
Prioritize Fit and Fabric
Choose:
- Linen
- Cotton
- Silk
- Cashmere
Trust me, these fabrics transform even cheap pieces into something luxe.
Avoid Excessive Logos
The second you remove loud branding, the outfit transforms from “influencer energy” to “old money elegance.”
Keep Your Accessories Minimal
Think:
- Gold hoops
- Brown leather belts
- Understated watches
- Neutral flats
Small details matter more than you think.
My Personal Old Money Summer Shopping Tips
Because I’ve tried way too many things and made way too many mistakes, here’s what I’ve learned:
1. Buy Linen Shorts With Structure
Elastic waistbands are comfy, but tailoring makes the outfit look intentional.
2. Always Check the Fabric Blend
Polyester-heavy “linen” just traps heat and wrinkles badly (and not in the cute way).
3. Invest in One High-Quality Neutral Bag
Not necessarily designer — just something with clean lines, solid stitching, and no flashy hardware.
4. Choose Simple Jewelry
You don’t need a whole collection. One perfect everyday necklace? Chef’s kiss.
5. Try Things in Two Sizes
Sometimes the more expensive-looking outfit comes down to choosing the slightly looser fit.
Ever wondered why your Pinterest inspo looks so effortless? Fit is doing 90% of that work.
Old Money Summer Beauty Vibes (Because the Makeup Matters Too)
Fashion and beauty always go hand in hand, right? So here’s how I keep my beauty game feeling elegant without going full glam:
Glowy Skin Over Heavy Coverage
Use:
- Lightweight foundation
- Cream blush
- Soft bronzer
Old money girls don’t try to look perfect — they try to look healthy.
Soft Blowout or Low Bun
Old money hair doesn’t scream for attention — it’s neat, polished, and effortless.
IMO, a simple blowout always works.
Neutral Nails
White, pale pink, nude, or soft beige always win. Every time I try a bright color, I instantly feel like I switched aesthetics.
Final Thoughts: Old Money Summer Isn’t About Wealth — It’s About Intention
If you’ve read this far (hi, love you), you probably care about curating a wardrobe that feels elevated but still… you. And honestly? That’s the whole point of old money style. It’s not about actual luxury it’s about quiet confidence, timeless silhouettes, and pieces that work year after year.
So try these outfits, mix them, repeat them, wear them on vacation or to the grocery store no one is judging. I promise.
And remember: if you feel like the richest woman at the beach club, you basically are.
xo,
Freya Weston