Look Like You Summer in the Hamptons (Even If It’s Just Your Backyard)
Okay, so you’re ready to glow up your summer wardrobe — but not with loud logos or TikTok trends that’ll be over by next Thursday. Nope. You want that quiet, classy confidence. That old money aesthetic. Think Grace Kelly meets modern-day muse, with just enough mystery to make people wonder if you own a sailboat.
Well, friend, you’re in the right place. I’ve rounded up 15 pieces that will give your summer wardrobe a major upgrade — without looking like you tried too hard. Let’s kick it off with the first five.
1. Tailored White Linen Trousers
Because Saggy Pants Are Not a Legacy Look
You know what screams old money? A pair of crisp, high-waisted white linen trousers that float around your legs like they were custom-made in Italy — even if you snagged them on sale.
- Go for natural linen or a linen-blend to keep things breathable.
- Pair them with a tucked-in silk blouse or a fitted knit polo.
- Add loafers, not sneakers. Trust me.
I’ve worn mine to brunches, garden parties, and even a casual wedding — and not once did I feel underdressed. FYI: they also hide the fact that I definitely skipped shaving that morning. 😅
2. Navy Blazer with Gold Buttons
Yacht Not Included (But You’ll Look Like You Own One)
The navy blazer is old money’s favorite cousin. Structured, elegant, and always makes you look like you know what vintage wine pairs with oysters.
- Look for structured shoulders and a slightly boxy fit.
- Gold buttons add that timeless preppy punch.
- Drape it over your shoulders when it’s too hot to wear it — that’s peak rich-auntie behavior.
I keep one in my car during summer because it instantly upgrades even the laziest outfit (read: tank top and denim shorts). It’s magic.
3. Silk Scarf (Worn as a Hair Tie or Neck Accent)
For That “I Own an Estate in Provence” Vibe
It’s amazing what a silk scarf can do. Wrap it around your ponytail, tie it around your neck, or thread it through your bag handle — and just like that, you’re giving “my grandmother gave me this from her Paris collection”.
- Stick to classic prints like florals, paisley, or geometric patterns.
- Choose neutral or pastel tones — leave the neons for someone else.
- Bonus points if it’s vintage or thrifted. Extra bonus if you tell people it is (even if it’s not — I won’t tell 😉).
I once wore a $12 scarf and had three people ask if it was Hermès. I said nothing. Let them believe.
4. Structured Straw Tote or Basket Bag
Not Just for Picnics, Darling
There’s something so effortlessly chic about a structured straw bag. It says, “I picked fresh lavender this morning” — even if all you did was go to Trader Joe’s.
- Opt for real woven straw or rattan, not the plastic knockoffs.
- Look for leather details, top handles, or buckles for that elevated touch.
- Use it with both casual sundresses and tailored outfits.
Mine fits my Kindle, sunscreen, and an emergency croissant. That’s what I call luxury.
5. Classic White Button-Down Shirt (Preferably Oversized)
Worn by Every Heiress Ever, Probably
A white button-down is the wardrobe MVP, no debate. Oversized? Even better. Tucked into shorts, tied at the waist, or thrown over a bikini — it works for literally every summer situation.
- Choose cotton or poplin for breathability.
- Go for a men’s fit or size up for that effortlessly relaxed look.
- Pair with pearls for the full old-money fantasy.
True story: I borrowed one from my dad once and never gave it back. Sorry, not sorry.
6. Silk Midi Skirt
Float Through Summer Like You Own the Vineyard
A silk midi skirt is that one piece that makes people double-take — not because it's flashy, but because it's just that elegant. The way it catches the light? Immaculate. The way it moves? Like you’re gliding, not walking.
- Choose neutral tones like champagne, blush, ivory, or deep navy.
- Pair with a crisp tank or that oversized button-down from earlier.
- Add understated flats or slingbacks for peak refinement.
I wore mine to a friend's backyard soirée and someone asked if I was “in PR or something.” I said yes, even though I have no idea what PR people actually do 😂.
7. Cashmere or Lightweight Knit Sweater (Even in Summer, Yes)
Trust Me, It’s for the Vibe
Alright, hear me out: yes, it’s hot, but an ultra-light knit sweater or cashmere pullover casually draped over your shoulders or tied around your neck? Chef’s kiss.
- Look for thin, breathable knits in cream, camel, or soft grey.
- Use it more as an accessory than an actual layer — it's about the illusion of coziness.
- Avoid chunky knits — unless you’re summering in Scotland, maybe.
Nothing screams “I grew up with summer tutors” like casually wrapping a sweater around your shoulders while holding a glass of white wine you definitely didn’t pour yourself.
8. Loafers or Leather Mules
No Heels, No Problem — Elegance Is Still Served
Old money doesn’t run around in stilettos. (Have you ever seen a trust fund baby sprinting in heels? Exactly.) That’s why classic loafers and sleek leather mules are non-negotiables.
- Choose soft leather or suede, preferably in black, brown, or beige.
- Minimal hardware — a tiny horsebit, max.
- They look fab with trousers, skirts, or even tailored shorts.
IMO, they say: “I own a library card, but I also drink martinis at noon.”
9. Pearl or Gold Stud Earrings
The Jewelry That Says, “I Don’t Need to Flex. I Am the Flex.”
You don’t need a chandelier dangling from your ears to look expensive. In fact, you’ll look 10x more elegant in a pair of tiny pearl studs or simple gold hoops.
- Stick to real gold or quality vermeil if your budget allows.
- Pearls should be classic round, not overly ornamental.
- Avoid blingy rhinestones or huge logos — this isn’t a music video.
There’s something quietly powerful about jewelry that whispers instead of shouts. Like… whispering, “My jewelry was probably passed down, thank you very much.”
10. Sundress with Structure (Not Spandex)
For the Garden Party You Haven’t Been Invited to Yet
The right summer dress doesn’t cling, it skims. It makes you feel like you should be holding a parasol and complaining about the heat while someone fans you with a magazine.
- Look for a-line cuts, sweetheart necklines, or wrap dresses.
- Stick to fabrics like cotton poplin, linen, or broderie anglaise.
- Keep patterns simple — florals, stripes, or solids in muted tones.
Bonus points if it has pockets — because power is also being able to sneak cookies from a party and stash them elegantly 😉
11. Wide-Leg Linen Trousers
The “I’m Not Trying, But Yes, I Do Look This Polished” Pants
If your summer wardrobe doesn’t include a pair of wide-leg linen trousers, you’re missing out on the MVP of old-money dressing.
- Go for high-waisted and slightly cropped or full-length — no capris, please 🙃
- Stick to classic shades: ivory, beige, navy, or stone grey
- Pair with tanks, button-downs, or even a blazer if you’re feeling bold
Bonus: they’re breezy, comfy, and somehow make it look like you actually enjoy going to brunch before 10am.
12. Vintage-Inspired Sunglasses
The Glamour Without the Logo Assault
Old money doesn’t scream designer brands in 100pt font across their face. Instead, they quietly stun with oversized tortoiseshells or angular metal frames that could’ve come from a 1950s yacht club photo.
- Opt for shapes like cat-eye, round, or aviator
- Ditch oversized logos — your style should shine, not the branding
- Try vintage stores for authentic finds that nobody else is wearing
Ever worn vintage sunnies and felt like you should be in a convertible with the top down and scarf blowing in the wind? Yeah… that.
13. Straw or Woven Tote Bag
For the Farmer’s Market (Or Pretending You Actually Shop at One)
The straw tote is the unsung hero of summer accessories. It’s casual, timeless, and makes it look like you definitely summer in the Hamptons.
- Choose structured styles with leather trim or canvas lining
- Skip cheap plastic or overly boho fringe
- Big enough to hold a book, your SPF, and maybe a tiny dog (kidding… kind of)
IMO, it’s the most low-key rich girl thing you can carry — especially if it looks like you’ve had it since you were 12.
14. Tailored Swimsuit or Retro One-Piece
Swimwear That Wouldn’t Make Grandma Blush
If your summer wardrobe isn’t beach-ready, what are we even doing? But skip the neon string bikinis — a structured one-piece or high-waisted bikini is the way to go.
- Look for scoop backs, underwire tops, or belted waists
- Stick to solid colors or subtle prints (navy, white, deep green, etc.)
- No ruffles, no rhinestones — this is not Coachella
Trust me, there’s nothing sexier than a swimsuit that fits perfectly without showing everything. It says: “Yes, I swim laps. No, I won’t do a cannonball.”
15. Panama Hat or Structured Sunhat
For Shade — Literal and Social 😎
Last but definitely not least: the Panama hat. It's the cherry on top of your elegant sundae. It's giving yacht, it's giving polo match, it's giving I-have-inheritance-energy.
- Pick one with a clean brim and minimal band
- Stick to neutral colors — cream or white with a tan or black band
- Pair with linen, dresses, or even your wide-leg trousers
And FYI, no floppy beach hats with sequined sayings like “Out of Office” — unless the office is Vogue HQ.
🎯 Final Recap: Old Money Essentials Wrapped in One Neat Bow
Let’s bring it all together. Here’s the full list of 15 old money-inspired wardrobe upgrades:
- White Linen Button-Down
- Silk Scarf
- Tailored Bermuda Shorts
- Boat Shoes or Leather Sandals
- Structured Blazer
- Silk Midi Skirt
- Lightweight Knit Sweater
- Leather Loafers or Mules
- Pearl or Gold Studs
- Structured Sundress
- Wide-Leg Linen Trousers
- Vintage-Inspired Sunglasses
- Woven Straw Tote
- Retro One-Piece Swimsuit
- Panama Hat
Final Thoughts: Quiet Luxury Is Loud in Confidence
Here’s the thing — old money fashion isn’t really about money. It’s about effortless confidence, classic tailoring, and knowing who you are without needing to flex. These pieces work because they don’t chase trends — they set the tone.
So, whether you’re curating your summer wardrobe for actual yacht parties or just leveling up your Target runs, these staples will elevate your look without making you look like you tried too hard (because that’s never the goal, right?).
Now go forth and summer like your last name is Vanderbilt. Or at least like you once dated someone named Vanderbilt 😏.