Let’s keep it 100: I am not old money. I am old student loans, a seven-year-old with expensive taste in cereal, and a wardrobe that sometimes doubles as my “new arrivals” content (because yes, I’ve styled the same blazer four different ways this month. And?).
But I’ll tell you a secret: you don’t need a trust fund to serve “quiet luxury.” Old money style isn’t about labels shouting from your chest—it’s about timeless pieces, subtle flexes, and a whole lot of confidence. Think Grace Kelly meets Brooklyn single mom with a knack for spotting $600 vibes in a $60 fit.
So let’s dive into 21 old money outfits that’ll have you looking like you summer in the Hamptons—even if you’re actually summering on your stoop with iced coffee and a thrifted linen shirt.
1. White Button-Up + Camel Trousers + Loafers
You can’t go wrong with this. It’s giving “I might own a horse” energy. Look for a crisp, oversized white shirt (mine’s men’s from the thrift store—$4) and pair it with tailored camel or oat-toned trousers. Loafers tie it together.
Style tip: Cuff the sleeves, add gold hoops, and slick your hair into a bun for max “trust fund” vibes.
2. Cream Knit Sweater + White Jeans + Ballet Flats
This is the outfit I wear when I want to feel expensive but also like I could read you poetry on a yacht. All-white looks rich. Even if your jeans are from Target. (Mine are.)
Throw a cardigan over your shoulders for an extra layer of “I don’t check price tags.”
3. Navy Blazer + Striped Tee + Khaki Shorts
Call it Ivy League Dad-core. I thrifted a men’s navy blazer and had it tailored. Add a boatneck striped tee (H&M has great ones) and structured shorts. Add loafers or leather slides and suddenly I’m at a country club in my mind.
4. Slip Dress + Oversized Cashmere Sweater + Mules
The cashmere is from Poshmark, the mules were $20 from Marshalls, and the slip dress? A random Amazon find. But layered together, this look screams Sofia Coppola levels of understated cool.
Bonus: comfy enough to chase your kid, classy enough to wear to an art gallery.
5. Linen Button-Up + White Wide-Leg Pants + Leather Belt
I wear this to feel like I live in a sun-drenched villa in Provence. Linen anything = old money cheat code. Add vintage sunnies and carry a woven tote for that “I buy fresh peonies every weekend” illusion.
6. Silk Scarf + Trench Coat + Straight-Leg Jeans
Silk scarves are such a power move. Tie it around your neck or in your hair with a beige trench and vintage jeans. Add a structured handbag (mine’s thrifted, naturally) and ankle boots. It’s very “I just landed from Paris.”
7. Sweater Vest + Collared Shirt + Pleated Skirt
Okay, this one is a little “prep school energy” but in the best way. It’s nerdy-chic. I got my pleated skirt from a secondhand uniform store (yes, really) and layered it with a thrifted vest.
Warning: You will feel like you know things about fine art when you wear this.
8. Cashmere Cardigan + Satin Midi Skirt + Slingbacks
Cashmere + satin is an old money combo I’ll never stop loving. Neutral colors work best—beige, sage green, dusty rose. My cardigan is vintage, and the skirt is from Zara’s sale rack. Looks luxe, costs less than my daughter’s dance recital fees.
9. All-Black With a Structured Coat
When in doubt, go monochrome. Black turtleneck, black trousers, long structured coat. Add black loafers or ankle boots. Quiet, mysterious, effortlessly rich.
I wore this to a work event once and someone legit asked me if I worked in luxury fashion. (Reader, I do not.)
10. Polo Sweater + Denim + Loafers
The ultimate blend of casual and expensive-looking. I found a Ralph Lauren polo sweater at a thrift store for $12. Paired it with vintage Levi’s and brown leather loafers and felt like I should be brunching in the Hamptons.
11. Long Skirt + Silk Blouse + Low Heels
My go-to for “mom style” that doesn’t scream mom style. Long skirts are classy. Silk blouses are grown-up. Pair with kitten heels and a soft updo.
And yes, my 7-year-old said I looked like a “fancy lady” in this. I’ll take it.
12. White Tee + Black Slip Skirt + Blazer
You already own these pieces. Together, they just work. Tuck in the tee. Add a delicate necklace and structured bag. Suddenly, you’re the woman who drinks espresso with one hand and signs checks with the other.
13. Beige Turtleneck + Wool Midi Skirt + Ankle Boots
This one is great for chillier days when you want to look like you own a summer home in Maine. Neutral tones keep it soft. I got my midi skirt for $9 and it looks like it walked out of a Ralph Lauren catalog.
14. Silk Cami + Wide-Leg Pants + Dainty Jewelry
Old money doesn’t over-accessorize. One necklace, maybe two rings. Done. A silk cami tucked into flowy pants is simple, sleek, and yes—silky.
Pro tip: If your cami has adjustable straps, it’s more versatile and flattering.
15. Monochrome Neutrals
Try this: oatmeal turtleneck, oat trousers, cream coat, beige heels. One color family, layered textures. You will look rich. Like, “my perfume costs $300” rich. Even if it’s from Marshalls (mine is).
16. Button-Up Dress + Minimal Sandals + Leather Belt
This is “museum date” material. Shirt dresses in neutral shades (white, tan, olive) are so timeless. Cinch the waist with a leather belt, slide into sleek sandals, and add a top knot. Très chic.
17. Cable Knit Sweater + Tennis Skirt + Crew Socks
Let’s be real, I don’t play tennis. But I’ll look like I do. This outfit is peak preppy—bonus points if your sweater is tied around your shoulders. Just don’t spill coffee on yourself like I did. White skirts are a commitment.
18. Black Turtleneck + Camel Coat + Vintage Jeans
There’s something about this combo that says “editor of an arts magazine.” I wear this when I need to feel pulled-together with zero effort. Add a messy bun and a bold brow and pretend you just came from a gallery opening.
19. Slouchy Blazer + Linen Pants + Tank Top
For when it’s hot but you still want structure. Slouchy blazers over anything make it fashion. My pants were $10 from a sidewalk rack in Brooklyn. Pair with a ribbed tank and leather sandals. Don’t forget sunglasses the size of your dreams.
20. Midi Wrap Dress + Classic Pumps + Crossbody
Effortless and feminine. I love wrap dresses because they’re adjustable, flattering, and look like you tried harder than you did. Keep prints minimal—florals or polka dots in soft colors. Let the silhouette do the talking.
21. Vintage Tee + High-Waisted Trousers + Oversized Blazer
Okay, hear me out. Old money adjacent. Take that vintage band tee (we both know you have one), tuck it into structured pants, and throw a blazer over it. Add pointy flats. You just mixed cool-girl edge with timeless elegance.
You’re welcome.
What Makes an Outfit Look “Old Money” (Even If It’s Not)?
Here’s the real secret sauce:
- Stick to neutrals: Ivory, beige, navy, black, camel.
- Tailoring > Labels: Fit is everything. A $30 blazer that fits trumps a $300 one that doesn’t.
- Quality fabrics: Cotton, wool, linen, silk. Even blends that look the part.
- Understated accessories: Think gold hoops, leather watch, classic bag.
- Confidence: The quietest luxury is feeling good in what you wear.
And remember—old money style isn’t about exclusion. It’s about timelessness. It’s the look you build with intention, not impulse. It’s the style that still works three years from now. It’s sustainable, wearable, and smart.
Even if you’re shopping your closet. Even if your kid calls you out for wearing that outfit again.
Before You Go…
You don’t need a new wardrobe. You need fresh eyes.
Next time you get dressed, ask: Does this feel like me? Do I feel powerful in it? Could I eat spaghetti in it without fear?
That’s the real luxury.
Stay tuned. Or better yet, stay stylish your way.
