💬 “They just looked like they belonged to another world. Not louder. Just… better dressed.”
I was in Milan, walking toward a tiny bakery that smelled like almond and warm sugar, when I saw them. The kind of couple that makes you turn your head — not because they were flashy, but because they looked quietly expensive.
He wore a tailored navy blazer and driving loafers. She had a crisp white shirt tucked into pleated trousers, tortoiseshell sunglasses halfway down her nose, and a scarf tied like she’d been doing it since the ‘80s.
They didn’t match. But somehow, they matched. You know what I mean?
Let’s Get One Thing Straight: It’s Not About Dressing Alike
You might think “couple outfits” means coordinated colors or his-and-hers everything. But old money style isn’t about that. It’s about complementing, not copying.
Imagine this:
- He’s wearing: A camel overcoat, a navy cashmere sweater, dark brown brogues
- She’s wearing: An ivory knit dress, slingback flats, and a vintage Hermès scarf
They’re not trying to look like a team. They just are one — and their clothes show it.
The (Unspoken) Rules of Old Money Couple Style
These couples follow a few quiet rules. Nothing is loud. Logos are… suspicious. Fit is everything. And they always look ready for lunch at the club, even when they’re picking up dry cleaning.
Here are five of their not-so-secret secrets:
1. Tailoring Is Non-Negotiable
Even a basic button-down looks expensive if it fits just right. For men, that means structured shoulders, no gaping collar. For women? Skimming, not squeezing. Think “ballet teacher in Paris” energy.
2. They Play With Texture, Not Trends
Wool, silk, leather, cotton. That’s their palette. You won’t catch them in vinyl pants or glitter mesh. But you will notice how his flannel trousers pair perfectly with her soft cashmere shawl.
3. One Statement Per Outfit
If he’s wearing a bold herringbone coat, she’ll go simple. If she’s wearing oversized tortoiseshell sunnies, he’ll stick to minimalism. It’s an unspoken rhythm.
4. Neutral Doesn’t Mean Boring
Greige, camel, navy, ivory — these colors do all the talking. And the occasional deep wine or forest green pops up like a plot twist in a good novel.
5. Shoes Tell the Whole Story
Loafers polished. Riding boots real. Sneakers, if any, are pristine, slim, and paired with ankle-grazing trousers.
Real-Life Old Money Couple Outfit Ideas (That Don’t Feel Forced)
Let’s play dress-up — but keep it subtle.
🍷 Date Night in the City
- Him: Gray wool trousers, charcoal cashmere crewneck, suede loafers, watch (leather strap)
- Her: Silk midi dress, kitten heels, top-handle bag, red lipstick and not much else
☕ Lazy Saturday at the Farmer’s Market
- Him: Rolled chinos, white OCBD shirt, navy cardigan, leather belt
- Her: Striped knit, denim culottes, basket bag, ballet flats
🏞️ Countryside Weekend Getaway
- Him: Barbour jacket, corduroy trousers, desert boots
- Her: Fair Isle sweater, wool skirt, tights, Chelsea boots
🕊️ Wedding Guest Vibes
- Him: Classic navy suit, pale blue shirt, patterned tie, brogues
- Her: Long ivory or sage green dress, dainty earrings, low bun, neutral heels
✨ For more inspiration, see our full guide on old money wedding guest attire
Budget-Friendly Ways to Achieve the Old Money Aesthetic
Getting the old money look doesn’t have to cost a lot. Smart shopping and a keen eye help. Thrift stores are full of vintage pieces that fit the old money couple style. I’ve found designer blazers and silk scarves for less than their original price.
For casual outfits, choose timeless basics. A white cotton shirt and khaki chinos are great. Invest in quality staples like leather belts and loafers. These pieces last long and make any outfit better.
To look like a money couple, focus on fit and fabric. Even cheap items look good if they fit right. Learning basic tailoring or finding a local tailor can help.
“Style is a way to say who you are without having to speak.” – Rachel Zoe
The old money style is about simple elegance. Use neutral colors and classic patterns. Mix high and low items for a unique look. Follow these tips to get the old money style without spending a lot.
Couples Who Nail It (Without Trying Too Hard)
Sometimes, you just need a visual.
I love getting style tips from influencers who show off old money looks. They give us great ideas for outfits that never go out of style. Gabrielle Caunesil is one of my favorites. She looks great in crisp white shirts and tailored pants, perfect for couples.
Image Source: Gabrielle Caunesil Instragram Profile
Aerin Lauder is another influencer I really like. She keeps it simple yet elegant. She likes neutral colors and classic shapes, great for couples who want to look good together. Her favorite pieces are timeless and help make a stylish wardrobe.
For men’s fashion, I look to Gabrielle’s husband, Riccardo Pozzoli and David Gandy. They know how to wear suits and casual clothes well, and shows us how to mix different textures and patterns in a way that looks good together.
Image Source: Riccardo Pozzoli Instragram Profile
Image Source: David Gandy Instragram Profile
“Elegance is not about being noticed, it’s about being remembered.” – Giorgio Armani
This quote really gets what old money style is all about. It’s not about being flashy or following the latest trends. It’s about making a lasting impression with quality, timeless pieces. By following these influencers, couples can create stylish and lasting wardrobes.
(We’ll share a roundup soon. Stay tuned!)
Let’s chat: What’s Your Go-To “Couple Look”?
Do you two have an unofficial uniform? Is it trench coats in spring or dark denim and loafers in fall?
Tell us in the comments or DM us on Instagram — we might feature your look on our next edit.
Old Money Style Is About Storytelling
At the end of the day, dressing like an old money couple isn’t about labels or money. It’s about the feeling.
The feeling of slipping into clothes that whisper, not shout. The confidence in simplicity. The intimacy of knowing your partner’s style — and choosing to look like you belong together.
And that… is timeless.
Questions and Answers for Old Money Style
Why is it called old money style?
It’s the kind of style your grandmother would smile at — classic, quiet, and completely unbothered by trends. Old money style gets its name from families who’ve had wealth for generations — the kind who wear cashmere sweaters from the ‘70s that still look brand new. It’s not about logos or being flashy. It’s about wearing timeless pieces that whisper, “I’ve been here a while,” whether or not you actually have.
What is the meaning of old money couple?
Think: the couple who looks like they walked out of a Ralph Lauren campaign and into a cozy corner booth for lunch. An old money couple doesn’t wear matching outfits, but their looks always make sense together — like a navy blazer with a silk scarf, or a camel coat with a wool midi skirt. It’s more about shared taste than trying to coordinate. It says, “We care, but we’re not trying too hard.” And that’s the magic.
When did the old money aesthetic start?
Picture the Gilded Age — long coats, silver hairbrushes, and estate homes with names. The old money aesthetic has been around for well over a century, taking cues from aristocratic Europe and preppy East Coast America. It’s the aesthetic of handwritten notes, heirloom rings, and monogrammed pajamas. Over time, it’s evolved into what we see now: tailored blazers, riding boots, and that perfectly worn-in tote bag that somehow makes any outfit feel intentional.
