Old Money Outfits You Need to Try! (Classy Looks That Scream “Trust Fund Baby”)

This post is all about the hottest Old Money Outfits

Hi bestie!
Grab your espresso and a buttery croissant, because today we’re channeling pure elegance. Whether you’re strolling through a European garden, sipping cappuccino at a French café, or pretending you just inherited a château from your great-aunt Colette, these old money outfit ideas will have you looking like a trust fund baby—even if your bank account says “girl, please.”

We’re diving into 10 curated outfits that are chef’s kiss for fall and winter 2024. Every look is timeless, tailored, and trés chic, with a sprinkle of sass and class.

Let’s dress like our family owns a vineyard in Bordeaux, shall we?

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1. Plaid Oversized Blazer + Headband + Mini Skirt + Tall Black Boots + Chanel Bag

Darling, this is autumn at Oxford energy. The oversized plaid blazer adds sophistication, while the black headband keeps it perfectly preppy. Pair it with sheer tights, a mini skirt, and those tall black boots that look like they stomp on heartbreak. Add a Chanel flap bag, and boom—you’re the main character of a BBC period drama set in 2024.

2. Cream Knit Sweater + White Trousers + Ballet Flats + Structured Black Bag

Clean, crisp, and utterly classic. This look says “I have a horse named Astor and I brunch in the south of France.” The cable knit sweater is the coziest piece of quiet luxury, and the tailored white trousers make you look like you’ve never spilled anything in your life (even though we both know that’s a lie, bestie).

3. Cream Knit Polo Top + Brown Leather Trousers + Loafers + Big Sunnies

This outfit is old money gone modern. The knit top is preppy perfection, while the chocolate leather pants scream understated luxe. Top it off with neutral loafers and oversized sunglasses—because we don’t cry, darling, we conceal with couture.

4. Gingham Blouse + Light Wash Jeans + Black Mary Janes + Silk Hair Bow

Country club cutie with a splash of Parisian playfulness. The gingham print and hair ribbon combo channels vintage coquette energy, and those black Mary Janes? Utterly adorable. This outfit is the definition of “old money on a city break.”

5. Puff-Sleeve White Blouse + High-Waisted Black Pants + Leather Belt + Rust Beret

Timeless meets bold! This is giving “1950s Italian film star turned modern fashion icon.” The statement blouse with puff sleeves is everything, and the rust-toned beret? She’s not just fashion—she’s a lifestyle.

6. Tailored Tan Jacket + Black Shorts + Sheer Tights + Black Heels + Lace Gloves

This one’s for the elegant rebels. It’s classy but slightly dangerous, like your trust fund came with a clause: “Must cause a little drama.” The lace gloves add that vintage glam, while the black shorts and tights combo keeps it daring and très couture.

7. Brown Tweed Blazer + Pleated Skirt + Button-Up Shirt + Burgundy Knit Over the Shoulder

Academia but make it fashion. The pleated skirt and tweed blazer scream “I fence and speak fluent Latin”, while the sweater slung over the shoulder is the cherry on top. This is your back-to-school outfit if your school is a private academy in Switzerland.

8. Burgundy Sweater Vest + White Blouse + Straight Jeans + Red Mary Janes + Woven Tote

Laid-back and luxurious. That burgundy sweater vest? Elite. The red Mary Janes? Old money whimsy. And don’t even get me started on the structured straw bag—it says “I summer in Cap Ferrat” even if you’re just popping to the corner bakery.

9. Black Blouse + White Trousers + Cream Loafers + Statement Belt

Sharp and stunning. This outfit is all about clean silhouettes with luxe details. The white trousers are crisp and tailored, while the studded belt adds just enough attitude. Paired with soft cream loafers, this is rich-girl chic at its best.

10. White Shirt Dress + Oversized Brown Blazer + Black Knee-High Boots + Dark Sunnies

Effortless elegance. This look walked straight off the streets of Paris. The white shirt dress keeps things simple, while the oversized blazer throws in a dash of masculine tailoring. And those knee-high boots? They’re walking all over mediocrity.

Bestie, there you have it—10 old money outfits that’ll have you looking like you just stepped out of a trust fund. Whether you’re sipping champagne or sparkling water, these looks are timeless, elegant, and totally wearable (even if your family tree doesn’t include a duke). The secret isn’t in your bank account—it’s in the tailoring, the tones, and the attitude.

So pull out your vintage pieces, your cable knits, your blazers and ballet flats, and romanticize the luxe life you’re building.

And if you loved this post (I know you did), don’t forget to subscribe to The Catalog by Celine for more fashion inspo, nail ideas, dreamy books, and lifestyle posts that slay on a budget. Trust me, you don’t want to miss what’s coming next!

With love and lace gloves,
Your forever fashion bestie.

Old Money Outfits:

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