How to Dress Old Money Style in Summer 2025 (Without Trying Too Hard)

🎀 How to Dress Like Old Money This Summer (And Not Accidentally Look Like You’re Trying Too Hard)

April 29, 2025

Let’s be real: in 2025, quiet luxury isn’t just a trend anymore—it’s a lifestyle. If you’re dreaming about yacht days, candlelit dinners, and looking like you were born into a trust fund (even if your actual budget says otherwise 👛), this is your summer to glow up your style game.

The best part?
Old money summer looks aren't about spending a fortune. They’re about looking intentional, polished, and timeless. With the right outfit formulas (and a little LookSky magic), you'll be channeling Old Money Energy without even trying.

✨ But beware:

If you don’t get the details right, you risk looking sloppy... or worse, like you’re trying to cosplay Gossip Girl 2008. 🚫 Let’s not let that happen.

Here’s your LookSky-approved guide to nailing the Old Money Summer vibe—plus outfit formulas, color season analysis, and cheeky "don't get caught slipping" warnings so you always show up camera-ready.

1. The Crispy White Classic

🖤 Outfit Formula:

• Clothing Type + Silhouette: Thick-strap white tank + crisp tailored white shorts + thin brown belt with gold buckle

• Color Palette: Bright white + warm brown accents

• Accessories: Minimalist gold hoops, dainty chain necklace, brown leather watch

• Shoes: Tan leather sandals or classic white sneakers

• Hair & Makeup: Sleek high ponytail + glowy skin + tinted lip balm

• ✨ Vibe & Seasonal Color Analysis:
This crispy-clean white outfit glows on True Summers and Light Springs (cool or neutral undertones who look amazing in icy or soft tones).

• ⚡ Don’t Get Caught Slipping:
Wrinkled white = instant downgrade. Steam or iron your outfit so you don’t show up looking like you got dressed in a laundry pile.

Woman in white tank and belted shorts summer outfit

🌊 2. Nautical Heiress Energy

🖤 Outfit Formula:

• Clothing Type + Silhouette: White ribbed tank + white structured shorts + navy-and-white striped sweater (draped over shoulders)

• Color Palette: Crisp whites + deep navy

• Accessories: Chanel-inspired ballet flats, structured mini leather bag, small pearl earrings

• Shoes: Elegant ballet flats (bonus points for cap-toe styles)

• Hair & Makeup: Loose center-parted waves + bronzy, glowy skin

• ✨ Vibe & Seasonal Color Analysis:
Gorgeous on True Winters and Cool Summers (girls who shine in cool, saturated tones and love a little contrast).

• ⚡ Don’t Get Caught Slipping:
Skip over-the-top sailor vibes. You want timeless, not "theme party."

Parisian chic striped sweater and white trousers outfit

🕶️ 3. Low-Key Luxe: The Off-Duty Heiress

🖤 Outfit Formula:

• Clothing Type + Silhouette: Light blue oversized Oxford shirt + crisp white shorts

• Color Palette: Pale blues + white neutrals

• Accessories: Hermes-inspired tan leather slides, raffia tote, oversized black sunglasses, clean stacked bracelets

• Shoes: Luxe-looking leather slides

• Hair & Makeup: Sleek low bun + natural glowy makeup

• ✨ Vibe & Seasonal Color Analysis:
Slays on Light Summers and True Summers—the soft blues and whites make you look effortlessly expensive.

• ⚡ Don’t Get Caught Slipping:
No giant logos on your tote. Raffia > designer print flexes.

Summer outfit with blue shirt and white shorts

⚓ 4. Stripes on Stripes (Yacht Girl Edition)

🖤 Outfit Formula:

• Clothing Type + Silhouette: Wide black-and-white striped sweater (draped over shoulders) + thin black-and-white striped tank + flowy white linen pants

• Color Palette: Crisp whites + black accents

• Accessories: Dainty layered gold jewelry, minimal earrings

• Shoes: Simple leather slides or barefoot for yacht vibes

• Hair & Makeup: Salt-sprayed beach waves + soft bronze highlight

• ✨ Vibe & Seasonal Color Analysis:
This one is perfect for True Winters and Summers—the sharp contrast plays up your natural brightness.

• ⚡ Don’t Get Caught Slipping:
If the stripes clash too much, it looks messy, not curated. Match stripe weights carefully (thick sweater, thin tank = chef’s kiss).