Fall Old Money Wardrobe Checklist: 5 You’ll Wear Forever
Okay, real talk—are you even living your best life if your fall wardrobe doesn’t channel a little old money energy? You know, that crisp, effortless elegance that says, “I summer in the Hamptons” even if you’re just sipping pumpkin spice in your backyard. If you’re nodding, welcome to the club. If not, buckle up because I’m about to change your life (or at least your closet).
So let’s talk about the Fall Old Money Wardrobe Checklist. These aren’t trendy pieces that scream “2025!” and then vanish faster than your motivation on a Monday. Nope. These are classic staples you’ll wear forever. Ready to give your fall look a quiet luxury upgrade? Let’s do this.
1. The Perfect Wool Coat (a.k.a. The "Rich Auntie" Layer)
Why It’s a Must
If you don’t already own a beautiful wool coat, what are you even doing with your life? Seriously. A tailored camel or charcoal wool coat is the crown jewel of any old money fall wardrobe.
How to Spot a Good One
- 100% wool or cashmere blend(don’t settle for polyester lies)
- Structured shoulders and clean lines
- Neutral colors– camel, navy, grey, black
- Mid to long lengthfor that dramatic walking-through-fallen-leaves moment
Personal Pick
The MAX MARA 101801 Madame Coat isn’t just a coat—it’s an icon.
Crafted from a luxurious wool and cashmere blend, this double-breasted beauty drapes like a dream and wears like timeless elegance. With its signature oversized silhouette and kimono sleeves, it flatters every body type and instantly elevates even your simplest outfits.
It’s not a trend—it’s a lifetime investment piece that whispers quiet luxury every time you wear it. Trust me, once it’s in your closet, you’ll wonder how you ever lived without it.
Bold tip: Pair it with loafers and a silk scarf. Boom, Audrey Hepburn.
2. Cashmere Sweaters (Soft, Luxe, Never Boring)
Why You Need Them
Cashmere is like the Beyoncé of sweaters. Soft, timeless, never goes out of style. IMO, a well-fitted cashmere sweatermakes anything look elegant—even your old jeans.
What to Look For
- Real cashmere, not acrylic knockoffs (you deserve better)
- Classic cutslike crewneck or turtleneck
- Colors: cream, chocolate brown, navy, soft pastels
Style Hack
Tuck a cream cashmere sweater into wide-leg trousers. Add a belt. Add a smug smile because yes, you nailed it.
FYI: Ever washed cashmere the wrong way? Me too. Hand-wash or dry clean only. Learned that one the hard way :/
3. Plaid Skirts (Academia, But Make It Chic)
Why It’s Still a Thing
A plaid skirt gives major old money vibes without trying too hard. Picture this: a pleated tartan mini with tights and loafers. Ivy League fantasy activated.
Choose Your Style
- Mini plaid skirtswith box pleats = youthful but polished
- Midi wool skirtsin muted checks = subtle sophistication
My Go-To
I have a Ralph Lauren midi plaid skirt from 2012 that I refuse to let go of. Every fall, I pair it with a cream turtleneck and knee-high boots. It never misses.
Bold move: Add a headband and a structured blazer for a Gossip Girl moment.
4. Leather Loafers (Because Heels Are a Scam)
Why They Matter
Real ones know—leather loafers are the foundation of the old money aesthetic. They say, “I’m important,” but also, “I walk everywhere because I’m grounded.”
What to Shop For
- High-quality leather(Italian? Even better.)
- Neutral tones: black, brown, oxblood
- Classic silhouetteswith minimal hardware
How I Style Them
With literally everything. Trousers, skirts, jeans, you name it. And they never hurt my feet, which is more than I can say for every heel I’ve ever owned.
Pro tip: Break them in with thick socks. You’ll thank me later.
5. The Wool Blazer (Your Polished Power Move)
Why It Belongs in Your Closet
There’s something about a wool blazer that just screams “old money heir to a publishing empire.” Toss it over literally anything and you’ll look 10x more put together. It’s math.
Features to Look For
- Wool or tweedmaterial for fall coziness
- Tailored fit, not oversized unless you’re layering
- Muted colors or patterns(think houndstooth or navy)
My Fave Look
White tee, vintage denim, tweed blazer, gold hoops. It’s giving CEO of her own destiny. And yes, it works for coffee runs and Zoom meetings.
Add a touch: A silk pocket square or brooch if you’re feeling extra bougie.
Final Thoughts: You Don’t Need to Be a Trust Fund Baby to Dress Like One
Old money style isn’t about having millions—it’s about looking like you do. And honestly? That’s the fun of it. These five staples will carry you through countless falls without ever looking dated.
Plus, you don’t need to buy new every season. Invest in quality, repeat outfits unapologetically, and wear your confidence like a Birkin.
So grab that coat, slip into those loafers, and strut through fall like you’re late to a board meeting you own.
P.S. Which of these pieces do you already own? And which one are you running to find ASAP? Let me know in the comments or DM me on Instagram—I’m always down to swap fall fashion faves. 🙂