Thanksgiving isn’t just about turkey and mashed potatoes anymore. It’s also about the fit. Whether you’re hosting, visiting family, or just pretending you didn’t burn the pie, you want to look effortlessly chic. And what says effortlessly chic better than old money fashion? You know the vibe: understated luxury, timeless silhouettes, and the kind of elegance that whispers, not shouts.
If you’ve ever looked at an old Ralph Lauren ad and thought, “Yeah, that’s the life,” this guide is for you. I’ve put together 10 old money-inspired Thanksgiving outfits that blend comfort, style, and that quiet wealth aesthetic we all secretly crave. Ready to look like you summer in the Hamptons (even if you’re just commuting to your aunt’s house)? Let’s get into it.
1. The Classic Cable-Knit & Pleated Skirt Combo
Nothing screams old money Thanksgiving like a cream cable-knit sweater tucked into a tweed or wool pleated skirt. This combo oozes refinement while staying cozy enough for second (and third) helpings.
Pro Tip: Go for neutral tones—ivory, camel, or heather gray. Pair with sheer tights and loafers or knee-high leather boots for that Ivy League energy.
Why it works? It’s simple yet elevated. The cable knit says comfort; the pleats say “I have a trust fund and impeccable manners.”
2. The Tailored Blazer & Trousers Look
A perfectly fitted blazer paired with straight-leg trousers is the unofficial uniform of the “old money” aesthetic. It’s sharp but never flashy.
To nail this look:
- Stick to earthy tones—olive, navy, beige, or charcoal.
- Add a silk blouse or cashmere turtleneck underneath.
- Finish with loafers or low-heeled ankle boots.
Ever notice how some people look expensive even when they’re wearing something basic? This is that outfit. It’s all about fit and fabric—choose quality materials like wool or cotton blends that drape beautifully.
3. The Cozy Cashmere Dress
Let’s take a moment to appreciate the cashmere sweater dress. It’s the ultimate “I look put together but I could nap right now” piece. Perfect for Thanksgiving.
You can belt it at the waist to give it shape or leave it loose for that relaxed weekend-at-the-cottage feel. Pair with suede knee-high boots and minimal jewelry for that quiet confidence.
Bonus tip: Add a structured trench coat or long wool coat to make the whole outfit scream old-money luxury.
4. The Chic Turtleneck & Midi Skirt Duo
If Audrey Hepburn and Princess Diana had Thanksgiving together, they’d both probably wear this.
A fitted turtleneck tucked into a flowy midi skirt creates that perfect balance of sophistication and ease. Choose a silk, wool, or satin skirt depending on how formal you want to go.
For shoes, block heels or elegant ballet flats do wonders. Add a statement belt or pearls (because why not?) for that rich auntie vibe.
And please—no bright neons. Stick to classic autumn shades like burgundy, forest green, or caramel.
5. The Monochrome Moment
There’s something powerful about wearing one color head-to-toe. It says, “I didn’t try too hard, but I know I look good.”
Try an all-brown, all-beige, or all-gray ensemble. For example: a camel turtleneck, matching trousers, and wool coat. It’s elegant, understated, and incredibly chic.
Why it works: Old money fashion thrives on minimalism and cohesion. Monochrome outfits look intentional—even when they’re incredibly simple.
6. The Preppy Sweater Vest & Oxford Combo
Want to look like you summered at the Cape? Then this one’s for you.
Layer a sweater vest over a crisp white Oxford shirt and pair it with tailored trousers or an A-line skirt. Add loafers (bonus points for tassels) and a headband for an extra preppy touch.
IMO, this outfit is a total win because it’s both nostalgic and trendy. You’ll look classic but also right on point for the current “old money aesthetic” wave on TikTok. :)
7. The Country Club-Inspired Knit Set
If your Thanksgiving plans include lounging after dinner but you still want to look presentable, a knit set is the way to go.
Think ribbed knit matching top and skirt or pants—preferably in cream, beige, or mocha tones. Add gold jewelry and a sleek bun for that “I just casually look perfect” vibe.
Why I love it? It’s basically pajamas in disguise, but no one needs to know that. ;)
8. The Trench Coat & Scarf Ensemble
Layering is where true style shines. Throwing on a camel trench coat instantly upgrades any outfit—from jeans to dresses. Add a silk scarf tied around your neck or draped over your shoulders for that Paris meets Connecticut flair.
Pair it with:
- A simple cashmere sweater,
- Straight-leg jeans or slacks, and
- Leather loafers or ankle boots.
You’ll look like you just stepped off a private plane (even if it was actually your cousin’s Prius).
9. The Plaid Power Outfit
Plaid and Thanksgiving go together like cranberry sauce and turkey. But there’s a fine line between looking like a 90s lumberjack and looking like a Vogue feature.
Here’s how to get it right:
- Choose muted plaid tones—navy, brown, olive, or gray.
- Opt for a tailored plaid blazer or skirt.
- Pair with solid basics (no pattern overload, please).
Pro move: A plaid mini with opaque tights and loafers = instant prep school royalty. Add a wool beret if you’re feeling bold.
10. The Velvet Showstopper
If you want something that says luxury without saying a word, velvet is your friend. It’s rich, it’s soft, and it catches the light in all the right ways.
Try a velvet blazer with trousers, or a velvet dress in deep jewel tones like emerald, plum, or midnight blue. It’s elegant without being over the top—and totally Thanksgiving-appropriate.
Top it off with gold jewelry or a simple clutch, and you’re ready to impress even the most judgmental relative (we all have one).
Accessorizing the Old Money Way
Let’s not forget—the details make the outfit. Old money style is all about subtle touches that quietly say, “Yes, this is cashmere, thanks for noticing.”
A few must-haves:
- Gold or pearl jewelry (simple, not flashy)
- Structured handbags (no loud logos)
- Classic belts in leather or suede
- Silk scarves for a pop of elegance
- Minimal makeup and polished hair—because understated always wins
Remember, the old money aesthetic isn’t about being boring—it’s about timeless taste. Think more “inherited style” and less “Instagram flex.”
How to Nail the Old Money Aesthetic Without Actually Being Old Money
Let’s face it—most of us don’t have family estates or vintage Porsches sitting in the driveway. But you can absolutely dress the part without the bank account to match.
Here’s how:
- Invest in quality basics – A few well-made staples beat a closet full of fast fashion.
- Stick to neutral tones – They mix and match easily, and they always look luxe.
- Choose classic cuts – Tailored silhouettes age better than trends.
- Accessorize minimally – Simplicity = sophistication.
- Pay attention to fit – Even the most expensive piece can look cheap if it doesn’t fit right.
And remember, confidence is your best accessory. Even the most polished outfit won’t shine if you’re uncomfortable in it.
Final Thoughts: Quiet Luxury Meets Thanksgiving Comfort
Thanksgiving style doesn’t have to mean sacrificing comfort for elegance. With these 10 old money-inspired outfits, you can look like a million bucks—without feeling like you’re suffocating in your clothes.
So this year, skip the sequins and loud prints. Go for timeless textures, muted tones, and classic silhouettes. Whether you’re sitting by the fireplace or helping carve the turkey, you’ll look effortlessly chic and seasonally perfect.
And honestly? The best part about dressing like old money is that it never goes out of style. Trends fade, but elegance sticks around. So grab that cashmere, pour a glass of wine, and toast to looking fabulous while eating your weight in stuffing.