21 Chic Old Money Fall Outfits For Women
Looking for some chic old money fall outfits inspo? I’ve got you covered!
When I scroll on Pinterest and see all these nice old money outfits, I can’t help but think I can’t afford to be this stylish.
Turns out I was wrong! There are plenty of options to embrace the Old Money look without having to break the bank.

And if you know me, you know how important it is for me to stick to my budget. After all, this is how I managed to afford my beautiful home mortgage-free this year!
Let’s take a look at the best old money fall outfits to nail the fall chic look this season with real and affordable pieces you can buy right now!
DISCLOSURE
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Looking for more old money inspo? Here are my top articles:
- 19 Old Money Summer Outfits for Effortless Elegance!
- 40 Best Old Money Winter Outfits For Women
- 16 Chic & Classy Rich Girl Outfits Ideas (For Every Occasion!)
23 Old Money Fall Outfits For Women
1.Long-Line Coat
A long wool coat is the one item you need to nail the old money fall look. Good quality and neutral tone, so that it goes with everything!

You can shop the perfect long-line coat here.
2.Trench Coat
The perfect piece when the weather isn’t yet, but you still want to look stylish. I love to pair it with simple jeans and a pair of low-heeled leather boots!
You can shop for the perfect trench coat here.
3.Wool Vest
The perfect item to nail layering with chic! Looks great over a shirt or blouse, practical under a coat when the weather gets too chilly.
This, my friend, is the one piece you need to fight chilly weather with style.

You can shop for my favorite wool vest here.
4.Wool Sweater
A staple of the old money wardrobe when fall comes. Endless opportunities to style it to perfection: over a shirt, paired with a silk skirt or mom jeans, the wool sweater will never fail you!
You can shop for the perfect wool sweater here.
5.Turtleneck
A turtleneck is an essential for any woman’s wardrobe. Under a blazer, a cashmere cardigan or knitted sweater, a turtleneck is the perfect item to combine comfort and style.

@fallon_king
You can shop the best turtlenecks here.
6.Knitted Roll-Neck
This piece is almost an accessory by itself, and is perfect for fall, as most of the time you do not need to wear a coat. And a chunky knitted roll-neck will pull your outfit together.
You can shop my favorite knitted roll-neck here.
7.Cashmere Cardigan
A cashmere cardigan is both comfy and stylish. You can wear it with a skirt or neat jeans and always look chic.
You can shop for this pure cashmere cardigan here.
8.Button-down Shirt
This is a classic and timeless piece for any wardrobe. Chic at any season, button-down shirts work great under a sleeveless wool sweater, under a blazer, or even tucked in mom jeans. Always best to go for white, blue, or subtle stripes. I love to wear oversized ones!

You can shop the perfect button-down shirt here.
9.Silk Blouse
This is a staple of a woman’s wardrobe, whether it’s for a work meeting or lunch with girlfriends, a silk blouse will always add a chic look to your outfit.
You can shop for the perfect silk blouse here.
10.Blazer – Old Money Fall Outfits For Women
There’s no specific season to wear a blazer, so if you don’t own one already, it’s time to buy one. This will be the perfect addition to your Old Money wardrobe.

You can shop for my favorite blazer here.
11.Silk Skirt
Perfect for the fall season, a silk skirt looks chic while being super comfy. You can go for a modern look and pair it with a sweater and trendy sneakers!
You can shop for the perfect silk skirt here.
12.Wide-Leg Jeans
More comfortable than skinny jeans, honestly. They balance out fitted tops really well. Great for long days when you still want to look cool.

You can shop for the perfect wide-leg jeans here.
13.Tailored Pants
These are my go-to for work or meetings. They instantly make outfits feel sharper while still being comfortable enough to wear all day.
You can shop for my favorite tailored pants here.
14.Knitted Dress
This is the perfect piece when you’re too lazy to match anything in your wardrobe. Plus, it’s warm and comfy, so it’s perfect for windy days.

You can shop for the most comfortable knitted dress here.
15.Long Skirt
Easy to style and works across seasons with different tops, a long skirt is a staple of the old money wardrobe.
You can shop for this beautiful long skirt here.
16.High-Knee Boots
These can turn any simple outfit into a breathtaking look. Leather is always a safe pick, but I like suede ones as well. I feel it’s the perfect material for the fall season.

You can shop for the most comfortable high-knee boots here.
17.Flats – Old Money Fall Outfits For Women
Practical and comfortable for everyday wear, they’re perfect when I have to walk a lot. Plus, they go with almost everything in my closet.
You can shop for the perfect flats to wear all day long here.
18.Trendy Sneakers
My most worn shoes, hands down. Good for errands, travel, and casual days. They make dressier outfits feel more relaxed and definitely more comfy!

You can shop for my favorite trendy sneakers I wear every day here.
19.Scarf – Old Money Fall Outfits For Women
An easy add-on when it’s cold or windy. It also helps make simple outfits feel finished. I always keep one nearby that I know goes with any of my outfits.

You can shop for the perfect scarf here.
20.Vintage Shades
Useful year-round, not just summer. They instantly add a cool touch to any outfit. But you need to pick classic ones to give yourself a serious look and not just a “summer holiday” vibe.
You can shop for the perfect vintage shades here.
21.Gold Stud Earrings
I wear these almost every day. They’re simple and reliable, as they go with everything and don’t get in the way. They don’t feel heavy and almost forget I’m wearing them.

You can shop for the perfect stud earrings here.
22.Leather Tote Bag – Old Money Fall Outfits For Women
My everyday bag when I need to carry a lot. Great for work, errands, and travel days, or simply hide all the baby stuff I carry around since having Niamh.
You can shop for the leather tote bag here.
23.Shoulder Bag
Perfect when I want to travel light. Easy, comfortable, and hands-free. My go-to for casual plans (meaning when I don’t have to stuff my bag with baby wipes and diapers).

You can shop for the perfect shoulder bag here.
More Old Money Outfit Inspiration
If you’re looking for more Old Money outfit inspiration for chilly days, you can check out these Old Money Winter outfits I put together.
I also have a guide on how to dress Old Money style during summer with outfit ideas.
Extra Tip To Nail The Old Money Fall Aesthetic
To nail the Old Money fall aesthetic, you have to pick quality materials, timeless items, and avoid flashy branded logos.
Pick the right materials
- Leather
- Wool
- Cahsmere
- Cotton
Pick earthy and warm tones
- Camel, Maroon, Chocolate Brown
- Beige, Cream
- Navy, Dark Green, Black, Grey
Less Is More
- Quality over quantity
- Minimal jewelry
- Subtle Accessories
Final Thoughts
You don’t need a black Amo or to empty your bank account to nail old money fall outfits. All you need are timeless pieces, worn with confidence and elegance!
Quality over quantity is the philosophy here.
And with these 23 Old Money wardrobe essentials, you have everything you need to wear the best old money fall outfits without overthinking it or breaking the bank.
Share with your favorite Old Money looks for this fall season!



















